May 21, 2012

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.

Got burning questions you’d like answered in a future blog post? E-mail

A Game of Pick-Up Check

11 thoughts on “A Game of Pick-Up Check

  • June 1, 2012 at 11:38 am

    Perhaps Jason didn’t see this as a date, but meeting someone for coffee to see if he liked them, and THEN scheduling a real date. What men resent most is the games and manipulation. On an actual date, men are prepared to pay, and it doesn’t need to be awkward. Sure, it was only 3 bucks. So PAY IT, and don’t read so much into it.

  • June 1, 2012 at 2:18 pm

    Timothy, I appreciate your comment. Generally, if you’re doing online dating, the first meeting is still your first impression of someone, so even if he was just testing the waters, it would have been better to pay for the coffee.

  • June 6, 2012 at 4:40 pm

    What an entitled attitude. If a girl makes a stink about paying for her coffee I can only imagine her seeing me as a walking ATM while we’re dating. Next.

    • June 7, 2012 at 3:26 pm


      Thanks for the comment. I think you’re missing the point a bit, though. It’s not about the money. It’s about the guy acting chivalrous on a date. That’s what we want.

  • Pingback:First Date Turn-offs — GTJ Dating Series with Erika E. (No. 44) — Gather the Jews

  • April 30, 2013 at 2:04 am

    I have to say, if a woman says thank you before I even look at the bill (on a first date) I’m going to view her as a gold digger. With the spread of feminism I take exception to women who pick and choose the old school gender roles that benefit her. If the woman doesn’t want to be called a gold digger to all oft friends when she reaches for her purse it won’t be in the hopes that I will offer to pay. It will be to grab that $5 bill she set aside for this. After all, it’s only a $3 cup of coffee and a generous $2 tip.

  • August 2, 2013 at 6:20 am

    You are so awesome! I don’t suppose I have read a single thing like this before. So wonderful to discover somebody with a few genuine thoughts on this issue. Really.. many thanks for starting this up. This site is one thing that is required on the web, someone with some originality!

  • November 16, 2013 at 10:16 pm

    Very nice article. I certainly appreciate this website.

  • October 9, 2014 at 10:48 am

    Erika says the first meeting is not a “real” date. It only becomes real when the check comes and the man should pay. A man should be “chivalrous” by scheduling his audition close to the women and letting her choose location. She double-books dates and feels entitled to free sushi dinner even when she knows she doesn’t like the guy.

    Quality guys avoid dinner whores. Enjoy the thirsty losers who tolerate it.

  • October 9, 2014 at 7:25 pm

    Erika’s reply to economical invitations: “We can have an extra appetizer with the money we’ll save!” Interesting choice of words, when she doesn’t pay anyway. It broadcasts her attitude that a woman is entitled to spend a man’s money.

    Erika dated almost 100 guys in a year before finding a boyfriend. Usually such women sleep with one guy, while shopping for an upgrade, and playing the other 99 guys for drink-buying suckers. Say it ain’t so, Erika. 😮

    • October 13, 2014 at 12:31 am


      You certainly have an interesting read of what I’ve written! I think you’re somewhat missing my point, though. It’s not the money at all. It’s the act of wanting to treat a woman and acting chivalrous that we crave.

      Thanks so much for reading!


Leave a Reply

Your email address will not be published. Required fields are marked *