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?

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