When should I pay??

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This topic contains 5 replies, has 1 voice, and was last updated by  T from NY 1 year, 3 months ago.

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  • #753467 Reply


    Some background: Met this guy on a dating app we chatted for a a few weeks or so, I gave him my number, he asked me on a date. He lives in NYC therefore does not drive, I do not so I do drive he lives about 40 min away. There is deff more to do in NYC therefore I agreed to drive to a place he picked. It was about 45 min away from me and 20 min away from him so he took public transportation to get there. We met up, it was cool and fun we had a few drinks. He paid for it. We have now gone three more dates where I meet him in NYC and he paid for those. Before the last one though I wanted to do an activity and offered to pay for it but they were all booked so we ended up going to a place he chose. We are planning on going on another date soon but I wanted to hear your input on if I should offer. He asked me on this date, it takes more effort for me to get to NYC tolls, gas, etc. So thats why I havent tried offering but I kinda feel abd. What do you guys think?

    #753469 Reply


    You’re doing all of the work… Do not offer to pay-

    A better questions to ask:
    When is he coming to your area?
    Do you think this situation is really sustainable?

    #753473 Reply


    That’s exactly why I haven’t offered. And yeah he is willing to come to my area but tbh there isn’t that much fun or exciting things to do that’s why I haven’t made a plan yet. Prob for date 5 I’ll look for things to do.

    #753479 Reply


    How about you let him look for things to do in your area?

    You are starting off on the wrong foot and the next thing you’ll start wondering, is if he is interested.

    Men are fully capable of planning dates and more than happy to make the trip to see someone they like.

    #753492 Reply

    T from NY

    I am sure there is a park for a picnic, hiking, biking, kayaking, pool table, comedy show, movies, etc etc (you see where I’m going with this) somewhere near you! I absolutely agree — the only way you’re gonna be able to gauge this mans true interest is to let him lead and give just a little air of mystery. I’m not asking you to play games! But there are A LOT of single women in NYC and if you invest too much energy too early some men take you for granted —then when you start asking for reasonable things (like for him to invest more effort and energy in you) they will balk and pull away because the pattern has been set.

    Be easy breezy about it. Next time it comes up – tell him you would love him to see your neck of the woods. If he asks for suggestions — give him a few — then say “I trust you! Looking forward to seeing you” then sit back and let him show you his interest!

    #753495 Reply

    T from NY

    ps A gentleman doesn’t let you pay for things on the first several dates or …. ever. I always offer but that’s to be polite. Every male dating coach I’ve ever read advice states that it is a beautiful thing when a woman offers and the man turns it down. I know there’s a lot of opinions about this —but men who really like a woman don’t allow her to pay — except possibly for little things here and there like a round of drinks, ice cream or coffee, but again, that’s later down the road.

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