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.

Coping with Loss Alone

At the end of May my last remaining grandparent passed away. Though distance had grown between my Grandpa Jacobs and me, he meant a lot to me. He was my first intellectual sparring partner and… so much more. His memorial service—which had an incredible number of planned and unplanned speakers—was breathtakingly beautiful. Looking back at a picture of my brother-in-law standing beside by father as he spoke during the service I felt a pang of envy.

Christa’s husband has shared in most of the notable events in her adult life and vice versa. Whereas my future husband (if I have one) has missed out on so much. There is so much of his life that I must be missing too.  It’s impossible not to feel a little regretful. Yet, I wonder if I would have been able to have such long and meaningful conversations that day with my grandfather’s pastor or two of my cousins that I rarely see or the pastor’s wife if I had a spouse of my own. Those conversations were as important to me as the ceremony. With the wrong man at my side, they definitely wouldn’t have achieved the same depth—if they happened at all.

In the past, I shared this quote from the movie “Shall We Dance” that I felt captures part of the beauty of marriage:

“We need a witness to our lives. There’s a billion people on the planet… I mean, what does any one life really mean? But in a marriage, you’re promising to care about everything. The good things, the bad things, the terrible things, the mundane things… all of it, all of the time, every day. You’re saying ‘Your life will not go unnoticed because I will notice it. Your life will not go un-witnessed because I will be your witness’.”

Over the last year I’ve realized that having a spouse as a witness to my life doesn’t mean as much to me as I thought it did. In fact, this sort of thing is exactly what I’m bad at.

Anyone who is friends with me knows that I’m great at being there during terrible things and wonderful things. It’s the mundane things you can’t count on me for. Forget about seeing me every day or even once a week! All of my relationships are defined by the quality of time spent together or in conversation, not by the quantity. Even when I’m living with people I can withdraw into myself like Sherlock when he’s deeply thinking or recovering from a particularly hard case. There have been people in my life who are exceptions to this rule but they are few and far between.

You could say that mundanity bores me. To some extent that’s accurate but that wouldn’t entirely explain why I’m disinclined to allow my friends or family to consistently participate in my daily life. The truth is that I guard my days like other people guard their secrets.  There is no more intrusive question to me than “What did you do today?”

I have often said that the quality of my life is defined by the quality of my conversations. That is what my life is made up of: anticipated and unanticipated conversations. What I truly excel at is developing deep connections with people quickly. Whether you need a shoulder to cry on or someone to debate with or are just looking for some entertaining banter, I’m your girl. I’m something of a chameleon in this way though I’m always distinctly myself. This is something that I treasure about my life, which is why I’m so protective of it. Bringing an extra person into the equation always changes the dynamic. Usually, the quality of a conversation (at least in terms of depth and sincerity) decreases with every additional person added. I can’t stand that.

Just as I cherish my time with people, I cherish my alone time. Anyone who has lived with me can attest that I think it is perfectly acceptable to be brusque when someone decides to talk to me when I’m not in the mood. It can make me a real pain to live with.

It’s really no wonder that I’m habitually single.

This is why its basically a prerequisite that I be wild about someone if I’m going to date them. Otherwise, their presence in my life-outside of work or an occasional get together-will feel like an intrusion. I didn’t choose to be this way. I didn’t wake up one day and decided that I wanted to have ridiculously high standards. It’s simply how I am. Just as you might find it impossible to strike up a conversation with a stranger, I find it almost impossible to be open to going on a date with someone unless we’ve already connected in a way that I don’t connect with most people or he’s won over my affection through a steady and charming pursuit.

I have tried to change this. Remember when I had that short lived relationship with a younger man? Or when I joined two online dating sites and went on a painful dud of a date? I was trying to play the role of another kind of woman. A woman who needs at least two dates to tell if a guy is a dud instead of one conversation. A woman who can take an online dating profile at face value instead of seeing the subtext. Someone who enjoys the experience of dating, even if it doesn’t lead anywhere. I love the idea of being like that but I’m not.

After failed attempts at changing (followed by a long season of beating myself up for being a boring loser), I’ve decided to embrace the way I am.

While I may envy Christa’s marriage a little, I’m also grateful for the life I’m able to live because I’m single. I do know what it’s like to share my life with the wrong kind of man. Once I had someone who mixed with my loved ones like oil and water. Had he been beside me at my Grandpa’s memorial I would have been torn between meeting his need for us to create a world-onto-ourselves in which he could feel comfortable amidst that sea of strangers and my desire to connect with my Grandpa’s friends and my extended family. I’m glad I didn’t have to make that compromise.

Feature image by Daniel Tseng.

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?

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.

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?

Don’t Let Me Down: The Limit to My Love

 “Love bears all things, believes all things, hopes all things, endures all things. Love never fails.”

I’ve thought about these words a lot this summer, even more since talking to Christa Sunday night. These words highlight the loyalty of love. She shared with me something from a Korean tv show that related.

She said that one of the characters in the show was constantly asking people, “What’s the most important: faith, hope or love?” The most common answer that she’d receive was love, to which she’d respond that the real answer is loyalty (I know, it’s a little grating that it isn’t even one of the options). Christa was struck by this. I was a little stung.

Frankly, I’m not a very loyal person. I’ve been baffled when friends have used this term to describe me. I internally cringed when a friend of mine, assuming my loyalty, said he was never afraid of losing me. Understanding that these comments were made in faith, that they were meant to be compliments, I played along (something I’ve realized now was somewhat misleading) while being internally discomforted.

It’s not that I ever plan to leave, nor am I just a fair-weather-friend, but I know it could happen. That the future can’t be predicted and that my loyalty to people has limitations.

The limit for me is disappointment. In time, I can forgive any insult or injury. I’m willing to mourn with you or face any battle. I’ll defend you fiercely. But if you let me down, if you seriously disappoint me…I’ve never learned how to do anything other than let go.

I don’t mean that in a petty way. It’s not like I’ll disown you for getting me an underwhelming present or flaking on me when I was really looking forward to seeing you. That’s all forgivable.

But if you turn out to be less than who I thought you were, if you let down my faith and trust, my heart will shut down and lock you out. Though I’ve assumed the nickname of Grace, I have not known how to offer grace in these relationships.

This is why the greatest love song to me is The Beatles’ “Don’t Let Me Down.” Its chorus is the internal refrain of my heart. It’s as much my warning as my plea. My well-developed self-defense mechanisms won’t let you shatter my faith twice.

I can’t explain why this is what hurts me most. Why disappointment is more painful for me than cruelty, but it’s been true since my childhood.

What Christa convicted me of is that this limitation of mine is a failure to love. That it’s a failure to bear, to believe, to hope and to endure when I should. It’s a failure to accept the human-ness, the weakness and fallibility, of the people who are closest to me. It’s an avoidance of the inherent risk and compromise of love.

As my friend Saundra recently said, “When you love someone you are giving them the power to hurt you. Though you are trusting them not to, you’re also promising to continue caring for them even when they do.” That is a promise I have not been willing to be consistently true to. Well…I don’t exactly stop caring, but I do it from a distance, behind the protection of firmly bolted doors.

I’ve been reminded of a message I received back in July from God. Feeling incredibly let down, I was ready to yet again shut another person out of my heart. I felt Him saying to me, “Lindsey, darling, when will you learn to accept that the people you love are not Me? They will let you down at times, just as you will let them down. If you put your faith in Me, if you put your hope in Me, these disappointments won’t hurt you so badly. ”

I’m continuing to struggle to keep my heart open, but I’m finding that my faith and hope is more firmly grounded in Him. He keeps reminding me of how He’s blessed me through my friend Lucy’s loyalty and of how He’s restoring my relationship with my sister, Noel (she’s been the one exception for me, and just barely-for a few years we were very much estranged). These relationships are illustrations of why love is not meant to fail. In time, trust can be restored and relationships rekindled.

I am trying to love without this limitation.

Taking Applications for a Male Sidekick or Thoughts on Online Dating


Entertaining (i.e. witty), charming, intelligent male companion who is a great conversationalist. Preferably has good math skills but a greater interest in literature and is slightly but not overly flirtatious. Excellent music taste (with a preference for indie and alternative rock) is a must. Preferably has a good work ethic and Judeo-Christian morals. Knowledge of the works of Joss Whedon and slight interest in geeky-things a plus but not necessary. Photo required. Must be between the ages of 22 and 32. All applicants need to include with their application a list of their favorite books and current play list. All submissions will be treated confidentially.   

Creeps need not apply. This is not a romantic ad (though romance may be a possibility in the future if you play your cards right).

Before you consider applying, you should know that this ad is just in jest (well…mostly). I simply couldn’t resist composing it for this introduction.

A while back I saw an ad for a dating site called HowAboutWe… Intrigued by the name, I had to find out what it was about. Basically, it is a dating site that’s been structured to have a similar feel and look to Twitter. You post your profile and, most importantly, you basically tweet dates you’d like to go on (i.e. How about we go wine tasting at Howell’s Main Street Winery and see where the evening leads…) and hope someone else will be interested in the same thing. Frankly, I love the concept. Except that it’s a dating site.

Ever since leaving NYC, I’ve been on the prowl for another Ben, a male sidekick who could potentially evolve into a boyfriend. I miss having a guy who would randomly text me to invite me on an adventure or who would get me out of my apartment when I’m feeling blue or who I could con into escorting me somewhere I didn’t want to go solo.

Ever since my junior year of high school, I’ve almost always had a leading man in my life who I look to both for quality time and emotional support (even if it’s just giving me something else to think about or talk about when I’m feeling down). Though this has often led to complications, I can’t help but be on the lookout for another one (who lives within at least a 30 mile radius, preferably).

For a woman who has only gone on one official date, I’ve gone on loads of unofficial ones.Though I keep saying that I need to be done with ‘unofficial’ because it gets messy and I usually end up being the one getting hurt. Though I’m tired of men relegating me to the ‘friend zone’ and being unwilling to even consider renegotiate our terms when our relationship has obviously evolved, it’s hard for me to imagine a formula for relationships that I’d find more comfortable.

Before opening myself up to the possibility of being rejected by some guy, I want to know whether or not I’d actually want to belong to him. That takes time. I enjoy lots of people when I first meet them but then the novelty wears off and sometimes I realize there’s not even enough spark for a lasting friendship. On top of that, it takes me a while to evaluate how much I really like a person versus how much I enjoy being flattered by their attention and affection. Then we have to figure out if we can trust each other. If we’ll be comfortable confiding in each other. If he can handle how exhausting I can be and I can handle when he’s boring. Etc. Friendship is practically my screening process.

I’ve come to realize this is why online dating has no appeal for me. I really wouldn’t mind it if I could use those sites as a way to collect a pool of male friends from which a relationship could one day potentially develop (it’s pretty hard to even find men my own age around here) but it isn’t structured that way. Most people are hoping for romance from the start. I’m not. The idea of letting a stranger have the opportunity to reject me after one or two dates, before I’m ready to even make much of a conclusion about him (unless he’s really dreadful), is entirely unappealing to me.

What are your thoughts on online dating?

If You Don’t Want to be My Boyfriend, Maybe You Shouldn’t Act Like You Are

A few weekends ago I was joking with a friend about writing a book with this title. But…it’s not exactly the first book I’d want published under my name. Still, I couldn’t resist using it for a blog post.

You know that I’m trying to swear off pseudo-relationships but this really is a hard thing for me especially since I want to date. Normal dating…well, it doesn’t really happen much anymore unless you join an online dating site. It seems like most couples start out in a pseudo-relationship or as friends-with-benefits before transitioning into actually dating. This really makes it a challenge to tell the guys who actually want you from the guys who just sorta want you. So I was also joking about making up a guide book/rules of engagement to give to guys who enter my life and seem serious about making a place for themselves in it. That title would be perfect for that booklet too.

Of course, that would be going overboard. It would be a terrible idea to start handing out little booklets to men who seem interested in me (though I do find the idea highly entertaining). Still I can’t resist posting a little guide for men who don’t want to cruelly lead on their female friends/emotionally take advantage of them (you know, we feel that being taken advantage of emotionally is almost as bad as being taken advantage of physically-just saying).

Instead of giving you a bullet pointed list, I’d rather give you a narrative illustration. When it comes to this, I feel that my friend Ben in NYC is a good example for others to model themselves after.

He and I started hanging out the summer he broke up with his girlfriend and when I was on a break from my emotional ball and chain. On the very first day we hung out he made it clear that we would only be just friends. No complications. That’s exactly what I wanted so I agreed to those terms. Throughout our friendship we’ve both made sure to stay within that boundary.

During that summer and first semester of our friendship, he was sort of like my play-boyfriend (not that I would have said that then). We went on non-date dates (he almost always paid and he even went with me as a platonic date to a friend’s going away party and did an excellent job of being a charming companion). I did his mending and stayed the night at his apartment sometimes (always on the couch). Every once in a while he’d call me just to chat. Most enjoyably, I got to play his personal shopper.

Despite the couple-ish things we could do, our relationship was never more than a good friendship. Sure, sometimes I’d toy around with the idea of us actually dating (crushing is one of my favorite past times). But all I’ve ever had to do is spend five minutes talking to him or with him to snap out of it. Jokingly I sometimes say it’s because, though he’s cute to most people, he has as much sex appeal for me as a doorknob. In truth, that isn’t the reason.

When we first met, we both had some emotional baggage separating us. As we got to know each other better, that diminished, still it became obvious that we are as incompatible as we are compatible. The last time he saw me he even said, “So, not that we would date, but I have this image of the two of us if we did. I’m sitting on the couch trying to watch tv and you’re trying to have a conversation with me. And I’m not having it.” Yeah, that pretty much sums it up. I want more out of life and out of him than he wants to have or give. So we’d frustrate each other to no end.

Just because there have always been lots of reasons why we shouldn’t date, this by no means determines that we couldn’t. Much less compatible people are even married to each other. This is why we’ve always maintained a safe distance. Five minutes with him reminds me that one thing I cherish about us is that I know exactly where I stand with him and exactly what I want out of our relationship: a platonic friendship.

I’ve never felt that he’s led me on in the least. First and foremost because he’s always respected my space. I’m not someone who talks to even a best friend everyday unless we live together. So unless you want to date me, you have no business texting or calling me every day. (Really, don’t most men know that communicating with a girl daily means, at least to her, that you’re probably romantically interested in her?) So he never tried to communicate with me daily and vice versa. We didn’t text dialogue and we never talked on the phone for more than an hour. For the most part, if we wanted to talk to each other, we hung out and never too many times in one week.

He also slipped in a lot of unsolicited rejections/neutralizing statements/relationship clarifications. Okay, sometimes it was annoying when he did it. Like the time he said he couldn’t comment on whether my hair was frizzy or not because he’s not attracted to me (we were looking at hair gel by the way and he’d asked my opinion on a product in his hair, which was a ridiculous question, whereas I was hunting for an excuse to buy a new product). It was a little grating, and I certainly got him back for it, but I did appreciate it. It was his way of making sure I knew we were still just friends, no matter how couple-y. I made my fair share of comments that got the same point across which I’m sure annoyed him a little.

Amused as I was by how he eventually started making up excuses to pay for a meal or made it awkward when he’d suggested we split the cost of something, I appreciated these gestures. He never confused me by competing with other men in my life for my affection and attention nor gave me all of his. These visible things, petty as they are, were indicators that, no matter how much he adored me, he wasn’t in love with me.

If you’re thinking that, no matter what I say, how much we felt a need to clarify our relationship means we’re attracted to each other, you aren’t wrong. I might not think he’s the hottest man in the world but he’s one of my absolute favorite people. He speaks my language better than almost anyone. I’m definitely attracted to him. Considering how much he obviously adores me, though I’m not the hottest woman in the world to him, I think it’s safe to say he’s attracted to me too. The basis of close friendship usually is attraction, that’s why it can transition easily into a romantic relationship. But just because you’re attracted to someone doesn’t mean you should date them. It means that if you want to be just friends you have to make sure that’s all you act like and are to each other.

Even though I used to tell him I wasn’t capable of falling in love with a man like him, capacity wasn’t really the issue. We’re not compatible enough for it to be a good idea, so I disallowed it and so did he. We never let like have the chance to turn into love (at least not romantic love).

If you don’t want to lead on a friend, you should try to be like Ben: clarify your relationship often, maintain space and don’t let it look like you’re in love with her.