How To Make a First Date Super Awkward


Name: Skyler
Question: Dear Moxie,
I have a money question that may have already been addressed on this site, I am not sure. So last month I met a new guy and he asked me out for drinks. For our first date we went out to a high end bar, and when the bill arrived I put down my credit card but he wouldn’t let the server take it. Then he asked if I had dinner yet, and I said no, and he suggested this casual Italian food place. When the check arrived I put my card down again, and he was like “no, no, my mom raised a gentleman. I can’t let you do that.” So I put my card away. For our second date, I brought cash with me so I could at least leave a tip. He again insisted on picking up the tab and I put down the cash for a tip. I received a text from him the other day, and it said: “Do you want to get drinks tomorrow?” I said “I can’t tomorrow, but I can meet you next week.” He said that was fine. So today I texted him and asked where he wanted to meet, and he said “Nowhere, I am sick of paying for everything.” So my question is, was I mistaken to let him pick up my tab those three times? I assumed it wasn’t until after the third date that letting the pay gets too excessive. Maybe I am just behind the times? When I go out on a first date with a new guy, should I insist on splitting the tab?
Age: 27


First, he’s a passive aggressive dick and possibly unhinged. His response was unnecessary and frankly kind of creepy. He sounds like the type of person that swallows his resentment until he can’t take it anymore, then explodes. He also sounds like he’s got a very fragile ego and may have felt slighted when you turned him down for drinks. Nobody needs a rage machine like that in their life. Any dude who whines about having to pay for “everything” after two dates is a bitch. Full stop.

Now, as for your question about whether or not you were wrong to let him pick up the tab those other times, here’s the thing: putting down your credit card is kind of bogus. What’s the server going to do, split the tab and charge each of your cards? Of course not. That’s too complicated and super awkward. My gut says you knew you’d be rejected when you put your card down, which negates the sincerity of gesture. It feels like a test. If I’m picking up on that, then he likely did, too.  I’m telling you, there are plenty of men out there who will sit back and say, “Okay, sure, we can put this on your card” just to see how you will react. I’ll also add that if you were the one to pick that “high end bar” to meet at for your first date, you shouldn’t have just offered to pay, you should have paid. Now, I know people will disagree with this, but that’s basic etiquette. You pick the place, you pay.  No guy is going to balk if a woman suggests a pricey bar for a first date. Why? Because he doesn’t want to look like a schmuck. In the future, let the guy pick the place if you expect him to pay.

I assumed it wasn’t until after the third date that letting them pay gets too excessive.

I don’t know where this myth came from, but it’s not a thing. There’s no number assigned to the process. It should be 50/50 from the get. Seriously, where’s the legislature that decides how many dates to wait before sleeping with someone or paying a god damn check? Most men will not let a woman pay just to avoid looking weak. Women know that. To take advantage of that expectation is wrong. If he insists on paying for the first date, let him , say thank you, then send a thank you text if you want to see him again. Don’t make a big deal of it. But on that second date? Don’t take no for an answer. Slip your card to the server and tell them to charge you if you don’t want to wait until the bill comes. Easy peasy. Buck up, literally, and contribute.



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36 Responses to “How To Make a First Date Super Awkward”

  1. UWSGal Says:

    Agreed on the guy being unhinged. Block that douche, bullet dodged.

    Disagreed on jumping through hoops such as slipping your card to the waiter etc. I always offer to pay (unless it is made clear to me from the start that the guy is rich. in which case fuck that, he’ll pay). But if a guy is like a normal NYC professional like myself i always offer. And wouldn’t hold it against a guy i liked if he took me up on it. But if he doesn’t because of his own ego, or fear of appearing “weak”, those are his issues, not mine. A guy who needs that much placating as to for me paying the check behind his back because he can’t stomach a split bill will require ridiculous amount of maintenance in the relationship and frankly i haven’t got the energy for that. There’s absolutely nothing wrong with giving the waiter 2 cards. When friends or families dine together this is how it is done. This is a very typical situation which should not result into any stupor on the side of the restaurant staff.

    Now if a guy refuses profusely and you like really want to “contribute” – there’re more gracious ways of doing it rather than bringing cash to leave the tip. Take him to a dessert place afterwards and pay for that. Pay for a cab ride. Pay for a drink before dinner the next time. Etc. Just say “this one’s on me” with a smile and decisively hand you CC to the bartender. Works like a charm.

    • Parenting Says:

      This. Ive seen both men and women write in to say that when the chemistry is lacking and there will not be future dates, they expect the woman to pay her half. If a woman insists on paying her half to the point of sneaking a payment, doesnt that say “not interested”? A geature that (in my opinion) fosters bonding and shows appreciation is insisting on “treating” desert, drinks or the next dinner as a show of your appreciation for his generosity. This is exactly what Ive always done with friends and family who bought me a lunch or a coffee.

      • Selena Says:

        ” Ive seen both men and women write in to say that when the chemistry is lacking and there will not be future dates, they expect the woman to pay her half.”

        Yes. If I want to pay my own way on a date the guy asked for, it’s because I don’t want to see him again. If he picks up the check and tells me what my share is, I’m going to think he isn’t interested in seeing me again. If he let’s the check sit there awkwardly long enough that I have to say “Shall we split this?” I’m going to think he isn’t interested in seeing me again, AND playing some sort of stupid game. If he splits the check with me and subsequently asks me out again I’m going to think he is only casually interested.

        Want to avoid ambiguity? If you are the asker you expect to treat. If you are the one be treated, be appreciative and reciprocate by being the asker sometimes yourself.

        • Rebecca Johnson Says:

          I think the idea that offering to pay means you are not interested is nuts. It’s a nice gesture that’s all. That yes usually the man waives away and yes the easiest way to make another gesture is to pay for dessert etc. But offering to pay, when I do it, is my way of saying that I’m not taking advantage of him or playing him. I respect him and his time and expenditure on me. I don’t take it for granted.

          But i am old. 48

          • Parenting Says:

            The difference, I think, is when you refuse his offer to pay and insist on paying anyway. That comes across as stand-offish. If a man picks up the check then asks me to pay half, clear sign he is treating me like his “bro” and not interested (or he is playing games). If I offered to pay on a first date and the man accepted, I wouldnt assume it means anything although it may leave me doubtful of his interest.

    • Eliza Says:

      Perfectly said…I agree..and it’s practically impossible to date or have any type of relationship with someone this passive-aggressive…where they don’t communicate and hold every little thing in…and then just explode like some volcano. He’s unhinged…and a waste of valuable time. Move on. He sounds too fragile, ego-wise and you need to tiptoe around this ass. Who has the time, patience for that? I ask when I go on a date, even if it’s a cheap lame coffee date, I always have cash on hand, to contribute. But if I insist, and the guy is adamant about paying … I’m not going to play some stupid game. I made a sincere effort of going dutch.

      • UWSGal Says:

        Passive-aggressive is one thing, but if he can’t handle a woman who pays without feeling inadequate it can only get worse from there. Say you’re in a relationship and you begin to out-earn him. Or he loses his job. Then what? Are you supposed to “pretend” that he’s the one who paid that rent check or for that vacation so that he can “feel” masculine? Are you supposed to still do everything at home even if he’s underemployed so that he can continue to feel “like a man”? Cause this is where this would be going. I think, men shouldn’t expect to have it both ways. If he wants to feel “masculine” and in his mind it is tied to money and paying, then he can pay up and shut up. But he better pay up. OR he can actually act like a normal evolved 21 century person and go dutch and still find a way to feel good about himself. Totally optional. What he doesn’t get is to have this “i am a traditional gentlemen guy who pays and feels dominant and masculine”-beating-his-chest-attitude, while failing to deliver – GTFO.

        • Eliza Says:

          Very good pint USWGal….you can’t have it all…to feed your vase-like ego. Women today, who have to work, go to school sometimes, and manage a home don’t have time to tiptoe around such fragile minded archaic little girly-men. Grow balls…and either pay, and SHUT UP, or deal. Or go dutch–the servers are cool with this…especially between 2 people. Now 4-6+ people…that can get to be too much.

  2. DL Says:

    “What’s the server going to do, split the tab and charge each of your cards?”

    This isn’t routine? I get that it’s super annoying if there’s 6 of you in the party, but I haven’t heard that a 2-way split is a problem for the staff.

    • myself Says:

      I do that all the time whether a date or friends or whatever, in fact around here (Montreal) servers never assume, they ask how many bills. I thought that was just standard.

    • Eliza Says:

      No problem at all…it is done, all. the. time.
      What is annoying is dealing with passive aggressive little pansies, that can’t seem to express themselves..yet get their panties in a ruffle.

    • Bethany Says:

      Yeah, I do this all the time. There’s nothing weird about this and I don’t think it’s fair to assume that the person who wrote in was just putting up a front.

  3. Yvonne Says:

    Skyler did nothing wrong. He invited her to have dinner and then insisted on paying. If he didn’t want to buy dinner, he could have left it at drinks. But even so, he refused her offer to split the tab. He sounds like a jerk. This is more about how to spot crazy behavior than about who should pay.

    • Selena Says:


      I also wonder if this guy expected sex on the third date and was pissed at Skyler because she wasn’t available on day he wanted? One of those “you owe me” types, who can only fake “being a gentleman” briefly.

      • Yvonne Says:

        I wondered about that too. Maybe he expected sex right away and didn’t get it? If that was the case, he’s obviously not going to tell her, so he comes up with something dismissive and outlandish.

        • Selena Says:

          Reading Nia’s comments about anger/control issues made me consider that might be what went on here as well. Guy is a gentleman who upgrades first drink date to dinner, pays for all and most of the second date (excluding tip) as well. For 3rd date, he texts “want to get drinks tomorrow?” That’s a casual, short notice invitation.

          Reasonable people would understand the person they are asking out might not be available on a specific day, especially on short notice, and not take it personally. A controlling person is more apt to get ticked off that the person they asked out is not available at their convenience. Perhaps even more so because they previous “paid for them”? Ugh.

          • fuzzilla Says:

            Yeah, and to add to the things to watch out for – guys who go on and on about being “a gentleman” are often rage machines full of resentment. Saying he’s a gentleman is often-not-always code for, “I mean, I’m jumping through the hoops you require, right?” Then the second he doesn’t get what he wants he flips out.

            A true gentleman doesn’t need to tell you he is and doesn’t throw a tantrum when he doesn’t get a cookie. He can feel disappointed, sure, but just think, “Ah, well, maybe next time” without exploding.

  4. mxf Says:

    I dunno… I was all down with the “bullet dodged, what a bad guy” stuff up until:

    “I assumed it wasn’t until after the third date that letting the pay gets too excessive.”

    See, I’ve never found it hard to pay for my share of dates, and I don’t find it that hard to read what the other person is really saying when they decline my money out of politeness. There are only so many scenarios:

    1. He waves away my money because he’s not an idiot and he knows he’s supposed to do that, so it’s genuine but not some deep philosophy. If you’re gracious and insistent, most of these guys relent and split the bill, so long as you let them off the hook of feeling cheap. “No really, MY mother raised me to be fair, please let’s treat each other and split dinner tonight, you can get the next one” whatever etc
    2. He waves away my money because he’s trying to nail down a second date, because he likes me or he’s having a hard time getting second dates in general. If I want to see him again, I’ll extract a promise that I get to pay for the next date, which I then absolutely do. If I don’t want to see him again, I’ll nicely insist back that I can’t accept his generosity, maybe another time, and pay my own way. Why should a guy I’ll never see again pay my bill?
    3. He’s so old-fashioned in his values he literally thinks it’s not my place to pay. Or work. Or wear pants, or swear, or have political opinions or any inconvenient demands in general.

    The OP is 27, I doubt she was with a Group 3 guy. And if she were, he would never get offended from paying anyway. Sounds like she was with someone passive-aggressive, who was going through the motions until he had a fit. But I just don’t believe people who say they tried and tried and tried to pay and simply couldn’t, especially not if they have a three-date window where they think it’s socially acceptable not to pay anyway.

    People who want to pay, pay. This guy said he wanted to pay and obviously didn’t, but it seems like neither did this woman.

  5. Nicki Says:

    Dodged a bullet on this guy, plain and simple.

    When it comes to paying on dates, I always offer. I will actually insist on paying for mine more than usual if I know I am not into it enough for a second date. If the date is drinks and he insists on paying then I’ll do the usual, “Next times on me!” If the date is dinner (which I try to avoid) then I’ll do, “Fine, but drinks are on me next.” I never assume that a guy is going to pay. This is 2017 and I kind of expect for things to be equal.

    Now recently I was dating a guy for a few months and we’d kind of switch off on who paid unless if it happened to be one of our turns and the other just spent a lot more… We’d just grab the check and pay regardless.

  6. Nia Says:

    The never ending debate :P

    I think simply putting one’s card down isn’t enough. Maybe “Please, let’s split this.” or “This one’s on me”. If he insists, then if the date continues “Okay, but next round/dessert is on me.”

    I find it kind of odd that there were no other red flags of any kind but it does happen.

    I once went out with a guy (there were some pink flags, but he talked me into it, a move I really regret) who showed up looking super rough. He confessed he had spent the night freaking out and sleepless because he “experimented” with a friends’ prescription Adderall. This is someone who worked as a grade school teacher and was over 40, btw.

    The date limped along, and he was out of it, and weird. I got upset and finally in the parking lot I asked him sharply “Why did you even come out on this date? It’s super clear you didn’t want to.” and he…flapped his hand at me dismissively as if I were an annoying store clerk.

    So…bad dates happen. People are weird and angry and do and say really out-there stuff.

    There’s no avoiding it, I think. My only advice is to a) pick a very inexpensive first date. b) ask the waitstaff “Separate checks, please” at the *start* of the meal. c) really be alert to genuine red flags.

    Red flags are different for everyone, but a short list:
    Out of proportion anger about anything
    Talks negatively or uses slurs or insults about women, any women, regardless of provocation
    Seems super interested out of proportion to the time you’ve known one another
    Seems vague, hard to pin down, you feel like you’re doing a song and dance to get him to agree to date
    Something about him makes you feel angry, sad, afraid, or jumpy “but you can’t put your finger on it”
    You’re ignoring stated deal breakers because of looks, job, location, or other “perks” (like he’s an airline pilot or something glamorous)
    He reacts out of proportion to what you say (ie, either gushing over you or freaking out over an innocent or stray remark and then profusely apologizing)

    Most of these are about men who are out of balance in one way or another. Men who struggle with temper and control issues. Those are the guys to really watch out for.

  7. splitting checks Says:

    I think the multiple credit card thing is very regional. In some cities, servers get annoyed. In others, it’s normal. I love in Phoenix now and servers are happy to evenly divide a check among 2, 4, 6… people. We don’t know where Skyler lives.

  8. KK Says:

    This guy is a dick, for sure. But how wad she giving a test? She put dowb her credit card, and he could do. Splitting the bill is easy. I have done it a lot.

  9. Astrid Says:

    This guy is a toolbox, and his attitude was creepy.

    I used to avoid this “who pays for the date” stuff by meeting for initial dates at a modest bar or coffee shop, or even an outing at a museum (here some museums have a free night) I’d pay for my couple drinks and he paid for his. Or, sometimes he paid for both because it ended up being so inexpensive and he could still feel like a gentleman for picking up the tab. We’d have fun and talk, but there’s no pressure on him to shell out for a woman he doesn’t know. As time goes on and if we liked each other, we have the dinners or whatever and switch off paying. It worked wonderfully. Does anyone else do this?

    • xyzed Says:

      Astrid…Not in NY or the surrounding areas. On all of my first dates, the women sit there expecting the tab to be picked up by the man. Some have even selected more expensive locations to suite their needs. What part of the county are you in? Maybe its time for a change in scenery?

      • bdjr Says:

        xyzed, I’m in NYC. Sorry bro, but you’re doing something really wrong.
        Although you must assume you will pay for the first couple of dates, they should be your choice of venue and within your budget limitations. Don’t even bother to meet any woman that won’t agree to your venue, she will be too much trouble.

  10. Angel Says:

    I wouldn’t want to sit there and go through a check line by line to see who owes what. That’s seems so cheap. I bring cash to make it as easy as possible for me to leave if things aren’t going well.

  11. sandra Says:

    I do not think there was/is anything wrong or impolite in allowing the man to pay. I do not even think it necessary to lay down your credit card. Let him pay. HOWEVER, since she claims she wanted to chip in, she could have texted after the dinner date or when discussing getting together again for drinks, that the next time the tab will be on her. I am not sure it would have changed the outcome since his actions appear unstable, but showing a willingness to pick up the tab beforehand after he has paid a couple times is reasonable and polite.

    • bdjr Says:

      Correct. Women should own their desire to pay or not, whatever it is. If you’re an entitled princess, then just sit there and be a princess. If you truly want to pay, then make it absolutely clear and DO IT(and men can tell the difference). The insincere offers just confuse everyone and disappoint.

      • UWSGal Says:

        How can you tell if the offer is “sincere” or not, can you read minds? And even if its insincere, what’s stopping you from accepting it anyway? Jeez. Quit projecting your insecurities on women!

        • bdjr Says:

          “How can you tell if the offer is “sincere” or not,”

          Because I’m a normal, socially calibrated adult. Not just my words, Moxie says it too. She calls it the “half-reach” for the wallet, among other things.

          • Parenting Says:

            If you want the woman to pay, just sit there until she reaches past the “half-reach” and make it all the way to putting her card on the table. Whether she does so sincerely or insincerely has no effect on the processing of her payment. It may effect whether theres a 2nd date or not but it sounds like you dont want to date the “half-reachers” anyway.

  12. Yvonne Says:

    I’ve been out on first dates where the man did not intend to pay. He either sat and did nothing when I went to buy my coffee, or when the check came, he said, “Shall we split this”? There was no fake show of chivalrous behavior, no game where he “pretended” to want to pay, or where he expected me to argue with him about his paying or read his mind. I either bought my own beverage or we simply split the check.

  13. Benny Says:

    Everyone I’ve known who has downplayed the importance of physical chemistry has either settled or cheated or both.

    • Nia Says:

      But physical chemistry isn’t always about looks.
      I’m not arguing that your friends or acquaintances or FB groups are unhappy, settled, or cheated/are cheating.
      I will argue that it’s not “downplaying” to acknowledge after a certain age that physical or sexual chemistry is *part of a bigger picture* and is not your top, most important quality in a potential mate.

      When you’re in your 20s, it’s understandable and fine to insist on fire chemistry. Hell, you can insist on it all you want up til the day you pass on!

      But what’s kind of self-destructive or counterproductive is to insist on it being the key or major thing in your relationship.

      Long term relationships are about shared values, friendship, support, laughing and crying together, and “bearing witness to each others’ lives”. You show up, you love them, and you’re there for them.

      Sure, blazing hot physical chemistry helps you form that bond and it helps one overlook day to day annoyances. But it’s not everything.

      Recently my BF confessed he wasn’t feeling very attractive and “up for it” because of some minor physical stuff and I told him (sincerely) “You don’t have to be “sexy” for me to want to be with you. Because being intimate with you is about more than ripping your pants off and stumbling around the apartment knocking lamps off the table. It’s about us, building our relationship, and me showing you my love.”

      My 2 cents :)

  14. Pina Says:

    Looks are temporary. Eventually through the aging process everyone becomes physically unattractive to some degree. Or what if someone you thought was hot becomes disfigured due to an unforeseen incident, do you just throw them away?

    I believe a person can change their mindset to overlook certain physical imperfections and zone in on the good points of the other person to find a relationship that’s a good fit for them. For me a sense of humor blinds me to a lot of physical flaws, like Louie C.K. for instance. He’s not textbook attractive but when I see him do standup I want to marry him.

  15. Smokey Says:

    Eh, every time I got out with friends or boyfriend or whoever we split the bill evenly over two cards. I’ve never encountered this being an issue in a restaurant before. I’ve done it on dates as well. Putting your credit card down and offering to pay for half is the right thing to do and she did it. Most normal guys would take her up on it at least on the second date. Not only that but she brought cash with her to the second date to cover her bases. I don’t think her gesture was insencire. He got mad about something else and sounds like a real creep. She dodged a bullet and didn’t do anything wrong. Your advice to seek out the waiter and slip him your card is the stupidest thing I have ever heard and your dating advice is usually spot on. Why jump through these kinds of hoops on a first date with a stranger? Offer to split the bill always and if they insist on paying who am I to tell them no? We have to read minds now? If I go out with a friend who insist on paying ill let them and I insist on paying myself a lot of times. I take people at face value. No time to play kind games especially with strangers on a first date

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