The 6 Types of Guys You’ll Meet Dating in San Francisco — Part 2
The warning signs always come out by the 3rd date.
A continuation of The 6 Types of Guys You’ll Meet Dating in San Francisco. As a single 30-something, I’ve collected my fair share of stories and I’ve found that there are a lot of common threads between my stories and those of my friends. If you’ve been on dating apps in the Bay Area for any significant amount of time, chances are you have some…interesting stories too. From startup founders, to eclectic artsy types, to polyamory, to fake marriages, there’s no shortage of characters here.
Here is a collection of my strangest dating stories from the last 2 years:
1. The “Woke” Oaklander Who Thinks Orgasm Reciprocity is a Ridiculous Heteronormative Expectation
We met mid-pandemic and spent hours on the phone getting to know each other. I liked his deep voice and the little song clips he’d record for me. He was a whimsical, creative type who lived in an eclectic household in Oakland. Definitely the type who goes to clambake parties.
We bonded over our shared love for the outdoors and Fenton’s ice cream. Our first several dates were dreamy, sunny days hiking to vista points and pontificating endlessly.
After dating for several months, I invited him on a 4th of July camping trip. On night two of the trip, we ended up sleeping together for the first time and it was about as okay as most first times are.
The part that stood out was that after he was finished, he rolled over and fell back asleep, without inquiring about me at all. Hmm…that was kind of weird, I thought to myself, but let it go since it was really late.
A couple days later on the phone I decided to ask him about it.
“Hey, so not a big deal, but I’m curious as to why you didn’t try and reciprocate for me when we hooked up?”
“Uhh, okay I didn’t know you wanted it”, he retorted with surprising defensiveness.
“What? Why wouldn’t I want it?”
“Not every woman is comfortable with orgasm. You should have asked, how should I have known?”, he shot back.
“Wait..what?? I mean…” I was at a loss for words. “I guess I could have asked? It’s just that reciprocation has always been a thing in my sexual experiences, I think that’s pretty normal? I don’t usually have to ask.”
“Ok well first of all, that’s such a heteronormative expectation”, he started and continued to rant about my unfair expectations.
We continued back and forth for an hour until I realized we were never going to see eye to eye. After that night, we never spoke again and I was left wondering about these women who “don’t want to orgasm”.
2. The Bearded Poet Who Forgets Who You Are After 3 Dates
He had to push back our first date by 30 minutes because he was coming back from his poetry group. Swoon. Men who are good with words are my kryptonite.
During our video date, he showed me the well-manicured miniature jungle he had in his apartment. And he takes good care of his plants!? He was witty in an understated, stoic way and I was immediately drawn to the way he’d take a beat before speaking. So thoughtful, I noted.
He told me how he’d dress up his adopted dog as a lion and tell little kids she was a real lion. We mused about funny costumes and bonded over our shared love of words.
We had a second video date that went equally well, which lead to a third date where we met for a walk in the park with his dog. He knew an amazing amount about local history, so we toured the park as he showed me a bunch of hidden areas I’d never been to. I was having a good time, except for the fact that his large dog was mostly off-leash and kept running up to other dogs and scaring the bejesus out of people. He seemed to not mind and kept letting it happen. This is unexpected for a guy who seemed so thoughtful, I noted to myself.
We ended the date with a hug. I had a feeling we might not see each other again, and felt pretty neutral about it, especially given the weird dog behavior. Neither of us reached out again, and he faded into memory.
Until a couple months later when I open up Hinge and see that he’s liked me. I thought it was one of those cheeky gestures when someone likes you just enough to come back around and say hi on a different app. So I matched with him and he messages me a flirty opener and I realized…oh my god, he has no idea who I am!!! After THREE dates!
I was aghast and had to know if this could possibly be real, so I messaged him back and lightly reminded him of our park date a couple of months prior. He never responded.
3. The 3 Months Out of a “Marriage” Guy Who Comes on Way Too Strong
We were knee-deep in meaningful conversation within a few days of matching on Hinge. He didn’t waste any time and asked all of the thoughtful, hard-hitting questions. What was my perfect Saturday like? Did I want kids? What was I looking for in a partner? How did I feel about tantric sex?
He realized how similar we were in lifestyle and ways of thinking and started dishing out heavy praise.
I can’t believe a woman like you exists, this is insane. I am so turned on all the time with you.
I felt so seen, it was intoxicating.
He revealed early on that he was relatively fresh out of a 5-year relationship, but that it had been “over” a year before they ended things officially. He was still friends with his ex, but they had just fallen out of love over lifestyle differences.
Hmm, seems reasonable, I convinced myself, as I careened off a cliff into an instant-relationship with him. He joked about me taking up half his closet after a few weeks, and I knew it wasn’t really a joke, and I loved it.
Eventually I started to feel a bit like I was filling a role that had been very recently vacated, so I inquired more about his ex. Well, they actually had a wedding, he admitted. But they never got lawfully married. Uh what? So he was fake married? He was 3 months out of a MARRIAGE!?
From there, our budding relationship began to unravel quickly. He kept trying to initiate sexually by saying asking “Orgasm time?” as soon as I’d arrive at his house. This clearly didn’t work for me after only knowing him a few weeks, but he took my slow pace personally. He couldn’t understand why I wanted to wait to have sex, why I felt a bit uneasy moving so quickly given the situation.
I felt him pull away. I asked about it and he seemed just as confused as I was.
“I thought I was ok being patient with sex, but I’ve just lost my excitement for you and I don’t know how to get it back”.
I was devastated. This had never been a problem for me before. How could he be SO into me a couple weeks ago and now cold and distant because I haven’t slept with him yet?
He never did warm back up, so we ended things and he apologized profusely, promising this was his problem and he’d go to therapy. And that’s when I learned the extremely painful lesson of burn-bright-burn-out relationships.
4. The Polyamorous Cofounder Who Really Wants You to Follow Him on Instagram
“I feel kind of sheepish asking you again, but I’d love to follow each other on Instagram”.
At the time, I was flattered. We had 2-hour video date a couple of days prior with a rare, palpable chemistry that somehow translated through our phone screens. He had just cofounded a green tech company — so hot. He also had a “Partnership Vision” document that he openly shared with his dating prospects. Different, but intriguing.
“Okay sure!” I replied back happily, with my Instagram handle.
He’d first asked to follow each other after a few Hinge messages and I explained my preference to get to know someone outside of a social media lens. But since he’d asked again and our virtual date went so well, I figured, why not?
A few days go by without any further communication. I happen upon his profile on Tinder and see that he’s polyamorous. Hmm, that’s an odd thing to leave out of a profile on certain apps but not others, I thought.
I’m not poly so I knew this was a deal-breaker for me. But I was still so curious about his behavior. Was he just collecting Instagram followers? Out of curiosity, I took a deeper gander at his Instagram. Aaaaand my suspicions were confirmed — most of his followers and photo comments were 20 to 30 something women who appeared to be single, beautiful, and honestly, really cool and interesting.
I smiled to myself and wondered if I’d ever hear from him again. I didn’t, but I did later see him breezing through Golden Gate Park on a bike, surrounded by fabulous-looking women. He still follows me on Instagram.
5. The Anti-Gentleman
We bonded over our shared passion for the outdoors. It seemed I had finally found someone who liked backpacking as much as I did! And he had the epic, mountain-filled Instagram photos to prove it. I couldn’t wait to meet him and gush about each of our recent trips to Yosemite.
Our first in-person date was at a fast-casual Mediterranean place in San Francisco. We perused the menu and laughed about both wanting the same dish. We also agreed on how incredible the frozen yogurt with Baklava toppings looked — more on this later.
He reached the register first and ordered his. When the person at the register asked “Anything else?” he made it clear he was only ordering for himself. Okay no big, I thought. It was nice when men offered to pay for a first date, but it wasn’t something I felt entitled to.
As we ate though, I started noticing he seemed generally disinterested in being gentlemanly in any way whatsoever. He poured himself water, but not me. He made very few attempts to ask about me. He mentioned he had little interest in traveling the 40 minutes from his small town to San Francisco very often. It became pretty clear we were both not very into it.
But then came the finale. As I mentioned earlier, we’d waxed poetic about the delicious frozen yogurt. My eyes lit up when he brought it up again.
“I’m going to go in and get some”, he told me after we’d finished our salads.
For some reason, in the moment, perhaps because frozen yogurt runs like $4, I guessed he’d probably get me some too.
He came back out with a huge cup of frozen yogurt, practically overflowing.
“Wow they sure give you a lot!” he bemused, eyes wide.
“Haha.. yeah they sure do!” I said, waiting to see if he’d offer to share. Or like, acknowledge anything about this very one-sided yogurt situation.
The offer nor any acknowledgement ever came. He sat in front of me polishing off his tower of frozen yogurt for 6 minutes, saying almost nothing. I’m usually quite conversational but at this point I was so turned off that I let the silence linger during the longest 6 minutes of my life.
As soon as he finished, he got up and said he better be going. About 47 minutes of date had elapsed at this point. I could not wait to be done. I am pretty certain we didn’t hug, but instead just turned and walked opposite directions.
We both swiftly unfollowed each other on Instagram, never to speak again.
6. The Effusive Frenchman Who Demanded His Gifts Back
We met for the first time in an airy, bright Turkish restaurant and as we ordered appetizers he made it known he was immediately smitten.
“I made this for you, a flower almost as beautiful as you”, he purred in a thick accent as he handed me a small rose he’d woven from a palm frond.
He sprinkled in lots more praise and affection as our date went on, on several occasions pausing to literally just.. stare at me. It felt a little strange, but also refreshing. Most men in San Francisco were much more guarded, only showing affection and clear interest after a few drinks. Here I had finally had clear signals!
For our second date, he picked me up and took me to a fancy dinner in the adjacent town where he lived. As we spooned up couscous and sipped Rose, I started to notice some possessive and off-putting comments.
“Oh was that your other boyfriend?” or “You never call me, are you too busy on other dates?”
He’d say “just kidding” but I could sense an air of discontent underneath. As our date progressed, I realized I was way less into him than he was into me. I started realizing I’d need to backpedal kindly out of this situation. Plus we’d been on the date for many hours, so I let him know I was tired and would like to head home. He agreed, no problem. But on the way, I realized we were going the opposite way of home.
“Oh we’re just going to stop by my house really quick, I have something for you”, he explained. I was mildly annoyed but it wasn’t much of a detour. Fine.
At his house, he gave me the tour and then handed me a small jewelry box. My gift. It was a small pair of teal and silver earrings, my favorite colors.
“Aww, thank you! This is so sweet”, I said with a bit of a forced smile, not quite sure how to receive this gift from a man I hardly knew.
“You still have your shoes on, I guess you want to just leave now?” he asked with a hint of annoyance in his voice.
“Um… yeah? I thought we were just stopping by for a minute?”
“Okay we can go, let’s go”, he reluctantly agreed.
After that date, we talked very sporadically and I eventually let him know I wasn’t feeling like I had time to go on more dates with him. This was my mistake — doing the classic female “nice let down” rather than just being fully honest that I didn’t want to date him anymore, at all, ever.
Months went by. I’d get a text from him every now and then. A happy birthday. A “hope you have fun in Europe!” nicety. I’d reply politely, and that was it. One day though, he asked to have a phone call to “catch up” after we’d both gone on Europe trips. I realized I had to really cut the cord this time.
“Hey, actually I need to be more clear. I don’t want to pursue anything further here and I think a phone call might send the wrong message”, I typed out and sent.
He then exploded on me over text, accusing me of leading him on for months, of lying, of hurting him. I apologized for not being more clear and left it at that. He continued to berate me. We hadn’t meaningfully talked or seen each other since the second date 4 months prior so I was shocked he felt so angry, but I didn’t think it was worth arguing.
Then he started sending me weekly texts demanding that if I really cared and was really sorry, I should give all of his gifts back. What? Is this guy for real? I was actually a little scared at this point because he knew where I lived. After the 3rd angry text, I blocked him and hoped he wouldn’t show up on my doorstep one day. He never did but I learned an important lesson in being crystal clear with rejections, even when it feels uncomfortable.
