How do I address the issue that my new flame doesn't offer to pay?
November 27, 2013 3:03 PM   Subscribe

I'm a 32 year old male, she's 28, and we're both NYC natives, if it matters. We get along well and we enjoy our time together. Generally, I'm ok paying for the first three or four dates, however beyond that it's clear we like spending time with each other, so I'd prefer that it was a mutual effort to cover costs. Otherwise, I feel like I'm paying for her time and presence, and it feels gross. We've been dating for almost a month now.

My relationships naturally end up with us sharing costs, without me having to address it. I don't see that happening with my new flame though. It appears I will have to specifically address this with her. My question is: how do I bring this up without coming off like a cheapskate or accusatory?
posted by anonymous to Human Relations (51 answers total) 11 users marked this as a favorite
Who is asking whom out? Are you the one suggesting dates? Even if I suggest an outing with a friend, I generally offer to pay as it is my idea, my invitation. While I don't make the same assumption when someone asks me to do something (I offer to pay for the activity, that is), maybe she takes it a step further than me?
posted by kellyblah at 3:09 PM on November 27, 2013 [1 favorite]

"Hey, would it be ok if we split the bill next time we go out?"

In current society, women aren't generally obligated to pay or offer to pay as long as men are offering, especially early on, and a month is still early.
posted by tylerkaraszewski at 3:09 PM on November 27, 2013 [14 favorites]

Next time you eat out somewhere and the check comes, as you go for your wallet nod to the bill and (pleasantly! casually!) say, "want to split this one?"

She should either say "sure!" or "I'll get the next one!" (The last one provides the opportunity for her to do something she's in control of the cost of, which is important if she's poor.)

If she balks, dump her.
posted by phunniemee at 3:09 PM on November 27, 2013 [16 favorites]

"Hey, let's share costs when we go out. Maybe I'll get one night, you get the next?"
posted by Stynxno at 3:09 PM on November 27, 2013 [4 favorites]

Does she ever initiate dates? That is, does she contact you and choose things to do, etc? If not, I can kind of see why you always pay - you're kind of driving the boat. That doesn't answer your question, but it might help you frame your discussion with her.

Instead of sitting her down for a relationship talk, I would be casual and say something like, "Hey, do you mind splitting this one?" at the start of your next date - and if you choose the place, pick somewhere inexpensive. If she blanches, or seems upset, that opens the door for a good conversation. You can just keep asking to split, but sometimes pick up the whole check, and she should figure it out.

If you do have to sit down and have a talk about it, I would stay clear from saying things like "I feel like I am paying for your time and presence, and that feels gross." Instead, I'd say something like, "I prefer to share costs with the people I date. It's how I've always done it, and I like it because it is more fair. If you'd like, we can switch off, so I'll get one, then you get one - I feel more comfortable this way."

You'll learn a lot about this relationship in this interaction, which is always good.
posted by k8lin at 3:11 PM on November 27, 2013 [1 favorite]

I would ask, but I'd ask before you actually get to the point of paying the bill. Don't just dump going Dutch on her after she's eaten - mention it during the planning stages so she can make an informed decision as to whether or not she wants to pay. And you'll be able to see how she handles this when she's not being put right on the spot.
posted by Solomon at 3:29 PM on November 27, 2013 [18 favorites]

- If you sprung this on me at the end of a dinner, I would think you were a shitty at communication and I would worry what other surprises to unexpectedly expect.

I would dump you in this scenario.

- If we were getting more serious and you talked to me about splitting I would enthusiastically agree!

- If you still wanted to date other people. I wanted to be more exclusive, AND you asked me to split.... Nah.

Do you see the differences?
posted by jbenben at 3:29 PM on November 27, 2013 [31 favorites]

two things missing from your question: how much money do you make relative to her? and, how expensive are these dates?

unless you make substantially more than her and you're going on dates that would be a significant cost to her, i think you should bring it up when you're setting up your next date.
posted by cupcake1337 at 3:29 PM on November 27, 2013 [7 favorites]

Generally, the asker pays for the askee. If this is indeed the case for you, is there a reason why she isn't asking you out on dates?
posted by Shouraku at 3:41 PM on November 27, 2013 [3 favorites]

You could stop thinking of it as paying for her time and presence, and think of it as an act of generosity/affection. You can spin it as the former to her, but I really think it's more of a signal of affection and appreciation.

I do think you should let her know ASAP, possibly during your next phone call, that you want to split costs so she can figure out if she wants to date you under those circumstances. It can give her insight into your financial expectations of her and she can decide if getting to know you is worth it for her.
posted by discopolo at 3:48 PM on November 27, 2013 [8 favorites]

The fact that she isn't offering to pay after a month of dating seems odd to me. The fact that it's being defended in this thread seems even odder, but I guess that shows there's a range of expectations in this situation.

You could try suggesting she plan your next date and see what happens. If she still expects you to pay for it, it's talk or walk.
posted by Georgina at 3:58 PM on November 27, 2013 [46 favorites]

And I think you're going to have to get comfortable with sounding cheap. There are a lot of guys who like to pay for dates/insist on paying even after being offered a split, and it's widely recognized as a sign of a gentleman, especially a guy who is older than 30 and has a job.

I'm afraid it might make you look like you're stingy, which is something some of us look out for when dating men. But if this is something that's going to gnaw at you, you might as well let her know you simply want to pay your half and not try to make it sound like you're doing it for her benefit (or that you're actually helping her not seem like a prostitute or escort, which is what you seem to be implying you're trying to do.)
posted by discopolo at 3:58 PM on November 27, 2013 [11 favorites]

If you do decide to ask her to split as a spur-of-the-moment casual conversation, I would do so before you order (assuming we're talking about a restaurant bill and not say, movie tickets) -- if she is having financial constraints you don't know about, she has the option to order something more modest and keep her burden lower while still agreeing. If she thought you were paying gladly and therefore ordered more than she would have on her own for financial reasons, it could make it harder for her to accept an unexpected spllt gracefully, even though on principle she would be willing.
posted by Mchelly at 4:04 PM on November 27, 2013 [1 favorite]

I'm often hesitant to suggest splitting bills when the guy offers to pay, even though splitting is what I legitimately prefer, because it gets awkward and I don't like arguing about it, even playfully. It's possible that your GF is in the same boat. Have you tried simply not offering to pay in the first place?

If you have tried this and she pointedly avoids looking at the bill or whatever, a good second step would be something like "I like to start splitting bills after the first few dates, are you OK with that?"
posted by randomnity at 4:06 PM on November 27, 2013 [5 favorites]

I think that the suggestion that you ask her to sort out your next date is a good one. It might be that she's just not that into you, in which case you're better off finding out quickly rather than slowly. Someone who doesn't put the effort into a relationship isn't someone to bother being in a relationship with. Part of the point of being in a relationship is complementing another person and putting in 50% of the effort to keep things going.

If you're happy being with someone who just takes, then that's OK, as long as you're actually OK with it. It doesn't sound like you are, though. I wouldn't be either, to be honest. Organising everything and paying for everything for another person skews things to a much more transactional type of thing, which I really wouldn't be comfortable with. I'd want my partner to show that they were committed to what we had, rather than deal with the expectation that because I'm male I should pay. This isn't the 1950's any more, and thank Jeebus for that.
posted by Solomon at 4:07 PM on November 27, 2013 [1 favorite]

Otherwise, I feel like I'm paying for her time and presence, and it feels gross.

This is something that you might want to work on thinking differently about by yourself, in addition to talking to her about it. There are lots of ways of thinking about why you'd pick up the tab, and this is maybe the least pleasant one you could pick: try on some alternatives, like "I like her, so I enjoy treating her to stuff" or "It makes me feel generous and kind to help my friends out with financial stuff" or whatever. Thinking about it like this seems like beating yourself up unnecessarily!

And it'd help just to recognize that different people can have very different ideas about the etiquette and ethics here. I mean, in addition to simple lack of communication or mere rudeness, it's equally possible she's letting you get the check because she is conservative in gender politics ("a gentleman always picks up the check") or because she perceives herself as poorer than you and has a proportional financial etiquette ("the better-off person should generally pick up the check"). This is not to say that you're wrong to want the equal split — you are very much allowed to want that, and to ask for it — but the equal split is not the one and only rule for everyone. You can acknowledge that when you bring it up ("so, I usually like to split things equally, but I know not everyone feels that way"), and it might help you feel/sound less accusatory about it.
posted by RogerB at 4:35 PM on November 27, 2013 [5 favorites]

Mod note: Answers to the question and not generalized complaints about relationships/dating, please?
posted by jessamyn (staff) at 4:53 PM on November 27, 2013

My relationships naturally end up with us sharing costs, without me having to address it. I don't see that happening with my new flame though.

Why not? Just because she hasn't started offering yet? Or because there's something about her that makes you think this is going to be a contentious or difficult conversation? That line somehow makes me think that you think she's avaricious or shallow or something (the feeling "gross" part adds to that) or that she's not as into you as you are her. If that's the case, you should probably to address those underlying issues; if not, Georgina's plan, or just a "Hey, let's split this," should work just fine.
posted by pretentious illiterate at 5:01 PM on November 27, 2013 [2 favorites]

This is a really really tough situation. It could be very awkward and result in the end of the relationship if you're not careful. Although if she's a decent human being, she should be more then willing...actually she should be start paying for some dates or at least splitting them. My philosophy on dating was the first date....I'm the dude I pay. The second date once again I pay. After that I at least expect her to make an offer to pay somewhere around the 3rd or 4th date. More then anything it could be a sign of what type of person she is or how serious she is about you. My wife started to offer paying on our 2nd date. And to me that spoke mountains of words as to what type of person she is. Now as for how to broach the situation....again difficult. Perhaps the best way is the next time the check comes I would casually say, "Let's split this one". Really at this point if she has a bad reaction it's not a good sign. Who knows maybe she feels she would offend you by offering to pay. Ya never know. Just don't make a big deal out of it. Hopefully all goes well!
posted by ljs30 at 5:07 PM on November 27, 2013

I'm pretty much breaking even each month (enough money for rent, groceries and bils). If a dude I had been seeing for a month (and had been paying the full tab) suddenly asked me to pay my half, it would prompt a whole other conversation about how I can't afford to go out in that way. Which for me would mean, let's do more free/cheap stuff together. So be ready for what you do together to possibly change.
posted by mandymanwasregistered at 5:07 PM on November 27, 2013 [3 favorites]

But if that dude told me he felt "gross" and that he was paying for my time, I'd know it was time to end the relationship.
posted by mandymanwasregistered at 5:08 PM on November 27, 2013 [13 favorites]

Just ask her if she'd be ok splitting the bill or alternating paying for dates going forward. Don't play games by asking her to plan a date and seeing if she pays.
posted by matildatakesovertheworld at 5:33 PM on November 27, 2013 [6 favorites]

I'm really really poor, but pass in my dress and mannerisms as middle class. Please do not assume that she is well to do, or middle class based on what she wears or how she speaks.

Be an adult and use your words. Either you will come across as a cheap and condescending jerk, or you will be understandable as a sensitive liberal gentleman. Keep in mind that even if you play this "perfectly," she may still be upset or "feel gross."

There are too many possible causes for this behavior (who's inviting, relative incomes, where you are eating, what she has been raised to expect, etc).

Some women have honestly, seriously been taught that any man worth their time will NEVER let them pay for anything on a date. I know this, because it is what my father taught me. I spent a lot of time digging into and unwinding those beliefs. If this is what your date was taught, then telling her that she is wrong, or selfish, or "gross" will NOT win you any points.

So, be objective. Frame this only as facts. "Hey, lovely ladyfriend, I have noticed that I have been planning/paying for all of our dates. I really like a more equitable (notice that word is not equal) split of relationship responsibilities. I really like you, and I want to spend more time with you. So it would feel really nice to me if you planned and took care of some portion of our dates. What kinds of things would you like to plan?" Her reaction to that will indicate how you might proceed to discuss the paying part of things. If she is already planning some dates but not paying for them, you can start by telling her how much you appreciate that she plans dates, but that you were raised to share costs equitably. Ask her if she is comfortable contributing financially to dating.

Do not do this on a date. On the phone is fine. Accusatory tone is not fine.

Brace yourself for the possibility that she may stonewall you or dump you. Respect her boundaries, and also your own.
posted by bilabial at 5:34 PM on November 27, 2013 [22 favorites]

fyi I just to have to respond to this: There are a lot of guys who like to pay for dates/insist on paying even after being offered a split, and it's widely recognized as a sign of a gentleman, especially a guy who is older than 30 and has a job. I'm afraid it might make you look like you're stingy, which is something some of us look out for when dating men.

I'm sure you are aware but there are tonnes of women that - absent radical income differences and literal inability to pay - insist on splitting costs for general dates etc. And they don't think it is stingy, but frame it as an equality issue, and they sometimes view guys who insist on paying for everything not as gentlemanly but as chauvinist and controlling.

Neither perspective is wrong, but it's definitely a values thing, and if the values are incompatible it bodes poorly for the future.

If it was me, and it was a small date/dinner under or around $20 bucks each, I would just say "are you okay splitting this one?" when the bill came - it's not a big deal to me, and I don't really wanna date someone for whom it is a big deal.

If it was more expensive, I would flag it beforehand for sure. Like if it was a concert or whatever when we were booking, I would be like "Tickets are sixty bucks, you wanna go?"
posted by smoke at 5:39 PM on November 27, 2013 [4 favorites]

Straight dude here. This seems like the kind of conversation that isn't easy to have, because if your date was inclined to understand your concern, you wouldn't need to have this conversation in the first place. I'm also assuming there aren't any cross-cultural issues that might account for why she isn't offering to pay.

Like others, I don't know how serious you are about her, and I don't know how your incomes compare. But if I were getting serious with a woman who was in about the same income bracket as me, I'd want to be with somebody who 1) I wanted to treat to dinner whenever I could afford to, with no expectation of a "return" dinner, and 2) wanted to treat me whenever she could, and was comfortable offering.

So toward those ends, if I were you, I'd be Mr. Generous with going out for a month or two--just picking up the tab right away--and if she didn't offer to pick up the tab at least a couple times, I'd take that as a sign of somebody who was either OK with letting me pay for everything without even pretending to want to take a turn, or not possessed of the same affection I was, and therefore not moved to want to pay out of her own feelings toward me. Those things, for me at least, are red flags that point to somebody who's selfish, or oblivious, or both.

From your post, it sounds like you and I might be different on this matter, but just thought I'd throw that out FWIW.
posted by Rykey at 5:40 PM on November 27, 2013 [5 favorites]

I don't know how many dates you've been on, but it sounds a bit cart before horse to go "well my relationships usually end up like so" and applying that to someone you are only dating.

I find it strange and off-putting that you've framed paying for dates as "paying for her time and presence," and I am not of the mindset that automatically expects for all dates to be paid for by the guy.

That being said, how does this usually come up? And are you prepared to break it off if she isn't into splitting? (Or conversely, if she breaks it off with you?)
posted by sm1tten at 5:56 PM on November 27, 2013 [4 favorites]

Maybe this is a micro-generation gap? I'm a woman who's few years older than you and have always always offered to pay or split costs on the first date - usually I covered coffee or drinks if the date lasted past dinner. Most of my dating happened in SF.

I think you may have different normals, so scripts that acknowledge that you may have divergent baselines are good. Talking about money seems weirdly hard in American culture. I have been lucky that my partners have always been generous when financially flush and I hope I have been the same to them. Good luck!
posted by spamandkimchi at 5:58 PM on November 27, 2013

I'm a lesbian so maybe I am not the best judge, but I think it'd ridiculous that a guy needs to keep paying if he asks a girl out and they've been dating for a while. I disagree that if he initiates he has to pay if they've been on many dates.

I might just try to make a joke of it to take the awkwardness away, like tease her "Hey, when is it my turn to be treated?" with a laugh. And then kind of move into saying it feels like you're paying to spend time with her and you hope she enjoys hanging out with you.

I don't think income disparity matters. Even if she makes less, she could offer once in while, no? My only question would be if she ever cooks your dinner or has you over and serves you drinks. My mom lets men pay for her when they go out, but she has them over and cooks for them, so it kind of balances out. If this girl is paying you back somehow, maybe it's not as imbalanced as you think.
posted by AppleTurnover at 6:01 PM on November 27, 2013 [5 favorites]

The point of all these disagreements you're seeing among our answers is that you have to talk to her about it. There is no one answer to "what is the right way to x when dating?" Where x is absolutely anything. Initiate the first kiss, pay, open doors, when to introduce to parents.

No one size fits all answers. Having these conversations is hard, but worthwhile, because you get to find out if your answers are compatible.

Very common cause of divorce? Disagreements about money.

There might also be some ask vs guess culture going on here, in addition to all of the variations in dating culture that have been mentioned above.
posted by bilabial at 6:11 PM on November 27, 2013 [4 favorites]

Mod note: Again, question is not "What do you think of gender roles and dating" but helping the OP with this specific question.
posted by jessamyn (staff) at 6:48 PM on November 27, 2013

I would definitely ask her about it. Not while you're on the date that you're discussing paying for, though. It should't be a big deal, but if it is, you have the right to know why.
posted by roomthreeseventeen at 7:20 PM on November 27, 2013

"Hey, it's getting kind of difficult for us to go out to eat so much on my tab. Can we do dinner in at my place tonight?"

That's a good way to start the conversation. If she's a reasonable person, she'll say, "Oh gosh, sure! And next time we go out, I'll pay," then you can say, "OK, or we could always split."

If she's an unreasonable person, she'll pout and demand a pony, then you have my permission to break up with her.
posted by mibo at 9:11 PM on November 27, 2013 [5 favorites]

Some women have honestly, seriously been taught that any man worth their time will NEVER let them pay for anything on a date. I know this, because it is what my father taught me. I spent a lot of time digging into and unwinding those beliefs. If this is what your date was taught, then telling her that she is wrong, or selfish, or "gross" will NOT win you any points.

I would also add that some men have been seriously taught that if they are serious about a woman, they will pay for everything, and that if they love her, they will take on some sort of provider role.

If you are a woman who dates those men, there will be a lot of pushback if you try to go dutch. It can cause confusion and anxiety, which can carry over into future dates. The first boyfriend I had after moving to a conservative town once asked me, with complete sincerity and worry, if I was thinking about breaking up with him...because I didn't let him pay at all for dinner one evening.

So...look. This could be a cultural thing. Really. If you are polite and adult about it, you can ask her. You may be surprised by the answer. Or displeased. Either way, you'd learn something.

I also think it's perfectly chill and easy to ask to split costs within the date, provided you do so before the date begins: "hey, I'm going to buy our tickets to show. Do you think you can get us drinks when we're there?" Or: "since you are a member of the Underwater Basketweaving Association, can you cover the entrance to the Basket-o-Rama festival? I'll buy lunch afterwards."

Disclaimer: this is just an opinion, and from someone no longer on the dating scene.
posted by sock puppet of mystery! at 9:46 PM on November 27, 2013 [6 favorites]

"Oh hey, I got this one, but can you get the next one?"

You can also mention things like not wanting to seem presumptuous, or ask her how she feels about dutch or alternating in the future.

But yeah, this is a discussion to have maybe on one date about the next one, not the one you're on then.
posted by klangklangston at 11:08 PM on November 27, 2013 [1 favorite]

I am broke as a joke, and I can't imagine just assuming that any guy would pay for all dates after a month. If there's a significant money-gap between me and my date - there usually is - and they want to go somewhere nice, they pay. Otherwise, we go dutch. Or I tell them that I can only afford to eat at a taco truck, and we eat at Taco Zone. Or we go somewhere else and they pay. Or I make a cheap dinner at home and they bring a bottle of wine. Or whatever. If an income disparity is an issue, there are ways around it other than one person paying for everything all the time

If she's too poor to go out, she can tell you that. She is, I assume, a grown-up who knows how to use words.

I like when a guy pays on a first date, because it generally clarifies that we are, in fact, on a date. I like it when a boyfriend pays for something every now and then without bean counting, because I do the same and it's important to be generous with the ones you love. I have no patience for the rules-y bullshit of, "If he's serious about me, he should pay! Take take take!"


Those things, for me at least, are red flags that point to somebody who's selfish, or oblivious, or both.

Yeah. For everyone who is citing potential cultural norms in conservative parts of the country, the OP says that they are both New York natives. I think never offering to pay is a major red flag, but if you like this girl, OP, talk to her about it.
posted by ablazingsaddle at 11:20 PM on November 27, 2013 [10 favorites]

I live in Canada, but I have almost never had a guy pay for every date, not even in the beginning. I always offer to pay. However, if you're doing the initiating and she's not financially secure, then she may not have the money. But, even in that case, if I didn't have much money, I'd invite you out for coffee, dinner at my place, a walk in the park, and so on. I'm wondering if perhaps she doesn't want to tell you that she can't afford to go to more expensive places or that she's afraid you'll think less of her if she keeps inviting you to cheaper places. (Some guys might think she's being cheap.)
posted by Chaussette and the Pussy Cats at 11:26 PM on November 27, 2013 [1 favorite]

"Hey since, I got dinner, coffee is on you?" is a not completely awkward conversation starter. And a conversation will have to be had; you can't rely on it just being changed if there's no sign to her that it's not working for you.

I usually offer to pay on date two just to avoid this sort of precedent being set.
posted by RainyJay at 1:08 AM on November 28, 2013

"how do I bring this up without coming off like a cheapskate or accusatory?"

Its going to depend completely on how she feels about paying for dates. You can certainly be polite about it, yeah- but if she is an "I don't pay on dates" kind of girl, then you will come off like a cheapskate, no matter how you frame it.

Also bear in mind that this lady may have had many dates before you and perhaps has never paid for any of them. If that's the case, she isn't likely to start now. I've discussed this at my large girls group and it goes half half- girls who have always split, and girls who wouldn't dream of paying.

I wouldn't look at paying for dates as paying for her company... I don't think most girls, even the "I don't pay on dates" girls, feel that way when a man pays.... and certainly don't frame it that way to her- if someone said that to me, well I would feel like he was calling me a prostitute.... and yeah, that would be the

For some women this is a really easy way to measure how generous a man will be... (accuracy unknown!) and you're also most likely fighting the science of women preferring well providing men for evolutionary purposes.
posted by misspony at 4:08 AM on November 28, 2013 [3 favorites]

I'm with klangklangston - a quick "I got this, your turn next time" gets the message across with (what should be interpreted as) friendly, fair intentions. My boyfriend likes doing the paying when we go out. He likes to feel generous. I value being independent and have almost always paid for myself. Early on I would do that and he seemed awkward about it, like he felt slightly undermined, as if by taking the check I was inferring that he didn't have the resources, or I wanted to symbolically separate myself from him and send we are not a close couple signals. Now I let him pay by default, I say thank you, and keep my ears open for when it's time for me to treat. He'll say, "your turn next time," or "I got tickets, you get snacks". The dynamic is much more comfortable. I definitely don't want to be a leech. I just need to know when it's my ball.

You don't want to be in a relationship with someone who isn't open to showing her generosity in kind, so if she gets offended with a gentle "next time, your turn" or even a cheeky "you should take me out! I like being wined and dined too!" you've probably dodged a bullet. You also need to be able to communicate comfortably when you are feeling overburdened in some way, because your date isn't a mind reader and she may have different experiences regarding who pays for what and why. Let her know.
posted by griselda at 7:38 AM on November 28, 2013 [1 favorite]

I'd like to second Smoke's advice; "if it was a concert or whatever when we were booking, I would be like "Tickets are sixty bucks, you wanna go?"".

Early on in a relationship a guy said a similar thing to me about an event that he had a comp ticket for, and we were deciding if we should get a second for me. He said basically "I can try to get another comp, and if not, we could split the $x ticket cost for the second?". It was a really straightforward and easy way to approach it.
posted by offrecord at 9:34 AM on November 28, 2013

As far as directly answering your question, this is what worked for me:

Years ago I started dating a guy and we started splitting the cost of dates from the start. I had no real problem with it, but when I mentioned it to a girlfriend she was appalled that he'd never actually "taken me out." She suggested that the next time we go out and the check comes I just sit there instead of immediately reaching for my wallet.

It was so out of character for me but I did it. It seemed like an eternity, but it probably just took him five seconds to pick up the check. After that I still continued to reach for my wallet, but he did start treating me to things, and I reciprocated.

I think maybe he was used to being taken advantage of, but either way, my friend's technique worked. I've never done it since. I couldn't imagine never offering to pay my share, so while it's nice to be treated to dinner or a night out I don't blame you for being irked by her behavior.

As far as the surrounding issues go, I agree completely with ablazingsaddle.
posted by Room 641-A at 9:58 AM on November 28, 2013

Also, I think "asker pays" is fine for the first couple of dates but I don't like keeping score in my personal relationships.
posted by Room 641-A at 10:00 AM on November 28, 2013 [2 favorites]

Lately I've been on a lot of first and second dates in New York.

If it is up to me to propose a date, I suggest a bar with a cheap happy hour where I am happy to pay for myself, take turns, or treat him, if I'm the relative big earner. But most of the time the guy suggests the place, and some of them have picked places way out of my price range. As in, I would save up and go there for my birthday and it would be a special occasion.

Who's suggesting the locations? Are you still doing all the legwork of planning, choosing, and inviting?

If so I think you do risk ending up in a relationship with a woman who has pretty different values from you, or ending up going on a lot of dates with someone who enjoys your company and likes you well enough to enjoy some free entertainment but is not into it enough to put her money where her mouth is.

I see a couple of ways to address this. First, consider how much space you've created for her to step up and invite you or choose a place. Are you travelling to her borough as often as she is to yours (this is an issue for me, living in Brooklyn and dating Manhattanites). You're probably fine on this, since you say it's usually worked organically in the past, but worth considering, just in case.

You could bring it up while you're hanging out doing something that doesn't cost money. So not during a meal before the bill comes, but out on a walk, or cooking together, or something. The topic is how she thinks money should work in new and less new relationships, and the goal isn't to change her or change anything but just to understand and get to know her better. I think the outcome of the conversation will tell you everything you need to know about whether you are compatible with her and whether this is something you can successfully talk with her about.

I have been racking my head thinking of other ways to do this but everything else I think of ends up sounding either passive aggressive or stingy.

The only other thing I could think of is a sort of more serious relationship-y conversation where you tell her that you're concerned about whether she's really into you, because in your experience in relationships it's a good sign when people start taking turns inviting and paying, and that you're really into her and if money is an issue you totally understand are happy to do any cheap or free thing that feels comfortable to her budget, and to take her out to enjoy fancy places on your turn. You better actually be really into her to go this route!
posted by Salamandrous at 10:23 AM on November 28, 2013

here's the problem. check-splitting can mean some level of "we're going to be doing this for a while." So its hard to bring up and hard for the other party to offer to split because it says "I think this may go on and it isn't fair long-term." Those things play into people's actions, sometimes unconsciously.

Keep that in mind
posted by Ironmouth at 12:03 PM on November 28, 2013 [1 favorite]

Another way. Ask for the check. Then get an E-mail requiring an immediate call to work, excuse yourself, then come back. If she hasn't even touched it, she's not for you.
posted by Ironmouth at 12:07 PM on November 28, 2013

i wouldn't lead with it, but if she accuses you of being cheap you can talk about how you believe in economic equality for women, and how you don't see it as gentlemanly/chivalrous but as more patriarchy. some people in this thread have put it better than me. that is, if you really believe that.
posted by cupcake1337 at 12:15 PM on November 28, 2013

I'd bring it up outside of a payment-required situation, and I'd make sure it was phrased as an inclusive idea that isn't focused explicitly on her - "I find it kind of weird that we don't split the tab when we go out" - and make it a general, non-accusatory conversation about paying conventions so you can hear what her expectations and assumptions are. Tell funny stories about dates where someone forgot their wallet or are otherwise humorous around the notion of paying, but make sure they're not jokes that make a non-payer the butt, this is just to keep the conversation light and easy.
posted by L'Estrange Fruit at 1:09 PM on November 28, 2013

Everyone has their own views on this.

My perspective is that economic equality if fine if you never have children.

If you have children then the mother will do a huge proportion of the effort, just from carrying the child in her body and breastfeeding.

Why is this relevant to someone you are dating for 1 month? Because you are both signalling what kind of partner you will be to each other...

By paying for drinks/meals you are signalling that you will a generous, supportive partner. Be careful how you ask her to pay... so IF that is what you want signal, it doesn't get obscured.
posted by zia at 2:03 PM on November 28, 2013 [2 favorites]

My question is: how do I bring this up without coming off like a cheapskate or accusatory?

You are only one month into the dating process, so you're still in the early stages of getting to know each other. This conversation probably feels stressful to you because you simply don't know her well enough (and vice versa) to feel ready to tackle such a loaded topic.

How about this? Invite her out on dates that don't involve money, or very little money. This will do two things: it will let you get to know her in a commerce-free environment, where money is theoretically a non-issue; and/or if she shows disinterest in spending time with you in a non-spendy way, you'll have a useful piece of info about her. Spend the next month doing creative, low-cost get-togethers, and lean back and observe.

(In your shoes, I'd be wondering why she didn't step up and spontaneously offer some small reciprocity, even if she is in broke-ass mode -- "Hey, you got dinner, let me treat you to an espresso down the street?" Etc.)
posted by nacho fries at 12:47 PM on November 29, 2013 [1 favorite]

If she's never offered, it's because she's used to not having to offer. Her last boyfriend probably paid for all of their dates and outings. If you really like her, you need to be careful in approaching this subject. Springing it on her after dinner in a restaurant is not the answer. She may not even have the cash on her to cover her half, or a card for that matter. Because you've paid every time, she won't expect that.

I think the best way to handle this is to have a conversation about it when the two of you are just relaxing at home or doing something very casual that doesn't involve dough. Ask her what she's accustomed to in terms of finances in relationships, and explain that you like for things to be a bit more balanced. She may be totally turned off by this, but at least then you'll know and will be able to move onto someone who's more appropriate for you.

I never paid for dates/outings with my boyfriends of the past, unless I was surprising them with a birthday dinner or gifting them in some way. However, I did always offer to split bills, especially in the beginning. I think it's just the proper way to go about handling things like that. That said, some women are very traditional and will take offense to a guy asking them to pay, so be aware of that.
posted by OneHermit at 4:44 PM on November 29, 2013 [3 favorites]

"how do I bring this up without coming off like a cheapskate or accusatory?"

Sorry, OP, on these facts, I don't think you realistically can. It's clear by now that going Dutch is not how she rolls. She likes the status quo of you paying.

I was raised with the old school/ upper middle class norm that @bilabial articulates above: "any man worth their time will NEVER let them pay for anything on a date" - which is so much an entrenched norm that hardly anyone ever says it out loud except to their own children - and not coincidentally, I'm happily married to a man who is a generous husband and provider from the same class background as me. So to folks like us (which possibly your date is), the goal behind your question (to suddenly reverse your established trend of paying for her on dates, without her judging you for it) seems... impossible.

By "impossible" I also mean consider well what @misspony said: "For some women this is a really easy way to measure how generous a man will be... (accuracy unknown!) and you're also most likely fighting the science of women preferring well providing men for evolutionary purposes."

I get how this all strikes you as "gross." But I would submit it is not really any grosser than men preferring nubile, proportional looking women.

BTW, this has nothing to do with feminism - if you drill it down, one could make a "real" feminist argument both for you continuing to pay for everything (distributive justice for your relative male privilege) and for her paying for everything (thus approximating the appearance of gender equality). The real unspoken issue is socioeconomic class. The fact you are "both NYC natives" means little - New Yorkers represent every walk of life.
posted by hush at 7:22 AM on November 30, 2013 [1 favorite]

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