Like most thirtysomething singles, I’ve been on my fair share of first dates. And yet, it doesn’t seem to get any easier to answer the unavoidable first date question — how to say goodnight?
Of course, there’s no right or wrong answer because so much of it depends on how the date goes in the first place. A recent evening out with OkCupid bachelor JC reminded me that more often than not, parting company can be more than a little awkward.
The date itself seemed to go well — decent conversation at a cozy wine bar, with a few laughs along the way. JC indicated he was disappointed that the bill came while I was in the bathroom. When I informed him the waitress brought it without any prompting from me, he said–
“The night doesn’t have to end here.”
And so, we went on to a nearby bar for one more round before heading toward the subway. As we approached the station entrance, JC said regretfully–
“Oh, this means our date is almost over!”
I assumed that he meant he’d like to get together again. Which is why I was more than a little surprised when his parting words were–
“Don’t be a stranger.”
I didn’t quite know what to make of that one. Did he want to get together again? Was he trying to gauge whether I was interested enough to make the next move? Granted, that’s one of the trickiest parts of a first date — who takes the leap of finding out if there’s going to be a second one? Experience has taught me that even though the so-called ‘rules’ say that responsibility belongs to the guy, men don’t always want it.
Not too long ago, another OkCupid guy ended our first date by handing me his business card. We didn’t exactly click, so I understood him wanting to put the ball firmly in my court.
Then, more recently, there was my final Nominate A Date bachelor Marcus. Despite asking several questions about whether I’m relationship ready, Marcus made it clear he wanted friendship only — inviting me to keep in touch about my dating projects (ugh).
But the most surprising conclusion to a first date I’ve ever experienced happened more than a decade ago. After hours of effortless, flirty conversation and palpable mutual chemistry, Southern Illinois cutie Steve said goodnight with….a handshake. I remember being completely floored (especially since I was so convinced about a forthcoming kiss, I’d discretely popped a breath mint minutes before).
Steve and I later had a good laugh about it after smooching at the end of our second date. And so began a wildly passionate romance that evolved into a friendship which endures to this day.
The longer I’m on this journey called singlehood, the more I realize that you really can never predict when, where or how romance is going to ignite. Sometimes a lukewarm goodnight means it’s just not happening, sometimes a handshake is a precursor to being completely smitten. And the only way to find out is by braving first dates, awkward moments and all.