Trying to Shake Off My Complacency with Singleness

Yesterday, I received a “love yourself” care package from my dear friend Lucy with books and goodies and journal supplies. The gift was prompted by our last phone conversation because we talked about how two men have re-entered my life that I had complicated relationships with once-upon-a-time (which is the reason they have been out of my life for the last few years). She gave me some practical advice that day about how to establish some healthy boundaries with them and mentioned three of her favorite books on the subject of self-love and dating: Daring Greatly, He’s Just Not That Into You & How to Get a Date Worth Keeping. She sent me all three with little post-it notes on them telling me the order in which to read them.

Unfortunately, the mug she sent got a little chipped in transit.

Lucy knows me so well that in her card she even wrote in parenthesis, “please, don’t brush [these books] off even if the titles seem abrasive/annoying/offensive—they’re so good, so totally worth reading.” Of course, she was referring to those last two because there’s nothing offensive about encouraging me to dare greatly. I can’t say that the title for the second book doesn’t sting a little or that the third book doesn’t make me bristle. At the same time, I’ve gleaned enough from our conversations about these books to know they are worth reading.

I started last night with the third book on the list (I’ve never been good at following instructions). I have heard so much from Lucy about Dr. Henry Clouds dating advice that I was impatient to see what more I could learn from actually reading How to Get a Date Worth Keeping. So much of what he has to say at the beginning are things that I have already learned. While I am going to keep reading and faithfully make my way through Lucy’s fall reading list for me, I feel like I’m in a different place than I led Lucy to believe during our phone conversation.

In college and grad school, I didn’t take much responsibility for my stagnant dating life. When my pattern of developing pseudo-relationships cropped up I felt like it was some sick fate that God was condemning me to. It was easy to blame my weight and the shallowness of men so I did that a lot publically. Deep down, I felt like there was something essentially wrong with me.  A fundamental truth I believed was that I was too exhausting to love. Or, to steal a line from my favorite Shakespearean play, I felt like I was too expensive to wear every day. Thus, I was relegated to be “the other woman” (though my affairs with men were only emotional because I don’t mix emotional intimacy with physical intimacy).

I’ve come to believe what Dr. Cloud espouses in his book: it is our own mental road blocks that prevent us from dating and developing the relationship that we want. If we want a different outcome, we have to change our mindset (I’m paraphrasing, of course, and being somewhat reductive but that’s the gist). I know that I have been the one holding myself back.

The summer I turned 25 I proved Dr. Cloud’s thesis. I felt beautiful and desirable. I had my heart set on getting my first official relationship and I left myself open to dating. For months, it seemed like I couldn’t go anywhere without meeting a guy who would eventually ask for my phone number.  It was great and led to that short-lived relationship with a younger guy.

It wasn’t discouragement or heartbreak that cut that season of dating so short. I’m the type of person who only needs to prove something to myself once. After I proved that I was dateable and loveable I was left with the question of whether or not I actually wanted to date or have a man in my life. At that time, I decided that the answer was No. I wanted to be single. My weight gain over the last year has been an external indicator of this internal truth. I wanted to clear my head. To learn how to be comfortable just being me without needing the validation of my male relationships. To focus wholeheartedly on getting back out on my own and out of my parents’ without distraction. It’s so exhausting trying to defend this stance (and, frankly, a very personal decision) that I’ve coped out and made excuses when undergoing scrutiny about my singleness. It’s so easy to blame my singleness on a lack of available/eligible single men. I’ve know that it’s a smoke screen. I could even list a number of opportunities that I’ve passed up during this time.

The re-entrance of these two men in my life has awakened a hunger in me that’s been dormant for almost two years–I forgot how nice it is to have a man in my life who will call me on demand and chat my ear off as I drive home from work so I stay alert. I forgot how easily my barbed wire can come down when I’m talking to a man I really click with. I know all of this is what is worrying my friends. It’s worrying me a little too. I don’t want to fall back in our old cycles. I don’t want to have my heart set on them. But I also know that it isn’t. I’m not as concerned as my friends are because that old pattern doesn’t tempt me anymore. Though I am still the same person and though I still care about these men, I have grown up. I’ve learned that I’m loveable and dateable. I know that I can live a full, rich life on my own. That knowledge makes it impossible to be willing to settle for someone who is just not that into me. Even though these men are reminding me of what I miss, even though they have awakened this hunger, I haven’t forgotten our history and I don’t expect them to satiate my hunger.

It feels so good to be regaining the desire to have a man in my life. Every time my exuberance is met with concern I get a little more annoyed because what I want my friends to pick up on is that I’m starting to shake off my complacency with singleness. I think that’s great news! I plan to put Dr. Cloud’s book and Lucy’s self-love kit to good use.

Feature image by William Stitt.

Not About Love

I’ve been really obsessed lately with the website 40 Days of Dating. Two friends, Jessie and Tim, with  opposite relationship issues—who also happen to be graphic designers—decided to date for 40 days and write about it. Part of what draws me into their experiment is the graphic element (I’m a sucker for bright colors and delicious fonts) but I’m also fascinated by the project itself. I relate to both Jessie and Tim in different ways.

Like Jessie, I grew up with parents who are deeply in love and have a strong marriage. Witnessing the beauty of the life they have made together and the bond they have with each other, it’s impossible not to want a relationship like that myself. Also, like her, I’m a romantic. I love the feeling of being in love (or being infatuated). And I’m equally uninterested, and frankly exhausted, by the idea of dating lots of men. But my reasons for being disinclined to date casually are very different from hers. This ties into how I’m like Tim.

Tim is a commitment-phobe because he loves his freedom.  He loves that he can do whatever he wants, whenever he wants, with whoever he wants. I can relate to that. As I recently told you, freedom is a requirement in all of my relationships. Though I am energized by having an extroverted job and love investing deeply in people, I am an introvert at heart who is very project oriented. I need a lot of quality personal time to unwind, reflect, recharge and work. When I’m sunk into a project or taking personal time even my loved ones feel like a huge inconvenience when they make the smallest demand on my time or energy (especially energy).  I prefer having relationships on my terms, in my timing.

All of my friends have said to me at some point or other, “I love that we can go months or years without talking and I know it’s okay. You won’t get offended.” Of course, I don’t get offended. This is how I like my relationships. The beauty of only seeing each other every once in a while is that it pretty much guarantees that when we do see each other it’ll be great! No drama. No boredom. No opportunity to take each other for granted. Since I jump quickly into deep conversation, we both get intimacy on demand. While these marathon hangout sessions usually take up a large chunk of time, it isn’t a habitual commitment so it’s easier to fit into my haphazard schedule. I get intimacy and freedom. But I don’t get anyone to consistently lean on or talk to every day. That’s the trade off.

Tim and I are very different in that my need for freedom and control leads me more naturally into pseudo-relationships than casually dating. I did give casual dating a try but I found it entirely unsatisfying because it didn’t offer me the intense emotional connection I crave. I don’t care if a relationship ends in marriage or if it just ends but while it lasts I want it to be deep, beautiful and meaningful. If it isn’t, there is no way I will find time for it in my schedule. Flirting is fun but I get my fill of it at work.

I have been “deep single” for the last year because I decided that my habit of pseudo-dating wasn’t healthy and that casually dating isn’t for me. I haven’t even allowed myself to hangout with guy friends outside of work because I didn’t want it to get complicated. While this time has given me a chance to clear my head and feel more centered, it has also left me craving intimacy. One thing I’ve realized about myself in the absence of close male relationships is that I don’t have the capacity to emotionally connect with women as deeply (I let my best female friend find out my grandpa died through facebook–you can bet I would’ve at least texted one of the leading men in my life right away had we still been on intimate terms at the time).

The 40 Days of Dating project speaks to where I’m at because I’m a crazy mix of both of these people: I don’t want to give up my freedom and I want a deep meaningful relationship. While they struggle to compromise with each other, I am struggling to compromise with myself.

Wednesday, I had what was supposed to be a networking meeting with life coach Jill Haas that practically turned into a therapy session. She observed that I’m a control freak which isn’t news to me but, somehow, I always seem to disconnect my desire for freedom from a need to have control (even though that is obviously what it is). She left me asking myself some good questions. I’m not going to pretend that I’ve come to a resolution. Instead, I’ll leave you with the main question I’m asking myself:

Is my need for a sense of freedom and control more important to me than my desire for intimacy and a healthy relationship?

Good question right? I wish I had an answer.

Taking a Chance with Online Dating


All winter long dating has little to no appeal to me. The cold seems to seep into all of my cells draining me of passion and energy. About all I want to do is curl up in a ball, in my cozy bed, and sleep until the snow melts away for good. Of course, I can’t entirely do this but I still practically hibernate. Few people see much of me in the winter. I’m entirely unmotivated to leave my apartment unless I have to. I especially won’t bother braving the cold to go out with a guy that I may or may not like.

Once I smell spring in the air, this starts changing. My craving for a male sidekick sets in. I instinctively begin hunting for a quality guy to hang out with. (I love my female friends but guys are really the best when you want to get out and have fun). Though winter won’t quite give up out here in Michigan, we’ve had enough spring-y days that the hunter in me has awoken.

Problem is that all the men I’ve been meeting fall into one of four categories: too young, too old, undereducated or married. Even if it weren’t for these disqualifiers, I haven’t met a single guy around here who I enjoy enough to want us to meet up outside of work. (Admittedly, I’m pretty selective about who I hang out with, whether they’re male or female – if we don’t really click, I don’t bother letting it be an option to have a relationship outside of work, unless I’m really bored). All winter just feeling like I had options, even benign ones, was enough. Now, I want more.

I’ve made multiple attempts over the last two years to find different environments, besides work, where I can meet some quality guys around my age (I’ve tried out like five different young adult church groups and frequently hang out at this trendy new café that has pretty high traffic). Nothing has been successful. It’s just not in my nature to completely give up on the hunt. As Judy says in “White Christmas,” “You know how honesty needs a little plus, well sometimes fate needs a little push.” I’ve decided that it’s about time I gave fate a little push. This is why, despite many reservations, I’m giving online dating a chance.

Alright, the decision wasn’t entirely this well thought out. It was kind of impulsive.

You may remember that I told you a little bit about this dating site,, last year. I saw an ad for it on facebook that I just had to click on because it fascinated me. It’s marketed as a dating site that’s more like a social network where you post date ideas like statuses and find potential people to go out with you. How cool is that? I come up with potential dates all the time. I miss having a go-to guy that I could con into taking me out. I fell in love with the concept.

I signed up for free so I could poke around the site. It was terribly disappointing. Most of the people didn’t take advantage of its awesomeness at all. They treated it like any other dating site. (Tons of the guys on there just post boring things like “Let’s just talk and see where it goes from there.” Psh. Lame! Not interested). At the time, I also was turned off by the idea of going out with strangers (spending the last year talking to hundreds to thousands of strangers every weekend has really diminished this hang up).  After satisfying my curiosity that day, I wrote off online dating.

I didn’t remember that my profile was still up until I recently started getting a number of emails from the site (I’m notorious for setting up online accounts that I never use but don’t bother to delete). For whatever reason, my profile began receiving a lot of attention. I got a string of messages throughout February letting me know that different men were “intrigued” by my date. Of course, that piqued my interest. I visited the site to check out these guy’s profiles but, annoyingly, I couldn’t see them without becoming a paid member. There was no way I was doing that! Still, after practically a year of silence, it felt like a nudge towards online dating.

After receiving yet another one of those emails, I set up a free account on the dating site Lucy uses. The next night, Heather convinced me to get on another dating site that she’s trying out.

I’ve had my profiles up for about two weeks now. I haven’t gone on any dates yet but I’ve messaged back and forth a little with a few men. I’m about ready to meet one and see if we get along as well in person as we do online.

I’m doing my best to keep an open mind but it’s hard. With an online format like this it’s too easy to go down the line and size these guys up quickly: Weirdo. Douche. Creep. Loser. Kid. Fitness Freak. Man’s Man. Etc. (All disqualifiers in my book). I’m doing my best not to just judge these men off of their profile pictures (though the pictures that people choose to put up can really say a lot about them). Men’s About Me sections and usernames play a big role in my assessment. I’m terribly inclined to immediately write off guys who say their primary interests are sports, exercise, or outdoorsy things (hiking, camping, fishing, hunting). I just can’t imagine having anything to talk about with these guys.

So far, the best thing about online dating is viewing people’s profiles. Some men’s pictures  scream douche bag so loudly it’s hard not to laugh. Plenty of Fish offers an extra level of amusement because each person has to have a headline for their profile. Some of my favorites so far are “Cougar? No Thank You.” “Add to Cart.” “Is eating a sandwich. Oh wait, wrong site…”  “I shower every day.” One of these days, I’m hoping to see a guy with the headline “Professional punner and proud of it.” I’d totally message that guy in a second.

Have you tried out online dating? What do you think of it? Do you think I’m judging these men’s profiles too harshly?

Searching for Mr. Good For Me

The posts that I wrote on relationships just before the holidays sparked a rather heated debate with one of my friends. After going back and forth on the topic, he eventually told me, “Sometimes it hits me that you and I having discussions about relationships is kind of like Forrest Gump and Penny (Big Bang Penny) debating String Theory.” I couldn’t help but chuckle and practically agree (I still don’t know whether or not to be complimented or insulted that he likened me to Penny).

Possibly the only relationship advice I’m qualified to give is on pseudo-relationships. Those posts on dating were primarily provoked by two things I’m very tired of hearing:

  1. Good guys always finish last because women go for assholes.
  2. Women have too high of standards. They don’t want to just fall in love, they want to fall in love like the movies.

Those are my paraphrases but I’m sure you’ve heard some version of these out there. I was trying through my advice to subtly challenge these ideas. I don’t know if that’s what I accomplished, so I might as well be more direct.

That first one really irks me a lot. It probably grates against me so much both because it’s what pick-up artists use to justify their jerky behavior (and to construct their rather ridiculous idea of the ‘alpha male’)* and because I’ve been accused of it. The accusation isn’t entirely unfounded. I have often been able to click with snarky, difficult, at times chauvinistic, men. That’s been true since middle school. I don’t necessarily think these are attractive qualities. We just had something of a natural affinity for each other. I’ve mostly outgrown this.

Setting aside my personal irks, I think it is a pretty inaccurate generalization. None of my female friends got the attraction between those men and I, even when one of the men was as gorgeous as a model. Maybe all the women I’ve befriended are incredibly singular but few of them find jerks attractive.

When I look around at all the women I know who are married, most are with kind men. Few settled for a charming asshole or blatant prick. There are some exceptions, of course. There are also strong women I know who chose men who are too nice for them. Men who’ve let themselves become doormats. If I’m honest, my tendency to seek romance with difficult men was, in part, an overcorrection. I was afraid I’d become like those women if I chose a man who wasn’t strong enough to push back against me. I’ve since learned not to misinterpret selfish stubbornness as strength. I don’t think it takes that long to figure out that a man doesn’t have to be douche-y to avoid being a doormat.

My biggest pet peeve with that statement, as I believe I touched on before, is that it assumes women all mostly want or are attracted to the same things. That’s absurd! If that was true pick-up artists wouldn’t have such a massive strike out ratio. They’re techniques would work on every woman they walk up to. (They may make it seem that way in their stories but it isn’t true. They just write off any woman who turns down their advances).

The reality is that every woman is attracted to different qualities and characteristics. Some women like men who are practically big, cuddly bears. Some women like introverted nerds. Some like artistic hipsters who look like waifish lumberjacks. Some like the classic, fit sports enthusiast. Etc. Most women, at least who I’m acquainted with, aren’t really looking for abstracted qualities. Sure, they’ve come up with an idea of the kind of man they’re attracted to or think is well suited to them. What’s wrong with that? What most of us are really looking for, in the end, is genuine connection.  Most of the people I know were surprised by who they fell for. No matter what idea they had in their head, they were willing to give a good man a chance.

I see no justification for nice guys to think women will rule them out just because they prefer not to act like douche bags. But maybe all the women I know are just the reasonable 10% who don’t mistake meanness for strength and prefer not to be treated poorly.

The second one on that list bugs me for two reasons.

The first being that I feel like it places all the blame on single women’s shoulders. Like Nichelle, Lucy and I are all still single at 25 because we keep chasing off our Mr. Good Enoughs because we’re waiting for our Mr. Perfect. That’s hardly accurate. It’s not true about any of my single female friends.

The second is that, again, I believe this is based upon a ludicrous assumption about women. I know that there are women out there like Lori Gottlieb, author of Marry Him: The Case for Settling for Mr. Good Enough, who have absurd standards.  Who will turn down going on a first date with a guy if he’s 5’7” instead of 6 foot something (which I find particularly hilarious cause I’m notorious for liking men closer to that height than 6 foot). Who will write off a guy immediately who seems like he’s too conservative or doesn’t have enough money. Who have a checklist of requirements that they believe have to all be crossed off before seriously considering a guy. I’ve been told these women exist. I’m sure I’ve even met some but I can’t fathom this. I find it hard to believe that these women are the majority.

Maybe I’m the exception. I don’t really have a picture of my Mr. Right in my mind. I don’t have this mental construct of what he’s going to look like or what career he’s going to have or what income bracket he’ll fall into. I haven’t predetermined what sense of humor he’s supposed to have and how I expect him to be romantic. I haven’t scripted out the ways I think he should display his attraction to me. All the things Lori Gottlieb claims are preventing most women from finding a partner to share their lives with.

I feel like I’m more at fault for wanting to settle for Mr. Good Enough than holding out for Mr. Perfect. Looking back over my history, I feel like I’ve been constantly trying to talk myself into falling for the best guys who’ve come along. When I say “best” I mean the ones with whom I’ve had the most chemistry or who were the most devoted to me and vice versa. Men that I genuinely clicked with and deeply enjoyed, or thought I enjoyed enough. I feel like the irony of my life has been that none of these men have let me settle for them. In the end, I’m always grateful for that because I don’t think I’m good enough at relationships to be able to live with someone who falls into the good enough category.

All my friends and family members already seem to know that. One friend this summer told me he didn’t think I’d be satisfied if I settled for someone who wasn’t on my level intellectually, spiritually, and emotionally. My friend Carrie told me around the same time that she feels like I’m an elephant who has been picking up sticks. When I asked her to clarifying that nearly insulting comment, she said that I’m a big personality meant for better relationships and a better man but I just keep biding my time with what crosses my path.

Over the last seven years, I feel like I’ve been schooled in what I can’t compromise on. I’ve learned how to recognize different characteristics and qualities that blend well with me. I’ve also come to realize that I have good instincts. At the beginning of most of my relationships, I’ve had a sense of the potential that it held for me. I just ignored it because I wanted the experience that was being offered me and there was no guarantee that my sense was right. I’m beginning to trust this sixth sense.

Most of my single friends are even more reasonable than me. They haven’t tried to convince themselves into settling for a bunch of Mr. Good Enoughs but they also haven’t been chasing men off with potential. They have a pretty healthy sense of what does and doesn’t constitute a deal breaker, though many have also been learning some similar lessons to me.

Dating, and pseudo-dating, are a process of trial and error that teach us about ourselves and about relationships. I’d like to believe that most of us learn what really matters in the process. I’d like to believe that what most of us are searching for is not a storybook romance but something lasting and worthwhile that we can commit ourselves to for a lifetime. We aren’t in search of Mr./Mrs. Perfect, we’re looking for Mr./Mrs. Good for Me. Maybe I’m giving people too much credit.

End comments:

*If I seem a little obsessed with pick-up artist, it’s because I find their philosophies as detrimental and dangerous as militant feminism. The friend who introduced me to The Game also used to send my blog links and articles by and about them. At first, I didn’t take them that seriously but, as their influence had a toxic affect on my friend, that changed.

Beating the Singleness Blues

I know! I know! Daily posts! You’re all going to be spoiled. It’s sort of my New Year’s resolution, that I’ve started on early, to have something for you every day of the week. Today I intend to keep it light and short.

After reading some of my friends’ comments on Monday’s post (which they left on it via facebook), I thought about how annoying I would’ve found a list like that when I felt trapped in singleness. I would’ve rolled my eyes at the idea that such advice was “helpful.” I still don’t know if I even believe in step-by-step instructions like those I gave. Primarily, my purpose was to convey principles and bits of wisdom that can’t guarantee you’ll find someone worth sticking with but might at least help you feel less stuck.The gist of my advice (Try!) is something I’ve had to take to heart myself.

Throughout this last year, that bit of advice has helped both my friend Lucy and I. Neither of us had dated until this year and we’d both felt a little trapped in singleness. In different ways, we both came to the conclusion that we needed to follow that simple maxim. For me, “trying” has sort of naturally resulted from a combination of things: losing weight, consistently looking nice, putting men through less shit tests early on, getting more comfortable giving men indicators of interest, toning down my intelligence and seriousness while simultaneous ramping up my absurdity and playfulness, and being more consistently outgoing. Some of these things I didn’t really do intentionally to start dating, still they’ve played a role in altering my circumstances. I’m still not dating tons, but that’s primarily because I’m choosy. Lucy’s story has been a little different. She has been much more intentional about trying.

Last year, after a long conversation about guys with her older sister, her sister decided that she needed a little help. She set up some online dating profiles for Lucy, gave her some dating coaching and then went through her closet. She took away all of her hoodies and men’s t-shirts. After that, she had Lucy try on all of her other clothes one by one. If a color looked bad on her, or a shape didn’t flatter her, that item of clothing went into the donation pile. Having rooted out her bad clothes, she kindly let Lucy go through her own wardrobe and she gave her some clothes that looked better on her. To complete the makeover, she taught Lucy more about makeup and convinced her to come up with a basic, daily makeup routine.

Lucy found all of her sister’s attention and guidance instructive and encouraging. Over the last year, she’s gone on more dates than she had in the previous six. Of course, most of her dates have resulted from her online profiles. Through this process, she’s become more confident that she’s date-able. While she’s always been a pretty flirtatious person, she never really took it seriously. The more she’s been dating, the better she’s gotten at discerning sincere but playful interest from platonic flirting. She’s still not in a serious relationship but finally she doesn’t feel trapped.

Lucy and I have a theory that believing you’re date-able is the base foundation for attracting interest and getting dates. Maybe we have it easier because we’re women. But, besides bad breath, teeth or hygiene, the most common reason women give for finding a guy initially unattractive is that he comes off as insecure or unconfident (which he may be conveying by being too shy to make eye contact or constantly seeking validation). I’d like the good guys out there to realize they have more of a chance then they think, just as we had to stretch our comfort zones a little and put in some effort, so do men.

If you’re feeling the singleness blues, and no-amount of effort is helping, I’ve found an amusing article to help brighten your day: 10 Ways to Dodge Questions About Singleness This Christmas. While most of these have the potential to make your holiday gatherings even more awkward, they would certainly be entertaining. My favorite being the suggestion to respond to the question of why you aren’t dating by “Conjur[ing] up a few fake tears, then look[ing] up quickly with a shout, ‘How long, O Lord!’” Another winner is “Pull a Mother Teresa: ‘The poor children at the shelter need me too much to spend time dating.’”

A Good Guy’s Guide to Get the Girl

Ghosts of Girlfriends PastOne of the Christmas-y movies I’ve been watching this season is “Ghosts of Girlfriends Past.” Matthew McConaughey’s character in it is a lady’s man, or pickup artist, who must have hundreds of little black books filled with his conquests. True to a good rom-com, especially one taking cues from A Christmas Carol, he sees the error of his ways by the end of the movie and gets with the woman he’s actually in love with. I must admit, partially I like it because he reminds me of some guys I’ve known. Watching his uncle teach him the art of “picking up dames” reminds me of reading Neil Strauss’ The Game: Penetrating the Secret Society of Pickup Artists. The best thing about this movie is that it illustrates that if you really want to fall in love, most of that pickup artists crap will not work for you.

The theory out there that good guys can’t get the girl drives me crazy. I think it is entirely untrue that women are naturally drawn to jerks. What we want is a strong, confident man who will make the effort to pursue. The primary reason pickup artist are successful is because they’ve learned how to manipulate women into thinking they’re stronger, more confident and more interesting than they really are. While they’re successful at one night stands, they’re hardly good for anything else. They aren’t as appealing as media can make them out to be (their strike out rate is very high). Even the woman who ends up with McConaughey’s character in the movie is entirely unimpressed by the persona that he’s put on. The only way he can be with her is by actually being himself. As well as by seeing her as a person, instead of a conquest.

There are some things that good guys can learn from pickup artist. Mostly it boils down to this: Try! What you’ll learn about women is that were pretty receptive to a sincere pursuit. Since I’m tired of hearing good men complain that women’s standards are too high, or that they have no chance because we’re inexplicably drawn to a man they don’t want to be, I’ve decided to come up with A Good Guy’s Guide to Get the Girl.

1. Become Intentional About Meeting Women – This is something that pickup artists are right about, the only way you have a chance to find someone to date is if you meet women you could date. This means getting comfortable approaching women you don’t know. Striking up a conversation with a woman in a coffee shop or bookstore, getting to know the women in your church or small group, talking to a female friend-of-a-friend at a holiday Christmas party. Or joining an online dating site. This is true for women too. If we want to date, we have to become better about meeting new people. My friend Carrie has always recommended finding environments with like minded people. When she lived in Dallas, she got very involved in the art scene to meet women there. I’m finding that I have more options when I leave myself open for lightening to strike where ever I go, meaning being comfortable chatting up strangers anywhere I am. We’re all different. But, you won’t find women to date if you don’t stretch your comfort zone a little.

2. Break the Ice – I know, starting a conversation with a stranger can seem hard or awkward. Usually, it isn’t actually as intimidating as you think it’ll be.(I say this as someone who used to find it very intimidating and now does it with ease). All you have to do is find an opening. It’s best to take a cue from your environment. You could ask her a relevant non-personal question (do you know where…is?). Say a witty comment that’ll provoke a response (but isn’t offensive). Make an observation about her that could spark a good dialogue (You’re reading Atlas Shrugged. I read that in high school, what do you think of it?). Etc. The more you do it, the better you’ll get. The best rule of thumb is not to be disingenuous. Be yourself. But bring you’re A game. Unless it suits the circumstance, avoid asking super personal questions too quickly. For example, Where do you live? Is an especially creepy question to ask too quickly.

3. Carry Yourself with Confidence – As Uncle Wayne in the movie says, “Cool comes from the inside.”  While we, women, are also suckers for a pretty face, we’ll give a homely guy a chance if he carries himself with confidence. Being cool doesn’t necessarily mean being cocky. It means having the courage to strike up a flirtatious conversation with us and conveying that you’re at ease both with us and yourself.

How do you convey ease? For starters, by not awkwardly seeking validation or trying too hard to impress. Pushing yourself like a used car salesman trying to get rid of a lemon isn’t attractive (I’ve got a guy doing this right now and let me tell you, no amount of persistence is going to wear me down though he is wearing out my patience). Instead of peddling your pros, let your personality come through in the conversation. Let your attraction be both a little obvious and tempered (it’s cute when we can see in your eyes how much you like us, it’s not cute when they convey ‘I’m so in awe of you I can’t consecrate on a single word coming out of your mouth. Marry me, now!’).

4. Good Grooming & Good Style are Winning – You don’t have to be an Abercrombie & Fitch model or look like you stepped out of GQ to get a girlfriend. While I personally go for more of the metro male, most women are just looking for a guy who takes good care of his teeth, showers regularly, matches most of the time and wears clothes that fit (too big or too small is not so hot). I’d say that’s a pretty achievable standard. If you’re really having trouble dating, I highly recommend asking one of your female friends to be your personal shopper and help you put together a good wardrobe. If there is no such woman in your life, I’m happy to offer my services. I’ll gladly send you a personalized guide if you contact me (I’m not joking either).

5. Get To Know Her Before Asking Her Out – I’ll confess, this one might be more of a personal rule. A guy doesn’t stand a chance with me unless he takes the time to get to know me a little bit (and gives me a chance to sense him out). We could just have one good, long conversation, or multiple little conversations but simply coming up to me, talking to me for a minute or two and then asking me out on a date or for my number is a sure fire way to get an automatic rejection. Even if you’re really good looking. I’ll be flattered you think I’m attractive, as long as you aren’t too creepy, I’ll nicely and humorously let you down. I don’t give out my personal contact information to strangers. I also don’t go out with people unless I know we can hold a comfortable conversation and that I’m at least somewhat interested too. I don’t think I’m alone in this. #MyFriendsAre Married is right there with me. There is a reason that online dating profiles consists of more than photographs. Women like knowing a little bit about who you are before we grab a cup of coffee with you and would like you to be interested in more than just what we look like.

6. Ask Her For Her Contact Information and Ask Her Out! – If you don’t make a move, you don’t stand a chance. Yes, in this day and age women can make the first move. Most of us prefer it when you make that move. In my experience, if a guy doesn’t get up the courage to ask for my number or other contact info it means one of two things: he’s not that into me or he lacks confidence/follow through. In other words, it’s not worth my effort. When you have the courage to make the first move it conveys that you’re probably going to be worth her time and emotional investment. (We tend to emotionally invest a lot in a even a first date, it’s part of why we can be so picky).

If you’re interested in dating her, ask her out soon after you get her contact information. Text, facebook message and instant messenge are all now acceptable ways to ask a girl out. Sometimes, they’re better than calling or asking her face to face. Then, if she happens to reject you, it’s much less awkward for both parties. If you are really obviously vibing and she’s already giving you physical indicators of interest (touching your arm, leaning in towards you, etc), feel free to be brave and ask her out then. If you wait too long to ask her out you run the risk of putting yourself in the friend zone or irritating her. The date doesn’t need to be fancy but it should be a neutral location. Don’t invite yourself over, or invite her over for a first date. That’s uncomfortable and forcing an intimacy that doesn’t yet exist.

 7. Accept the Risk of Rejection – I know, it sucks to be rejected. I’ve had my fair share of rejections and it always stings a little. You get over it. The sooner you let it happen, the sooner you’ll recover. Harboring feelings for someone for months or years before asking her out then finally getting rejected, when you’re incredibly emotionally involved, will be much more painful than getting rejected after two or three conversations or a month or two of dating.

While it’s normal to wonder what you did wrong, and in some cases this is a legitimate question to ask, you should also remember that chemistry and compatibility aren’t entirely controllable. No matter how interesting, well dressed and wonderful you are, that doesn’t guarantee you’ll really click with someone. Or that you’ll work out long term. Some connections, though genuine, don’t really translate well to romance or a long term relationship. Even if you’re both physically attracted to each other. It’s sucks when you feel it works and they don’t but you don’t want a person who doesn’t return your feelings.

Don’t let the potential of rejection get in the way of taking a risk.

8. Be a Student of Relationships – Let your past relationships teach you about the quality of people that you click with. You can learn both from your romantic relationships and non-romantic relationships. Like, while I never was attracted to my friend Ben, he has qualities that I know are a good compliment to me. I’m finding myself more attracted to guys that have those qualities. I don’t recommend having a checklist of requirements, that’s always struck me as a little childish and impractical. It’s more about honing your senses so you’ll better know who is worth going out with and who isn’t.

Wrestling with Myself: An Exercise in Managing My Neuroticism

I told you last week that I’ve been more on the silent side because I’ve been wrestling with my mother and with myself. Then I just swept that last point under the rug, I focused solely on what I’ve been learning about how to honor my mother right now. The next day I sort of changed topics. I’m going to let you into that other struggle.

You’ve got to remember that I’m totally neurotic. Meaning I’m plagued with utterly irrational fears. Then remember that I started dating, and have a history of being with guys who only almost date me (it may help to know that one of those guys also had this tendency to just withdraw from me for no apparent reason at different times) now maybe you can begin to get a sense of my inner turmoil. For about the first month of dating, on the inside I was like “Is this really happening?” I kept preparing for him to just completely drop out of my life at any second inexplicably.

I knew it was just my condition flaring up. That these fears were utterly ungrounded. As I told you, we put our cards out on the table in our first text dialogue. There was nothing unclear. We were actually dating. By like the third week of dating he called me his girlfriend. That was that. Nothing to stress about.

It was all feeling too good to be true. Usually, in my life, when things seems too good to be true it’s because they aren’t true. Either I’m being led on, or leading myself on, or a combination of the two. I’m not used to relationships with men in which the nature of our relationship is clear and uncomplicated. New territory is always a little frightening and hard to trust. On top of that, I’m not really overly trusting of men in the first place.

In a great display of self-control and person growth, I didn’t let any of my neuroticism leak out into our interaction. No obsessive texting. No awkward clinginess. It helped that I could go back and read some of our text dialogues, in which we were both really honest about our commitment to give this a chance, when I was starting to get really panicky. (If there is one good thing about all the crap we’ve gotten about our age difference, and we’ve gotten a good amount since it’s so unconventional for the guy to be the younger one in a relationship, it is that it prompted these conversations). When even that didn’t help, I’d tell myself that if people are gonna run away you should let them. I’d resign myself to simply accepting that possibility.

Then, one day, my fears dissipated. I can’t tell you exactly why it happened, only when. I’d shown up to work that Saturday having been especially neurotic all week after our Tuesday date. He’d been a little withdrawn that afternoon. Though my mind told me that there were probably other reasons (and had a good idea what those reasons were), my emotions were like ‘It’s a sign of the end. Brace yourself.’ So, I had. (I admitted I’m a little crazy, right?).

As I handed out packets of tea for customers to try at home, I felt a tap on my shoulder and turned around. There he was smiling at me. When I saw his face I was overcome with relief. And awash by just how much I like him. I haven’t worried since that afternoon a couple of weeks ago.

Being that neuroticism isn’t governed by logic, it wasn’t reason that settled my fears. My mind had kept pointing out that our relationship is nothing like the pseudo-relationships of my past. That he is so very far from those guys (he’s actually dating me, that’s a big difference right there). It was telling me that for the first time there were no warning signs, so why was I so worried? (especially when I’d survived ignoring warning signs before). More powerfully than any argument, that look on his face and my corresponding internal reaction conveyed exactly what I needed to know: this is real. Come what may, that’s all I needed.

Still, being a Cancer, I can’t help but be cautious even in my happiness.Time will only tell if this really works out. I’ve just stopped second guessing whether this is actually happening or not.

A Tale of Two Sneakers

My laptop inexplicably decided to stop charging on Tuesday. ‘Til I resolve the problem (which is probably going to involve me taking apart my computer and replacing the power jack-you can tell I’m the daughter of an IT guy right?), I’m stuck borrowing my dad’s. It’s lucky for me that I can use his computer but I feel a little at a loss without my own. As if my creative juices need to be greeted by a more beautiful background image and are reliant on the “right” feeling of keys beneath my fingers (I know, I’m a little ridiculous).

Yesterday, I tried to write a witty and interesting post for you all about casual sex and chastity but I couldn’t bring it together quite as I wanted. I spent so much time on it that I got a little behind on my other projects for this week; as a result I’m tight on time today. When time is tight, the best option is always to tell a story. So, I’m going to introduce you to the new man in my life.

Before introducing you to him, I have to go back to middle school briefly. Back when we were living out in the country in Indiana. Stranded out in the sticks, there were very few people with style. All the guys at school fell into pretty much two categories: preppy or poor. There was one guy at my church who actually broke the mold. He was a few years older than me and played in the band. He had mild punk/indie style. What stood out the most were his shoes. These well loved, military blue suede Vans (I’m assuming now that they were Vans). They might sound simple but they really exuded personality. That was Frank. I totally had a crush on him. Well…on his shoes (even back then I made the distinction-his personality was a little on the muted side, which is not my thing).

You have to know about Frank and his shoes so you’ll understand me better when I tell you that I first realized this guy might have potential on account of his shoes. We’d chit chatted a little before then. I already had a sense that he liked me. I thought he was cute. But I was still on the fence. He hadn’t entirely made an impression yet. I also hadn’t noticed his shoes yet.

It was the Friday of Labor Day weekend and I was feeling stressed and spacey. Noel was in town and I was dog sitting a lovable but very neurotic little pug. I wasn’t in the mood to be working that night and I was stuck with a terrible talking demo. I was in the back of the store handing out coupons for paper plates and plastic silverware (totally lame!).

When I’m really not in a people mood, I have a tendency to spend my time mentally shoe shopping off the live models walking by. That’s when he walked up with these good looking, canvas-y orange and royal blue sneakers on and started chatting with me. I don’t always like loud shoes, especially on men, but I like these. They gave me a sense that when he’s not in his Meijer uniform (so…he might be a tad younger than me and be going to school and working at Meijer) he likes to look sharp. Most importantly, they have a lot of personality. I perked up a bit.

Despite not being in a tolerant mood to talk with most people, we talked along easily that evening. There was no small talk, we just talked like we already knew each other and were friends. This was as attractive as his shoes (easy, almost automatic connections are the best). Unlike Frank, he proved to have as much personality as his sneakers.

That’s when I finally learned his name (which I’m still withholding until this is a little less new). Throughout the rest of my shift he kept dropping by to talk. When we weren’t talking, I followed his shoes with my eyes (I said I was in a spacey mood right? And I find bright, beautiful colors calming). It was an evening that reminded me of the first night Julie and I clicked, when I knew she’d become my best friend. From that moment on, I had a sense he might become the next leading man in my life.

I don’t really notice his shoes anymore. He stands out much more than they do. But I wasn’t wrong that they were a sign that he’s got style. (On our second date we went shopping, I’ve never had that much fun looking at and trying on clothes with a guy, and I’ve gone shopping a lot with guys…but that’s a story for another time). And personality.

Dating vs. Pseudo-Dating

Relationships are just going to be the theme this week because that is what is on my mind. Next week, I promise, I’ll have other things to talk about (I have a mental list that has been growing). I just have to gush a little right now because, after so much pseudo, it is beyond refreshing to have something real. To have something mutual. I cannot help but celebrate the beauty of actually dating over pseudo-dating. Here are all of the little things that I’m reveling in so far:

There is No Question about What’s Going On

When all of those other relationships started, I never knew what those guys were after. They were clearly attracted to me, they got attached to me quickly but it was hard to determine the nature of their interest. While all the women in my life would be like ‘Men don’t text dialogue all day with women they don’t want to date’ or ‘Guys don’t just leave voicemail stories for girls they aren’t interested in’ or ‘Having an eight hour long conversation is pretty serious, no guy would do that if he doesn’t want to date you.’ These things were always debatable. Our relationships were always more emotionally intense, time consuming and possessive than a normal friendship but it was never clear if they were moving towards romance. I never even really knew if I actually wanted something romantic with them. I was as confused as our relationships were confusing.

In this relationship, there is no debate. We’ve both been obviously attracted to each other for a while (though he definitely fell for me first) and, since our initial text dialogue, we’ve been honest about what we want. I’ll admit that I sort of set this tone of honesty but he’s proven to be just as forward and frank as I am. It’s incredibly refreshing.

You Each Own Your Attraction

None of those other men in my life would ever really own their attraction to me: “I just like talking to you.” (That’s why you practically stalked me, cause you could tell I would be an amazing conversationalist?!) “I just really admire you, like a mentor.” (Really? Who sees their mentor cry and kisses them on the forehead?!). Even though they always initiated our relationships and set the tone, they ultimately made it out that any attraction was simply on my side. I wanted to be like “Honey, I’m a great reader of attraction and I saw it in your damn eyes so give me a break.” But you can’t force someone to own their attraction when they’re set on denying it. I couldn’t point out these things and, until I was ready to throw in the towel, I had to hide my attraction as best I could.

This man owns his attraction to me. And so I’m able to wear my attraction to him (being coy doesn’t really suit me –plus, my eyes totally give me away).

You Don’t Have to Consciously Maintain Your Distance

While those guys would definitely invade my personal bubble, I never felt like I had permission to do it back: “Why are you sitting so close to me?” (Um…who was just invading my physical space like fifteen minutes ago?! I’m pretty sure it was you). Besides maybe initiating a hug when we said goodbye, I had to keep my distance. It was frustrating that I couldn’t just be comfortable being close to them. That I had to create artificial space between myself and the few men I’ve been comfortable enough to not want at arms length (when most men enter my bubble I either physically withdraw or internally cringe, these men are a rare exception).

I don’t have to worry about that now. I can stand close to him. I can put my hand on his arm. Etc. I’m able to be at ease. There is no need for me to constantly police my sense of comfort.

You are Wanted for You & Vice Versa

Most of the men who have been attracted to me have never really wanted me. It wasn’t even just that they didn’t want to date me. They only wanted aspects about me. What I could give them. How I made them feel. They’ve wanted me to guide them, to entertain them, to inspire them, to make them feel alive, even to love them. They wanted to wear our intimacy like a badge of honor. But they never wanted to give me as much as I gave. They never simply wanted me for me as just me. In all of my human-ness. Even that first guy I went on a date with after getting back from NYC would fall into this category. I could tell that I couldn’t ever have been more than a concept for him (frankly, that was the biggest turn off). For me, those men were always projects. I consented to the nature of our relationships because I wanted to save them, to mold them, to help them become the men they could be. But I’ve had enough of that.

I can tell that I’m not a concept for this one. I’m just me. Beautiful, radiant, ridiculous and needy me. He wants our relationship to be about us instead of about him. He isn’t asking for more than he’s willing to give in return. I don’t want to help him become the man he could be, I just want to be with the man he is.

All of these are refreshing changes. Breaks from what had been my norm. They are the signs of the start of something undeniably healthy and good. Don’t think that these are all the reasons that I like him. I’ve refrained from gushing about all the aspects about him and about our interaction that make me rather wild about him (If this works out, maybe I’ll tell you about them in the future). These are some of the pros of exchanging pseudo for something real. An exchange that can be frightening (and hard to believe will actually happen) but is entirely worthwhile.

What to wear? Oh, what should I wear?!

I feel like I should reach for greater heights with you this week, my dear readers. But, let me be honest, this question has been a big one on my mind lately. I’ve been wishing Hilary or Nichelle were here to consult as I’ve been rifling through my closet trying to settle on what to wear… Maybe I should back up. I think you all need the right context to understand why I’ve been agonizing so much over my meager wardrobe.

Last you knew, before I headed off to NYC, I was on the cusp of dating. Since then I haven’t brought the subject up. You might have assumed that my life had reset to my usual norm. That I slumped back into a placid and eventless singleness. In the past this would have been an excellent assumption. Not this time.

So as to avoid jinxing myself, I neglected to mention that both of those guys I confirmed liked me asked me out before my trip (and, okay, maybe I should confess that in my mind a race was sort of going on to see which guy would ask me out first). The week I got back, I was a little preoccupied so we didn’t get to go on those dates until last week.

Though I’d resolved to give both guys a chance, I have to admit that I already knew my favorite before either asked me out (I can feel my eyes practically shining when I talk to him, really there was no contest). Even though the other guy technically won the race and asked me out first, I knew it was a mistake to have said yes (all I can say to explain why I didn’t decline is that I finish what I start). The moment I agreed, everything in me told me that I didn’t want to show up for that date. Not because I don’t think the guy is cool but because I already knew the nature of my interest. Having been led on so many times myself, let me tell you, I was overwhelmed with guilt to do it to someone.

During my NYC trip, the guy I really like and I had text dialogued a little. Meanwhile, I was agonizing about what to do about the other guy: Do I go on the date? Do I cancel? Do I cowardly blow him off? The friend I made on the subway advised me to go through with it and then politely let the guy down. “Lindsey, any guy who is interested in you will be able to handle you being honest with him. Even if he doesn’t realize it,” he said.

That was the first date I went on after returning. Okay, I didn’t exactly worry too much about what to wear. During the date, I spent pretty much the entire time internally berating myself for being an awful person and trying to figure out the nicest way to let him know my interest in him was merely friendly. Not that he would have been able to guess this. I thought it was only fair to be my normal, friendly, chatty self on our date (Though I gave him some subtle cues: I bought my own tea, I maintained a rather wide berth from him, I kept conversation incredibly surface-y and I might have struck up two animated conversations with strangers).

I just couldn’t bring myself to turn him down verbally. So, at the end of the date, I had to endure two hugs – one in which he picked me up (I don’t overly love being touched by … most people so I think God was paying me back for my vanity with that discomfort). I texted Nichelle and Lucy, practically as soon as I left, that I’d learned my lesson not to lead someone on ever again. Later that evening, I gently let him know I was only interested in being friends via text (which I think was less awkward for both of us than doing it in person).

Finally, I was free to go on my date with the guy I like without guilt. But his life had gotten particularly hectic and we hadn’t been able to figure out a time that worked. I didn’t want to push it, even so, I had my heart set on going out with him Saturday evening. I had an engagement party to go to that night, it seemed a shame to not invite him since my invitation had been made out to Lindsey + Guest.

After my years with the Rafetto boys, I’ve learned the value of patience and seemingly spontaneous plans. So I decided I’d just show up to my demo job Saturday looking particularly cute and, when we ran into each other, I’d casually invite him to join me at my friend’s party later that night if he was free (yeah, I’m not above a subtle con).

Here is when the conundrum began. What do I wear?! Half my wardrobe doesn’t even fit me anymore. Of the half that fits, most of them are summer clothes. All of those were out since that weekend was particularly chilly and rainy. The engagement party was being held outside, rain or shine, so I absolutely couldn’t ignore the weather. Plus, I had to choose something that I could wear to work. After completely ransacking my closet and trying on every possible combination, I finally settled on skinny black jeans, a cute grey tunic and teal, button-less cardigan. I chose subtle, complementary jewelry.

All of my agonizing and scheming paid off. Last Saturday night, we indeed went on our first date. Yesterday we spent more than half of the day together (which was, of course, pre-gamed by more wardrobe angst – this time I opted for something casual that looked effortless but was great colors for me). If this keeps going, I think I’m gonna need to invest in some new clothes soon.

Do you also find yourself at a loss when trying to dress for a date?