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.

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13 Comments on "Your Call: Is It Okay to Always Let Him Pay?"

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Serba Serbi Berita

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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!


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.


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?

Madamoiselle L
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… Read more »
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… Read more »