I wasn’t always such a good dater. It’s funny because these days I co-run TRY ME, offering private dating coaching and throwing events for the unattached. But just a few years ago, things were different. In fact, I forced myself to sign up for OkCupid when I was fairly new to San Francisco and in dire need of romance.
My first online date was also my first date after a five-year relationship. I was nervous to the point of nausea. I left the apartment as my roommate said, “I can’t believe you’re doing this.” (Online dating was still weird in 2007.) Still, I felt enough excitement to get myself out the door to meet my date at a bar. I remembered how to flirt, and we ended our date with a make-out sesh outside my apartment.
And so it began, my love affair with an online dating site. San Francisco’s dating scene can often leave a girl longing for more, but on OkCupid I had a whole catalog of males to choose from. In my early days, I got trapped in pen-pal-style romances with my e-suitors. They were never as impressive in person, though, like the time I met up with a cute redhead who couldn’t hold his liquor and revealed he was married. I learned to keep emails brief, set a date by the third correspondence, and hope for nothing more than good conversation.
In the five years I was on the site (yeah, I said five), I went on an average of two dates per week, minus periods of exclusivity, which means OkCupid set me up on more than 250 dates. Only a handful were horror shows, the aforementioned ginger included. Lucky for me, OkCupid loves to reward its most dutiful users with new matches. When I’d start to see the same profiles again and again, I would log some activity by editing my profile or answering a new question.
As time went on, my mastery of OkCupid developed. I used more features of the site, like QuickMatch, chat, and star ratings. While I’m not sure I trusted OkCupid’s compatibility scores, I did find its quizzes to be pretty revealing. A guy’s profile may look fantastic until you realize he thinks a woman should never be the breadwinner in a relationship. Guess who won’t be buying dinner!
Sometime around 2010 it seemed all of my single girlfriends had joined OkCupid. This made it way more fun but presented challenges when we started targeting the same guys. In some cases, this was helpful, like when my friend recommended I cancel a date because the guy was six inches shorter than the height he had listed and an A+ grump. She knew because she had gone on a date with him the week before. We started a shared Google Doc, where we could list who we had dated and leave comments about what the next girl might encounter.
With the site now part of popular culture, there are tons of OkCupid fanatics out there, each with his or her own strategies for how to manage online dating. I chatted with Jayne, who at 39 looks like a way-hot 29-year-old. She went online because she was only meeting men too young for her taste. She liked the idea of “dating backwards” or, as she describes it, “Getting all the details up front, smelling them last.”
Jayne claims OkCupid’s $5-per-month A-list membership is worth the meager investment and believes a positive attitude is the key to success in dating. Her openness once led her to a four-day first date when she invited her “dream man,” who was unfortunately located in Idaho, out to San Francisco to meet in person. Jayne’s best advice is to start off with a phone date as it saves a lot of time and awkwardness by screening for compatibility.
Then there’s Richard, a three-year veteran of the site. He chose OkCupid after seeing tons of cute, interesting guys around the city but not meeting any of them in person. Richard isn’t into the hook-up scene and feels OkCupid is better for those seeking a relationship (over other options like Grindr). Like me, Richard believes in taking communication offline within a few messages and meeting up as soon as possible.
As for the tricks up Richard’s sleeve, he taught me to take a screen capture of a date’s profile so you don’t have to keep peeking at it online. Brilliant. As for his success online, Richard is still dating (check him out@treestremble, he’s cute!), but he found a best friend and a cofounder to launch his forthcoming nonprofit,PsychedelicSF.org, via OkCupid.
I also met Nat, who is a force to be reckoned with on OkCupid. Nat has been using the site on and off for about four years and initially joined due to a maxed-out schedule that prevented her from meeting people organically. Although she currently has a boyfriend, when she was listed as single, Nat was checking her account up to four times daily with its iPhone app. Nat says, “You cannot approach OkC like spearfishing. You gotta trawl it like a vast ocean.” Her skills paid off when she started booking three to four dates a week.
She believes that success starts with your profile. Avoid being cliché (ladies, no more pics with fake moustaches) by taking a look at your competition. In order to get good matches, you have to stand out. Nat outsmarted the dreaded OkCupid slump by creating a new account entirely. With her new profile, Nat turned up in more searches and saw her traffic spike by 30%. Nat says a secondary account, or a “creeper account,” that you use to look at profiles anonymously is a must-have.
According to Compete.com, more than one million people visit OkCupid daily. And as the number of online dating sites grow, so does the feeling of not knowing where to start. Alicia Ostarello and her partner saw their online business, Vow Muse, grow after expanding from crafting custom wedding vows to writing online dating profiles.
Alicia feels profiles should have enough information to interest a visitor, but they shouldn’t reveal your life story. They should be easy to read and have responses of varying lengths. Turnoffs include profiles with overpowering sarcasm or phrases that show a lack of confidence, like “I can’t believe I’m doing this.” Avoid pictures of yourself with someone more attractive or those with someone cut out of them (creepy!).
If you’re single and think San Francisco’s dating scene sucks, it may be time to go online. Just be warned: You may get sucked in like the rest of us. As for me, I retired my account six months ago. I finally met a guy online who was dreamy enough to break me of my addiction to OkCupid.
