By Rhys Alvarado
Photos by Jessica Worthington

People say I’m old fashioned.

And I don’t blame them.

I listen to old soul cuts of Sam Cooke and The Nat King Cole Trio religiously. I drink old fashioneds when I go to the bar (a good measure of a good bartender). And I’m still searching for the thief who’s been snagging my weekday subscription to The New York Times.

Maybe the last one’s just me getting old. Regardless, I’d say my peers are right.

Even when it comes to finding love, I’ve always relied on chance or meeting people through friends. But living in a “get-it-or-get-out” kind of city like San Francisco, where I’m attending class four days a week, interning for a social media startup and waiting tables on the weekends — I find myself too busy to find love. Having been single for almost a year while trying to keep up with a to-do list that just never seems to end, the idea of creating an online dating profile has only sounded sweeter as the gap between me and my last girlfriend has grown.

I was timid about putting myself out into the digital spectrum of finding love —and sometimes lust— over the internet because I didn’t think I knew anyone involved in a successful relationship that began online. I thought wrong. One of my aunts met her husband in an online chatroom. My current roommate met his girlfriend on Match.com. My old construction boss met his fiancee online too, with plans to marry in the spring.

Hindu astrologers would pick mates based on the stars back in a time when matchmakers were once a staple in all cultures. But in today’s fidgety gadget-grasping age, the internet is the way 40 million out of 54 million singles in the United States are trying to date. A 2010 study by Match.com reveals that one in five committed relationships have begun online. There are websites that help users find a compatible partner based on personality tests. Phone apps like Tinder that use the GPS in your phone to meet people nearby, NOW. Today, matchmaking websites are tailored to everything from women looking for a sugar daddy to sea captains seeking a first mate.

Bay Area dating coach Jessica Engel is in the business of helping people find successful relationships in person and online. Most of her clients are males in the tech industry who don’t have the skills to put themselves out in an attractive way and busy professional women who aren’t satisfied with the men that they’re meeting. Engel promotes to her clients that online dating is one of many avenues for people to connect. Engel says that the negative stigma of online dating mostly lies with older generations while younger ones that grew up with social media seem to be more accepting.

“A lot of people have this inculturated view of love that says we have to wait for fate for it to happen, but we don’t have the same structures we were used to. We’re no longer being matched by our parents or through church groups,” Engel says.

Matchmaking in the 90s

Robby Robbins has worked in the advertising department for alternative weekly publications for more than 20 years. In the glory days of personal ads and the classified section, weeklies like the Indy Week in Durham, North Carolina, capitalized on $40,000 in revenue each month. Following Craigslist’s spread to cities across the nation in 2000— and its widely accepted use— advertising revenues in the personal and classified sections immediately shrunk.

“Still to this day, this was the ugliest web fight. We went from $40,000 to $5,000 overnight,” Robbins says.

Each day, Robbins would assist people in placing personal ads in the newspaper who were in search of anything from a fling to a full-fledged relationship.

“It was a phenomena going on across the country, and in Durham we had a massive audience of busy professionals approaching 30 who weren’t married yet,” Robbins says. “It was a ripe opportunity for this system to work.”

The system catered to mostly single men, who Robbins says were not in tuned and did not have the social meeting skills to introduce themselves and say “hi.”

“I used to tell folks that the answer is going to be ‘no’ until you put yourself out there,” Robbins says. “If you’re direct about what you want, you may be surprised about what you’ll find.”

Robbins managed what were called Blind Boxes, where customers could establish pen pal relationships by paying $10 a week to have mail forwarded to them. Robbins was also in charge of promoting the 900-number services, where people created a voicemail for others to leave a message on at $1.99 per minute.

“We promoted it as a safe way to meet people,” Robbins says.

In order to know what he was promoting, he created a voicemail for himself.

“I did, because as a gay man in the south, meeting a real person was difficult. In the south, you’d get your ass beat if you hit on the wrong guy,” Robbins says.

Having just left a serious relationship, Robbins wasn’t looking for anything serious. Neither was caller No. 4, Bryan O’Quinn.

“He just sounded nice. You can tell a good bit from someone’s voice,” Robbins says.

Four months later, Robby and Bryan moved in together. In 2000, the couple drove to Vermont during a massive snowstorm to engage in a civil union. In 2006, they moved to California and were legally married in 2008.

“All the hoops that we jumped through—14 years and we’re finally legal,” Robbins says.

Dating in the online era

Kathy Sepulveda and her boyfriend Phil Van Stockum have become online dating evangelists.

The couple, who have been dating for two and a half years, take every opportunity they can to tell friends about how online dating is THE way to date.

“Online is really like a large bar where the options are endless,” Sepulveda says. “You already know going in that you’re seeing someone you’re already compatible with.”

Sepulveda was able to convince her high school friend to try online dating. He’s now expecting a child with his computer love. Whenever and wherever they can, the couple is trying to remove the negative stigma against online dating.

“People ask me how we met, and after I tell them we met on OkCupid, they say ‘that’s okay,’” Sepulveda says. “Like I need reassurance that it’s okay. I know it’s okay.”

Sepulveda says that she knows of couples who have met online, but are ashamed to admit they did. Instead, they say that they met elsewhere.

“Some think people who use online dating need it to meet people,” Sepulveda says. “I feel like it’s a smart way to meet people.”

What started out as an obsession of taking online personality quizzes, turned into a way of making friends while attending college in San Diego. It wasn’t until Sepulveda moved to San Francisco in 2009 when she used OkCupid to find dates. Kathy and Phil began chatting with each other a year before dating. At the time, Kathy had started to date another guy exclusively and backed out of a date with Phil last minute.

“A year later when that didn’t work out, I messaged him again and we’ve been dating ever since,” Sepulveda says.

For their one-year anniversary, Sepulveda put together a book that pieces together their earliest online conversations.

Before meeting his girlfriend on campus in September, SF State BECA major Ryan Johnston used online dating for four years to find one-night stands, friends with benefits and casual dates. For Johnston, this was an extra avenue aside from meeting people at parties or shows. His roommates swore by it. Soon after, so did he.

“I liked it for the fling aspect,” Johnston says.

Nightmares in online dating

Deborah Berk, whose real name was kept on the condition of anonymity, is a personal trainer in San Francisco who struck a cold streak of bad luck when she used dating sites like Fitness Singles, Match.com, OKCupid, Let’s Date and Tinder.

Berk admits she’s a freak and former online serial dater who went on more than 40 dates, sometimes as many as four per week.

Berk used the speedier dating sites like OKCupid, Let’s Date and Tinder for quick hookups and/or adventures where she’d do anything from dinner, hiking and camping. But after ringing in the New Year, Berk decided to start searching for a serious relationship on Match.com. The first couple of dates were dreamy. But once she gave into having sex, Berk said that the guys she thought would be her next boyfriend would disappear for good.

“They led me on to the point where you think you’re going to be included in someone’s life, then you’re not,” Berk says.

Berk says that some guys who sign up for determined matchmaking websites can’t handle the weight of a serious relationship.

“There’s so much pressure to commit and get into something serious that they freak out once they find someone who wants that,” Berk says. “It hurt me enough to say ‘I hate online dating’. It’s because of the ones who went into it seriously initially.”

Apps like Tinder and Grindr use the GPS in your phone to find other users who may be looking to chat and meet up. Users can quickly flip through small profiles with short one-liners where people can either be liked or discarded. Messaging between two people on Tinder is only possible after both users like each others profiles. On Grindr, an app targeted toward gay men, users can be tracked within feet of you. And anyone can message another user anything unless they are blocked. According to the company website, Grindr’s mission is to get you “0 feet away.” Michael Villanueva, a 26-year old San Francisco native, has used Grindr as a way to pass time or hook up on late nights when “in heat.” He’s also met one of his best friends through the app.

“How fast do you wanna go?” Villanueva says. “It’s another way to help you with whatever you’re looking for.”

But on one late night meet-up, Villanueva visited a man who was a completely different person than his profile had shown. After bolting, Villanueva has taken a more cautious approach to using the app. He now asks for a phone number, to see more pictures and whether or not they have a Skype account so that he can confirm their identity before actually meeting up.

“As far as I can go, I’ll play Colombo,” Villanueva says.

He says that there were even a few instances when people lied about their age. Villanueva says that the speedy hook-ups that quick-firing apps like Grindr and Tinder can lead to, could be risky to underage people who can access these conversations.

“Technology is moving so fast, I’m scared for the youth to have physical contact. It’s so easy for the youth to have this access—it can be dangerous,” Villanueva says.

My Date

What better way to pass the time on Muni than to sweep through random women’s profiles, x’ing them out or giving them the green light? After a few weeks of chatting on OkCupid and Tinder, I was able to line up a date for a few drinks in the Tenderloin.

Waiting at the end of the bar at the Owl Tree my palms were sweaty, my pulse uneasy as if I was interrupting life’s flow and forcing fate. I waited 20 minutes, gulping away at a pint of Lagunitas faster than usual, my buzz not coming quick enough.

Would her profile look anything like her? What if I choke up and can’t find anything to say? Am I about to find the girl that I’m going to spend my whole life with right now?

Then there she was, standing at the doorway, black hair and back facing me. I stepped up from my barstool and made my way toward her. As if my move had cued hers, she turned around. She looked nothing like she did in her profile pic. One word: sideburns. My sources warned me about this.

But that was okay.

Although I wasn’t physically attracted, we chatted over a couple beers during happy hour and made our way to another joint for a farewell cocktail. We laughed. Related. I walked her to BART and said goodbye.

Phew. What a relief. Online dating might be right for some, but a little much for me. Who knows? Maybe we’ll all look back 50 years from now and find that online methods of matchmaking lead to the most successful relationships.

But what’s a good journalist without a good story?

I think I’ll stop looking so hard for love and let it find me.

I’d like to hold on the romantic idea that I’ll find someone doing what I love, lost on my travels, coming around a street corner the same time as she. We’ll bump into each other and she’ll drop a copy of Hemingway’s “Old Man and The Sea.” We’ll agree that it’s our favorite book and spend the rest of the evening on a blanket near the ocean talking about the trials and triumph of the old man’s noble catch. Or something along those lines.

That sounds like a better story to me.

Bartender, you know what I’m having.