40 + age group: Is offering to pay when a man asks you out insulting or emasculating?

I am addressing this question primarily to men (and women) in their 40s and older, because I believe it's a bit different for us, though I welcome feedback from all ages. I am 43 and he is 52.

A man who I know from different concerts and online music forums recently invited me to a concert. We have known each other for at least 2 years and we have hung out together at a couple different concerts (we went separately and met there). Recently, we've been calling and emailing each other a lot more and talking about planning to go to another concert together. It's clear to me that he is interested and I guess he sees that I am interested in him as well, though that took a while as he is pretty shy and reserved.

He saw that one of the artists we both really like had some local shows planned and so called me to ask if I'd like to go. I f course said yes enthusiastically and was really happy!

I asked during that call that night how he wanted to handle the tickets (he lives about 100 miles away) -that I'd book them or if he would prefer to. He said he'd like to and early the next day, he emailed me to tell me he got the tickets. I responded immediately to thank him and said I'd send him the money for the tickets, just let me know where to send.

That was more than a week ago! I haven't received a reply from him... what happened? Did I offend him? Put him on the spot? Make him feel like I didn't view it as a date or he as someone I'd date? I didn't mean any of those things, I just thought the polite thing to do is not presume he will pay my way or front me the money for over a month! I know he's not working right now (his dad is elderly and he takes care of him... he used to live/work about 20 miles away). I don't want to break him or put him in a difficult position or insult him like he can't handle the price of the tickets.

And that's another matter... tickets ranged from $39-69 + fees. He knows I am a front row fanatic, esp for this artist! I don't know if he got high-end tickets or what price range, and he said nothing about it - I didn't know the tickets were of varied price till I checked the website the next day (after his email saying he got the tickets), so I have no idea how much he shelled out.

He is a gentleman. I know this, but I didn't want to seem presumptuous, and wanted to be considerate. It's not like him to just not reply, so I am guessing he doesn't know how to!

Also, I had a long-term relationship with a guy his age in the past - in fact they are a month apart! At first, I offered to pay quite a bit until that guy told me he felt it was 'emasculating' when I offered to pay when we went out and he'd prefer to just pay - he strongly insisted! So I let him. I liked that, but felt it was not really fair to him. I did other nice things for him, cook meals etc.

Other guys my age vary as to whether they pay, but most will say if they plan to treat, but seem surprised if I offer.

What do I do to get him off the spot?

Updates:
For the record, I don't get upset about men wanting to pay, I like to treat as well. I HATE paying 50/50 when the check comes - very very tacky! I'd rather just pay! And I don't mind if we agree ahead of time to trade off or if that naturally works out.
I'm really cool with whatever men prefer, but I wish they'd be clear about what that is - I hate this kind of awkwardness. I'm fine with it, just let me know so you don't feel offended, put-upon or embarrassed.


So how do I fix this?
Well, he called today, Valentine's Day, & HE fixed it - sweet! :) He said the tix arrived, so I mentioned my email & asked what he'd like to do about the tix. He said "how about just let it be my treat?", which I accepted & thanked him for a lot!
Now a new ?: That concert is 3 days after his b day, but there's an even bigger, rare show that we'd both LOVE a couple days before that, which would be a great b day gift, & don't know if it'll be around again. I don't want to steal his thunder?
All of you are giving great answers! That's why I haven't picked a 'best' yet! Thanks for all the feedback!

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Most Helpful Guy

  • Okay. Here's the deal with guys, gifts, money, and women.

    It doesn't matter if the guy is 15 or 50.

    Somewhere along child-development, for whatever reason, boys are lead to believe that girls ONLY value gifts. You never see a cartoon or hear/read a story about the princess that falls absolutely in love with the prince simply because he's so gorgeous. No. It's always something he DOES for her, or GETS her, or GIVES her. (a powerful idea, deeply implanted in the male unconscious mind, at a very young age)

    As boys get older, the media, and women, don't really do much to dispel that idea as false or untrue.

    It's pretty much understood, that UNLESS you PAY for a first date, there will be no second. That UNLESS you GET a girl something for valentine's day, you will not have a valentine. (a powerful association between gifts, getting, giving, material things, that cost money, and love)

    In short, boys come to believe (and conclude) from a very early age, that the only form of expressing affection to girls that's important and meaningful (valued by) to girls is that of getting and giving her material gifts or gestures that represent some sort of time, money, effort sacrifice.

    This never allows for guys to learn how to express their affection or interest in women, in other ways (or believe that it will be appreciated).

    Later on in life, guys eventually get better at math.

    Days, weeks, months, years go by in a relationship, and they look at how much they have both respectively been investing in the relationship:

    Guy: $28,386

    Girl: $892

    That's where conflicting emotions start taking place, and something so simple turns into something so complicated.

    On one hand, guys aren't creative. For guys, it takes a HUGE amount of mental effort and time to muster up the kind of creativity it takes to think of "other" ways of expressing his affection or interest in someone he cares about, that doesn't have a price tag on it. And since most guys are lazy, they just find it easier to BUY things. It's literally the price to pay for being mentally lazy.

    On the other hand, nobody wants to feel used or taken advantage of. And for guys, after just a couple of dates or months in the relationship, is pretty easy to start feeling this way when he's extended $1,000 of himself and the girl hasn't even extended $100 of herself in the relationship.

    Because men are so conflicted on this issue, it's sadly, a VERY thin line to walk on.

    If a woman is TOO receptive, he starts to become afraid of being used or taken advantage of, and starts to lose interest and checks out emotionally. If a woman isn't receptive AT ALL, he takes it as her way of saying that she's not interested in him; period. (as if rejecting his gift or gesture is the same as rejecting HIM)

    The truth is, he only made ONE offer, and you only rejected ONCE. It's not like he asked you out to dinner & you said NO, then said NO to the tickets, and NO to coffee, etc. I don't think you did anything wrong here.

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    • SEE? You said I REJECTED! But I didn't! I was soo happy he asked and told him so - I just offered to cover my ticket! I am glad he called back on Valentines Day and said he'd like it to be on him. I'm also glad he accepted for the tickets I bought, though that was a tricky situation too, because it ended up being 2 days before the one he asked me out to.

      I wish these rock superstars would time their tours better so as not to put me in such awkward situations! LOL!

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    • Wow, a straight guy, in touch with his emotions, able to communicate them so accurately and well, and be completely open and honest about them. this is priceless. I'm going to spam the sh*t out of your mailbox just so you know. don't say I didn't warn you ; )

    • Indeed amazing insight... I wonder how you do it

      on topic I would (unless its value exceeds your and/or his comfort-zone) make an effort to pay for dinner afterwards or do something similar of approx. equal value to repay him, this will create balance while already setting things up for a next time & gives you a chance to show your gratitude for his effort...

What Guys Said 4

  • its all in a guys head, but if a guy asks a girl out, he plans to treat her. So when she offers to pay, it comes across as a small sign of rejection. If a woman cannot accept the gift of his company in the spirit it was given, then Houston, we have a problem.

    and if the guy is insecure, it will affect his decision to ask you for a second date

    the gift of paying for dinner, should be no different than if a guy bought you flowers.

    you don't offer to reimburse him for the cost of the flowers too do ya?

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    • UGH! That's what I'm afraid of - I didn't mean it as a rejection - I am so glad he asked me out. I was trying to be considerate. If he took it as a rejection, how do I fix it?

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    • (ran outta space) but a man who lives with his parents beyond a certain age women assume " something must be wrong with him"

      your fighting centuries of stigma that its a man's job to take care of a woman.

      so a woman can take care of herself...for crying out loud if a man likes ya...let him spoil ya!

    • LOL, there would not be a fight - he is a really easy-going person. I just was worried that it was taken as a rejection, but HE called and fixed it. See my update above.

  • He's 40. Just be blunt with him; the child games ended years ago. Say "let's go, I'll treat!" and if he starts huffing and puffing just explain that you like to contribute to; he'll agree for one of two reasons:

    1. To make you happy and feel a part.

    2. It eases his financial burden.

    Selfish or selfless you win.

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  • dont steal his thunder, besides, he may have other friends and family who may have theor own plans.

    if you and he are meant to be, there will be other birthdays

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    • K, thanks!

      I got worried it might diminish what he is doing for me AFTER I'd already asked him if he was free either of those days, which he will let me know about. D'OH! Now I've got myself in another spot!

  • I'm not 40+, but I'm going to leave an answer anyway...

    I'm sick of women who believe men have to do more, to be equal to women... The only way to emasculate me, would to physically beat me at something that requires strength...

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    • I don't believe this. I am saying some MEN, especially those in his age category (early 50s), do believe it and it is awkward for me, because I feel wrong not offering to pay my fair share, especially if they don't make it clear if it's a "date". Even when that is clear, it feels wrong to expect men to pay. Then when I do offer, it makes them feel bad or rejected or put into the friend zone. Do you see my dilemma?

    • Yes, I am aware that older men think this way.... they should stop being sexist.

What Girls Said 2

  • It is totally emasculating to offer to pay. It makes him think you are putting him into the friend category. It is hard for me to hold back from offering to pay because I can pay and I don't want to look like a gold digger, I guess, but in reality it's a mistake, at least in our age range. I have even noticed with younger guys (I date younger) if a guy is in to me he totally wants to pay. If a guy is just looking for a romp in the hay, the would prefer you go dutch.

    I think that offsetting a guy paying by inviting him over for a home cooked meal or doing other feminine things is the way to go. I do think there is a point in the dating, certainly when you are in a relationship, where it would be okay to pay without fear of making him feel less a man.

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    • Yes, it is very hard to hold back. I've always been taught to be fair and to contribute my fair share... I feel really weird just not even offering. Especially for something as expensive as many concerts we both enjoy.

      So, do you think it will be a bad idea to buy tickets for the other concert for his birthday, given that concert will be 2 days before the one he asked me to? I think I painted myself in a corner here since I already asked if he'd be free that night for a concert - he is!

      HELP!

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    • As you have been dating ask him over and cook dinner. Maybe after you've gone out a bit you could say on a dinner date "Can I get this?" and see what he says. Some guys are just going to be very old school and they won't want you to pick up a check. Just some ideas from another old school gal trying to figure out this whole dating scene :)

    • So I got the tickets today for his birthday and called him and told him about it, so it won't be a surprise. It is awkward that it's going to be 2 days before the concert he is taking me to, but at least I ended up getting crappier seats than he did! LOL.

  • You could just be over-thinking this. You have only stated that he didn't respond to your e-mail asking if he wants you to pay him back and that he never does not respond. Perhaps he didn't receive the e-mail? I think the two of you are at an age where you can communicate honestly and openly. I

    think you should CALL him, mention the e-mail he sent you about the tickets (not the one you sent, the one he sent) and casually bring up the price of the tickets you saw online. You could say something like "hey, I got your e-mail that you bought the tickets and I had looked on-line and saw they could go up to $70! That is pretty steep. If you want, I can pay you back when you get here." I think, if you ay something like this, you are letting him know you respect his wallet and you are at least willing to pay your own way. And you are also allowing him to refuse your offer an making the decision his and he will feel manly. You are also avoiding showcasing your panic over him not responding to that e-mail.

    You will have to ask him how he feels about it.

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