[I wrote this a couple months ago for the October Syllable night. It is based on a true story, one that happened in 2011. I tweeted tonight that I hope Santa Claus will send a Mr. Darcy my way. I post this as evidence that I’m not just sitting around wishing and dreaming.]

Will you have a drink with me?
I’m not sure I have ever uttered this question. At least, not to anyone other than the Winnie the Pooh, with elf hat, that Ellie gave me for Christmas senior year of high school. Sometimes I put a blue Michigan hat on Pooh because, well, Alex doesn’t wear an elf hat. Alex. Tall, intelligent, funny, Alex.

“Hey, Alex, will you have a drink with me?”
I’ve practiced it numerous times.

“D @alexinwindycity hey…what’s happening tonight…wanna get a drink?”
How hard would a tweet be? I haven’t even managed that.

We met about a year ago; a little more than that, actually. He is also friends with Ellie and Jack, and was part of our mini-gang cruising Lake Shore Drive on our bicycles. Once a year they close the road to cars and it becomes a sea of cyclists. I know we chatted, somewhere between Randolph and Wacker. But with the 5:30 am start, and my lack of a caffeine drip, the rest of the details are rather fuzzy. Since then, as I’ve continued to meld into the mini-gang, we’ve seen each other quite often. Never just the two of us, always a crowd.

Today Alison and I are enjoying cocktails at the Field Museum. You know, one of those events where they try to convince ‘young professionals’ that museums are cool by providing overpriced drinks after work. Alison and I may be pressing the limit on the ‘young’ portion of the phrase tonight (we think the music is too loud) but we both wanted another glimpse of the shoe exhibit.
We are waiting for the band to take a break so we can have a conversation. Alison traces stains on the caterer’s tablecloth. I’m staring at Sue, the museum’s famous T-rex, debating another trip to the appetizers. I always think Sue will be larger than she is. Alison’s finger has traced its way to her Chardonnay. She takes a quick sip, then announces, “Here comes Alex.”
With my thumb and forefinger I break the rim of the styrofoam plate in front of me, grateful Sue’s unimposing stature has distracted me from another tower of cheese cubes. Alex is here. My hair is a mess. Well, at least I don’t have any competition tonight. Alison and I are the only mini-gang representatives, and she is dating Ross. Often Marni is here, with her perfectly curled lashes and…wait, Alex is here? Didn’t he just tweet a photo of…well, he is certainly back now.
I don’t know that I’ve come out and told anyone I want to date Alex. Would I be laughed at? Encouraged? Never again invited to hang out at the bar? I can’t be hurt keeping it to myself. I’ve been here for three years and have had one date, Sam, another friend of Jack’s. Sam doesn’t bike, and the only thing I could talk about with ease was my recent trip home to Connecticut. He found his whiskey glass more appealing than my description of spinning down Old Mountain Road at over 40 miles per hour. Why did I think dating would be less onerous in Chicago? It hadn’t been any easier moving from Connecticut to Michigan, either.

Will you have a drink with me?
Seven syllables. Yet, in a year and a half, despite having his phone number, email, Twitter handle, probably even snail address, the possibility of a “no” answer paralyzes me. That possibility is real, isn’t it? If he were interested, he would have asked me out by now, right?
I wave and smile as he approaches the table. If anyone knows about my interest in Alex, it’s Alison. She certainly hadn’t announced Sam when he walked over earlier in the evening. Other than alerting me to Alex’s presence, though, Alison does not let on that she knows anything.
The three of us converse about our friends, high and low points of our days at work. As the band begins another set, my thoughts drift back to dinner, a few months ago, with Alison, Ross, Sam, and Alex. Who knows what we talked about. All I remember is Alex and I laughing at all the same things. I no longer recall what was humorous, only the moment I realized that though there were others at the table, it was just two of us sharing a laugh.
After that dinner I started daydreaming. Well, continued daydreaming is probably more accurate. Maybe I could get a group together to visit my grandparents’ cabin in Wisconsin. I imagined fishing, rounds of golf, cocktails on the porch. No, I should keep it simple. A drink, just the two of us.
As the song ends my thoughts return to the present. How can I get to know him better? How can I persuade him to spend time with me? When will I see him again? Suddenly my helmet is strapped on. My feet are clipped into the pedals. The chain is in the big ring and I am ready for the descent. Tonight I will ask him out for a drink. Then my mind switches gears. Maybe we could go to a football game. Does he like football? I don’t, but he went to a university with a good team. Maybe he’d go to the Michigan game with me! They’re playing at Northwestern soon.
I ignore my own advice. I don’t keep things simple. I look across the table and find myself asking, “Would you be interested in going to the Michigan game with me?”
My heart doesn’t even have time for the proverbial pounding. He answers immediately.
Outwardly I try to keep something resembling a smile on my face. I play it down. “No problem. I was just curious.”
Alison manages to segue the conversation, to what I do not know. I am busy cleaning up a world record size case of road rash; convincing myself it is football he doesn’t like, not me. I should be proud of myself for making the attempt, facing the twin fears of dating and rejection. Instead I want to offer myself to Sue as a snack.
At least I asked late in the evening. A few more minutes and Alison and I are descending the exterior marble steps. “I had to ask. Otherwise I never would have known.”
“Yeah,” Alison replies.
I take that to mean she understands, that she has been in similar situations. Alison neither berates me nor offers false hope. I’m grateful, as it keeps me from dwelling on the topic, at least until I get home. I open the door and see Pooh grinning at me, Michigan hat and all.
Careening downhill at excessive speed doesn’t phase me. Asking anyone other than a stuffed animal out for a drink: petrifying.

[And no, I do not have routine conversations with a stuffed animal.]