A Game of Pick-up Check – GTJ Dating Series with Erika E. (week 34)

You know the scenario well: The check comes.  No one moves.  You look at each other.  You smile.  The check sits there.  This, my friends, is what we call a little game of “pick-up check.”

The question is: Should a woman offer to split the bill on the first date?

Notice that the question isn’t: Should a man pay on a first date?  The answer to this should be an unequivocal “yes.”  While I’m a huge advocate for women e-mailing men on online dating sites, and I’ll even dare to say that a woman should suggest meeting for a drink if the guy is trying to have an e-lationship, I am a stickler for the old-fashioned tenet that the man should pay on the first date.  That said, should the woman at least offer to pay?

When the bill comes, the woman has a few choices:

1. The “reach” (going for her wallet to see what happens)
2. The offer (saying “May I contribute?” or something similar), or
3. The assumption (just saying “Thank you so much!”)

Given that the date should only consist of a drink or coffee (no dinner on a first online date) and should not be too expensive, I’d actually opt for #3.  It avoids the awkwardness, and you get to show your gratitude immediately.  #2 is a close second.  Just hope he doesn’t take you up on it!

Men, generally when women offer to pay on the first date, we don’t want you to take us up on it.  Even if we know there won’t be a second date and feel guilty for taking the free drink, deep down we still hope that you’ll pay because it’s still a date after all.  The last thing you want is to accept our payment offer and then be labeled as “cheap.”  Yes – she offered, but when it comes to paying on a first date, yes almost always means no.

I had one particularly memorable experience with the “pick-up check” game, and I’ll tell you off the bat that the results weren’t good.  The scene: A JDate at Tryst.  We planned to meet at 3:00 for coffee on a Sunday afternoon.  When I got there, I saw a guy who looked vaguely like the guy I was expecting, but he was deep in thought on his laptop, and he was drinking a nearly-finished coffee.  Was this my date?  I went over to him and asked, “Are you Jason*?”  It was, in fact, Jason.  He had gotten there early to do some work.  I certainly didn’t care about that, but when the check came for my latte (a whopping $3 and change), he never even looked at it.  Apparently he had already paid for his drink, so he took no responsibility for mine.  Awkward, to say the least.  “Pick-up check” failure.

Ideally, the man will reach for the check before the woman even has the chance to decide between options 1, 2, and 3.  Then, even if it’s not a love connection, she’ll tell her friends how generous he was.  Let’s avoid the game of “pick-up check” and end the date on a more positive note… planning the second date.

If you’re curious, the experts agree.

*Name has been changed.

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