20 September 2015

Date check…mate?

By: Jessica B.
Tagged: Random

I love going out but I hate the many-times awkward moment that occurs when the check arrives. The “Oh how much did you have? Okay does that include tip? Do you need change” moment where conversation can die and damper the evening. Because after you argue over who had three mimosas rather than coffee or how much did Sarah REALLY eat of the calamari appetizer, you’re kinda like, so….the weather today was great!

But while I’ve been able to maneuver the social check situation with friends, I am a bumbling awkward idiot when it comes to that moment on dates….or “maybe” dates.

The first real guy I dated, never paid for me. Ever. We always went Dutch. He said that he “didn’t want to insult me because I am a progressive, independent woman.” It took me years to realize he was being a cheap fuck. And that scarred me to any future dates and not knowing if a guy would actually pay for our meal or drinks.

I’m not kidding.

And while I’m a progressive, modern woman who makes a good living and can financially support herself, I want chivalry. I want old fashioned romance and dates where the guy steps up like a fucking man and pays. Especially if he asks me out. I’ve been in relationships where I’ve picked up the tab at times but in the early stages of dating, IMO, the guy should pay.

I always offer to leave tip, or take my wallet out as a genuine gesture to pay, and every single time after cheap as fuck college guy, guys will take care of it or tell me no. But, I like to offer.

So, fast forward to Saturday night and being on date #2 with a guy who gives great text and has a lot of common interests as me, and after a pricey meal at a place he chose (with wine and apps), the bill arrives and he says to my face, “so let’s just split it down the middle, that’s fair.”


Conversation was good, but not THAT good. And, the date didn’t really start out on a good foot when he (dressed in jeans, polo and a suit jacket – a big step up from his Bristol Renaissance Fair-like outfit from date #1) said “thank you” to my compliment about his outfit, then proceeded to look me up and down and say nothing in return. Ouch. BURN.

After that moment of settling up the bill, he’s like, “let’s go for a nice walk.” To which I accompanied, and he made no effort or even cheap attempt to hold my hand. And, then I realized, I don’t have to fucking stay out here and walk around making small talk. I paid for my meal, I’m going home! So after about 15-20 minutes of awkward post-check conversation (where the fact that we split it felt like the biggest elephant sucking the air out of the room), I said, “yeah I’m tired, I’m going home.”

I wasn’t tired, but I was ready to go home. Oh well, one down.

How do you handle the bill situation on dates?



  1. Oh geez. I still feel like we don’t handle this the best even after being together nearly 4 years. Sometimes we both reach for our wallets. Sometimes only one of us does. Sometimes we both look at it. Not that either of us can’t pay its just that we have this weird nearly joint hold of each others finances yet we don’t live together. You would just have to be with us to get it because I can’t articulate it but more than one friend has commented that its like we have joint checking. Yet we don’t.

  2. Bethany says:

    On first dates, I generally expect the person who did the asking to do the paying: if you wanted to take me out, I would think that it’s fair to assume you actually, you know, want to take me out, not just want someone to accompany you to dinner/drinks/whatever (or, vice versa, if I were the one doing the asking, I think I should expect to pay AT LEAST for myself, if not for him, too, because I was the one who suggested it. Not that that happens, like, ever, but you know. In theory. Haha.). If I’ve been set up with someone, however, I think it’s fair to split the bill on the first date, because an outside person “forced you” to go out (obviously either one of you could’ve said no, of course, but I think being set up is different than being asked out). I don’t date for the free meals, but it does rub me the wrong way if the GUY suggests we split the bill, rather than if I suggest we split the bill.

    And for the record, I HATE going for ~walks~ with guys I’m dating when they don’t even try to make the teeniest, tiniest thing resembling a move. Come on, man! Do something to indicate you’re at all interested! I don’t want you all over me by any stretch of the imagination, but even “accidentally” brushing my arm a couple of times feels a lot better than both of us acting like the other person has cooties. Though if a guy is that unwilling to pay, I suppose cooties aren’t out of the question…

  3. Adav says:

    Chivalry is tough … I guess, in my mind, there can be some variations of how chivalrous a guy can be while also being considered a stand-up dude and someone worth dating.

    Regardless of that, even with my friends, I feel like money sometimes makes things weird. Like, if you’re itemizing your bill and how much you owe, it seems like everything else from the night gets itemized, too. And feelings can get hurt or things can get weird. I like at least taking turns – whether with friends or when I was dating, I’d get this dinner, my friend would get the next. Or buy drinks after. My guy would pay pretty much all of the time, but with times changing, I don’t know if it can still be a deal-breaker unless he’s a total douche or loser otherwise?

    What do I know? Just my thoughts. A very interesting topic!

  4. howie says:

    chivalry lives. guy always pays. no questions asked, but it was a nice gesture on your part to take out your wallet. as far as holding hands, which is always nice, he may not have wanted to force that on you. nothing wrong with you asking: would you like to hold hands. you are a classy lady, Jessica. if a guy doesn’t see that, move on.

  5. I think it’s about much more than the money. It’s about how willing they are to be a bit generous and whether they reciprocate your own generosity (i.e. like when you complimented him and he took it without considering what he could say/give to you). His loss for sure!
    You want to be with someone who is willing to go outside of just 50/50. You want someone who knows a relationship is a fluid give/take situation x
    I think that if someone asks you out/organises the date they should pay and the other person should offer. Most of all, when you meet the right person the rules won’t matter because you’ll reach an understanding without having to do that awkward dance. What you decide together in that moment will make sense – even really early on (in my experience anyways) x

  6. Caz says:

    pretty much what you do. I offer to split it, pull out my wallet, and often on a first date won’t bat an eye if we do go Dutch. (When dating online, first dates often feel like a ‘meeting’ more than a date -where you’re feeling the other person out and evaluating if you do maybe want to go on a date with them)
    But, a guy definitely does get extra bonus points if he picks up the check on the first (few) dates, and even more points if it’s dinner and not just a beer or two.
    If I quite liked you, splitting the bill wouldn’t be a deal breaker, but if I was already meh about the situation it certainly wouldn’t help. I take the dude offering to pay as a (possible) indication he may like you and/or be interested in another date.