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Dating Someone With More Money

Group Therapy: Dating Outside of Your Tax Bracket

This question comes from Group Therapy in our TrèsSugar Community. Add your advice in the comments!

I have recently been on a few dates with a guy who is fantastic! Our first date was nonstop conversation for four hours about everything and anything. I'm a rather shy person at first so it is incredible that I have been able to open up to this guy so readily. He has been the textbook definition of awesome so far. The only problem is that he comes from old money. I am rather middle class and have no clue how to fit into his world.

He doesn't flaunt his money at all, only contextual clues have led me to believe he is wealthy. I'm fresh out of college and struggling to have ends meet. In my past relationships I've always paid for the majority of our activities, and while it may have annoyed me at times I actually enjoyed paying for things and deciding what to do. If I can't afford to do something I simply don't do it. It's empowering. So when he wants to take me to a fancy restaurant, where I need to Google the etiquette for multiple utensil use, I freak out because I know I won't be able to afford dinner there. I never want to expect him to pay, although he has every time. He is also the type of guy who seems slightly offended by me suggesting I pick up the tab every once in a while. It feels strange because every Disney movie has told little girls this is the prince who will save you, but I feel intimidated by his ability to afford nicer things. I always expected I'd be the breadwinner in the relationship. How do I repay him or get over this? What does a girl do here?

Have a dilemma of your own? Post it, anonymously, to Group Therapy for advice, and check out what else is happening in the TrèsSugar Community.

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weffie weffie 5 years
If you decide this is a dealbreaker, can I have his number? :P
mix-tape mix-tape 5 years
Thank you SO SO SO much everyone for the advice! He is a pretty great catch and I keep telling myself I deserve this break in life. I brought up the idea of me cooking him dinner at my place soon as a way to repay him for taking me out and he said "we'll see" which was always my mother's code for "no." haha I think I am going to be adamant about doing something simple for him even if it takes me asking a few times. I don't think he's used to girls like me. Last date he described me as the 'type of girl who gets shit done" which is pretty accurate because I've had no other option in life except to get my "shit done." And yes, I always imagined myself as a breadwinner because I couldn't imagine myself being a stay at home mom and not having any major input with a family budget. Probably some control issues there :/ Anyways, he is pretty fantastic- intelligent, hilarious, attractive, conversationalist, animal lover- total gem. Thank you everyone for helping me not screw this up! Wish me luck!
postmodernsleaze postmodernsleaze 5 years
Even though it wasn't a money issue, I keep thinking of that episode of Sex and the City when Carrie can't handle Aleksandr's grand gestures and they end up at McDonalds. Haha.Accept his gestures with class and gratitude. If it really bothers you to have him pay for everything, just let him know that you might not be able to take him to a five-star restaurant, but you are a 21st century modern woman and would like to treat him to a night out once in awhile. I don't think he's trying to be rude or patronizing by treating you to nice dinners and dates, I think he's just trying to be a gentleman. Man, I wish I could find a guy like that!
postmodernsleaze postmodernsleaze 5 years
Even though it wasn't a money issue, I keep thinking of that episode of Sex and the City when Carrie can't handle Aleksandr's grand gestures and they end up at McDonalds. Haha. Accept his gestures with class and gratitude. If it really bothers you to have him pay for everything, just let him know that you might not be able to take him to a five-star restaurant, but you are a 21st century modern woman and would like to treat him to a night out once in awhile. I don't think he's trying to be rude or patronizing by treating you to nice dinners and dates, I think he's just trying to be a gentleman. Man, I wish I could find a guy like that!
GlowingMoon GlowingMoon 5 years
I agree with Spacekatgal. Just accept his generosity with graciousness. He's being a gentleman. Be a lady -- accept his kind behavior, and be appreciative. Truthfully, every man I had a good relationship with (including my husband) behaved this way to a certain degree. By the same token, with my husband, his gentlemanly behavior carried over to our marriage. That's just how he is (and it's one of the reasons I love him).
GlowingMoon GlowingMoon 5 years
I agree with Spacekatgal. Just accept his generosity with graciousness. He's being a gentleman. Be a lady -- accept his kind behavior, and be appreciative.Truthfully, every man I had a good relationship with (including my husband) behaved this way to a certain degree. By the same token, with my husband, his gentlemanly behavior carried over to our marriage. That's just how he is (and it's one of the reasons I love him).
boredgourdless boredgourdless 5 years
I agree with the others who are telling you to talk it over with him. I would add that when you do talk about it, try to frame it positively. Let him know that while you love being treated to wonderful dates, it feels good to reciprocate. That you would like to give him something--a fun date--as well. If he understands that you want to give too, it may not feel confrontational.
medenginer medenginer 5 years
I would say your due for a discussion about finances if you think this relationship has a future. I'm sure he will understand that your a normal middle class woman trying to make it in this world that hasn't had all the opportunities he has had. I'm in a similar relationship. He makes significantly more than me but I still bring things other than money into the relationship. I believe it's not necessarily what you spend on some one it's how you treat them that matters. You need to realize you can provide for yourself but it's alright to let someone help you as long as you don't abuse it. I think he's also old fashioned and use to paying for dates.
starbucks2 starbucks2 5 years
leilani, I thought that too, and that I thought it was actually pretty cool of her to expect that. Most man expect that...obviously she's had her mind set on becoming so succesful, it would be hard to keep up with her! You go! I'm gonna dig deep here and here's my inner therapist speaking: Soungs like you enjoyed having the upper hand so far in your reltionships. You were the one with money so you got to decide what to do. Now, you're worried this guy might take the upper hand because he's got more money. Don't worry, you sound like you have a good head on your shoulders so you'll be able to stick up for yourself even if he's a Rockerfella and it just sounds like he was raised traditionally were the man pays (especially since the money spent won't be missed...) Let him know how you feel about this, that you appreciate him doing this for you, but you'd like to pay ever once in a while. A real man doesn't mind!
starbucks2 starbucks2 5 years
leilani, I thought that too, and that I thought it was actually pretty cool of her to expect that. Most man expect that...obviously she's had her mind set on becoming so succesful, it would be hard to keep up with her! You go!I'm gonna dig deep here and here's my inner therapist speaking:Soungs like you enjoyed having the upper hand so far in your reltionships. You were the one with money so you got to decide what to do.Now, you're worried this guy might take the upper hand because he's got more money.Don't worry, you sound like you have a good head on your shoulders so you'll be able to stick up for yourself even if he's a Rockerfella and it just sounds like he was raised traditionally were the man pays (especially since the money spent won't be missed...)Let him know how you feel about this, that you appreciate him doing this for you, but you'd like to pay ever once in a while. A real man doesn't mind!
leilani-s leilani-s 5 years
Does anyone else think it's odd that she always expected to be the breadwinner in a relationship? I can see expecting to split expenses (that's what my husband and I do) but why would you want or expect to be the sole breadwinner?
gymgoddess32 gymgoddess32 5 years
if you are worried about being stuck with the bill at a too-expensive dinner, before you go you can say something like "i am so excited for this date, next date i'm taking YOU out!" i don't think he would expect you to pay for a place he picked out,especially when he is aware of the difference in finances.Don't worry about it, you aren't a mooch. I hope he feels comfortable in your world as you become more comfortable in his!
gymgoddess32 gymgoddess32 5 years
if you are worried about being stuck with the bill at a too-expensive dinner, before you go you can say something like "i am so excited for this date, next date i'm taking YOU out!" i don't think he would expect you to pay for a place he picked out,especially when he is aware of the difference in finances. Don't worry about it, you aren't a mooch. I hope he feels comfortable in your world as you become more comfortable in his!
brindey brindey 5 years
Hey Cinderella, You are worth a million dollars. If it bothers you, talk to him. Clearly he isn't shallow, and will probably understand.
brindey brindey 5 years
Hey Cinderella, You are worth a million dollars. If it bothers you, talk to him. Clearly he isn't shallow, and will probably understand.
schnuppi schnuppi 5 years
I would also let him know how you feel about, just like you told us here. Maybe you guys can go on a couple of cheaper dates (movies and popcorn is fun too LOL). It sounds like your guy is raised pretty old-school where he has to pay for dinner. But Im pretty sure he wont feel too bad if you pay for his movie ticket and it will make you feel better too. It sounds like he doesn't have a problem with paying for you so you shouldn't be too hung up about it either. Just show him that you care about HIM and not about the money.
schnuppi schnuppi 5 years
I would also let him know how you feel about, just like you told us here. Maybe you guys can go on a couple of cheaper dates (movies and popcorn is fun too LOL). It sounds like your guy is raised pretty old-school where he has to pay for dinner. But Im pretty sure he wont feel too bad if you pay for his movie ticket and it will make you feel better too. It sounds like he doesn't have a problem with paying for you so you shouldn't be too hung up about it either. Just show him that you care about HIM and not about the money.
JoeTyndall JoeTyndall 5 years
OP,This is what I call a 'serious difference' between you and him. As with all serious differences, you need to sit down with him, lay it all on the table, and discuss this serious issue in great detail. It is essential that he listen to how you feel about this, and he shows that he can respect your feelings on this topic. If left undiscussed, this topic will lead to trouble. Even worse, if he shows that he will not respect your feelings on this, it cause trouble. I have been in the same predicament. I am a guy, I was dating this one lady, she was practically broke, and as far as she was concerned, I had tons of money. We did <i>not</i> work this out between us, and it led to bad feelings between us. Please do not let this happen to you. When all else fails, communicate. Sit down with him and lay it on the line. Let us know what he says.
JoeTyndall JoeTyndall 5 years
OP, This is what I call a 'serious difference' between you and him. As with all serious differences, you need to sit down with him, lay it all on the table, and discuss this serious issue in great detail. It is essential that he listen to how you feel about this, and he shows that he can respect your feelings on this topic. If left undiscussed, this topic will lead to trouble. Even worse, if he shows that he will not respect your feelings on this, it cause trouble. I have been in the same predicament. I am a guy, I was dating this one lady, she was practically broke, and as far as she was concerned, I had tons of money. We did not work this out between us, and it led to bad feelings between us. Please do not let this happen to you. When all else fails, communicate. Sit down with him and lay it on the line. Let us know what he says.
sarah_bellum sarah_bellum 5 years
Nevaeh's advice is spot on. It sounds like you are a little too hung up on the material aspects of dating, which I can understand worrying about when there's a significant income disparity. You shouldn't be worrying about keeping an even tally as far as dollars spent on each other. If he takes you out to a fabulous restaurant and you can't afford to reciprocate, next time prepare a nice picnic and head to the park or something. You said in the beginning of your post that you were at ease opening up to him, so if you feel comfortable enough talking to him about it try casually bringing it up sometime, but carefully in a way that won't bruise his dainty male ego. Then maybe you guys could then start occasionally exploring the funky offbeat restaurants (that are usually cheaper) in your area on a quest to find the best ones. And if you're still feeling weird about it, hang in there and eventually you'll feel more comfortable with things with time. He sounds like a catch, regardless of income.Good luck.
sarah_bellum sarah_bellum 5 years
Nevaeh's advice is spot on. It sounds like you are a little too hung up on the material aspects of dating, which I can understand worrying about when there's a significant income disparity. You shouldn't be worrying about keeping an even tally as far as dollars spent on each other. If he takes you out to a fabulous restaurant and you can't afford to reciprocate, next time prepare a nice picnic and head to the park or something. You said in the beginning of your post that you were at ease opening up to him, so if you feel comfortable enough talking to him about it try casually bringing it up sometime, but carefully in a way that won't bruise his dainty male ego. Then maybe you guys could then start occasionally exploring the funky offbeat restaurants (that are usually cheaper) in your area on a quest to find the best ones. And if you're still feeling weird about it, hang in there and eventually you'll feel more comfortable with things with time. He sounds like a catch, regardless of income. Good luck.
liquidrops liquidrops 5 years
I agree with the above and I have to mention also that you don't have to stress too much cause he could see that and u don't want to! act natural show him that you enjoy simple things in life like a walk in the park but also an exclusive restaurant and as I've read you have been only on a few dates...concentrate on his personality and on what he has to offer to a relationship and by acting naturally everything will arrange by itself;-)
Venus1 Venus1 5 years
I agree with the above.Maybe let him know this concerns you. Then the ball is in his court. Clearly he likes you for you so providing you demonstrate you care I don't think this should be a problem.
Venus1 Venus1 5 years
I agree with the above. Maybe let him know this concerns you. Then the ball is in his court. Clearly he likes you for you so providing you demonstrate you care I don't think this should be a problem.
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