by Katie Sweeney
Bring up the subject of dating with any single person in San Francisco and you are sure to be met with all kinds of eyerolls and horror stories. Depending on the day and my mood, I could cringe, dive into a story about the Greek diplomat who made me pay for his drinks because I showed up late, gush about the sexy text relationship I'm in, or cry about the city's lack of decent, available men. Dating sucks, and lots of people will try to say that dating in San Francisco sucks more than most places. Case in point: I've been living in the city for eight years and I've been single and dating the entire time. You know what else? 39 percent of this city is single and living alone. 39 percent. Tell that to the next person who asks, "Why are you still single?"
I've been on a dating detox since May and now that summer is over it's high time I get my single, early-thirty-something self back on the dating wagon. I will be sharing my dating chronicles here with you, but before we dive into things, let's go over some dating basics for S.F.
Do experiment with technology. San Francisco is ground zero for dating apps like OkCupid and Hinge, so upload a couple of cute selfies and start meeting people and making matches online. If you've already exhausted the aforementioned popular sites, consider doing what I'm doing and just joining SeekingArrangement. At this point I am not above entertaining a sugar daddy.
Don't think you'll never run into the people you've dated. San Francisco is a small city. Even if you aren't in the same circle of friends, you will run into exes, one night stands, and everything in between, everywhere, like the crowded wine aisle of Bi-Rite Divis or the empty bar of Black Magic Voodoo Lounge. When it does happen, you'll be far happier if you never spent a drunken night texting pathetic things to this person.
Don't judge anyone by the neighborhood in which they live. Not all guys who live in the Marina are douche bags (really!), just as not all girls who live in Bernal Heights are lesbians. If you don't want to date someone because he lives in Oakland, you're limiting yourself and could be missing out on something great. Because I care a little too much about my appearance and can be kind of frivolous, guys automatically assume I live in the Marina. I do not. I live on the north side of Cathedral Hill.
Do pay for the first date, straight gentleman. It doesn't matter that it's 2014, a woman will always want a partner who can take care of her. Go ahead and pay for the first drinks. Trust me there is nothing more unattractive than a first date who makes you go to the ATM at Lush Lounge to pay for your $5 glass of crappy Cabernet. (If you're not sure where to take her, here are some great ideas from our resident Foodinista.)
Don't pick a place that is too pricy. If your date lets you decide on the first date location, choose someplace fun and unpretentious where the cocktails aren't $15. Neighborhood spots like Amelie on Polk, Madrone on Divisadero, or Social Study on Geary are a some personal favs. Want to enjoy some craft cocktails? Head to a long-standing bar like Elixir or Rye; their drinks are cheaper and faster to get than newer hot spots like Dirty Habit or Bar Agricole.
Do plan your evening. If you make it past the first couple of dates and are ready to get it on in the sack, select a going-out location that is just a few blocks to one of your houses. If your date has been seeming kind of passive in this regard, better make it your house.
Don't judge a techie by his hoodie. The seemingly stuffy sommelier could actually have tattoos all over his legs and be a stallion in the sack. The buttoned-up blonde who teaches computer training could actually be a beach babe who grows marijuana in her back patio. The friend of a friend who drives Uber and parties hard could surprisingly be a real estate heir. SF is a city full of open-minded chameleons and Burning Man attendees who do hallucinogens at least once a year, so get to know your date before you stereotype them.
Do get out of the city and explore. From wine tasting in Sonoma to hiking Mt. Diablo to bar hopping in downtown Oakland, you should be renting a Zipcar and putting some effort into this if you like this person. If there's one thing people who've been dating for too long tend to be, it's lazy and unimaginative.
Don't have a first date routine. Taking all your first dates to Mission Bowl is lame and people will catch on. The staff will notice and your date might too.
Do order your date a ride home. One good way to win anyone over is to get them an Uber, Lyft, or Sidecar at the end of the night. It's a simple gesture that goes a long way.
Don't spend too much time talking about work. App ideas are not pick-up lines. Describing the start-up or venture capitalist firm you're killing it at does not make for stimulating conversation. Mention what you do briefly and then move on.
And most of all, please realize, this is a marathon and not a race, and in this marathon, nobody really wins and half of you will get divorced anyway. I hope to see you all out there.