Last year my company, which shall go nameless, went public. Since I was employee number 44, I now have more money than I know what the hell to do with. Obviously, this is not something to complain about, given that so many people can't make ends meet, but it has become a dating problem. When I invite women to my house, a large renovated Victorian in Noe Valley, or take them to a really nice dinner, they seem to become intimidated. I bought all these great new clothes like a Label Under Construction suit, but I feel like I can't wear them without looking pretentious. How do I present myself so I stop scaring people away?
He Said: I have half a mind to tell you to stop dating until you get your values together, Gloria Vanderbilt! Alas, that is not my job here, so I'll try to formulate an answer. You have two options. One would be to find another Google, FB, or Twitter bunny who has plenty of dough and is your equal, at least financially. The better option is to simply go modest and downsize your life. You are a young single guy in SF: What the hell are you doing living alone in a modern McMansion? Get rid of the house (but save the fabulous LUC!), and find a comfortable spot in a more mixed 'hood such as the Mission and mingle with ordinary folk of the female variety. There are plenty of modest but good ethnic restaurants on every corner to treat your date. There's no reason on earth to let anyone know your net worth until you have gotten serious with them—and learned how to be serious about giving it away to more deserving causes.
She Said: I don’t think you have to sell your house or stop going to great restaurants. Rather, I think you need to get straight about (a) what kind of lifestyle you really want to lead and (b) what kind of woman you want to date. Are you living in Noe Valley, eating at Saison and wearing Italian suits because you really love those things, or because it’s what you envision rich people doing? If the answer is the former, all you need to do is start dating women who also love those things—and I am here to tell you that San Francisco is chock full of them. In fact, I’m having trouble imagining where you’re finding these dates who become so easily flustered at your big house and expensive dinners. By and large, San Franciscans are a sophisticated, tasteful lot, and even those who don’t actively seek the luxury lifestyle are well able to appreciate it when it comes their way. A few ways to find a less easily intimidated woman would be to go a little older, a little further north (I’m thinking Pac Heights and Cow Hollow), or to meet and mingle at some of the city’s arts-related and philanthropic events such as the opera, ballet, and museum galas. These worthy organizations will be delighted to take your check for a table and the ladies you meet there won’t blink at your deep pockets.
Now, if none of this appeals to you, then by all means stick to the Mission and SoMa, hit the dive bars, rock out at the Independent. Or maybe you enjoy mixing it up: highbrow one night, lowbrow the next. That’s all fine. But know your audience. If you’re having a first date with an SF State co-ed who lives in a studio in the Lower Haight, take her to Suppenküche, not Gary Danko. Wear your LUC military jacket, not your suit. Take her back to your place but instead of giving her an architectural tour, pour her a beer and ask her about her life. You know, be subtle. Understate your Number 44ness. You’re not alone. There are a good number of millionaires walking around the Mission quietly funding fat retirement accounts (and yes, big donations to great causes, please get on that ASAP).