An awkward situation

In midlife dating, we sometimes encounter situations that are just too awkward to have a ready-made answer. I remember one from early in my dating re-entry. I wish I could forget it. I’m not sure I would have an easy answer if it happened again.

The gentleman and I were dating a few months and neither of us were exploring dating others, not because of any overt exclusivity discussion. More because we were busy and not unhappy with the relationship, although I wouldn’t say I was happy either. It was a relationship of convenience — at least for me.

We saw each other at least once on the weekend and once during the week. At first he paid for all dinners, and I’d pay for the movie or after-dinner drink or dessert on the way home. Then I stepped up and took turns treating for dinners, too. Although at the time, my divorce had taken a major economic toll on my life. When my ex left, my expenses doubled immediately and my income went down dramatically as I just couldn’t market my services with much gusto.

So when it was my turn to treat, I’d suggest a modest restaurant. When it was his turn, he nearly always chose an upscale one, as he liked wine and fancy meals. Not that I mind those, but he was more insistent about them than me.

One day he asked, “Would you like to go to the Peobo Bryson/James Ingram concert?” I like those artists, but not so much that I would drive the hour to see them and pay a high ticket price. But my beau liked me to accompany him to events like this, so I said yes. He made an attempt to buy the tickets online, but couldn’t complete the transaction. He called me: “I have a client call in 3 minutes and I can’t complete the online transaction. The concert is almost sold out. Can you go online and get the tickets?” What was I to say? I said yes.

The tickets cost more than I would have spent considering my economic situation. I assumed he would pay me back, although he never said he would. When we arrived at the event, he suggested I go to will call while he parked the car. If I did this, I’d miss the opportunity for him to say to the box office, “Can we put this on my credit card?” So I said I’d wait for him at will call while he parked. When he arrived, we asked the clerk for our tickets. Since I’d already paid for them, there was no discussion of payment.

I’m a tad embarrassed to share that as I sat through the concert, I couldn’t shake dwelling on the high cost of the tickets. And I wasn’t enjoying the show that much — probably because I was obsessing about the cost of the tickets.

I felt uncouth and chintzy to bring up the reimbursement for the tickets, so I said nothing. My guy knew I was barely scraping by. How could he not know that this expenditure was more than I’d have volunteered to take on? I stewed and fretted.

It never came up. He was generous to me in some ways, so I justified that I was evening up the score. But I couldn’t shake that if I were going to treat for a high-cost event, it would have been for an artist for whom I was a big fan, not just sort of liked. I felt a little duped to treat for an evening I would have never offered to spring for.

This same man had earlier suggested we go to Paris together for vacation. I told him that my finances could not support such a holiday and perhaps we should wait until I could split the costs. He said he understood my situation and would pay for everything if I would use my frequent flyer points to get us business class tickets. So it wasn’t as if he didn’t know my situation. (We ended up not going because we couldn’t get tickets that fit our schedules.)

The tit and tat of finances during dating can be dicey. More so when you are going out together a lot and/or seeing each other for a while. I now know that this is something that should not be taken for granted but discussed if there is any discomfort.

How do you manage some sense of fairness about dating costs when you’ve been dating someone for a while?


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22 responses to “An awkward situation”

  1. Karen Avatar

    I think this can, unfortunately, be a deal-breaker.

    It’s not so much the actual wealth of the people involved, but if they have different expectations about what constitutes a “good time” that can be the problem.

    For example, even though I have a very good income and have all my finances in good order, I would never consider spending more than $100 on tickets to see any artist. I think concerts are the worst place to appreciate music (you can’t really hear it) and I hate crowds. I’m also not very enthusiastic about attending sports events–I’m not a fan–even if the seats are great/very expensive. I also think going on a cruise would be a total bore (and waste of money).

    On the other hand, I’ve dated men who had less money than me, and I’m sorry but I don’t want to spend most evenings watching Netflix on their TV because they can’t afford to go out! Also, sharing a meal in a nice restaurant with wine etc is one of most wonderful ways to spend time and get to know someone. But eating anything in cheapo chinese restaurants or all-you-can-eat buffets with zero ambience is worse than eating cold cereal at home IMO. Honestly, I’d rather just skip it.

    It’s not always about money. I have dated men who made less money than me who were lots of fun because we valued doing the same things.

    We heard great music on the cheap–chamber concerts at churches and universities, and great new bands in dive bars. We snuck into jazz clubs (there’s no cover if you go late enough), attended gallery openings and open-air art fairs, roller-bladed at the park, went to the art museum on free Thursdays, took coupons to great restaurants, stayed home and cooked gourmet, went out only for drinks and dessert, scored student rush (cheap last minute) tickets to broadway shows, and traveled all over the country on the cheap by driving and staying in campgrounds etc etc.

    So, I think ideally you should be matched with your dating partner in terms of what you like to do, and it’s not just about the money.

  2. Karen Avatar

    Your situation with the tickets was awkward, yes, but on the plus side it was very educational! You learned something very important about this fellow–that he’s cavalier towards others (including you). I don’t think you can assume he “forgot” or that it was an accident. He knows what he did & it’s OK by him!

    I’ve dated (& been married to–ulp!) men like that, and they are bad, bad news. The behavior is, at heart, narcissistic—they believe they deserve to be treated better than other people, as a matter of course, because they are special in some way. The behavior trends with other behaviors—lying, infidelity, using others. I’d say that’s a dealbreaker—a man who would do that is not a man you want to be around.

    Chalk it up to experience (you’ll never see you $ again) and thank your stars that he revealed himself before you got too involved. Worth the money.

  3. Karen Avatar

    And what do you do if your sweetie buys you an outrageously expensive gift and you can’t afford/don’t want to reciprocate? Also awkward.

    If I’m dating a man seriously for 6 months or more, than I’m OK with spending $3-400 on a birthday or Christmas present for him. That’s more than I’d typically spend on my children for Christmas (I come from a fairly frugal family) and about what I used to spend on Christmas/birthdays for my ex-husband. But I’ve found that when dating men expect something large/symbolic. It kind of kills my budget, but OK I go along. But then, I’ve had men spend much more than that on me! So odd! For Christmas, one guy I was dating bought me a diamond necklace & earrings (OMG) and another (in another year, obvs) bought me an iMAC computer. (I kept the jewelry from the one guy after we broke up, but I made the other fellow take the computer back).

    I’m never sure what to do. The sensible thing would be to discuss the gift issue before the holidays, but that doesn’t always work. The diamond guy had actually told me before Christmas that he was uncomfortable by the whole commercial aspect of the holiday and he hoped I wouldn’t “go crazy” with gifts. So I almost didn’t get him much of anything! I finally decided on some normal-looking but high end sports gear that I knew he needed. And then he came out with the diamonds! Thanks, but, grrr (teeth grinding). I was flabbergasted, but I thought the most graceful thing to do was to accept the present & pretend I didn’t know how much it cost.

    And I’ve also wondered what to do with men who buy expensive presents for my *children*. Again, I try to avert it ahead of time, but if they come out with it anyway (& my kids like it), I just gracefully accept.

    I wish there was a “norm” re gift-giving in dating relationships. (I also wish the “norm” was a little less $!)

  4. Samantha Avatar

    I wouldn’t have cared about the ‘consequences’, and would have said ‘i’m sorry i can’t get the tickets because it’s too much of a squeeze for me.’

    I know that my boyfriend brings home so much more than I do and has a much lower mortgage payment than I. So, finances aren’t an issue for us. He understands my situation and seems to be the type of guy who doesn’t mind spending most of the money. Even still, I feel uncomfortable sometimes but continue to contribute what I can afford. I also ‘pay back’ by helping him in other important ways in his life. I have mentioned this in passing to him… that my way of contributing is to help in this other way.. he has a big yard that needs a lot of care. I have helped him clean things up tremendously. So, I feel I am earning my keep.

  5. Mike Avatar

    This can be a deal breaker because it makes both of you talk finances which most people don’t like to do. Over the years I’ve had women tell me what they expected and others we just fell into what we thought was balanced. Whether we go back and forth or as Samantha put it someone makes dinner or some other contribution. How they handle this tells a lot about a person.

  6. Mark Avatar

    I usually plan on paying, but I don’t pick expensive places. Sometimes the woman will treat, and that’s ok too. I can’t imagine a concert deal like DG had though — I would never do that to a woman. Now, on the other hand, if it was a concert she wanted to go to and asked me and said she’d get the tickets, I’d probably be ok with that.

  7. Anna Avatar

    DG, since he asked you to the concert (his choice of band) then it was just bad form that he did not offer to pay for the tickets at the Will Call. That was his opportunity to make things “right”. He might have been feeling a bit bitter all along that he was paying more for outings (in his mind) and this was his way of getting some type of mental balance score. I don’t know, I am only guessing. It IS difficult these days to get the financial thing right. However as we women still deal with the glass ceiling and its a known fact that we still earn only 78 percent of what men earn in similar jobs, I think its still fair that men shoulder more of the dinner bills. And in terms of basic evolution, surely men feel better about themselves by being the “provider” I know most men I have met seem to feel that way. And the few I have met that do not and appear to be cheap then I won’t see again. I am financially independent and work hard and can afford to buy my own dinners but when I am on a date, I do expect the man to pay if he has asked me out. Similarly if we are dating for a while. I may get shot down here by the men (I will risk it!) but we women do have to spend more on general upkeep… do’s, clothes, make up, etc to put on that style that makes a guy proud to take you out to dinner. And yes the woman can treat the guy now and again, no harm in that if he is comfortable with it. She can also do as you do DG and buy dessert or movie tickets, that seems the fairest way.

  8. Mitsy Avatar

    I think I would have been upfront about the tickets being out of my price range from the beginning. I would make it clear that the credit card was on ice so there was no misunderstandings later. Also, for what it’s worth, I think most concerts are overpriced. You don’t have to spend a lot to have a good time. Also, a guy who only wanted to eat at high-end restaurants would not work for me either. There are many restaurants that are nicer than McDonald’s but don’t break the bank. Also, what’s wrong with Chinese restaurants? That’s probably my favorite restaurant to eat at. I don’t eat steak or prime rib so those ultry-expensive places would not be my thing either.

    I think it’s fine to take turns on treating, but if you are short on cash, a home-cooked meal is ALWAYS appreciated and is a way to reciprocate without spending a lot.

    I think in this particular situation, the money issue should have been talked about upfront. Also, I think downplaying a concert you aren’t too interested in would make more sense than coughing up money you don’t have and then go & not enjoy it anyway.

  9. Samantha Avatar

    I dont want to get caught up in wanting to be with someone to the point that I can’t open my mouth and say something. It’s really OK to just say no sometimes. You just do it – say you can’t. I feel that learning how to handle sticky situations is healthy and helps one learn how to navigate and maintain a long term union.

  10. Mike Lowrey Avatar

    I would agree with Mitsy,
    Two things went wrong.

    1) He was wrong for not making sure he gave you the money for the tickets since it was his idea.

    2) You should have been assertive in saying hey you know my situation can you reimburse me for the tickets. Real guys wouldn’t get offended, especially if it was our idea to go in the first place.

  11. Mark Avatar

    At some point the equation about the whole money thing is really simple. I will relate an episode from my own life.

    When my marriage broke up a few years ago, I was talking about it with a dear friend I’ve known since I was six years old. One of the things I said to her was along the lines of, “I am not looking forward to dating. Just look at my car, a banged up, 10 year old mini-van with nearly 200,000 miles on it. I know a lot of women wouldn’t even want to date me once they saw my car.”

    What my friend said to me was this: “Any woman who wouldn’t want to date you because of your car is a woman you wouldn’t want to be with anyway.”

    She’s right. I do like to pay for dinner. I pick inexpensive yet interesting places. I don’t mind paying for something expensive now and then, but the norm is the date isn’t going to cost a lot. The attraction isn’t what we’re doing, but us being together. We can have a wonderful time taking a walk or doing any of a number of things that are cheap if we care for one another.

    What kind of relationship would it ever be if it relied on me paying for entertainment? A shallow one.

  12. Mitsy Avatar

    So true, Mark. And I will echo your friend’s sentiments about the car. My car is also old (1996) but it’s paid for. I owe money on other things and on my house. Sometimes a guy could have a fancy car and it won’t be paid for. There might be very little money to go out on because of that fat car payment. So, there’s 2 sides to look at here. Sure, I like a decent looking car but it doesn’t have to be new or anything special. It just needs to get a person around.

    When I was dating the alcoholic guy, one thing I definitely did not appreciate about him was his lack of maturity when it came to money. He spent foolishly on things that he did not need (booze for starters) and stuff I would deem as “toys” for a grown man. Oftentimes, he didn’t have the cash to take me out or we ate at his house a lot (which I didn’t mind for the most part). However, I was always 2nd place in his priorities. Unfortunately, it took me 2 years to figure out that his priority was really booze and there was no room for a woman in his life. Now, I hope he and his booze and his financial mess are quite comfortable together. :0

    So, if you aren’t scraping by and drive an old, but paid for, car, then I think you have more going for you than a lot of guys.

  13. Matthew Avatar

    Yea, it seems like being up front about not affording the tickets right away would have avoided a lot of the awkwardness. Simply assuming that a guy is going to pay for everything is not a good dating strategy in my opinion.

    Relationship finance situations are certainly tricky and of course even more uncomfortable when the two parties are in vastly different income brackets. It’s tough but necessary to communicate about this type of stuff up front.

  14. Richard Avatar

    “How do you manage some sense of fairness about dating costs when you’ve been dating someone for a while?”

    Who said life is fair?

    50 years ago, it wouldn’t have been an issue. It is only one now because women feel the need to be equal that the problem arises. Guy takes the lady out to a nice restaurant. Gal makes him a nice home cooked meal. That was the quid pro quo. Not “equal”, but he showed interest by taking her out, and she showed interest by taking the time to cook.

    Since this is a forum for people over 40 dating, I say: If you can’t afford the stakes, don’t play the game. 20 year olds may have a different set of expectations. But people over 40 should feel comfortable playing by the old rules (and if he doesn’t, do you want to date him anyway?)

    Regardless, I think a general rule of thumb is: Whoever does the inviting pays for the date. In general, he invites, and she is sensitive to not suggest something outside of his ability to pay (“let’s go out to dinner, where would you like to go?”). If she is going to pay, then she can invite him. If she can’t pay, then she plays the game by letting him know where she would like to go in the future, and waits for him to invite her (“Phatom of the Opera is comming to town, and I love that show.”).

    Regardless of whether you are trying to maintain a “The tit and tat of finances during dating”, the rule still applies. But, when you do “tit for tat”, it is your obligation to maintain your end of the bargain (you invite), and not for the other person to force it upon you. Since he invited, he clearly has the obligation to pay, regardless of whether it was your turn to pay or not.

    In your situation, the embarrasment stems from calling him out, and not for anything that you did wrong. That’s always a difficult situation, and some people have a way of doing it with more tact. Unfortunately, I don’t, so I can’t give you any suggestions on how to deal with it better in the future.

  15. Mitsy Avatar

    I think this merits further discussion. What I’ve experienced is that I’m most comfortable in paying for some meals or doing my share of cooking (even though my last guy was clearly the better cook). One of the many problems I had in my last relationship was the misguided notion that my guy thought that because I worked 2 jobs, that I had a lot more extra income than he did. I did likely make more money than he did but I also owed quite a bit more and my house payment was 3 times what his was. Nevertheless, he was quick to let me pick up the check more times than I thought was considerate. He was also the one who had the drinking problem. He seemed to have money for booze but seldom ever took me anywhere to dinner unless it was a holiday or something. In the end, his love of booze won over his love for me but I often think about the other issues I had with him aside from the booze that made him seem selfish & inconsiderate. Indeed, it’s hard to decipher what was booze related & what was plain old lack of thought on his part. But, regarding the money issue, maybe more women would be willing to pay for more things if they felt their guy didn’t always expect it or realize that some gratitude on their part would go a long way in making sure the expenses stayed fairly even for each person.

  16. Brad Avatar

    At worst the “gentleman” was conniving and at best he was extraordinarily careless. I can’t help but feel that fairness was being prioritized over relationship (which I suppose if fine if the motivation at the time was to simply not be alone). Any healthy relationship can’t ignore each individual’s personal situation just for the sake of fairness, financial or otherwise.

    If I had a friend in this situation today, I would recommend that she confront the situation directly letting the “gentleman” know that the situation was unacceptable. Were she uncomfortable doing this, I would recommend she ask him out to dinner and leave her wallet at home. When it comes time to pay…”Oops! can you grab this one?” Rinse and repeat until the equilibrium of “fairness” has been reestablished. Perhaps this would give a good measure of his character (possibly revealing some ugly hypocrisy) or it might indirectly bring to his attention how his actions were unacceptable.

    Again, I don’t see fairness as a good way to build a relationship but every couple is entitled to operate however they see fit.

  17. […] An Awkward Situation Over at, a story is told how a man, by all appearances, fooled his date into paying for an expensive event that he asked her to go to. The question is asked: “How do you manage some sense of fairness about dating costs when you’ve been dating someone for a while?” […]

  18. Mark Avatar

    “Were she uncomfortable doing this, I would recommend she ask him out to dinner and leave her wallet at home. When it comes time to pay…”Oops! can you grab this one?”

    I think that’s a bad idea. It’s being manipulative. The situation DG described really needs to be discussed by the two people involved. It made DG uncomfortable and you simply have to let the other person know about your discomfort.

  19. Samantha Avatar

    I read DG’s post to my boyfriend, and asked what he thought. He said, “she should have said, OK but I need you to pay me back.” Guys really can take a straight forward request such as this. My BF also volunteered the comment that he wouldn’t do that (call to ask the gal to get the tickets).

    He also said he’s old school and thinks that he should be paying for everything. I like that, but I dont take advantage of him.

  20. Mark Avatar

    The whole “who’s paying for what” thing really comes down to what you’re looking for in a relationship. If what you want is companionship, if you find a good person who fits you try to make it work even if you have to work around money issues. Maybe you can’t work around the money issues, but why would anyone who is looking for companionship above everything else want to ditch a man or woman who didn’t have a lot of material wealth?

    OTOH, maybe you’re looking for going out on the town. Maybe that is why you want to date. Broadway plays, nicer restaurants, enjoying a nice bottle of wine, etc. — if these are what you’re looking for, then maybe you need the guy who has the money to afford to pay for these kinds of dates.

    And I understand that many want both, and there’s nothing wrong with that, but you may spin your wheels for a long time trying to find that perfect match. I’d hate to pass on someone just because she wasn’t my ideal.

  21. Mitsy Avatar

    Mark, your post brings up a lot of things that I’ve thought about many times in the past. In my past 3-4 dating relationships, it seems that the guy was good about taking me out in the beginning and then once he knew he “had me”, he quit making much effort but more than once it seemed to be tied to financial issues. In other words, they wanted me to be around but disliked spending money on me or simply didn’t have any extra. I remember telling the last 2 guys that I didn’t need expensive dinners–that Wendy’s or Hardee’s worked at least part of the time. Their lack of effort was astounding at times. It was like they wanted a girlfriend but ONLY when it was convenient or when they decided to take me out which got to be seldom as time went on. My last guy was the alcoholic who always seemed to come up with $ for his booze though. I’m convinced that a lot of his financial problems were due to his addiction more than anything else.
    Incidentally, I saw him Sat. night at the store where I moonlight. He smelled like beer & was still in that angry mode–he made mention about me not taking his phone calls. I told him it was too painful to talk to him. He hasn’t changed and this encounter confirms that he’s no closer to sobriety than he was a year or 2 ago. Sad…when people let an addiction ruin their lives.

    But, on the money issue, it doesn’t have to break the bank in order to date. I did want to go on some vacations with a guy, but it never got to that point, but if it had, I would have paid for my expenses and not expect the guy to pick up the tab on everything.

  22. Mark Avatar

    Mitsy, any woman who is willing to eat fast food once in awhile is more than reasonable. I’d rather fix her something at my place than take her out for fast food, but that’s nice of you to have that attitude.

    There’s no doubt that we are on our best behavior initially when we are getting to know someone. We want to impress. And I’m sure that the natural impulse when we feel secure in a relationship is to relax and worry less about impressing. You do need to continue to try, though. It’s not so much about impressing the other person, but showing the person you care and you care about her having a nice time.

    I think it’s one of the real challenges when it comes to sustaining a relationship is remembering to put in that effort. It’s easy to let things slide.