Anon asks: Hey Isaac, I was hoping for some insight. I like this girl but the problem is that I’m afraid of asking her out because she comes from a much wealthier background and I’m scared of embarrassing myself. Any advice or experience with this sort of thing?
Hey, gidday mate! I love this question and I love you for asking it.
I’m trying really hard not to jump into extreme stereotypes, but…
Is she the snooty princess who expects diamonds and helicopter rides and dinner at Michelin starred restaurants?
Is she the black sheep who wants to make Daddy angry by dating the bad boy from the wrong side of the tracks?
OR MAYBE… Is she just a normal girl whose parents happen to have made a lot of money and she’s out here looking for love like you and me and everyone else we know.
I also can’t stop thinking of that Gossip Girl episode where Dan takes Serena out on a first date and she’s all excited about hitting an underground gig in Brooklyn or an arthouse movie at Film Forum, but he spends every dollar he has on a limo and an expensive restaurant and she gets disappointed because of the inauthenticity of the date.
So keep Dan and Serena in mind when you ask this girl out. And you should ask her out. If she’s a down to earth humanoid who cares more about things like personality and sense of humor over finances, then she’ll be interested in getting to know YOU, and won’t be worried about how much money you’ve got.
And if she’s more interested in outward appearances than emotional value (as many people are, male or female), then she’s probably not the right one for you.
One caveat: If you’re a person who’s easily intimidated by things like other people having stuff that you don’t, then she might not be the right one for you for that reason, too. If you’re going to get insecure when you hang out with her friends and feel less-than everyone around, then for your own personal sanity it might be a smart idea to swerve.
But if you can keep cool, then by all means go for it. You’ll never know until you know. Throw caution to the wind. Be bold! And who knows: If you ask her out, she might just say yes.
Got a question you want answering? Ask me here!
I LIKE YOU!