“Jenny’s” dating profile says her weakness is “super smart polymath builder/makers.” I look up polymath to confirm that I know what it means. Ironically, doing so also confirms that I’m probably not what Jenny is looking for. She likes complex cocktails – also not my thing. She has starlink and works remotely for weeks at a time. Yes, I too would like to be less tethered, alas, I am not. We both like pitbulls, and hers looks like the one I used to have. Knowing we’d be a long shot, I pass and swipe left.
I do this a lot – pause over profiles, read carefully, look for ways that we might match, read between the lines… and of course look at the pictures. Quite often, I find myself mumbling, she’s too much for me. Quite often, I’m facing the uncomfortable admission that I’m not enough for her. Quite often, I pass and swipe left.
At the bar, I elbow-nudge my friend and nod in the direction of “Lisa” who is half dancing at the end of the bar. With each twist of her hips she reveals a little side boob. Lisa is celebrating her birthday and wearing a silky, maroon top with a neckline that plunges to her midriff. In addition to being cute and braless, Lisa is too young for me or my friend. That doesn’t stop us from trying to make eye contact, and/or looking her way. We’ve seen her in the bar plenty of times before though never connected. In my head, I write The Onion headline, “Dirty Old Men Grow Weary of Ogling Younger Women at Bars.” With her cohort of equally attractive but too-young female friends, Lisa leaves for the bar down the street. My friend says we should follow. I say no. We stay. We toast a round of shots with a new crowd of friends who come in. The bar kicks us all out at 2am. I fall asleep on my sofa, fully dressed – the light still on in the bedroom where I’m not sleeping. When I wake, groggy in the morning light, I think, “this is not the look I’m going for.”
“Nicole’s” profile says that she’s the founder of a consulting firm and is an IPO advisor. I take that to mean that she has some money and is tangentially, if not deeply, involved in the tech scene. She describes herself as a “disher of sarcasm and exploiter of the gullible.” Based on this one line, I ascertain that Nicole is not a nice person. One of her pictures is in front of a canal which looks more like Amsterdam than Venice. Another picture is outside of a hotel – there’s a faded bronze colored, metal plaque on the brick wall behind her. It reads, “Small Luxury Hotels of the World.” There’s a picture of her skiing, a picture of her mountain biking, a picture of her tied to a neon green nylon rope, pick-axes in each hand, as she’s about to descend a crevice in a glacier. Aside from not liking that she’s an exploiter of the gullible, I acknowledge that I stay at crappy, cheap hotels which I don’t think would meet Nicole’s standards. I don’t ski. I don’t mountain bike. I pass and swipe left.
She waves at me and comes over to say hello. She asks me how I’ve been. I say, “you know, hangin’ in there.” I ask her how she’s been. She replies, “same.” We talk for a minute and she walks back to her bar stool in the middle of the bar. My friend gives me a nudge, “who’s she and how do you know her?” I tell him without telling him, “We have history.” She’s young, very attractive in the alluring way that foreign women tend to be attractive: dark hair, olive skin, bright red lips, seductive eyes. My friend gives me an atta boy nudge, “good for you, wow.” I shrug with embarrassment. She and I were tipsy. I assume that under normal, less-inebriated circumstances, she has better judgement. I think that because I refused her advances a few different times when we first met, I became a challenge to her, a puzzle to solve. She used to ask in her clipped South American accent, “why won’t you date me?” I always told her she was too young for me. My general rule, one that I have only violated since moving to San Francisco, is to not date or hook up with anyone who is closer in age to my daughter than they are to me. She and my friend both think my rule is stupid. Meh.
When the rash first showed up, I googled, “can too much alcohol cause…” Psoriasis? Hives? Eczema? The results were inconclusive, and well, I didn’t want to look at any more pictures of rashes. I order a topical cream anyway and hope for the best. Guess I won’t be bringing anyone home anytime soon. Not that that happens all that often or is even my intent, but one never knows. Once again, I think, “this is not the look I’m going for. I need to get my shit together.”
“Stan” and his boyfriend of seven years, “John,” recently broke up. I was friendly with both of them, but Stan is keeping the house they were renting – I doubt I’ll see John again, at least not anytime soon. Within a few days, Stan is hooking up with anyone and everyone. He’s meeting guys in the park for sex, sleeping with his 19-year-old neighbor, trying to date a lawyer, trying to date an heir to a condiment fortune. He’s giddy when he talks about his exploits, especially his 19-year-old sidepiece. He shows me a picture of tan and chiseled abs, he tries to swipe to another picture and “accidentally” shows me a bare ass. Even if I wanted to, I don’t think I could be as free or promiscuous as Stan. Maybe my age rule is stupid. This is San Francisco where everything and anything goes, right? I should probably loosen up.
It’s after 2am and were standing outside in the cool San Francisco night. She tells me she thinks she’s probably going to leave her boyfriend. He doesn’t seem to have any interests or passions. He’s nice, but boring. Also she’s not sure where he went, he kinda ditched her a few hours ago. I suggest that we often think the grass is greener elsewhere, maybe don’t overlook those good qualities. I tell her he seems like a decent guy. She says he is, then looks at me and says she’s had a thing for me for a while. I know this, we’ve “hung out” a couple of times before. I flirt back. We make out on a side street not far from the bar. I offer to walk her home. Her phone is dead and she can’t get into her building. She dials several numbers using the building’s buzzer system. Man, I’d be pissed if I was one of her neighbors. She drops her phone, I pick it up and put it in my back pocket. Finally, someone lets us in. I walk her upstairs, and when she opens the door she whispers, “ah, he’s here, I was worried where he went.” She rushes in, shuts the door, and I go home. Halfway home, I realize I still have her phone in my back pocket. It’ll have to wait until morning.
Over a beer with a friend after a city hike along the Embarcadero, I tell him that I’ve been feeling stuck. I tell him that I think everyone I’ve dated has moved on better than I have. They’ve either found love, gotten married, or found fulfillment in some other realm. Meanwhile, I’ve found a bar that feeds me free shots until two in the morning. “This is not the look I’m going for.” This isn’t the type of thing you write home about. This isn’t the type of thing you brag about on social media, much less share on your dating profile (though a personal blog that nobody reads is probably fine). He reminds me not to judge my life by the way others live. He tries to use parent logic on me. If all of your friends were getting divorced, would you want to get divorced too? A better equivalent would have been, if all your friends were getting divorced and bragging about how awesome single life was, would you get divorced too? His logic fails. I tell him, I think there’s more to life than what I’m currently doing, but for now, I’m ok with the holding pattern. He tells me not to worry about it. Worry isn’t the right word. I like what I have and also want something different.
I can sense her sizing me up, deciding if she wants to chat. She does. The conversation is innocuous at first. She’s just took a job at a restaurant in the neighborhood, and isn’t sure where she wants to live or what she can afford. Rents are crazy. She moved here from LA, but has lived all over the world (London, New York, Bogota). She chats in Spanish with the Colombian soccer fans. It’s the world cup. We talk about the neighborhood and the city, and eventually dating in the city. I tell her that in my experience, the dating scene seems pretty bad, and that I’ve pretty much given up. I share that for better or worse, everyone thinks it’s bad and at least there are plenty of other things to do. She asks me what I’m looking for – men or women? do I chase twenty-somethings? Woman, and no. I tell her my rule is to not date anyone closer in age to my daughter than me. She asks how old my daughter is, and I say 30. She’s 27 and seems disappointed. She says she’s open to dating older men and open to dating just about anyone, but has never had a relationship – ever. She seldom gets past the first or second date. I find this hard to believe. She’s cute, well-traveled, articulate. She says she’s dating with intention and if things don’t work out within the next three years (she wants to get married and maybe have kids), she’s gonna move to a cabin in the mountains and be solo. I ask if her independence, while admirable, might scare some men away, and I say, yes, everyone seems to be dating with intention. Collectively, we might make more connections if we were a little less intentional. She smiles at this, tells me not to give up, I’m too young to give up and I seem like a decent dude. I say, maybe giving up is the wrong phrase. I don’t make much of an effort because nobody seems to make much of an effort. Besides, I have a ton of friends here at the bar and lots of things to do in the city. She finishes her drink, says she’ll see me around, and leaves.
“Teresa” lives in Santa Cruz. Under normal circumstances, I’d say Santa Cruz is too far, but because I was feeling stuck, I figured maybe I should change things up. I reach out. She replies. We exchange a few texts and then she says she’s going on a week-long retreat in Big Sur. I tell her I had to skip Big Sur when I was driving up the coast (it was closed), I wish her well or something like that, and ask her one or two more questions about the retreat and what she does for a living. The week passed, then a few more days passed. That’s where the conversation stalled and got moved to the “expired” list on the dating app. I could have reached out again and asked how the retreat went, but pride or stubbornness or the reality that maybe it’s too much work for having only exchanged a few texts kept me from doing so. Santa Cruz was probably too far, and well… the ball was in her court. Meh.
When I check the app in the morning, I see there’s a new match. “Audry,” who I had swiped on the night before, is very cute lives nearby, and swiped back – hence the match. Her kids are almost grown, which is also a plus. I send a message through the app telling her it was pleasant surprise to see the match and asking her the innocuous and generic, “any big plans for the weekend?” I end by saying I hope we can connect. I get no response. I’m pretty sure we matched one other time, maybe a year or two ago. I’m pretty sure I reached out back then and also got no response.
I was paying to use one of the apps. In doing so, I could see who sent likes and choose accordingly. It gives you a little more control and a little less exposure to rejection. Online dating involves a lot of rejection. The rejection is seldom an outright no, it’s more along the lines of slowly letting things drop. Everyone fades away. Because I’ve been lax and because the experience has been mixed, I let my subscription expire. Prior to moving to San Francisco, I had met everyone I had ever dated through an app and had never met anyone at a bar. Since moving to San Francisco, I seem to have only connected with people at bars, and I don’t think I’ve ever had more than two dates with someone I met on an app. Most of the app connections fizzle out before we even go out. There are lots and lots of “expired” conversations. On the app that I didn’t renew, there are currently twelve expired conversations and two more that will expire in a few days if neither of us communicate. There were more, but I deleted those. Of those twelve, two were from out of town, seven were dropped by the other person (meaning that in the last text message, I asked a question and never got a response), two were dropped by me, one was a date in which I said, text me later and she never did. Normally, I would assume that I’m the common denominator and therefore, I’m the problem, but I think it’s the collective fatigue with the apps that’s the problem. Shrug, fatigue.
In her profile, “Nancy” had a link to the article, “Against Chill.” I read it so that I could reach out and comment. I try not to comment on people’s pictures or looks and prefer to go for something more substantive. What better way to show interest than to read an article she thought was funny. “Against Chill” isn’t the only screed out there taking issue with the chill mindset that has overtaken modern dating. The general criticism is that people who are chill are overly dispassionate. They roll with the punches a little too much. They don’t take risks because taking risks isn’t chill. As I read the article, I noticed similarities with my current approach to dating – I might be described as chill. When I reached out, I told Nancy that I read the article, thought it was funny in the nervous, ha ha, no no I’m not chill like that sort of way, but maybe a little. We texted once or twice, she asked if I had plans for the summer. I said not really, and asked her the same question. That was a couple of days ago. I may or may not hear back, and it’s too soon to write it off. I can be chill about it.
The apps are intentionally misleading. Their goal, I believe, is to keep you hooked and keep you swiping. When I was a paying subscriber, I could see who had swiped on my profile. I had whittled the number down to just over 150 people. There were a lot of nos for a lot of different reasons. The rest were maybes. There were very few hell yeses (what’s the plural of yes). I wish there were more hell yes types. No sooner did I let the subscription lapse and the number jumped to over 400 likes. They want me to believe that I’m missing out or that my connection is just around the corner. I secretly told myself that when the subscription lapses, I’m gonna delete my profiles – take a week or two or three off. I’ll give the “active” conversations another day or two… but at this point, I’ve probably written them off. Momentum is difficult to establish when you wait two, three, or seven days for a response.
And that’s the thing – chill is the collective sigh from a dispassionate online dating scene. Chill is the result of dozens of small rejections or missed connections or conversations that go nowhere despite everyone saying they want to have deep conversations. Chill is a defense mechanism or, only slightly better, a way of managing expectations. Chill is cynicism masquerading as being too cool for school. Online dating, at least through the most popular apps, has become a race to the bottom, a competition in who could care less (cue the Ben Folds song). I don’t think most people on the apps are being intentionally guarded or aloof, it’s just that nobody seems willing to extend effort because nobody else seems willing to extend effort. Where before (meaning a few years ago) everyone agreed that online dating sucked, at least then they seem to hold out hope for something better, fight for those last few shreds of possibility. Now, people are still in agreement that it sucks but instead of fighting or trying or hoping, there’s the well-worn shrug of acceptance, “it is what it is.” It’s not that not caring is cool, it just seems to be the only option left.
There was a time in my life, maybe seven or eight or nine years ago, when connecting with people was not only a priority, but was fun. It was less chill and more purposeful. Risking something seemed authentic. I met and went out with a lot of interesting people. Some of them, I really liked. Some of them had partnership potential. The many who weren’t good matches helped me better define what I was looking for. None of that rings true today. Now, the only thing I seem to be learning from the non-matches (and everyone seems to be a non-match) is a deepening sense of indifference. And because of the years that have passed, I can’t tell if it’s a me thing, a them thing, or a this is just how it is thing. I’d say it’s exhausting, but that would imply far more effort than is being expended. The truth is, I seem to rule lots of people out before we even begin, and then when I “try” the effort or interest isn’t reciprocated which only reinforces the “chill” approach, only reinforces the feeling of, “meh, whatever.”
With the twenty-seven year old at the bar, I said, I think it’s a numbers game. She hated that I was putting “love” or finding your person in such crass or practical terms. She wanted to believe that connections are magical and natural. I used to believe that too, maybe still do. I didn’t outright disagree with her, I just said that you may have to wade through a lot of meh to find that magic. It’s a numbers game. Out of the over fifty or sixty people that I went out with, maybe four or five or six held real possibility. I didn’t keep track of how many non-starters (expired conversations that never materialized into meeting up) there were back then, but it seems like there were far fewer of them. This seems to be the choke point now. I still think it might be a numbers game, and while I may want the end result (everyone says they want the same end result – someone to adventure with someone to share life’s ups and down with), I’m wondering if I’ve grown too chill to play the game. Maybe, like her, I should get the cabin in the woods or the van by the river and just chill out. At least then, I wouldn’t be telling myself, “this isn’t the look I’m going for.”