What It Means When an Older Man Spends a Lot of Money on First Dates with Younger Women

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QUESTION: What do I do when an older man wants to take me out to din­ner at a very expen­sive, fancy restau­rant? I do not want to come off as a gold dig­ger, but how do I go about it if I like him and he likes me and is intensely attracted to me? (So he says.) 

CHELSEA SAYS: Con­trary to what many peo­ple think, not every age gap match has to do with money. So just because an older man wants to take you out to a nice restau­rant, it doesn’t always mean he just wants to be your sugar daddy. And accept­ing his offer does not make you a gold dig­ger. Maybe he gen­uinely likes you and wants to impress you, and there’s noth­ing wrong with that. Think about it this way: how would you feel if this older man asked you out to a fast food restau­rant? Not so appeal­ing, right?

If you like this older man and you’re gen­uinely inter­ested in see­ing where this can lead, you should def­i­nitely go. Plus, he’s the one who offered, so it’s not like you’re actively pur­su­ing this age gap match because of his money (I’m assum­ing). I say go, have a good time, keep an open mind, and for­get about what other peo­ple think. They’re not the ones on the date, you are. Just remem­ber that you’re in no way oblig­ated to this older man—just because he’s treat­ing you to a fancy, expen­sive din­ner, you should never feel like you have to give or do any­thing in return.

Also keep in mind that although there’s the poten­tial that this is a gen­uine age gap match based on more than money, there might still be a chance that he’s look­ing for a more casual sugar daddy/sugar baby rela­tion­ship. Avoid any con­fu­sion by just being open and hon­est on your date about what you’re look­ing for in a May-December rela­tion­ship. He’s more likely to do the same and then you can decide if you’re inter­ested in a sec­ond date.

TRENT SAYSHe wants to take you out? Already you’re not sound­ing like a gold dig­ger. This actu­ally sounds like a good age gap match.

Now, had you asked him on a date and demanded that he pick you up in a Bugatti, told him that you only eat ille­gally imported Kobe steak, drank only vin­tage Caber­net Sauvi­gnon, and hated when dates didn’t appre­ci­ate your love of Birkin bags, then I’d say you’re com­ing off as a gold digger.

As it stands, he asked you out. You can only take him for his word that he is intensely attracted to you. So enjoy it. Let him lav­ish you with praise.

Con­versely, show him you aren’t a gold dig­ger.  Com­pli­ment him and ask him lots of ques­tions about him­self. The more orig­i­nal they are, the more he’ll think you’re really, really into him.  For exam­ple, after find­ing out how his day went and all that, ask him what his ear­li­est mem­ory is, what his favorite child­hood Christ­mas present was, his favorite vaca­tion spot, what his ideal day would be, and so on.

If the night is going well, ask him fun ques­tions, like what fea­ture he notices first on a woman, or what exactly it is about you that he finds intensely attrac­tive. Tell him to give details.

Get dressed up. Go out. Have fun. And let us know how it goes!

  • Ryan Cham­bers

    Older men gen­er­ally have money any­way, younger women want them to spend money on them, it works both ways.