The First Date Dilemma

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.

Category: dating rules, first dates, OKCupid, online dating, Southern Illinois 4 comments »

4 Responses to “The First Date Dilemma”

  1. JT

    It falls on the guy to make the move or end the date.

    Me personally? You can find out here what I’m about-

    http://www.getgirlsnotgame.com/sex-on-the-first-date-yes-this-is-for-me/

  2. Melissa

    Agree completely. And what I should’ve added in my post is that when a guy is interested, he usually does make the move. What baffles me is why people — and I think we’re all guilty of this at times — feel the need to pretend there’s going to be a second date. If there’s no mutual chemistry, why pretend otherwise? Yes, it’s easier to just say goodnight and nice meeting you when you know both parties aren’t interested, but I just think honesty goes a long way toward not wasting anyone’s time.

    As for your post about your approach and all girls being open to sex on the first date, we’ll have to agree to disagree there.

  3. Brainy Pint Sizer

    “Don’t be a stranger”? Was he channeling his 12-year old-girl tween self? I haven’t said that with a high-pitched, syrupy, Mister Rogers aura since forever. Such an awkward ending to any date. He could have said something else if he felt there would be nothing in the cards for a future date. Actually, reading the post, it seemed even more strange since he made the comment about the date not having to end there. That’s peculiar. If he’s not interested, why make the comment and proceed to another venue? His signal was confusing.

    Strange and stranger.

  4. Melissa

    Major mixed signals indeed. His actions said he was interested, his parting words communicated otherwise. Not surprisingly, there was no second date LOL


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