How To Date Someone Richer Than You!

How To Date Someone Richer Than You!

“He’s so much richer than me,” my college friend told me, as if money stood between her and true love.
It reminded me, some time ago, I myself was sitting across from a girl who made a lot more money than me. I think it happens more as you approach your thirties. It’s nothing really new though. Some of the first dating stories in the Bible are about a guy named David falling for girls way beyond his class. He elevated his status though by just killing a lot of Philistines. Not recommended, don’t kill Philistines. In my case, somehow what should have been coffee ended up being a dinner I would have bought my parents for their 50th wedding anniversary. She and I weren’t celebrating an anniversary; this was just a first date.

The bill came, I did some quick calculations and realized that this single meal depleted pretty much my entire monthly dating budget and even dipped into my gas budget too. Of course, she offered to help out, which would have been the most practical thing since she probably made more in an hour than I did the entire day. Agreeing to split the check though after seeing the check is like asking her to finish your lap on the treadmill because you had no idea the hill workout would be so difficult. Besides I’m just not in to splitting the check. I get the sense that if you split the check dating you’ll both end up measuring how much the other spends; then paying for your own food; then paying separate rents when you’re married. Splitting doesn’t come across as bonding.

Preferences aside, however, I realized that there was a very simple, practical, material obstacle between the two of us being able to go out. It didn’t matter that we were both spiritual, semi-sophisticated with several things in common. It was simple. Over the conversation of the evening I realized that she spent more money on happiness than I did. And I don’t blame her, if you’ve got it spend it.

The first option was to stretch thin, keep a straight face, and always choose valet. I had this vision of myself in the near future siphoning funds out of my haircut budget, clothing budget and IRA so I could eat out and hit the entertainment venues that she liked. I’d rather just be friends.

The second option is just to admit, “Sorry sweetie, the well is dry, we just need to play marbles and get a coffee.”

At that point she’ll say one of three things: “I don’t want to go out with you anymore because you can’t afford me.” Understandable. Or, “OK, we’ll just take a walk.” In which case she’ll learn some simplicity and you’ll learn humility admitting that you’re just a normal middle class guy and not a trust fund kid. Or, finally, she’ll say, “No worries, I’ll pick it up this time. My treat.” You can let that happen if it’s your birthday, hump day or she gives you a good reason, like she thinks you’re really awesome. And if it does happen she’ll learn some magnanimity and you’ll learn some— humility, again—because we all know how much guys like to be in control. It’ll also make you reflect and think about what else you have to offer besides money (but not Philistines, no not the Philistines).

How to date someone richer than you? Just be you. Always offer what you have and never what you don’t.