Should The Man Pick Up The Tab And Pay On a Date?

Who pays the check? By Colleen Kong Savage
Illustration by Colleen Kong-Savage

The following is a guest post by Colleen Kong-Savage, a graphic artist in New York City. She writes and illustrates at Konga Line: Children Are BeastlyLet's discuss should the man pick up the tab on a date.

I am on the dating scene again after sadly breaking up with my boyfriend of two years. But lemons into lemonade, and rainclouds into silver lining, I am looking at the situation as an opportunity to write this here essay and ask, On a date, should women still expect men to pick up the tab?

When we first met, my ex-boyfriend paid whenever we went out, but after a month we were splitting the bill and taking turns paying. I confess, I had to adjust my mindset when we made the change. Before my ex-boyfriend, I was in a 13-year marriage, in which I was completely supported by my partner.

In that relationship, I had worked in my ex-husband’s company until he suggested I quit to pursue a career in art while he supported me. What a gift! Truth be told, I suspect he was just tired of having a lowly graphic designer (that would be me) brawling with him in front of his other employees. My ex-husband always paid on dates because my own work paid me a piddle.

What Do You Think? Should The Man Pick Up The Tab?

I relish the efficacy of online dating versus floating about in a bar. The activity of filtering through profiles has the curious flavor of voyeurism and processing job applications. For the most part, I like dating, meeting interesting men with interesting stories over drinks or a good meal.

If I’m lucky, my date even asks me questions, which leads to two-way conversation. Hopefully we are at a restaurant, where I can feed the cuisine to my face without destroying my appeal. Hopefully he can too. Then it is time to wrap up, and there is that slightly awkward moment of settling the bill.

I admit it: as a woman, I believe in equality among the sexes and that expecting the man to pay is wrong, but secretly I do prefer the man to do so. As a matter of fact, every time I ask my date if we can split the bill, the old-fashioned side of me wishes the idealist within would just shut her big flapping trap.

For this post, I surveyed a bunch of friends, mostly a politically left-leaning bunch, to see what they thought of the tradition of the man picking up the tab on a date. Is it gentlemanly? Or is it outdated in this age where the average Josie works alongside the average Joe (albeit at 78% of his pay rate)? Is it unfair and out-and-out sexism? Are other women as conflicted in their opinions as I am? Here are some thoughts…

A Case For Why The Man Should Pick Up The Tab And Pay

Sweep a Woman Off Her Feet Or At Least Make a Good Impression

Jake, a director for packaging comps, agrees with his wife. “On the FIRST date, the man must pay or give the lasting impression that he is cheap for whatever reason. After the first date, anything goes—splits, pay the tip, whatever. I will say, when my wife and I dated I paid, always, happily.”

Most men expect to pay on the first date. There is an inherently romantic element to the gesture. To have a date take you out feels very different from when your buddies take you out. Of my seven first dates, only two agreed to split the bill. And one of those splitters had turned our coffee date into a work meeting when he whipped out his laptop to show me different programs he thought I’d find useful in my work as an illustrator. Useful information, but computers are a mood-killer.

Keri, an opera singer, says she always offers to split, but like me, is pleased if the man gallantly declines her offer. “I try not to let the ‘splitter’s’ choice impact my impression of him, but unfortunately it does.” I get that. However, what if we stop seeing the male splitter in a vaguely negative light, and simply grant bonus points to the fellow who picks up the check. I find generosity attractive in a man (or anybody for that matter). The ability to give is a strength, and the desire to give is a kindness.

Pick Me a Breadwinner

Higher income men get more attention
Source: OKCupid

Some individuals seek a provider, someone who will be the breadwinner while they manages the home and mind the children (I hazard a guess that the homemaker-hopefuls are mostly women). Some individuals are simply in search of “life-sponsors,” as a friend put it. And some individuals are happy to support someone they find worthwhile.

Related: How To Get A Rich Man To Be Your Boyfriend Or Husband

Only a minority of people list income in their dating profiles. I find the detail so crass, like looking at a stranger’s underwear. But there are people who want to know because they are looking for a wealthy provider (being the beneficiary of one of those providers I cannot judge others who want the same)… or avoiding a mate who will bleed them financially dry.

In some ways men like sugar-mamas as much as women like sugar-daddies. However, if you look at the statistics on dating sites, there’s a subtle difference in the money-attraction. Women think, the richer the guy, the more desirable he is. Versus men thinking, I do desire a rich woman, but if she’s not rich then it doesn’t make a difference whether she earns $20K or $80K, according to 

A man paying for dates is a basic signal that he is open to that traditional model of a husband supporting the wife or future family, which is the kind of mate many women seek.

Reasons Why A Man Should Not Pick Up The Tab And Pay

Because It’s Just Not Fair

A few friends believe unequivocally that the man should pay for the first few dates, regardless of income level. This bias doesn’t sit well with me. At the very least there should be exceptions. If you remove gender from the issue of who’s paying for the date—as would be required if you are gay—you are left with these following arguments against one individual carrying all the responsibility to foot the bills.

Whose big idea was this?

First of all, who asked who out? Marketing consultant Kathy says, “If the woman asks the guy out, she should pay or split—yes, I’ve done that. It’s bolder, faster, smarter.

The Fatter Wallet

We want him to pay,” comments Muna, a philanthropist. “But he does not want to anymore, understandable given the current economic situation.

It makes more sense that the person with the greater income picks up the tab more often than the one with less income. David, a game designer, writes, “ The women I’ve dated since 2011 have all been financially more secure than me. I believe it has to do with profession—artists are more unstable.” David habitually picked up the tab on the first date, but the rest of the time he and his dates would take turns or go dutch. “Now my girlfriend and I have a shared account for hanging out,” and both individuals contribute roughly the same percentage of their income to the date-fund.

Power Play

I don’t like uneven power dynamics on dates,” says Lily, a graphic artist. “So I’ve always split the checks with people at first, whether the person was the opposite gender of me or not.

Money is a power. Money calls the shots. Even if the payer is not a bully, the recipient feels an obligation to repay the act of generosity.

In my twenties, I was an artist’s model. One artist I worked for had designs on me. He took me out for meals, to museums, invited me into his figure-drawing group for free, and use of his studio. Because I was a grad student without much cashflow, I naively accepted his material generosity. What I didn’t realize was how emotionally exhausting it was to feel obligated to grant my friendship, loyalty, and company to an employer, 25 years my senior, married, and who kept hoping to get intimate.


On the flip side, the payer has to worry about being manipulated and used. Is she really interested in me? Or is she using me as a free meal ticket? “Beware the cheap person, on both sides of the table. The clues are often right there if you have the eyes to see them,” says Jeff, former marine and university administrator.

Greater Expectations

Man pays on the first date,” declares Dan, massage therapist and artist. “If a woman pays then it’s not a date.

One man I met online drove into New York City from 70 miles away just to have a date with me. I had initially hesitated to accept because who drives 70 miles for a first date with no guarantees? But considering his history of going to extremes to accomplish some amazing feats, he pointed out that a 75-minute car trip was not a big deal. Unfortunately the chemistry wasn’t there. I wanted to be the one to treat because he had schlepped in from way beyond the borders of the five boroughs just to meet me. Yet he insisted on paying, deftly snatching the bill and sending the waitress off with his credit card. Chivalry is alive and well.

I showed him Grand Central Station, careful not to be flirtatious. I had a really good time… with a friend. He was baffled and bitterly disappointed when I told him I wasn’t feeling it. Perhaps it would not have made a difference if I had been the one to treat, but in allowing him to pay, but I felt like I was leading him on.

Related post: Career Or Love? Be Careful Working Too Much

What's The Rich Choice?

Our society expects men to make more money than their female counterparts. We even pay men more than women in the same jobs. We are moving towards an age where gender roles are interchangeable, but we are not there yet. When I go to a PTA meeting, 90% of the parents in attendance on a weekday morning are female because their male counterparts are tied up with work, being the main breadwinner of the family.

I imagine the idea of having someone treat you to a lovely night out on a regular basis would be as appealing to a man as it is to a woman. However, despite our enlightened states of mind, we still bow to society’s expectations.

Male egos are tied more closely to their paychecks than are female egos. For example, we know intellectually that in marriage, it should not matter who brings in the majority of the income, but some men admit feeling emasculated they must rely on their female partner’s income when economics change. Whereas I don’t hear that same self-esteem issue coming from women who rely on their male partner’s income—or at least women don’t feel it as intensely.

In the end, what is the purpose of the date? You are meeting someone you hope to know better and hope to like. Or you are doing something special with someone you care for. On the question of who picks up the check, my friend Susan sums it up best, “My opinion remains that it is up to the individuals. If two people can’t figure that out between themselves, they’re doomed when real hurdles arise.

Who should pay for the bill? (choose up to 3)

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Readers, should a man continue to pay for the check in 2015? When do you think it'll start being the norm for women to start paying most of the time? What is your mindset paying the check before going on a date? Should both parties at least offer to pay? Thanks Colleen for writing this post!

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65 thoughts on “Should The Man Pick Up The Tab And Pay On a Date?”

  1. I always offer to be gracious but if the guy does not pick up the tab, I will not take him seriously as a future partner and will not see him again.

    Who cares about the segment of men who thinks this means I’m a certain kind of girl? They are always coping about the realities and claiming this is unfair. 100% of them want attractive partners and we want partners who can provide.

    It really is that simple.

  2. We even pay men more than women. STOP. Leave the online world of feminist lies. And go outside.

    Are women paid less or equal in the legal industry.. equal. Accounting.. equal. Medical.. equal. Programming, engineering, education.. equal, equal, equal.

    If it were true women are always paid less, why wouldnt a boss hire only women and saved lots of money. DUh.

  3. Sam,

    I apologize for my language on my deleted post. The question I pose. Do women want to date John Wayne or George Kastanza? Guess which man pays for dinner?

  4. Simple .. who ever asks the other party on the date. If a Man asks a Woman out .. then it is the Man’s responsibility. Vice-Versa works as well.

  5. I think the person asking should pay on the first date. After all, you wouldn’t invite a friend over to watch a game and then expect him/her to pay the pizza delivery guy. Expecting a guest to pay is just tacky.

    Once it’s actually a relationship – talk about it! Communication is important, especially about money. As long as it works for the two of you, there is no wrong allocation.

  6. gary martins

    paying for a first date is almost like paying for sex. you don’t really want to buy affection, do you? What type of precedent does that set?

  7. Interesting topic.

    I always offer to split on the first date, but if the guy insists on paying it’s a plus in my book. I don’t know why. Maybe because it shows he can take charge. And because he asked me out on the date – if I was the one asking a guy out on a date (has yet to happen) I would expect to be the one paying for the date.

    If I find on the date that I have no interest in the guy, I will insist on paying for my half, because I don’t want to feel like I owe him anything or that I have been leading him on.

    Going forward, I am happy to split, or maybe rather take turns paying. If one person makes significantly more money, I think it is reasonable for that person to pay most times (but not always). I have been the one making significantly more and paying most times.

  8. Dating has got so much more complicate now.
    It was so nice, my still current husband paid on every occasion he took me out (2years 9months)
    That is now part of my good memories when I think of our time together, which is now 36 years.
    He now get’s to sit while I go and put our Hungry Jack’s order in, & I pay with our money.
    It makes us who we are today. Good memories and time together
    I now see Dating through my Daughters eye’s and I am not very impressed.
    Hope the next generation can do something about it….

  9. Pingback: What They Don't Tell You… - Konga Line

  10. I think it’s a two way street. If the guy picks up the tab on the first date, maybe the girl should offer to pick up the tab on the second date. When I went out on my first date with my later-to-be wife, we ended up splitting the bill at end of the night. She thought it was different but understood the reasons.

  11. I think the male should pay for the first three dates. When I was single, I would often spend lots of money to get ready for a date… a new dress, a blowout, and nice makeup. I would argue that I would spend more on the date than the man picking up the tab! And certainly more time! I think a lot of NYC women are like me – we really try to primp for these dates. Men just throw on an old outfit and hopefully shave. After the third date, women feel they can be a bit more natural and then I think the paying can alternate. Going dutch just doesn’t feel like a treat. It is much better to make the other person feel cared for by paying for their meal. Things will never be 50 / 50 but it is nice to be treated and it is nice to treat.

  12. Probably depends on what you want out of the relationship. If you want to be a stay at home spouse it probably isn’t a bad idea to date someone who is willing and happy to pick up the check. My husband makes the money, I do everything else include managing it. He has no interest in how much we have or where it is. I save every penny I can to honor his work and would never consider asking him to do a household chore. We don’t fight about money or house and yard work ever. I also know of a couple who would never drive the other’s car, and everything is divided down to the nickel. I think the most important thing is to know what to expect down the road. Do yourself a favor, do not pretend to be something you are not while dating!!!

  13. Todd Guthrie

    I think a lot of it goes toward simple rules of attraction, where I think the differences between men and women will take a lot longer to normalize than they will for salary differentials.
    All else being equal, women are typically attracted to men who are confident and who take charge (by for example choosing the location and paying the bill), while men are typically attracted more by looks.
    I think that’s why women usually put on all the fancy dress and makeup for a first date, while men usually don’t, and why men usually pay the bill for the first date, while women usually don’t.

    Personally, as a man I would always offer to pay on the first date, but I would give major points to a woman who then offered to split it.

    Btw, interesting comparison to gay dating, where gender roles are not obvious. That’s a good control for any hypothesis…

    1. You’re right. People do read the act of paying the bill as taking charge. In that light it’s interesting to see how that might explain why some men do not like women paying the bill, i.e. having someone else take charge. And why some would-be feminists still have that gut reaction of wanting a man to pay because that take-charge gesture indicates confidence, which IS attractive. Altho I wonder why men don’t find this take charge confidence in women as appealing—men who do appreciate confidence in a woman.

  14. Great question! When I was dating, I would definitely pay for the first date, but I always appreciated it when the woman would offer to split it or pay the tip. In fairness, I believe whoever asked should pay, but I would always offer and be prepared to pay even I were the “askee”. I just believe that’s gentlemanly. When I met my wife (via online dating, which worked out well for us!), I paid on the first date, but of course she offered as well. On the second date, she made it clear that it was her turn and I certainly appreciated her generosity. I think splitting each check takes a bit of the romance out of the air, but taking turns seems quite reasonable. It wasn’t very long before my money and her money became our money, but in a longer-term dating situation, I would hope that whoever had the better financial situation might take a few extra turns over time.

    1. I agree with you that the split does take the romance out of the date. There is something beautiful in the act of giving to someone else, whether man to woman or woman to man.

  15. I’ve always paid for dates. Although it doesn’t any logical sense. I can practically hear my dates saying, “We want to be equals with men – but you are still going to pay for my shiz, right?”

  16. First dates, or any date really, don’t have to cost anything at all. I can think of expensive dates and free ones. Ultimately, two people are either interested in each other or not. And trying to impress with expensive things is generally ill advised. My wife absolutely never wanted to feel like a charity case when we were dating. And I don’t blame women for feeling that way, most men never realize that some women may feel awkwardly and unnecessarily indebted.

    Removing gender from the equation really does spice this debate up. I would buy popcorn for that.

  17. If that were the case, I think most men would agree that they would be waiting a very long time for a free first date meal :)

  18. Great post. If the guy asks the woman out on a first date, which I believe is the man’s role call me an old fashioned millennial, I believe he should pay. On the next few outings however, I like to split things up. Just my way of subtlety stating, that while you have the pleasure of pursing me, please know that I can support myself, so what else do you have to offer?
    If things progress well and a steady relationship develops, I guess you both work out a system that seems natural. Maybe one night one person pays for everything, the other night the other person does, with the higher income earning person picking up the greater share of the bills.
    Since I believe in dating with purpose i.e. must be leading somewhere, none of this date forever no legal commitment in sight, I believe couples eventually get to the point where they start thinking about long term financial goals. Ideally goals align (recipe for disaster otherwise) and each couple works out a system that best suits their needs.

    Ultimately while I do believe in splitting things up, I expect, and respect is earned for chivalry. You cant ask me out and then expect me to pay for things. I’m a fair girl however and will relieve you of that responsibility from time to time. Bonus points if you can actually afford to keep me in the style I’m accustomed too though, how cute (but unnecessary) that you actually might like to try.

  19. I like the idea of the person who initiated the date being the one to pay. After the first date though I think it’s fair for the pair to split the bill. And if someone feels strongly about paying in full that’s fine too but I think it’s fair for the expectation to be splitting the bill from the second date onwards.

  20. I’d always offer to split on the first date, but if I guy accepted, I might for some inexplicable reason be less attracted to him. The only time I’ve insisted on splitting is when I knew I wasn’t interested – then I’d prefer not to feel obligated in anyway. I also think cooking a meal for second or third date rather than paying is a nice gesture – more appreciated and less awkward than fighting over the bill!

    1. Yup, it’s that “lizard brain” instinct Tamara was talking about a few comments ago. Kind of like instinctively wanting a guy to be taller than you, even though you know good character cannot be measured by height.

      Meanwhile I find cooking a meal a lot more intimate than going to a restaurant, especially since it means one of you is in the other person’s home.

  21. When my wife and I were dating before getting married, if we went out I would pay, but then if we stayed in, she would cook. Worked out well.

  22. BeSmartRich

    Hm. In Korea, typically men pay about 95% of time at the beginning of dating. If women are considerate then they help pay some of the cost. Interestingly, in Canada, I realized men pay about 60%-70% of time.

  23. Traditional “dates” are old school. Lots of baggage and expectations; just look at this article and the comments. Much of this can be avoided.

    The point is to meet up, learn a bit about each other, and look for chemistry. Expectations should be modest and realistic. The focus is the human connection.

    For a first meetup, I invite my girls to something casual and informal: e.g., drinks, coffee/tea, frozen yogurt, etc. I don’t call them “dates.” I don’t have dinner on a first meetup.

    Often, chemistry can be ruled out in the first hour or less. If the vibe is not there, it’s easier (and more merciful) to exit the meetup early, if it’s an informal, casual one.

    Yes, I always pay — but obviously it’s not much. More investment in time and money can come later … if and when things develop.

    1. Sure. But at some point you will need to go on a “date” or whatever label you want to assign to it – spending a decent amount of time with the other person with the intent of developing the beginnings of a relationship with that person. I dont think you can build up anything meaningful by continually “hanging out”. And people need to eat. And… food costs money… :)

  24. I’ve been conditioned since I was a kid to always pay for the bill. It didn’t matter whether the person was a boy, girl, friend, potential partner, or client.

    It started off with trying to woo girls in middle school and high school with my $4.25/hour McDonald’s income. Then I graduated from college and had to entertain clients for the next 13 years on my corporate card.

    I always feel super weird when someone, anyone, pays, so I just pay. But, if on the rare occasion they absolutely insist, or they sneak to the bathroom to actually pay, then I am always grateful and will do MORE to make up for their nice gesture than just take them out.

    And to prevent any sort of awkwardness when I pay, I always tell them “Just take me out next time!” to keep the relationship alive, even if I don’t plan to let them pay :)

    1. That’s so sweet.

      But on the other hand, what would happen if you were in a relationship with women like commenter Des, or my friend Lily, who are wary of the power dynamics of money?

      1. I can answer that :)

        Most men are accustomed to footing the bill, so there’s a bit of an exchange, but the scene typically looks something like this:

        (Bill comes to the table, I reach for my purse, he reaches for his wallet.)

        Him: “Oh don’t worry, I got it.”
        Me: “I appreciate the offer, but I can pay for my part.”
        Him: (accustomed to paying the bill) “You don’t have to do that.”
        Me: “That’s very sweet of you, but I insist. 21st century woman and all that.”

        Most men will see at that point that it is important to me and consent to split the bill. Or if the date is going really well I might get something like:

        “How about I get this and you buy drinks at the next place?”

        That is acceptable, assuming I want the evening to continue. Drinks often cost as much as a meal. I’m not trying to keep everything even to the penny, but I make good money on my own and feel weird taking what feels like charity from a near-stranger.

        If a man pushed past my “I insist”, it would not be well received. That’s dismissive and domineering. It isn’t a hard deal breaker (it could just be a faux pas) but it would be notable. I have yet to encounter this – the men I date are usually quite progressive.

  25. I’m not going to breakdown this topic using logic, numbers and common sense. Instead, I’m going to resort to the primordial lizard brain part of us. The man should pay if he’s hoping to start a romantic relationship instead of a platonic one. It’s not because buying a meal can buy a woman’s heart (not guaranteed) or that he earns more (he may not). It’s simply because while most women, myself included, THINK women should pay for dates or at least go halfsies, the unconscious part of us that assesses potential mates may default to the “traditional mindset”–fair or not.

    Unless the woman absolutely insists on paying, the guy should at least make a show of offering to pay. In a semi-related note, I know lots of women who insist on paying for a date when she realizes she has no romantic interest in the guy. Somehow, it just doesn’t feel right to have him pay when there is no chance of a second date.

    If the relationship gets serious, then the resources of both parties are pooled together anyways. There’s no more “yours” or “mine”.

    1. To your point, guys should watch out for women who insist on paying for the date so they can free themselves from “obligation”!

      I think this makes a lot of sense. Nobody likes to reject others.

    2. Yes! Lizard brain! I’m there!

      Sam, I guess it’ll be “wait and see” for a man to know the answer because there is more than one reason why a woman would insist on paying.

  26. I guess I’m confused how this is still a thing. I want an equal relationship with a partner, not a sugar daddy. I always pay my share or split the bill on the first date. It would be super weird not to – I have a career of my own, a house of my own, investments of my own. Why am I all of a sudden thrown back to 1950 just because it’s a first date? I don’t want a 1950’s style relationship, so why start off on that foot? Especially with someone I don’t know yet. Money creates power dynamics, and I want those dynamics to be equal.

    Also, I need a partner with good self esteem. If a man feels emasculated by my paying my own way, we can just weed him out at the start. If he is off-put by my bucking outdated traditions, we aren’t going to get on very well. I don’t color in society’s lines well and I need a partner who finds that refreshing, not unnerving.

    I think it should become the norm to go dutch on the first date. If men want to pay for future dates (and their women also want that) fine. But on a first date you don’t really know this person yet. What if you let them pay and you don’t want a second date? That seems very rude. I wonder how many second dates have occurred because a woman felt “beholden”.

    1. How can it NOT be an issue with society still pushing for the traditional model? Even with your recognition of that money dynamic, other people still have their expectations. And so many women still prefer being homemakers to having a lucrative career.

      Again, I do like the principle of the first date being dutch so that both people stand on level ground in that initial meeting. My knee-jerk reaction however is still, it’s a treat to be taken out. I never thought about being “beholden” for that second date… if you’re feeling beholden from the first date, wouldn’t you feel even more so on the second, so why would an obligated damsel go there? I’ve actually heard a number of men complain about women who have no qualms being wined and dined repeatedly, even if they weren’t interested in the man. I’ve also heard a few female friends have no issue with the man treating whether or not interested.

    2. Practical Patty

      Well put Des! I completely agree with all of your points. I was looking for an equal as well and am lucky enough to have found a great one who felt the same way.

  27. First and foremost, great post Colleen!

    Very interesting topic, indeed! Let’s answer Sam’s Q’s:

    1) Should a man continue to pay for the check in 2015?

    I’d have to say, yes! It is the least gentlemen like thing to do when taking a woman out on a date. I, myself, have had a long number of relationships, and while my travels have taken me to different parts of the world, I’ve been able to meet different women from different cultures, etc. In line with the aforementioned, I recall my time whilst in NYC where a cousin of mine took me out to a lounge in the meat packing district, and I noticed something very different about NYC women, compared to women from Miami (where I am originally from)… They had no trouble or hesitation approaching men, period! I was approached by at least 6 different women that night, which is something unlikely to occur in Miami, at least. I know you’re probably thinking “what in the world does this have to do with anything?”… it just goes to prove that things are changing in the world. Women are becoming more independent, and are no longer sitting around and waiting for men to do all of the legwork. While this does not apply to every woman out there, in my profession (Medicine), it’s very noticeable, even with nurses. While I was raised to ALWAYS front to check whenever I am out with a woman, regardless of the where, I still firmly believe that men should continue to front for each check whenever out with any lady (but that’s just my opinion).

    I know of instances where women become offended when they offer to pay for dinner (or whathaveyou), because the man turns down their offer. And while I can understand their reasoning for wanting to do so is to show appreciation and wanting to do something nice in return, it’s a bit difficult for me to accept at times. But, every now and then, it’s totally acceptable to allow a woman to pay for a thing or two (w/in reason, of course). But let me be clear here, it doesn’t matter who asked who out on the date originally, the fact that the woman has taken time to dress up and look exceptionally beautiful that night for you, you better be paying for that dinner and everything else that night for that woman.

    I once dated a woman I met in England, London, while engaging in my undergraduate studies before applying to medical school. I donned and gave her everything in life. She asked for the stars, I’d reach out for the moon; she asked for the Sun, I reached out and gave her universe. We were in love… deeply in love. I never allowed her to pay a single thing. I’d pay for her tuition, I’d take her shopping (LV, Chanel, etc – she was a model in Canada before pursuing her career in Medicine), and we’d take amazing trips around the world together. I recall one time she swiped my AMEX and charged $16,800 USD at the Chanel store at the Bal Harbour Village Resorts and Shops, in Miami, Florida. At any rate, 2009 rolled around, and guess what happened to my steady flow of income?… you guessed it right, it went away right before my eyes! So not having a single penny to my name, we were getting ready to relocate to Connecticut for our Internal Medicine rotation, and I didn’t have the resources to pay for both of our tuitions, so I asked if she’d be able to pay for our tuitions and that in about 60 days, I’d be back and running w/ my flow of income. Keep in mind we’d been together for 5 years at this point, and had had talks of getting engaged later that December (this was in April of 2009)… her response to my “cry for help” was “I can’t pay for you, in my culture it would be frowned upon if they my family found out I paid for anything for you…. Why don’t you call your mother, tell her to sell her Mercedes Benz, and use that money to pay for your tuition?” I don’t think I’ve ever been that hurt like that very day, such that every ounce of love I had for her vanished almost instantly that very moment. And yes, that relationship ended very, very soon after that occurrence.

    Which brings me to…

    2) When do you think it’ll start being the norm for women to start paying most of the time?

    Simply stated, not anytime soon. You have to remind yourself that we follow and comply w/ everything society has placed upon us. Take for example, Love. Is love a feeling or an occurrence? Most people will answer that love is an occurrence, and that is completely and utter wrong. Love is an emotion, a feeling! But society has branded in our heads that it’s socially unacceptable to tell someone you just meet 1 month ago that you’re falling in love w/ them… everyone will call you crazy, and say that you’re nuts, that you’re confusing love w/ lust, blah, blah, blah! So were subconsciously suppress this feeling when it first comes about and we wait, and wait, and wait until it’s socially acceptable to tell someone you might be falling in love w/ them, which is about 6 months to a year’s time. So what did we just do right there? We took love, being a feeling, and made it an occurrence, because now at the 6 months to a year’s time when it’s socially acceptable to tell someone that you’re falling in love with them, you’re forcing that emotion right back but it’ll never be the same at that point. Anyone will argue, well if you loved them at 1 month, you’ll still love them at 12 months so that doesn’t make sense. It sure a hell does, and I’ll let you think about it! So back to the question, we’re still stuck in our ways whereby society finds it socially unacceptable to ever allow a woman to pay for dates, despite a minute notable trend where some women are paying more and more nowadays. I think it all depends on your upbringing and culture. Once you’ve been in a relationship that’s established, then it’s okay to allow your girlfriend or wife to pay for an outing every now and then.

    3) What is your mindset paying the check before going on a date? Should both parties at least offer to pay?

    I always walk out of the house knowing that I will be paying for the check on any date. If you don’t have the money to go anywhere fancy and expensive, then make sure you stay w/in your budget and go somewhere affordable. A real woman that’s interested in getting to know you will not be interested in where you take her, she’ll be interested in knowing whether there is any chemistry or not (among other things). Like I said before, if she took the time to dress up and look as beautiful as she can just for you that night, you better make sure that lady brings nothing but her license/ID, lip-gloss and/or lipstick (for touchup purposes throughout the night) in her clutch purse.

    If she offers to pay for that evening, like Sam mentioned earlier, thank her for your gesture and offer, but let her know that this dinner is on you and that you’d let her pay next time. That way she doesn’t become offended by the fact that you turned her offer down.

    I’ll close this off w/ the following as a food-for-thought. I recently asked a good number of girl friends of mine what they would do if a guy asks them out on a date, for which the get all beautified for, only to find out that the guy takes them to a McDonald’s or something of the like. Unbelievable, every single one of them told me “I’d never go out with him again.” Which I found interesting. I returned and said, what if he was testing you just like you were clearly testing him? What if while at the McDonald’s you guys have the best time and conversations ever, rendering this the best date ever? You prematurely nexted him, w/o given him an honest chance.

    Great topic, again!


    1. Wow Dex, great comment! That totally stinks that the moment you asked her to pitch in, she said no after 5 years of you financially taking care of her.

      Is she a Doctor too? Perhaps her culture + her expectations of big bucks convinced her it was OK for you to always pay, and for her to swipe $16,800 at Chanel from your credit card. Yikes… maybe I need to write a handbag spending post guide. I’d think one would need to make at least 25 X $16,800, or $500,000 to spend $16.8K on a bag!

      Are you doing well now 7 years later? I wonder if she regrets her decision.

      I had the same thing happen to me in college. My GF received a $10,000 scholarship to go to China for a semester abroad, and I was pumped for her. And when I applied to a $500 scholarship, I got denied, yet my Mandarin was top notch. I looked to her for sympathy and support, and she gave none. My love for her vanished instantaneously. I was a dashing young man during college, and ended up with another attractive girl the very next week. She was not happy.

      Funny how money gets in the way of relationships. In my case, I didn’t need her money. I needed her support.

      1. Sam,

        Life is amazing now. My career in medicine has been rewarding beyond my expectations. And yes, she, too, is a Doctor… She moved back to Canada somewhere. Funny thing is, in 2012 she contacted me asking for me to do her the favor to marry her so that she can get her Residency in the United States to stay and practice… I’ve never laughed so hard!

        She spent the $16,800 on multiple items, not just a purse… Imagine that! But hey, you live and you learn, and trust me, I learned. Sorry to hear you went through something similar, but I think someone came out on top here and we both know who that is.

    2. Dex,

      1) Personally, I LOVE the gentlemanly gesture of a man paying for dinner. And I do love a man’s appreciation of a woman dolling herself up. However, I would imagine the man is ALSO making an effort to look good. Or at least I hope he is.

      I have no problem with a woman wanting to pay for a meal, but it does seem a little silly if she becomes offended with your refusal to let them do so. Yes, New Yorkers are an aggressive lot, aren’t they, men and women. I love that women can take initiative vs. passively waiting around and hoping.

      Your England romance is quite a story, and her spending habits and response to your request for help seems embarrassingly obscene.

      2) In re Love: it’s all labels, but I suppose what society is trying to do is dictate your actions in a relationship. I love that crazy high of falling for someone, but it does take a good number of months before their true nature comes out. People tend to be on best behavior in the beginning. I imagine it took a while before Ms. Chanel did her $16,800 swipe.

      3) But it’s McDONALD’s. Forget about cheap, that stuff is nasty! You were basically asking your female friends to kiss the frog prince!

      1. Before getting married I always went on super cheap first dates. Not McD’s, but usually dive eateries with character.

        I found that it screened out the high maintenance, materialist girls quickly and effectively. It saved a lot of time.

        Now happily married to a gem.

  28. Gen Y Finance Guy

    I admittedly have not spent much time in the world of dating since I have been with the “ONE” since I was 18. But I always took pride in being able to pick up the tab. However, it was always nice to have the other side at least offer to pick it up or split it.


  29. No Nonsense Landlord

    It always seems like the guy pays on the first dates. I am not sure why. After being with the same GF for 25+ years, we swap paying quit a bit. But I pay her CC bill, at least the meals charged, so I am still typically paying.

    I want to find out how to be one of those guys that just goofs all all day, and have the woman work, pay rent, cook and clean. I have seen that type of guy in some of my past renters…

  30. I still believe in the man paying for the meal. While women are making huge strides in the job and income department, it is still the responsibility of the man to provide for his spouse and family. This responsibility is first demonstrated in the dating scene. If the man sits there like a shlub, expecting the woman to pay for the meal, then this displays a lack of leadership on his part for the future as well. Women, if you are dating a man that never reaches for the check, I would be very cautious in pursuing this man as a life partner.

    1. Fair enough. If the man has a responsibility to be a provider, it follows that a woman has a reciprocal responsibility.

      What is it?

    2. That is what I am dealing with now. I don’t know how to broach the subject. I am typically very frugal.
      He will say- you don’t have to cook tonight m, let’s go to dinner instead. I got excited! He is going to take me to dinner. It ended up at my expense.
      Another scenario, you have worked so hard this week and done so much for others this weekend, we’re going to the mall. Guess who ends up finding something and who ends up paying?
      One may example, I need to stop and pick up lunch items for work this week. Get to the checkout counter. I didn’t bring my wallet.
      I feel like I am paying him to be with me.

      What do you all think? I make 3 times more than he does. I still think he should pay once and a while. Or we just don’t go out 3-4 times a week and stay home.

  31. You both should try to pay for the bill on the first date and be gracious about letting the other person pay, or splitting it. When I was single, I’d pay for my date’s dinner, but if my date didn’t even attempt to pay, no second date.

    In the long run, you both need to chip in. If neither of you cooks, then you need to be splitting the check regularly.

    And since this is a website about finances, let me state the obvious: learn to cook a few meals and save money. Dining out regularly is both expensive and unhealthy.

    Back to your first date. If he pays for the nice meal and you would like to see him again, then offer to make him a nice meal for your second date.

    1. I second this. I feel like if we want to have a more egalitarian world, it should extend to our personal lives. While I have paid for first dates, it’s refreshing (and often a better indicator of the type of person I’m sitting across from) to see someone either offer to help or request to split it (I don’t tend to buy the attempted grab for a wallet or purse). In fact, in my current relationship, my girlfriend thought it was important that I split the first check with her, and while we don’t keep tabs, we tend to be equitable (or at least proportional to our incomes) in terms of how things are split.

    2. Fantastic second date suggestion. Living in SF, where there are so any amazingly good restaurants close by, it is so rare to have a home cooked me.

      Home cooked meals taste 10x better due to the amazing effort a loved one puts in. Take notes!

      1. Thank you for recognizing the value of a home-cooked meal! I’m a pretty damn good cook, BUT as time is limited and I’m often depleted of energy, I think it’s pretty special when someone puts their effort and talents into feeding someone. So much easier to pay for a meal.

  32. “Josie works alongside the average Joe (albeit at 78% of his pay rate)”

    From experience, observation and statistics, my opinion is that the gender wage gap can be largely explained through different career choices. I find it hard to believe that widespread sexual discrimination is practiced by employers in this day and age of instant media dissemination and lawyers champing at the bit.
    Whenever I encounter these attitudes I always ask – if this were true, and employers were getting away with paying Josie less and getting the same level of expertise and experience as Joe, then why not fire all the Joes and rehire them as Josies?

    I believe that the “Who pays on first date?” issue goes deeper than the issue of picking up a single cheque. It boils down to the issue of inequality in courtship. Similar to alimony, I feel its an issue of inequality that has been brought over from gender roles of our previous generation, but which society has yet to address/correct.

    1. Firing all the Joes to only hire the Josies to save 20% for the same work. Never thought about that. Brilliant!

      Maybe there isn’t that big of a gender wage gap given hiring only women to save money would be a logical business move.

      My theory still comes down to creating EQUAL paternity leave for men and women so employers can’t discriminate as easily against someone who takes time off to raise a child.

    2. Have you seen this Forbes article about the income difference between genders among Hollywood actors??

      Inequality in courtship is a reflection of inequality in income. As for alimony, the law states that whoever is the higher wage earner is responsible for paying alimony, regardless of gender. Society is moving towards equality among the sexes, but we’re not there yet.

      Sam, I think paternity leave is a great idea. Not necessarily EQUAL paternity leave because logistically women do need that extra time to give birth and recuperate from all the nasty things childbirth does to their bodies, but otherwise, paternity leave would be great.

      1. Thats interesting. What percentage of America’s workforce can you say are multi million dollar earning hollywood celebrities? Even if you build a case that sexual discrimination is being practiced in hollywood (and that article does not) it still does not lend itself to proving that widespread sexual discrimination is practiced by employers across America.

        The wage gap myth is a classic example of confirmation bias – unfortunately this bias makes it hard for many people to understand that correlation does not imply causation. For example – I can see that in london, many jobs which are menial in nature such as floor sweeping, table waiting, etc are taken up by polish. Can I then draw a conclusion that employers are racist? Similarly, there seems to be a gap in the average earnings of men and women (before controlling for any other factors). Therefore can I say that employers are sexist?

        What you will find is when you control for more relevant factors like experience, skills, industry, full time/part time, etc, the wage gap between men and women falls to about 7%.

        Here is a more insightful study of the issue:

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