TL:DR: Known this guy for three weeks, he initiated the first two dates without any expectation for me to pay since he planned them before asking me. I initiated the third, should I offer to pay?

I (25f) met this guy (32m) around 3 weeks ago. He asked me out initially and ordered all my drinks for me and before I even asked, put all my drinks on his tab. After the first date, he immediately planned a second and said it was already confirmed and booked so I didn’t have to pay either. In the past, I’ve been really shy and it’s hard for me to initiate dates, but I’ve been working on it. So this time (before he could plan something) I asked if he wanted to do something that you have to buy tickets for. He said to let him think about a date and he’ll figure something out. My question is, when he “figures out” which day, should I just offer to pay? Since I’m the one who asked right?


14 comments

  3. I think he doesn’t want you to pay, he seems dominant (in the best way possible) saying he wants to think about a date means he probably will pay again, but you can always say “let me pay this time” when it’s time for it and see his reaction. If he wants to pay, let him, maybe he lives comfortably

  4. I’d say you can offer to pay and see how he responds, or alternatively just buy the tickets yourself and see if the topic even gets brought up, the money bit can always be sorted out later. Its also not the first date anymore, you initiated this one (and I think its normal to say that the person who asks the other person out gets the burden of dealing with the bill).

  5. Who asks/invited pays generally. But generally, if I know I work for significantly more than my date, I pay. That’s just my personal choice though…

  6. I think that’s nice for you to say you’ll get this one! Especially since you planned it and he paid for the last 2 dates. Lots of guys would appreciate the gesture. However, it sounds like he may push back if he has a more old-fashioned idea that men should always pay.

  7. 100% agree. Start with offering to pay (I got this. I asked you out his time) and pay if he says ok/doesn’t object, and then follow through. Sounds like he’s more likely to decline and he’ll say he’s got it, but even showing him that you’re willing to pay will send the right message. Then, on later dates, you can start paying for things here and there, even if it’s just small things, like coffee, buying tickets to something ahead of time, etc. Then you both can sort of ease into a natural balance over time.

  8. If you have to get tickets in advance, then it’s up to you. You can even ask “shall I get the tickets?” And he will tell you

    Me personally, I always pay for the tickets in advance because the other person will just buy you a drink or a meal afterwards. So it usually evens out.

  9. In that instance, when I invite them, I say…”hey, would you like to do this? My treat!”

    And then he can respond with…”that sounds great!” Or “I would love to go, but I’m buying, okay?”

    Keeps things clear. Especially if he has been buying most or all of the time prior to that. He has the option to agree or say he is fine with continuing to pay.

    Either way, he at least understands that you are not taking him for granted and you appreciate it.

  10. I’ve stopped seeing women if they don’t bother to handle a date themselves. I’m just going to assume you’re only hanging out with me for outings if you don’t do that from time to time.

  11. Let him pay off but asking if it is OK? When I was dating man (I) paid for everything. I was broke sometime she wanted to go somewhere so she foot the bill.

Leave a Reply