Two years ago I came back to San Francisco in possession of a new job, unfortunately single again, in denial about relying upon dating apps. They worked but at a cost: they frame thought in 2D, rely on fleshy filtered visuals, cookie-cutter wit, and louder signals than you'd ever use in the wild—they are poor indicators of real chemistry. To presume to sense a soul through metal and glass. Giant HAHA. A joke. Right. But. They are tools. They serve a purpose. They hold the network, they are the dating pool. Our lovers are stuck inside, drowning. It is our job to dive in, match, get their number, and crawl out.

I met a nice Texas gentleman who restored my faith in dating, at least for three months, before he stepped away to care for a parent entering hospice. Before that, my last great relationship withered at the end of COVID when my boyfriend of two-and-a-half years asked to move with him to Barcelona, and I, in return, asked for a ring. Though partly spurred by an upbringing in a conservative household—LIVING WITH A BOY BEFORE MARRIAGE WAS BLASPHEMOUS—I more so, just wanted to marry him. I still believe that within a couple years of dating, you should know if you want to. We met on Bumble.

I used the apps a couple months this year. Then I deleted them all, except Hinge. The free version allowed checking the matches of men who—God, bless them—spent time swiping and 'liking' first. That meant I could spend less time on my phone. Big whoop. Worn out and hating my addiction to checking if someone liked a mirror selfie, I eventually deleted Hinge too.

What follows are selected stories of meeting people in various ways, organically, which is better for you, they say. The tales I tell are similar to those told to me by friends in Europe, and New York. Dating in San Francisco is hard, but so is dating anywhere. Gurus try to help, but I think they just add to the confusion, saying to maximize surface area, reach for those most emotionally aware, never lower standards, date at least four men at once, at all times. In good faith, and since I'm the one sharing, let's reframe dating as brave. A noble endeavor. Really a hellish landscape, also, if you're doing it right: giving others the benefit of the doubt—at least once!—acting in love and not fear, getting crushed, inevitably, if not first hardened into an A-hole stone. Note: I know not to expect a prince. Still hoping for a knight (with thin armor).

May you enjoy, and not take pity upon my soul. I assure you, I don't.

Twitter Is the New Dating App

My first connection through X (formerly Twitter) came from lurking in the replies. A user proposed publishing the names of men with accounts on Only Fans, and I retorted that shame isn't good at changing habits when weaponized. (I'm right, by the way.) He seemed to concede, liked one of my Substack essays, then slid into my DMs. His profile picture a cartoon, I may have been naïve in approaching the interaction with an open mind. But one must try! Would it be that different than a blind date? He'd be in town soon, and we settled on meeting at a nearby coffee shop. I went to bed thinking how nice.

The next day I logged into X and saw 5 blue notifications. It was like Christmas. Turns out I was tagged in multiple posts containing strange, furry anime porn and a video (apparently) showing this user's face. The user tagging me was a girl, she was badmouthing him. Shocked first to see a wolf with breasts, I blocked them both and reported the content. My excitement about meeting him gone, I grew angry at the user who tagged me. I don't know what happened between them, but I'd very much like to be excluded from their narrative. The jarring visual surprise reminded me of being twelve, using Napster, and opening a music file that was actually porn. I decided to take a break from X.

Reading at a Bar

The first intentional foray was bringing a book to a bar. I had never done it before, which is how I convinced myself to, despite how silly it sounded. Bars. are. not. for. reading. They are for talking! Drinking! Dancing! I fought back single lady librarian vibes and donned a skirt and tights, committing myself to the mission. It's not cringe if it's a social experiment.

The bar had two televisions. The sound was low. The bartender tatted. We struck up a conversation about LIFE. I settled into my bookmarked page with a beer, in the corner, comfortable. Over time, the place filled, and a very nice-looking couple—smiling—asked if I was using the chair next to me. We started chatting and soon found out she used to work where I did! A relief. I too, am like the nice-looking people. We talked about the book I was reading—A Brief History of Intelligence by Max Bennett—and about her husband's work at Apple, where they met. Things were lively. We exchanged Instagram handles with the intent to run into each other again. No other new conversations were had. My book had done its job.

I told my sister how unsuccessful I was at attracting a suitor, and that I had made two new friends who were married. She asked if I thought they were trying to pick me up. "Like a throuple?" I said, suddenly unsure about the encounter. "A lot of married people in SF do that," she countered. I didn't think my new friends were like that. But I also wasn't sure that they weren't.

Whatever the intent, I had had a good time.

Church Networking

I told my mom I didn't want to, which meant I had to: I signed up for a singles event at church. It was a blind dinner, organized by a staffer, based on our local neighborhoods in the city. We could choose the closest one. I'd meet eight to ten people of mixed but equal genders.

Arriving on time like a grownup, I took BART and walked past the junkies at 16th and Mission selling cabbages out of a suitcase. I came from work, trotted through the front door, wearing a trench, denim with boots, and a buttoned-down blouse. The waitress found the reservation and led me to a long table. I chose a seat by the window, sacrificing easy access to leave for a well-positioned view of judging the others as they arrived. Ten minutes passed with many people arriving, though none sat by me. My eyes would follow their steps to a different table, there were two couples, five large groups, and Carol's Birthday Party in the back, outside. I ordered a beer. I double checked the restaurant name and time. I read my book. As the minutes passed, I decided to order dinner. After another thirty minutes, I downed the hummus and kebabs, sipped the last of my beer, and emailed the organizer to let them know.

I was the only attendee.

At least, I told myself, I had tried.

Walking home, I passed the junkies again, still selling produce. It didn't look like they had any takers so far. I knew how they felt—excluding the drug use.

Sidewalk Connections

Life continued and I moved from Mission to the Marina. Walking around on sidewalks, I learned I could look anyone in the eye. In the Mission I had witnessed a kidnapping and was aggressively followed by a large man, to the point where I had to run and ask others for help—shoutout to the door host at Trick Dog, Josue, now a firefighter!

The fact that my dog is cute affords me a lot of new rando connections. She's also slow. One morning she was paused sniffing, and I overheard an old woman speak Spanish. Later when she happened to join the line I was in for coffee, I asked (in Spanish) if she's from Spain. She was Italian—en serio!—and we conversed accordingly before she invited me to meet a few younger friends she had. Maybe it's the fresh air, or the blue water we can stare at, but there is what I call a 'Marina Effect' where everyone on the sidewalk at least acknowledges a "Good morning" or "How are you?" if you put it out there.

One of my favorite organic boy-meets took place over concrete, aided in large part by a fashion choice.

My new friend E reached out spontaneously—we had gotten each other's number the day before—and I went with the flow saying 'yes' to a meetup at the night market at Fort Mason. She was headed there, and I was walking my dog, in a coat with jeans covered in rhinestones (a recent purchase from the Zara in Milan). They are happy pants, loose-fitting and stylish in ways that get me stopped. Hint: clothing is a great catalyst for conversation.

We headed towards the picnic benches to listen to the band when a loud, "YO SPARKLE PANTS!" carried over the crowd. I love a good YO. A guy standing next to two women by the light pole looked me dead in the eyes. "You got some nice pants there." I replied, 'Thank you! Did the rainbows catch your attention?" Twirling by the lights, the concrete sparkled too. He said they did, and E and I were content to stand with them, chatting into the night. We got beers, then walked to a wine bar, eventually pressing phones together until they vibrated and flashed each other's data. The boy who liked my pants made it clear he liked me too. He invited me to a weekend in Napa, and Big Bear, and to see his boat. I told him I was a slow mover and rejected weekend plans in favor of drinks at a local bar. He was fine with that. He hosted parties, and E and I went, having a great time. I didn't feel natural chemistry, but wanted to give it time. As it turned out, Sparkle Pants Guy and friends had been on shrooms when E and I met them, which was fine, and funny, in fact. It felt amazing to be let into a circle of friends, especially in your thirties.

When Sparkle Pants Guy invited me to do drugs, there was no pressure. He respectfully listened. We continued to get to know each other. But one night I heard a rumor. That he had had sex with a girlfriend in our group. Which wouldn't ordinarily affect my opinion of a guy, except that he had introduced her as being like his sister. She was recently divorced and once showed me a list on her phone of all the men she slept with this year. There were nicknames and descriptors. I was honestly impressed. Divorce must be an absolute hell to go through. I respect Sparkle Pants Guy still, and we remain in orbit, and in group chats.

Pitch Night

Months ago, a friend texted me a link to a dating pitch night. I had no idea what it was, but he said it'd be fun, and that he couldn't go—to please, take his ticket and try it. The ticket said to bring booze. The location was fifteen minutes away.

Why not.

Friend texted again to "have fun!" and said these events were well-run. I walked in boots to Marina Market and snagged a six-pack of Pacificos. At the venue, I knew no one. The pitches had started, and the slides were bangers. I saddled up to a table with an empty chair and took a bottle opener out of my pocket, motioning to the others to please take one, if they wanted. Someone whispered, "You brought your own opener?" and I nodded. It was not my first rodeo. Apparently, no one else brought booze. The event had a bar. I was told I was generous, awarded instant smiles from the half-moon of strangers around me. Wow everyone here is nice. Presenters continued and the room filled with laughter and claps continuously. Breaks were forced, to mix up seating arrangements, and I soon ran out of Pacificos to pass out. I stayed the whole night, enjoying the concept of someone pitching their best friend. You could hear the love. Witness the humor. Anyone willing to go through such a ritual in public is a worthy contender, if they have friends, the type of which who want to publicly shout about them.

At the end a QR code was displayed for gathering information to stay in touch. Exhausted, I did an immature thing. I left the venue quickly, after thanking the host. I had been uplifted by the energy and attitudes of everyone. But I hadn't met anyone who drew me in, who was interesting enough, or mysterious enough, to make me want to see them again. At least in the context of romance.

The Old-Fashioned Approach

There was a day that a young man stopped me on the sidewalk and told me I was beautiful. Context: I was walking my dog. Dog is old, fifteen, close to death. I let her sniff whatever she wants. Strolling Chestnut for one block takes thirty minutes. Paused for potentially her last sniff ever, I noticed man in a black coat glancing over. Sully continued. Then stopped. Once again, at a plantar. The young man raised his voice, and that's when he said it. And I refute the naysayers! I love catcalls. Even from homeless people. But back to this man. Ok. Looking at his face, I realized he was young, dark eyes, very thin, with sharp features. He was not attractive, despite being miles ahead of any boy I've made eyes with on sidewalks prior. He deserved my friendliness. And I thanked him for the compliment. When he began asking questions, I replied in kind, for he was nervous, a little shaky, I could tell. When he asked me out for a drink sometime, I smiled and said yes without pausing. He got my number, and there was no regret with giving it, he deserved all the numbers.

Texted my bff immediately. Can you believe this guy? He just stopped me on the street to tell me I was beautiful. No way. They didn't believe me. That never happens. I wanted to tweet about it—prove to the world it happened—but the thought of soliciting 'likes' on a statement about being called beautiful made me hate myself. Dear men: you will never make a woman happier than randomly complimenting her on something, anything, especially how she looks.

We decided to meet at a wine bar on Union. I performed my getting ready ritual, opted for jeans (not sparkly) and a silk white and black polka-dot top, red lipstick. We sat by the door on barstools, I craved a Coke but ordered Chardonnay with ice. Within thirty seconds it was evident this would be a bad date. It wasn't our age gap, he could make eye contact. He just couldn't keep it. His eyes wandered to every girl in the room. Each one entering. There were long stares. Barely looking at me as we talked. Said he was an actor from LA. OH. Asked what he had been in, and he said not much, he was looking for the 'right' material. I asked him why not take Shakespeare into the auditions to read. He looked confused. I went on, saying he could probably write his own script using AI or whatever, any material he wanted, put it on YouTube. He said he was focusing on his craft, working with a coach, his eyes continued to dart. Following them led to an attractive brunette, a younger girl, with wavy hair and a deep-plunging top, leaning across the counter. I looked back at him and smiled. He looked at me and said: "You give me bi-sexual vibes."

A compliment or twisted come-on, I couldn't tell, ok I could, but part of me wanted to run with it. If I replied to say I'd never been with a woman before I'd be giving into the thought play, and if I replied 'yes' that would be an overshare he doesn't deserve to know. I cocked my head to the side and smiled. He did that eye squint thing that happens when the other person doesn't answer. Perhaps he wasn't all that bad. Perhaps he grew up with sisters, picked them up after school, helped them with their homework. Next, he asked a question which he should have known the answer to, "Where do you think this is going?" I replied, "This date?" He invited me back to his place. I laughed. Things unraveled quickly, but I was comfortable in the silence, watching him struggle to come up with something to say. "You look like you're not happy with me," he said. "What makes you say that?" I asked, keeping calm. "Your face looks mad." I confessed his comment about my bisexual vibes was slightly offensive, that we had just met, that I found it crass. His eyes darted past me. We spoke as couples who argue in public do, stupidly, and I realized I didn't even owe him that.

I did that cool thing where you stand up, wave a hand in the air, and signal to the bartender WRAP IT UP! I HAVE TO GO! He offered to pay for my drink. I thanked him, and promptly left. A block away from home he texted to apologize for being rude. A gentleman, sort of.

Twitter as a Dating App – Part Deux

Having put time and distance between me and the anime porn, I logged back on X, with the intent to enjoy myself—the only way to use it.

One day I got surprised, again, by a user sliding into my DMs. Someone I followed who I'd replied to. Another cartoon profile pic, I had learned no lessons, was wary but still open-minded. When we met at a bar, his looks matched the image populated in my phone when he texted. He was tallish. No slight man boobs. His voice was the same as online, and my defenses lowered to normal dating levels.

We had a fun first date. Went to multiple spots, then a late dinner. When I asked what stage of dating he was in, he replied that he was looking for a wife or someone to talk to. We had more drinks, assembled furniture, went to a sports game, and I even cooked dinner. He was funny. Smart. Busy leading a startup. I liked hanging out. He smelled nice.

Sipping soup together one night—he brought it to me when I was sick—he asked if I thought he was autistic. I've lived in the Bay Area and been around lots of interesting people. I'd never discussed autism, potentially their own, directly with someone. Frankly, I wasn't sure. I replied that I didn't think so. (As a woman, I've found that saying "I don't know" about things you're not an expert on invites a better conversation.) The next day I bought a book about dating people with autism.

There was some odd behavior. I've seen weird things before, like a man wet himself for attention, and a child who yelled CUNT! until her mother brought a stuffed duck to comfort. It can take me a day to process some things. A single something did happen. And days after it, I called him to check in. The first words out of his mouth hit me like a speed train. They were direct, completely out of left field, undiscussed before, and hit a personal topic of past shame. Knowing he wasn't aware of how his words hurt—and having healed years before—I asked a couple questions. He said he needed to think. In the same breadth, he said I had asked dumb questions at the sports game, then he said I wasn't tenure. He asked if I knew what tenure meant and I replied that I didn't, not in this context (again, it's good to allow men to explain things), so he continued, saying it means I'm not long-term material.

The conversation ended and as I hung up, I scoffed and shook my head. The door was closed, clearly, on me. At least he picked up. At least he hadn't ghosted.

His words hurt though. I don't need to be treated like a piece of glass but it would be nice to be held carefully.

Fast forward three months. It's 9pm. Walking to a party. My phone lights up. It's him. A text. One short sentence: NEAR YOUR HOME.

I ignore it. It landed like a threat.

Still weeks after that, I received another text asking if I had blocked him on X (which I had). This time I decided to engage, and wrote that I wasn't interested, I wished him luck. I meant it. His reply? "Well…I thought we had a good conversation last…but okay."

Was he being manipulative? Clueless? Does he have a different definition of good than me? I don't know. Honestly, I don't care.

Conclusion

Dating apps are horrible. I don't blame anyone for using them, though. I will say, the bar has never been lower for men to approach women, as sending a simple DM—one text—can invoke the feeling of being pursued.

Perhaps you shouldn't take anything I say too seriously. I am, after all, still single. Typing in front of Réveille on Chestnut. Sipping my latte. Reflecting on the fact that I just met a nice man in line for coffee. They still exist! All I had to do was compliment his sweatshirt, then we talked about the neighborhood, and my dog. When I gave him my name he gave me his in return. No numbers exchanged, but perhaps I'll see him on the sidewalk again, as I keep stretching my surface area in 3D.