Online Dating For the Romantically Hopeless (Pt.1)

The title for this series comes from a book I had as a child, Country and Blues Harmonica For the Musically Hopeless. It was part of the Klutz series of books. Other entries in this series offered instruction on how to juggle, do hacky sack, and play various card games. I had them all! I never learned a single one!

A self-inflicted crisis with universal causes

On Substack, the British writer Ian Dunt posted a newsletter entitled "How to be a Man." On Bluesky, he teased it by saying "the left is completely silent on the issue of men getting laid," which is just very funny. Imagine Keir Starmer (since Dunt is in the UK) or Joe Biden releasing a 10-point platform intended to address the growing crisis of men not getting laid. Also, note the choice of "getting laid" rather than "finding love." Even as Dunt provides perfectly serviceable advice to young men on how to exist in the world and interact with women (or other men, for that matter), he still presents it using the language of vulgarity and objectification. He still presents women as means to a certain end and not an equal variable in a complex equation. While claiming to offer a counternarrative to the "manosphere" – a nebulous constellation of podcasts and fitness influencers for which Joe Rogan acts as a synedoche – Dunt immediately cedes the rhetorical ground.

I do not, personally, have much investment in men getting laid. But as many people responding to this have pointed out, very few of the things Dunt discusses here are exclusive to men. Rejection is hard on everyone. No one is having a good time dating. The difference is that other people's loneliness is not seen as a national crisis. It's seen as simply a fact of life. Young men – and let's be clear a certain subsection of young men – struggle so much partially because they have been raised to believe that they are entitled to the women of their choosing as a reward for being such good boys. This belief prevents them from doing the very things that would help them be more appealing to the women they desire. Patriarchy is the cause of these young men's problems and also why the rest of us must care that they are such failures.

However, I am also someone who has historically really struggled with dating and I know it sucks. In addition, many of the issues that plague these young men — entitlement, self-pity, a general inability to see others as fully formed humans — are increasingly present in other populations: adults, queer people, women. I think apps — and not just dating apps but apps more broadly — have brought about a type of cultural narcissism. Our dopamine-addled brains have been so conditioned to convenience and ease, to seeing ourselves as the center of an algorithmic universe tailored to our needs that we have lost the capacity to connect with each other in authentic ways or to accept disappointment, loss, or frustration. Therapy culture has told us we need to “protect our peace” and set boundaries with “energy vampires.” Our friends should not burden us with their problems. Our partners should be more appliances than people — there to provide validation on command and shut off when we’d rather be alone. If a relationship fails, it’s because our ex was avoidant or a narcissist, not because we were incompatible or failed to treat them well.

Everyone is very down on dating apps and I don’t blame them, exactly. But they’ve been a really useful tool for me and I think most people’s issues are their own, not that of the apps. Similarly, a lot of the therapy concepts that get distorted on Instagram are also real and useful. It’s just that people use these tools to justify their own dysfunction and vilify others. They use them to avoid accountability. Everyone’s healing but nobody’s getting any better.

But I’ve gotten better. And not just at dating. Like, dating is just one avenue of life. Most of the skills you need there you need everywhere else. (And when I say I am closer to being "good at dating," I mostly mean it no longer fills me with dread and anxiety.)

A Series of Unfortunate Events

Let me establish my bonafides re: dating. Three years ago, I was pretty much ready to give up on the enterprise entirely. Two years after the end of a five-year relationship, I got back onto dating apps and found myself immediately falling into familiar patterns that had dogged me during my last sustained period on the apps (when they were just websites), sometime in the Obama era.

During that time, I went out on many pleasant but unpromising dates with perfectly lovely people. I met two women who I genuinely seemed to connect with and who I thought I would enjoy spending time with. I never really got to find out. They could never commit — either to consistently going out with me or to leaving me alone. Much like Charlie Brown and Lucy, I extended them benefit of the doubt again and again and every time they did the same thing they had done before. One of them — the Grad Student — would just disappear for days or weeks after our seemingly great dates before sheepishly reappearing with an overwrought apology. I would relent. We'd go out again. She'd disappear again for days if not weeks. Lather, rinse, repeat. She eventually just disappeared forever. I didn't take it well! (She randomly showed up a while back on Instagram in a photo carousel of a writer I follow. Never go out with anyone associated with Harvard!)

The Frisbee Player would say she would do something – get in touch, follow up, etc. – and then just not do it. I would assume – as I generally assume when someone shows me so little consideration – that we were done. And then she'd reappear, a few days to a week later with no acknowledgement that she had failed to do what she'd said she would, or even any acknowledgement that she'd ever said she would do it. This continued for some time and each time this happened, I grew slightly more deranged. I finally grew bored of her after she butt-dialed me one night and left me a several minute voicemail that recorded her talking about me (in the very casual way you talk about someone when you are certain they cannot hear you) to her friend. I was honestly deeply relieved but that relief – and what seemed like clarity – was cut short when she reached out to me mere minutes later via Gchat...to not take any accountability for this, either. We somehow ended up hanging out one more time for reasons that remain baffling to me more than a decade later. I looked her up some years ago. She married some Frisbee-adjacent dude. (Like, this girl played in some rather elite co-ed team that would do a lot of traveling and that was part of some broader, very insular Ultimate Frisbee "community." It's why she could never hang out!)

I guess these might be what the kids call "situationships" but honestly they were just really unfortunate situations that left me feeling rejected, confused, anxious, and stupid. And that lasted forever. Together, the Grad Student and the Frisbee Player took up a year or more of my life.

It was only as I approached the end of my time in Boston (this was in Boston) that I finally met someone — not on the apps, but rather through the only group of dykes who have ever been vaguely nice to me. (I treasure you!) My therapist knows this person as my “good girlfriend.” (And even she just stopped returning my texts six or so months after our mutual, amicable breakup.)

Going even farther back, there's Maureen, the first woman I was ever involved with. Things were great – if very undefined – between us when we were on different sides of the Atlantic Ocean but floundered as soon as we were in the same ZIP code. I can’t confirm it but I believe that Maureen took a last-minute transatlantic flight because I told her I would be in her hometown, Columbus, Ohio, ahead of a potential move there that fall. She had, up until a few days before, been planning to go to Spain from Belfast, where she was getting a master’s degree in English literature. (Why? Great question.)

The visit did not go well. Beyond the fact that I simply did not appreciate being ambushed like that, she got sick from her flight and could barely talk, our online rapport completely disintegrated in person, she and my future roommates didn’t get along, and she insisted on going out dancing (it was Pride weekend) only to completely shut down once we got inside the club — after standing outside in the drizzling rain for 30 to 45 minutes following a long day spent in the sun — and refuse to speak. I was like, "Hmmm, maybe not."

In the year in which we lived in the same city, we mostly took turns being mean to each other. (I also managed to develop an aversion to Dr. Who, one of her favorite shows.) I remember one night, towards the end, when she invited me out with her and one of her roommates, a twink named Jamie whom she did not particularly like. (In Jamie’s defense, Maureen hated everything!) I was even supposed to serve as some kind of buffer. Miraculously, and coincidentally with me as a sacred witness, she and Jamie connected in ways they had never connected before. Laughing, joking, just having a grand old time. I was not included in the fun, however. Maureen would occasionally glance over to confirm I was taking it in but I was never invited to participate in any meaningful way. I said maybe four or five words the whole night. I eventually wandered off. Later on, when it was clear that I was hurt (she did eventually notice I was gone), she was remarkably put out, like “God, you don’t have to take it so personally.”

Come August, I moved back to Boston and she went to Philadelphia for law school. The week before our respective departures, Maureen set her iChat to display her current iTunes song (I had showed her how to do this), and then listened to “Call it Off” by Tegan and Sara on a loop for hours for several evenings in a row. (Just an extremely 2008 sentence.) I was like, “I will not be engaging with this childishness.” As soon as hundreds of miles were between us once again, she was very eager to reconnect and eventually drunkenly declared her love for me over Gchat. I blocked her.

Then there’s Rachel. Rachel was the first woman I met from the internet. She immediately dumped me for someone else but asked if I wanted to stay friends. I had just moved back and didn’t have many lesbian friends, so I said yes.

When we hung out, Rachel would mostly complain to me about Natalie, the person she had dumped me for. I got tired of this, and hoped that our “friendship” would just peter out if I did not nurture it. Unfortunately, Rachel would allow only about three weeks to go by without hearing from me before she would reach out. We lived very close to each other. It was winter. I faced a choice: spend a slightly awkward hour with her at a pub in Washington Square or explain to her over email that I did not like her as a person. I kept choosing the first thing.

Eventually, I started going out more — and I cut my hair off — and Rachel’s attitude toward me began to change. She had dumped Natalie by this point — and I came to have a lot of sympathy for Natalie, Rachel was something of a sociopath — and was seeing someone named Mikey. But she was getting increasingly handsy with me. This was quite awhile later, after the women I’d met online had been so disappointing, so I was feeling pretty wounded and was generally compliant. One night, possibly on the way home from a Robyn concert at the House of Blues near Fenway, Rachel informed me that she was going to break up with Mikey so we could date. I was like, “Hmm, I don’t think that’s a good idea.” But I didn’t verbalize this to her because it would be awkward. It's hard to tell someone that they aren’t really into you, they’re just into your perceived unavailability and once the obstacles are out of the way, they will realize it was the obstacles they found intriguing and not you. So I didn’t say it. I was like “If that’s what you want!” So she dumped Mikey, immediately regretted it (she looked frankly bereft when she arrived at my apartment), we had one of the most awkward sexual encounters of my life, and that was that. It did allow me to stop returning her emails, however.

There was other, more minor drama, like that time I got involved in something of a love triangle between the two members of this folk pop duo. I liked one, who I think liked me back, but the other one really liked me and I was like, “This is stressful, I will simply not date either of you.” Oh, and my friends really liked the one who really liked me and kept just inviting her to our social events, which I did not enjoy. She eventually dated one of those friends for a couple of years and, well, let’s just say I dodged a bullet there. (It's nice for my taste/judgement to get a win once in a while. Among the reasons I wasn’t interested — though these things really aren’t rational — is that Atlas Shrugged was one of her favorite books.)

What about more casual things, Lauren? Well, that’s not really my jam, either. The one time I can remember taking someone home with me from a night out, it was very stressful. (I randomly went out to GQB….by myself?) Like, first off, she had to talk me into it. There was a lot of coaxing. I was very drunk. She was a sexologist from Montreal (they apparently have those there) and very nice. I figured since she lived in another country, there was little risk. Like, what’s the worst thing that could happen?

The next morning, I woke up so hung over I could barely open my eyes. I received a text from her asking if I would come meet her before she got on the train to go home. I told her the truth, which is that I was so hung over I could barely open my eyes. She did not believe me because she kept asking, with greater and greater urgency, which caused me, already not in a great state, to get more and more anxious and upset. (I don’t enjoy disappointing people but there was no universe in which I could rouse myself and go out in public and certainly not for a woman I barely knew. I was not even to the Gatorade stage of my recovery.) Like, was something wrong? If there was, why wouldn’t she just tell me instead of insisting I come meet her when I had told her again and again that I couldn’t? What was I supposed to say, when the truth did not satisfy her? (It's low on my list of grievances, but the fact that women so rarely believe – or take seriously – the true things I tell them is very annoying. ) The more she insisted, the less interested I was in going (and going was already impossible!). It was such a hassle that I basically decided I would never take anyone home with me ever again. It was just the same annoying bullshit I got from dating, but with additional helpings of stress and anxiety.

So, like, it’s just not been a fun time. Women get very weird about me. They both are never casual about me and also are incredibly and deliberately casual about me, to the point of cruelty. “Oh, sorry, did you expect me to include you in this conversation just because I invited you here? Whoops!” “Oh, yeah, sorry I did not return your text for five days — had more important things going on.” "I need you to come meet me no matter what's going on with you, which I don't believe anyway."

When I got back on the apps in 2021, my only real goal was to...not do any of that stuff again. No more ambivalent people who can't make up their mind or give me the slightest bit of consideration.

Unfortunately, I proceeded to do something like "that" three times. The last one was particularly upsetting and, while I congratulated myself at the time on not wasting months of my life being jerked around by this person only to be unceremoniously dismissed (this particular Lucy only got a couple of additional opportunities to yank the football away), it was still pretty discouraging.

I thought it was probably just time to retire from the game entirely. Like, what was the point, if this was just going to keep happening? I could learn another language, adopt another cat — literally do anything that was even slightly rewarding instead of more of this.

But there's something about being ready to throw it all away that opens up a new sense of possibility. Maybe I could try something different. If there was nothing to gain with the old way (ya know, Winging It), there was nothing to lose with a new one. Like, statistically speaking, it seemed there had to exist, somewhere, a woman I would connect with who would not treat me like a toy she could just pick up and put down as it suited her.

In the three years since, I’ve done a lot of stuff. But the most important thing, the thing that undergirds everything else, is that I had to take responsibility for my own experience. Maybe you can even see that in the stories I’ve told in this post. In most of these situations, I could have put a stop to things — to my confusion and misery — at any time. With Rachel and Maureen, especially, it wasn’t until they made a huge mess that I could even bring myself to cut them off, long after it had ceased to be anything resembling fun (to the extent it had ever been fun at all). With the Frisbee Player and the Grad Student, I could have simply stopped responding and saved myself a great deal of suffering.

And a lot of people seem to have similar problems but not much self-awareness. On our relationship-obsessed social media platforms, I see a lot of Charlie Browns complaining about how they charged at the same old football at full speed and, wouldn't you know it, their own personal Lucy – or the latest iteration – humiliated them again. And, well, I've never seen this show, but I think I'm using this GIF correctly:

And the Lucys of the world do bear responsibility for their part in things. But, as we know from years of Peanuts cartoons, Lucy isn't going to change. (And sometimes Lucy is an actual person and sometimes she's just a set of circumstances.) Lucy enjoys the football gag because of how gullible Charlie Brown continues to be! Charlie Brown keeps going for it because it would, in fact, be nice to kick the football. It'd be nice for Lucy not to be so mean. But that is not the reality. The only way to earn Lucy's respect is to stop taking the bait, and to do so, you must accept that you will never kick the football. There's no magical solution where it all works out and you get what you want. Some things simply cannot be resolved and certainly not by doing the exact same thing and wishing for a different outcome.

This metaphor is getting away from me a bit, so I'll wrap it up. In my next post (published who knows when!) I'll talk about one of the core tenets of Buddhism, Realistic View, which requires you to embrace the inevitable unpleasantness of existence. Til then!