Asking someone out is always going to be awkward.

My first crush was named Molloy. He was one of those really tall bean-pole style people, with a messy mop of blonde hair and dark-rimmed glasses. Compared to most of the boys in high school, he was incredibly attractive, and his locker was only eleven lockers down from my own. I walked up to him one afternoon when the hallway was empty and he was digging something out of a folder and asked him to the homecoming dance. He said no, and it was awkward.

Ten years later I was working for a theater company in Chicago. One show we produced required an elaborate paint treatment, and we’d had to post in the wanted ads for a scenic painter. We ended up with Tom. Tom was stout, but with a cute, dimpled smile and I adored the way he looked intently at his design, and then up at the set, studying it. I had been unabashedly watching him work every opportunity I could since we loaded in to the theater, but hadn’t spoken to him beyond “hellos” and “goodnights.” On opening night the production team went to the bar to celebrate and after two beers I decided to take my chance. After a few minutes of my exuding drunken compliments on the brilliance of his painting while draped over his hightop, he also said no.  It was awkward, and then we did three more shows together in relative silence.

Some years after that, a few things happened. First, I got married (to someone who said YES). Then I discarded all of my accumulated skills at asking near-strangers to do things with me. And then I met John.

John worked at the same theater I did but in a different department. Our duties did not intersect and we mostly didn’t speak to each other, except that my desk was right next to the door to John’s office. He started saying “hi,” and then I started saying “hi” back, and pretty soon we were having whole conversations and going for coffees. (Now remember, I’m married, and John knew I was married, and we were not trying to do anything underhanded about that.) Then a sign was posted for the company canoe trip, along with instructions that each canoe needed a team of at least two people. Of course John was my logical choice for co-canoer, and I decided to ask him after lunch one afternoon. As we walked out of the café, my palms started sweating and my stomach clenched. I could barely get the words out! All of my previous awkward invitations and rejections came back as a tidal wave of memories convincing me this was a bad plan. I stood there with my mouth hanging open. After an eternity he politely responded that he would think about it. I let out the breath I was holding, turned to walk away, and walked into a street sign. Bam. Awkward.

But all of this old history really comes up because last week I was, at the last minute, gifted a pair of tickets to a bike race. I have never been to a bike race, and this sounded like a good time. My spouse was not available, and, though I asked around my friend circuit a bit, I couldn’t find anyone who was free on the short notice. Figuring I’d have better luck with people who were on the same schedule as me, I thought about what co-workers I could possibly bring. Stephen came to mind right away. He’s this very geeky, very kind, quiet fellow that I’m pretty sure no one pays any attention to and I thought that made him kind of safe. I cornered him at the end of the day, took a deep breath, wiped my sweaty hands on my pants, and asked. His response, which I should have anticipated, was to the effect of, “Don’t you have any better friends than me?”

“I asked my usual friends,” I replied. “None of them were available, so I started on my… un…usual friends.”   Then I smiled real big and tried not to die of humiliation.

So it seems that no matter how old I am, how married I am, and how many times I’ve tried it, asking someone out – even casually as friends – is awkward for me. My palms are always going to sweat. I’m always going to hold my breath. And chances are very good that somewhere in there I’m going to put my foot in my mouth (or maybe walk into a pole). But I keep trying because at the end of the day I really like people, and I especially like it when we can get pas the awkward parts and be friends. Not that that’s ever happened. But… tomorrow’s another day.

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