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 SAYS: He 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!