I am sitting in The Creamery, a cafe in SOMA that’s really popular for people to “get coffee”, which is something I just did myself, and am about to walk to my second of three dates. The Creamery shares the intersection with the 4th Street Caltrain station. As you sit in The Creamery you don’t really notice the trains from the peninsula roll in — they glide in, almost eerily, as if sneaking into the city. But you do notice when the intersection floods with commuters that disperse into SOMA’s arterial sidewalks, to offices, co-working spaces, lofts and apartments originally built to be warehouses. Considering San Francisco’s human capital balance with the rest of the tech-focused peninsula, and with a highway-280 on ramp that runs right from here to Sand Hill Road, you could argue this stretch of 4th Street is today’s Port of San Francisco.

I had “met” all three women on Hinge. If unfamiliar, Hinge is a smartphone app (very similar to the more famous Tinder) and if Hinge were real life you would have a single file line of potential partners at your doorstep. Each woman carries a 3X5 notebook card with information about her. You glance over the notecard. No one is around to judge how you are judging her. You can tap her on the face to change her appearance. Perhaps now she’s doing dancer pose at the beach or looking sexy in a cocktail dress or hugging her BFF or enjoying a sunset or kissing a baby (it’s her nephew, her notecard clarifies). If you are interested in talking to her you pull a lever to the right but there is a catch: She has been making the same judgments about you. You were in a queue too! And if she didn’t pull her lever to the right, you aren’t allowed to talk to her. But if she did, then you can. But she still may not be interested in talking. You may say something nice — “Where did you catch that amazing sunset?” — and she may ignore you because what you actually are, is one more message. You’re not a person saying hello, or a friend being introduced by a friend, or a kind face at a bar, you are another notification on her phone.

The Creamery is filling up and I beeline up 4th street, away from the trains and turn left on Market Street. You feel Market, before you step into it. Humanity’s maw. A jazz trio covers a cheesy rock song. A street vendor sells glass pipes. Another sells kettle corn. Another sells bracelets. BART trains whoosh through the pores underneath. Two girls take a selfie in front of of the Westfield Center, a mall. Through the chaos weave commuters, slicing practiced courses with strategic shields. There are the sunglasses. There are the earbuds. There’s the apparel: long black jackets, scarves, tall socks, hats, boots and sometimes gloves. Throw some gum in your mouth and the only sensory neurons exposed to the world can be in the lower half of the face.

I cross 5th and think through the first date I had today. It was at Sightglass, another popular San Francisco coffee shop. We both appreciated the outdoors and liked to dork out on data, but there wasn’t a spark. I would text her later, saying maybe we won’t fall madly in love but it’d be fun to hang out again as friends. She texted right back agreeing, wondering why it’s possible to detect a potential for love so quickly. It’s true. Maybe we need to make it socially acceptable to end a date after ten minutes. This sounds harsh but if you’ve traversed the dating scene you know what I’m talking about. Some call this a “Tinder Tossback.” You could have fun sex but, for whatever reason, glaring or vague, there’s no chance s/he’s meeting your friends much less ringing wedding bells. Pointing this out should be okay! There’s a very good chance the feeling is mutual. Of course we don’t because — at least at our current point in history — this is too much optimizing. It’s mean. But anytime I throw out the idea, a lot of single heads start nodding. Can city life be so busy, so cluttered, so chaotic that spending an evening with a new human when there’s no potential for sex or partnership has become a nuisance?

A skateboarder snaps to a dismount so close that I throw up a stiffarm. He doesn’t look at me. A troop of tourists check a map and figure out where they are. A biker zooms behind me and just misses the trolley tracks that run down the center of Market Street. The grooves of these tracks grab bike tires and hurl cyclists to the pavement. A few years ago, as I biked to work at Wired, my tires slipped in. I only remember careening forward — but my body hovering at 45 degrees. The impact cracked my helmet down the middle. Some cyclists stopped to make sure I was okay.

I check my phone to be sure my second date hasn’t pushed things back. There’s no guarantee someone’s will show for an app-borne date until you’ve laid eyes on them. I pass The Warfield, home to some of the best performances in rock history, and it has a line for Madeon, a scrawny young French DJ. Everyone in line looks twelve. These kids in line seem jumpy, like they can’t wait to get inside. This is the Tenderloin; though the ability to say that — “This is the Tenderloin” — and have the meaning ring with clarity has started to dissipate. The San Francisco economic tide is raising boats; it’s just not clear whether folks living in the Tenderloin were invited onboard. After the Warfield, I pass healthy people snapping selfies by a recently-cut wood tunnel filled with mirrors. “That is not art; it’s ugly. What is all this?” someone demands. This is the Market Street Prototyping Festival, a sign clarifies. I pass a ragged fellow, smiling, selling ornate fur covered wooden canes on the corner. No one pays attention to him.

Should I feel jerkish for scheduling three dates in one day? This runs through my head. There’s so many obligations. Things are always happening! Busy San Francisco. Facebook invites. Email chains. Meetup events. Meetings. Coffees. Secret parties. Street parties. Networking Things. Meeting People. Who are you? Nice to meet you. I wanted to take a full Friday to (try to!) find That Someone. Yet shouldn’t I be able to find someone at all those other things I just listed? Exhausting, time consuming, that search, and so far these apps’s actual ability to create a match has been, for me, suspect — that optimization: suspect. The overall math doesn’t actually work, I think, most people searching for the longterm are still better off trusting setups or breaking ice at a party. Hinge or Tinder are not really motivated to find you love because then they lose two users. I’d say there’s a reason when you match with someone that Tinder doesn’t ask “Keep Searching?” but instead, “Keep Playing?” Gamifying love. Disrupting love.

I’m almost off Market Street. Underneath construction scaffolding a wide-shouldered man in a Giants windbreaker speaks intensely with a teenager. “That’s not enough,” he says as I pass. “If you can’t pay me today,” then he lowers his voice when he sees me. I turn right at Civic Center plaza. Cops stand around chatting. There’s a band covering Super Freak. Kids dance in a bouncy castle. The sun sets behind City Hall and a man stares at the pastels. His mouth hangs agape. His eyes are vacant. He has a shopping cart. Small huddles of people lay against the concrete walls around the San Francisco Public Library. One girl eats Cookie Crisps. Her fingers are stained brown and she’s wearing a filthy torn Stanford hoodie. My phone is getting low on battery. I pass the Bill Graham auditorium. People sleep in blankets against the walls. City Hall. Symphony Hall. The Opera house. Distinguished families and couples cruise to their shows. Someone leans on their horn. I pass Boxing Room, a fancy restaurant, and a well-dressed woman implores to the person on the phone that “We just have to rise above this” and I briefly consider giving her a highfive but she looks too serious.

I’m into the womb of Hayes valley. Outside the little market where I used to buy groceries is a huge black and white portrait of Louis Armstrong and Nina Simone. I lived up the street from here 2009 to 2012. Hayes Valley was half-delicate then. Now, it is ninety-five percent delicate. The date venue is called Noir, an overpriced lounge; it was Fritz when I lived here, an overpriced crepery. Inside is more delicate. Perfect haircuts. Tight jackets. Small cocktail glasses. Though she pushed the time of our date back twice because she was at the beach with friends, my date is now fifteen minutes late. Optimizing! My phone is almost dead. She shows up. Noir is too packed. We walk to Brass Tacks which is also packed but not too packed. More pretty cocktails. More pretty faces. We have a nice connection around surfing and being Bay Area natives and this is a good example of the Tinder Tossback being a jackass idea. The spark wasn’t there, but it was nice to chat with a fresh face for a couple hours. She heads to a dinner with friends.

I consider bailing on my third date and walking to my buddy’s house in the Mission for an impromptu jam session. But that’d be dick. I agree to meet her at Brass Tacks — yes, the same bar — optimizing — and at that moment my phone finally dies. I step into Sugar holding it gingerly, like a dirty rag, and without a word the bartender plugs it in behind the bar. She smiles. We share a moment of understanding that phones, in the end, suck. Even still, I worry it will be stolen if I don’t watch it — but everyone else in the bar has an iPhone too.

[This was Walk 3 of a seven part series where Caleb Garling takes a stroll through 2015 San Francisco. Walk 2: Footholds and Walk 4: Almost There. Follow the collection at https://medium.com/seven-walks.]