Your Call: Is It Okay to Always Let Him Pay?

Share your advice for this reader in the comments section below…

Dear Em & Lo,

I’ve recently started seeing this older guy. So far we’ve been on three dates, and he always insists on paying for everything. I feel a bit guilty, but on the other hand he does have a pretty good and well-paid job, while I’m a student and can barely make ends meet. I’m really glad he wants to pay, otherwise I couldn’t even afford to go out with him that often, but I’m worried he might start to expect something back in return — as in, sex. And I really wasn’t planning on sleeping with him all that soon, because I prefer to take things slow and get to know him first.

So, is it okay to let him pay?

— Free Rider

What should Free Rider do? Share your suggestions in the comments section below.


  1. Thanks for taking the time to talk about this, I feel strongly about it and love studying more on this subject. If achievable, as you gain experience, would you mind updating your weblog with more info? It is very helpful for me.

  2. maybe this is just because I’m super stingy with my money, but I would let him pay as much as he wants. I mean free food? Alright!

  3. I had this same issue with my boyfriend. He always pays for everything and wont even let me leave the tip. I finally asked him one day and he said that he wants and will always pay. He believes in chivalry and will always pay. Knowing that and having that discussion has helped out! Don’t be afraid to talk about it with him.

  4. As a single woman, I am always interested in this topic. This seems like a pretty easy case, though; he makes a lot more than she does, so of course he pays. The question is: What if the situation was reversed? I make decent money, but hate it when a guy expect to split the bill on the first few dates. Is that so terrible?

  5. Cadence, you are right, free or low cost amusements can be a LOT of fun. (My Man and myself and our kids and one girl’s bf went to see a show My Man’s friend puts on with Tesla Coils and electricity last Saturday Night (yeah, we’re nerds) the entire cost? Nothing! It’s fun to do things like this. But, also, when a man has money he often likes to be able to take his date to nice places sometimes, too. We certainly don’t have the disposable income we had before children, so we don’t go out as much, but a man who is used to “nice things” (or a woman who was used to them from her own family) does like to occasionally get dressed up and go out.

    There can be a happy medium between the different kinds of amusements. Sometimes, some take out and a movie from On Demand is better than a dinner at Morton’s and a live show. (MMMMMM Morton’s…..)

  6. I certainly agree with the people above that talking to him about it can only be a good thing. Maybe he does feel that because your income is so much lower, it’s no problem for him to foot the bills.

    However, another option is to suggest doing things that are cheap, or free. Pack a picnic lunch, or go for walks, or stay in one night. There are plenty of museums, galleries etc around that are free (obviously depending on where you live). Even just go to the movies on the cheapest day. There are loads of deals around if you look for them.

    My boyfriend and I try to do free/cheap things whenever possible specifically because there is such an income gap and I feel uncomfortable taking money from him, and we find it really helps to make us both feel equal.

  7. My Man is older than I am, and he makes very decent money at a job he has been at for more than 25 years. Although I am a nurse, I have spent many years at home as a stay at home mom. Of course I let him pay. I let him pay when we were dating (occasionally, for a treat, I would take him out to dinner, but usually he footed the bill) and he has a much better income than I do, and he doesn’t mind paying at all.

    Don’t feel like you have to “pay” for your date with sex. Sex is not a commodity, sleep with him when you are ready, but if you feel you don’t want to eventually have sex with him, don’t keep him just for the free eats! 😉 There should be no pressure to have sex simply because the other person is paying.

    He has more disposable income than you do, he doesn’t mind spending it, let him.

  8. My goodness gracious; I may have the vapors.

    In the dear dead days of my youth, gentlemen always paid for dates since it was not expected that young ladies could afford it. The young ladies reciprocated with theater tickets they had happened to get, or opera tickets, or movie tickets, or small inexpensive gifts, perhaps found in resale shops. (Unexpected presents do not need to be expensive to be as romantic and sexy as hell.) They might, quite innocently, offer to cook dinner.

    The idea that spending money bought sex was–and is–disgusting. All that is needed is emotional parity.

    As I said, this was in the dear dead days of my youth. But it was really quite a bit of fun to have an extensive flirtation complete with stolen kisses and “will she/won’t she” before deciding you liked someone enough to let him see you naked.

  9. I too dated someone older & very well paid. I make decent money, but could not afford to take him as frequently to the types of places he took me. I got self conscious, but then he explained he much preferred going anywhere with me because he could be himself. He could relax, which with other people, he couldn’t do.

    I would suggest you find out what he appreciates that doesn’t cost as much. If you keep dating him and really like him, maybe make a loaf of fresh bread. Buy a decent bottle of wine and go over with a movie. Find out when he does laundry and just talk while you help fold clothes. I know those sound kind of corny, but my guy was most appreciative when I shared something with him that took time and consideration that other people didn’t make the effort to do. If you show you like him when he’s not spending money, that will mean the world to him.

  10. It sounds like you feel you have a problem with him paying all the bills. Therefore, there is a problem even if he doesn’t see any issue.

    Simply ignoring the situation won’t improve things.

    Maybe you just need to talk to him about it? See how he feels?

  11. Now that I am the older breadwinner in my relationship, I feel uncomfortable taking money from my girl, knowing that she makes so much less than me and she needs what she earns.

    I’m not hung up about it. Occasionally my girl is quicker with the check than me, and it doesn’t offend me. Sometimes she buys me drinks after I buy her dinner. Sometimes pride gets her and she insists on paying. I just say “thank you” and don’t make a thing out of it. I’d consider it a small red flag if a guy was really uptight about this.

    When I was broke, older friends and family who made more money took care of me. It was embarrassing, so I do understand both sides of this issue. But in the end I appreciated the fact that my friends wanted me around enough to buy me beers.

  12. My current boyfriend (who is almost 10 years older than me) insists on paying for everything, even though we’ve been together for about a year. Because I initially felt uncomfortable, I attempted to grab a check every once in a while or pay for our bar tabs, which he became incredibly offended by. It took a long time for me to get used to it – mainly because I’ve always tried to split things down the middle, even when I haven’t been financially well-off. Now that we have a year behind us, things have settled to much more even footing, mainly because we are more comfortable in our relationship and there’s less of that whole posturing and trying to impress each other with silly gestures.

    For some guys, the need to always pay is a point of pride or the way they were raised to be able to pay for everything. I’m not discounting that there are men out there who would use paying for dates, meals ect. to leverage sex in return.

    I guess the bottom line is that you have to discern what type of a person you’re dating, and if he ever suggests sex is a requirement because he’s bought you a dinner or two, set him straight and walk away. Taking things slow and getting to know someone before having sex with them is absolutely not an unreasonable request, and any person who doesn’t respect that quite frankly isn’t worth a second glance.

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