Empire Date: Testing Out HowAboutWe, citysbest.com

Empire Date
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Howaboutwe.com puts a new twist on online dating, taking the focus away from profiles and onto the actual date. The suggested activities range from the surprisingly inventive (orchid show, trapeze) to the relatively prosaic (coffee). Coming up with date ideas, my imagination took flight, running through images of gallivanting through the city hand-in-hand with an exuberant partner like characters in a romantic comedy.

Through the site, I accepted an invite to improv at the Upright Citizens Brigade. I’ve been meaning see UCB for a long time. The inviter, Alan, seemed decent; “out-of-the-box” and quirky, but responsible. Pretty much how I view myself.

I met Alan at a Starbucks. He came in, and as usual, I wasn’t sure it was him, having only taken fleeting glances at his profile picture. Alan had a business book and a notebook with him. I liked these accoutrements. They made him seem thoughtful. We matched a little in this — I had my journal on me, too.

“Is that a Moleskine?” He asked.

“No!” Alan had inadvertently broached one of my favorite conversational topics: Why I Don’t Like Moleskines. After wrapping up my carefully thought-out argument against Moleskines, we still had 45 minutes before the show. I learned some facts about Alan; I got the impression he wasn’t too happy with his current job, but he didn’t dwell on it. Instead he spoke of some entrepreneurial activities he had, many involving the web.

I liked Alan, and I felt we had a good intellectual connection. But there was something hidden about him, and I wasn’t sure I was the person meant to find whatever it was. As we walked to UCB together, I felt a faint instinct to widen the distance between us. Though I was still considering Alan in my mind, I felt like my body language was saying something different.
What a relief to get to the show, where I didn’t have to worry about any of my feelings. I laughed at the weird randomness of improv, and I heard my date laughing, too, which was nice. Alan was laid-back, and having the HowAboutWe activity took pressure off both of us to make conversation.

But, when we left UCB, I felt that familiar urge to go home. In hindsight, it probably would have made more sense to schedule the coffee for after the show so we’d have time to talk then. Instead, I was tired and wanted to go home. Plus, to be entirely honest, the night before I’d met a person at a party I knew for sure I was into. Just having so recently experienced real attraction was making it hard to convince myself it was here.

Alan wrote and asked me out on a second date. I declined, citing the lack of spark. He wrote again, suggesting that we just meet again and get to know one another as potential friends. I’m still considering that option.