NOTE: Please don’t forget to tell me your favorite Dating Dad columns from the last 10 years! I might just take you to dinner!
I always thought I’d move to San Francisco after Simone goes to college (in THREE YEARS!), but the summers here are just too fucking cold for someone who lives for hot weather and warm water (more about that next month).
But, as I sit in this funky coffeeshop on Russian Hill, the baristas behind me debating the merits (and lack thereof) of this summer’s batch of franchise blockbusters (props to Mad Max, disappointed by everything else, and fully sick of Captain America), the cool breeze that drifts through the open door is actually quite refreshing. It’s carrying the scents that let me know I’m in Northern California — all eucalyptus and sage and salt, taking me back to my college days at UC Santa Cruz, when the early fog would burn away to ocean views, the sea lions down in the harbor barking away, their calls echoing up into the hills like a summons.
This morning, I took a long walk down to the marina, where the Golden Gate was just emerging from the mist. The park area was full of cyclists and runners, the occasional elderly woman smartly striding her way along the path, people with dogs and strollers and dogs in strollers. I stood on a little knoll, breathing in the sea air, and glanced down to see a ridiculously pretty woman laying in the grass a short distance away, her chihuahua taking notice of me and yipping until she quieted him down. I thought about walking over to say hi, maybe calming the dog with a gentle scratch behind the ears, but of course I didn’t.
In my mind, I said, “That would be creepy. She’s having a nice moment with her dog, and she hasn’t sent any indication that she wants to talk to you. Don’t be that guy.” I could make any excuse I wanted for why I didn’t walk over, but the truth is that I was just too rooted to my spot, too shy to make any sort of approach.
I don’t naturally talk to strangers.
Sure, I’m social and outgoing, and if someone else starts the conversation, I’m happy to roll with it, but striking up a chat is an act of will for me. I’ve learned to force myself to do it, but my natural state is to sit quietly and wait for someone to talk to me.
I’m naturally warm and smiley and loving, so people tend to be surprised to learn that I can also be painfully shy in certain situations. I’m not a proficient small-talker. A conversation about the weather is just a crutch, to be avoided if at all possible. I’m good with eye contact, but unless you give me an opening (or I’ve planned some topics of conversation), my brain will flail and self-flagellate until I can come up with something meaningful to say. I’ll ask questions to take the focus off of me, but even that can ring hollow after awhile.
I hate networking events as much as I hate singles events because your one job is to talk to as many strangers as you can. “What do you do?” “Where do you work?” Blah blah blah. Everybody there is looking to score — a date, a new client, some validation. Mixers are painful and free of any meaningful context. They feel like free fall for me, untethered by a reason to be there, I get paralyzed, sipping at my cocktail, looking at my phone, until I force myself to step up to a small group of people already in conversation. Awk. Ward.
Last night, I ended up solo at one of my favorite San Francisco bars, lucky enough to settle onto an open stool just as things were getting crazy. I had a fun, quick conversation with one of the bartenders, but the people on either side of me were coupled up, so I contented myself with drinking a stellar cocktail and ordering a salad with duck prosciutto on it (so good). When I looked up from Instagramming my dinner, a pretty woman had just taken up the spot to my right. She didn’t make eye contact, and seemed to know the bartenders, so that gave me an excuse to, you know, not say anything.
When a dude reached between us to grab his beer in a can, I said to her, “I can’t imagine coming to Trick Dog and ordering a beer.”
She laughed and said, “Yeah, not the best choice in a craft cocktail bar.”
And then went back to texting.
It didn’t matter, though, because I was so proud of myself for talking to a stranger at the bar.
And then a different woman stepped up behind me and ordered herself a cocktail. I swung around just enough to take her in — long dark hair, with thick, chunky glasses, big brown eyes, awesome lips. I couldn’t tell if she was alone, or with friends. Not that it mattered, though, because I wasn’t going to talk to her.
But then she was just standing there behind me, sipping at her drink, so I offered up my seat.
“Do you want to sit here? I already ate, so I don’t need the spot anymore.”
She politely declined, and turned away from me. But then the stools next to mine opened up, and she took the one beside me, pulling a menu in front of her and glancing at the small bites.
“What did you eat?” she asked.
That started a very short conversation. She was meeting friends at another bar, and had stopped in for a cocktail and a bite. We didn’t say much more than that, and when she was finished, she wished me a good night and went on her way.
If she’d invited me to go to the next bar with her, I would have, just to see what happened next. But the opening didn’t come, and I, well, didn’t have much to say. As usual. I’m pretty bad at realizing when someone is interested in me, but I’m fairly certain I didn’t miss any signals, this time.
But I went to bed happy with myself for talking to not one, but TWO strangers in one evening. It’s a start, right?
I’m on the flight home now, sad to leave the city, but so looking forward to sleeping in my own bed tonight. Last night’s adventures ended around 3am, and I’m damn tired.
But it was worth it.
See, I was enjoying an early solo dinner at a new restaurant, sister spot to one of my favorite restaurants in the whole world. I wasn’t sure if I’d be able to get in, so I showed up just after they opened and staked out a spot at the bar. The place was busy, but not packed, and my first cocktail and round of small plates came quickly. I dug right in, so happy for some stellar bites. The place began to fill up as my third cocktail and a couple more dishes arrived. A tall young woman with dark, curly hair took the seat next to me, smiled and said hello, and started looking over the menu. She had one of those darling, open faces that tells you you’re in the presence of a very sweet person. A couple on the other side of her asked the bartender about one of the cocktails, which just happened to be the one I was drinking, and I spoke up (!) and told them it was delicious.
That opened things up for the four of us to talk a little (the couple was scandalized that I was on my third drink of the evening), and then the young woman next to me asked what I liked on the menu. It turned out she was in town for a trade show, and we ended up talking companionably for the next hour. When she mentioned her boyfriend, I smiled and asked about him, as well.
“Okay,” I thought, “That was really nice, but it’s time for me to move on.” So I asked for my check. Just to be polite, I told her I was going to grab an Uber downtown so I could stop in at two bars where my friends worked, and that she was welcome to join me.
To my surprise, she wanted to tag along. “If you don’t mind,” she said. We had already talked about the concept of surrendering to an evening or an opportunity, and I’d already invited her. And, anyway, it was refreshing to have someone join me in my carousing.
We stopped in for a cocktail at the bar I’d visited the night before, where the GM greeted me by name (yep, I’m doing my best to build a network of beloved bartenders in San Francisco, too!). Our drinks were perfect; so was the conversation. We talked about our career trajectories, our love of travel, the joys of entrepreneurship. I regaled her with stories about world travel with the girl, and asked her some questions about her boyfriend (just to make it clear I understood the landscape).
And then we walked over to my friends’ cozy bar, Benjamin Cooper, which is hidden away in a boutique hotel. My friendship with Mo goes back years, to his time cutting his teeth as a bartender in Denver. In some ways, he was influential in my learning how to drink a proper cocktail, and I always make a point of visiting with him when I’m in the city. His business partner Brian is equally warm and friendly, so I was greeted with hugs and hearty back pats when I arrived. They hugged my companion, too. I could see the warm treatment agreed with her, which spoke volumes about her graciousness.
The two of us shared a range of spectacular craft cocktails while I caught up with Mo. We were treated to more drinks and sips and shots before we realized it was after 2am and we were the last people in the bar. Mo and Brian ushered us out through a secret door to the street, I promised I’d be back soon, and we started walking.
I told my new pal I’d accompany her back to her hotel, of course, and when we got there, she gave me a hug, thanked me for introducing her to my favorite spots, and said goodnight. I swiped an Uber, exhausted but happy and surprised that my evening had turned out to be so fun, so full of good company, drinking and discussing all manner of subjects until the wee hours of the morning. I’d surrendered to whatever the evening had in store, and, as usual, I was rewarded with magic and surprises and new friendships.
So, yeah, I know the benefit of talking to strangers, and I’m rarely disappointed when I actually make an effort. I have friends who can talk to anyone. My mom is the same way. They have a skill (or a personality trait) I admire and wish I could emulate. Even though I know the rewards are many, and even though good things happen just about every time I put myself out there, it’s a struggle to start the motor running.
Next time I’m feeling tentative, maybe I’ll remind myself of my last few days in SF, and say something witty to a stranger nearby.
Or, you know…maybe I won’t.