Overthinking overthinking my love life

I have a problem: I think too much. I try to solve problems by thinking that are better solved by acting. Then I try to solve my overthinking problem by thinking about how to solve it.

Or, maybe it's more correct to say that I am bad at overthinking.

I'm going to try and remedy this by overthinking my overthinking.

I.

Lately I've been thinking a lot about my love life.

I started partner dancing to meet women — I had lots of other good reasons to do it that, in some sense, may have been more valuable, but I probably wouldn't have picked it if I didn't expect to meet women that way. I wasn't and am not out only to seek whom I can pick up — but that does matter to me as much as the fun of dancing itself.

So I find myself reflecting on how that's working out for me.

In one sense, it's working: Dancing certainly brings many wonderful women into my life, some of whom are (potentially) singles I am interested in dating. Some of those live close enough that it is logistically possible, and some of those seem not clearly opposed. I've met one such lady that I think is actively interested. That's a huge leap forward from where I was in early 2024.

I'm not content, though, to have women I'm interested in dating merely passing through my life. My dance partners don't have to like me back, but I haven't advanced my love life if I haven't met any who like me back. That would suck.

And it's not exactly the case — but it feels like it isn't so far from the truth. I've been dancing for eight months now. I met one woman I liked who liked me back enough that I think she might be interested enough for a first date. That's a flow rate of at most 0.125 first dates per month. It would be foolish to simplify my whole love life down to a flow rate, but it's not a great sign for my love life's health.

It's not that the time went to waste. I really enjoyed it! Even if dancing never gets me a date, I have had a great time and I want to keep dancing. But dancing doesn't for me a whole life make. I want to have a love life, too — and clearly something is going wrong with that.

The question is what.

II.

I'm going to think about my love life like a sales pipeline. I know very little about sales, but I have a vague understanding of how pipelines work and I'm going to run with it.

I think I'm placing an okay number of "women of interest" into my life. I count about ten so far. It works out to about one a month. Though in another sense this is undercounting them, because I met probably another four to ten who showed up for a few classes and then vanished — so maybe it's more like one and a half to two a month. So, one to two a month.

Is that flow rate good or bad? I don't know, I know nothing about other people's love lives, it's certainly a lot better than I've had in years... but actually I think this is the wrong question.

I think what I mean is: Should I be trying to make that number go up or not? And that's a question of tradeoffs. So maybe let's try exploring other dimensions and circle back to that.

I've met one woman who seemed clearly mutually interested out of ten to twenty I met in eight months. That's a conversion rate of 5-10%. I'm tempted again to ask is that good or bad but the question is really what can I do to increase it and is that worth doing right now.

I haven't gotten as far as landing one first date, so that's as much of the pipeline as I have to analyze right now. Silver lining: That makes this simpler.

So, there are two dimensions I could work on here: Meeting more women or increasing my conversion rate. I could work on these independently. I could go to different, more popular events and venues, or more different events that have different associated communities, and might make "number of women I meet" go up. Or I could try to improve my conversion rate — a much gnarlier problem that I'm not totally sure how to approach. These are interconnected in a funny way, though, and I worry that it's very much suboptimal to treat these as two independent problems.

When I say it's suboptimal, I mean maybe I don't need to meet more women, maybe I need to meet a similar number of women who I like, but in a different context where they generally like me better. In other words, maybe I'm in the wrong context. Maybe I can find a context where my strengths shine more clearly.

Unfortunately I have no idea what context that would be. My other strengths are mostly in nerd shit like programming. Nerd spaces are notoriously not a great place to meet let alone pick up women. I am good at writing, but not impressively good. I don't think I'd fare better in a writing group than in my dancing groups. And I might be forgetting something important but I think that exhausts my list of other strengths (that have an associated local community where one could meet women). So that seems like a non-starter.

This suggests I should work on the two problems independently.

IIa.

Plausibly I could meet more women if I went to bars/clubs. (I'll just say bars going forward; honestly I'm not sure what the difference is.) I have a dancing friend who says it's a better place to pick up women than the dancing scene. Going to bars is not my favorite idea, though.

I worry bars aren't the right place for me to meet more women, on several levels. I'm an autistic nerd and I don't drink. I could start. The idea of starting to drink worries me. I have toyed with the idea anyway, with setting guidelines for myself to keep me from getting into too much trouble. That doesn't totally assuage my worries. But there are other issues, too.

I want to meet a woman who, among other qualities, wants to have kids and who might make a good mother. Will I find her in a bar? I am skeptical. My cousin in college used to go out to bars with friends and often saw herself as her group's "mom." If I squint I can see where the "group mom" role might correlate with wanting to be a mother or making a good one. My cousin doesn't want kids, so it's clearly not a slam dunk, but okay, maybe there's something there. But that role could also signal bad qualities — maybe she is enabling her friends' bad habits, like maybe they drink more than is good for them, and maybe she takes too much responsibility for them in a way that's bad for her. And outside of that I think being in a bar is a slightly negative sign for parenthood qualities.

I'm not saying a person is a bad parent if they drink. I know at least one mom who drinks, and she seems like a good mom. I know at least one dad who drinks, and he seems like a decent dad. But it's a slightly negative sign. Drinking is optional, it's not great for one's physical or mental health, and the fact that you're doing it anyway says something about you. What exactly it's saying depends on the person — some people are social drinkers and they seem to manage it in a way that's healthy enough for them, and for those people all it says is "this is how I hang out with people." But drinking says something about everyone who does it, and many of the somethings it can say are not very good re: fatherhood or motherhood.

Arguably that is a skill issue. Maybe I could find the responsible motherly types by paying attention to how they are drinking — what, how much, how quickly. Maybe the right way for me to go about meeting women in bars is to meet them and abandon ship if she drinks more than I find reasonable. I am unhappy to admit that that is an entirely sensible argument and I ought to be compelled by the strength of logic presented — 'cause I don't wanna go to bars to meet women.

Because I don't drink, I've got a couple problems to solve if I decide to start drinking to meet women at bars. I've got to find something to drink that I am not tempted to drink too much of. I've got to learn bar norms. And most importantly, I've got to get comfortable spending time in bars, otherwise I'm going to have a horrible time and won't do a good job of flirting and won't want to go back the next night to try again.

Going to bars is probably the most promising in terms of increasing the raw number of women I meet. I keep seeing headlines about how Gen Z drinks less than any other generation, and I'm right on the edge of counting as Gen Z, so that's potentially a downside to this venue. But I don't know of any canonically more popular place for women to hang out and potentially meet men.

I can think of lots of other venues that are likely to have women with more interesting qualities. Art galleries, art shows, local music events, bookstores, book clubs, coffee shops, athletic classes and clubs, cooking or baking classes... okay, maybe I have run out of ideas but clearly are other options. But I doubt if they are better places than a bar or better than dancing as places to meet women I'm interested in as potential dates. I think they'd present environments roughly as challenging as dancing – if not moreso because there's no excuse to touch each other. Given all that, I don't think it makes sense for now to try anything beyond dancing events and bars.

(I might be wrong but if so there is some other factor I'm overlooking and obviously I haven't thought of it myself, so please tell me if you see something.)

I do think there's some gain to be had from attending other kinds of dancing events. I met that one lady I like who I think likes me back by going to a Latin party, where I normally frequent two or three venues that hots recurring ballroom and swing dancing events. I could branch out a little more and attend e.g. the Hepcats event, or spend more time at Latin dancing events, or go to Louisville where I know there are probably at least (checks notes) four ladies I like who haven't shown anything I read as disinterest. I could go to the line dancing events more often — I know of one lady I like who goes to those sometimes, and I've seen two or three I might like at the events I've been to. There are at least two other dance studios that host parties and I could check those out sometimes. I've got options for branching out within dance events, and I've already made plans to check out some of those options.

The elephant in the room is dating apps. I've said before I don't think those are a good option, and a friend who would know from experience and who I trust has seconded that opinion. I don't see any reason to explore apps further at the moment — they seems like a lot of work that fail to generate matches that are in any sense successful.

IIb.

That's every option I can think of for increasing the number of women entering my life. What about increasing the conversion rate? I said that's a gnarly problem and I didn't know what to do about it. I meant it. I can think of options, but they all seem like a lot more work than my options for meeting more women. Generally though I think this all boils down to improving my "game."

"Game" means flirting, in part. But it also means actually attempting to play the "game," and that's a challenge in itself.

I'll give an example. I met a lady a few months ago. I thought right away she's kind of cute. I knew off the bat she's creative because of what she's wearing. I danced with her, it's fun enough. I talked to her a little bit and learned we have a shared familiarity — maybe a shared interest. So I'm kind of interested, and at this stage she's not obviously uninterested.

I don't show that I'm interested, though. I make friendly conversation but that's it. I don't go out of my way to talk to her. I don't touch her except as necessary for dancing. I don't give any compliments that I can remember. I don't do anything at all that would hint that I'm interested. Hell, an older guy passing by overhears about our shared familiarity and he makes a joke in a way that sets me up for some fun with her — which I appreciated — and I don't do anything with it. I'm asleep at the wheel — I'm not even in the game.

And this is not an isolated incident, this is a regular occurrence. This is how I generally deal with women I meet and like: I show interest only if they show it first. Otherwise, it's just friendly, and fairly distant at that — I have no interest in being a Nice Guy, or being just a friend to women I already know I'm interested in as more than that, this being a serious risk factor for becoming a Nice Guy. Unfortunately this default strategy for dealing with women I like isn't working well for me on any level.

It isn't working well for me in at least two ways. The obvious sense is that I'm not getting dates by hiding my interest, and I'm also not crossing women off my list of candidates. The other sense is that things get to feel awkward with the woman. Things feel awkward for me, sometimes intensely so, and I think our interactions feel awkward at times for the woman too. I don't know what it is, it's nothing obvious to me, as I said I avoid interacting much with them so it's not that, but maybe it's in my body language. In any case, it seems I am not excellent at hiding my interest and that makes things tricky for both of us. It must be much better to be up front about it.

So, what I really need to do is get in the game. I need to get in the habit of playing. I can't succeed at flirting if I never try.

Unfortunately, I know only heavy-handed ways of showing interest. The one I'm most comfortable with is personalized variations on You're cute and I'd like to take you for coffee. I've only used that line once and only contemplated it in two other cases, because it seems like such a leap from you're cute to I'd like to take you for coffee. I barely know her, and I like her but do I like her that much? It's not that much financially, or even time-wise, but it feels bigger in terms of the emotional cost of saying this. Maybe that's a skill issue — I can see where maybe if I did it more often it would feel less sudden and under-justified, just a thing that I do, just the way that I am. Maybe I should act like a man with a hammer and just do a whole lot more hammering.

I have one softer option. I'm happy giving compliments and I often do, and sometimes it even seems to register as flirting. I am working on that last part. Switching from "I like that [dress, nose ring, etc.]" to "that [dress, nose ring, etc.] looks great on you" seems like a promising direction to work with where available — it's subtle but seems like it better indicates more-than-friendly interest. This isn't an option with every compliment, though. I'd like to have more tools than this and the date-hammer.

One option would be to touch women I like more. The easy option that every dating advice post I've ever read has mentioned is the arm — gently touch her elbow, for example, to emphasize a point in whatever you're saying. That's only barely out of my comfort zone — it's not too scary, I could do that with a little effort. But my comfort zone with women has been well inside the "safe zone" (friendly zone) for a long time now, so I find that is actually a bad sign rather than a good one. I figure that if this level of touch is just outside my (very safe, just-a-friend) comfort zone, it is not direct enough. I am hoping for something that a woman could recognize as more than my just-friendly way of treating women so she can respond accordingly as she's interested or not interested.

The harder option is the lower back, and as previously discussed, that's an exciting but terrifying option. That seems plenty direct. It is maybe too direct! Or maybe it is just the right amount of direct — it's not an ass grab (obviously too much, unwanted in 99.9% of cases it's attempted) and yet the small of the back is clearly not a place a man touches his sister. I am almost certain it is not too subtle a sign of interest. In theory, I could see it being either too far ("that's really close to my ass, it might as well be my ass!") or just far enough ("hmm, close to the danger zone but it's not in the danger zone, I'm okay with this"). Probably it varies by the woman. I think touching a woman's lower back is worth trying in real life to see if it is a good idea or a terrible idea in practice.

Banter is the canonical way to flirt. Banter includes teasing and game-playing. I think teasing is not a good fit for me, and here's one guy's case against this form. That leaves playing games, primarily verbal ones. (I think other games also count as flirting but not as banter.) Unfortunately, I don't understand the kind of games that I think of as banter — telling white lies so she can pretend to be offended, or saying outrageous true things so she can pretend to be offended. There are probably a lot more but I can't think of any off the top of my head. I expect I'd be pretty bad at games like the ones I've listed, and probably many others I haven't thought of too. I might be able to learn to play them but I am not sure where I would start. Ideally I'd start with a simplified game that is still fun enough and branch out from there but I don't see anything like that that would fit naturally into a conversation. I'd love to learn about better options for me, but as it is this seems like a dead end.

Besides "let's go on a date" or compliments or banter or touch, another option might be body language. I worry this is too subtle a game for me to play though. I'm not sure if I could get out of my head enough to (a) display the right signs, and (b) recognize the body language I'm getting back from her as interested or not, unless if were very clear(ly interested). The advice is out there and seems reasonable enough. This seems even harder to work on than the lower back touch thing, though, because it's so subtle. It might be worth learning anyway, but I would like to consider other options.

A Second Person post discussed ideas for getting better at flirting. Maybe that's worth taking seriously. I paid for it, after all.

I started this by talking about flirting and "game," but there are other things I could do to work on my conversion rate. I think I'd look and feel a hell of a lot better if I gave up on my hair that's falling out and shaved my head. It's not that weird anymore, it's not a skinhead thing, I know five different guys with shaved heads and it looks good on them. I think it'd look good on me, too. I could dress differently — I think I dress quite well in a dancing context so it's not worth doing there, but I could dress nicer for everyday occasions, for outings like going to a bar. I could try and fit strength training exercise into my day, although that's a heck of a challenge between everything else I do with my day (dancing, SRS flash cards, meditating, work, reading and writing). Maybe there are other things.

It ought to help to improve my mindset. Proceed as if they already like you, that's what one post I read recently suggested, and a recording from another source agreed as discussed in another post. Maybe that's something to try on and see if it helps.

I didn't mention working on my confidence/comfort level/anxiety, did I? I am already going to therapy and meditating and dancing. I've taken an improv public speaking class and some coaching. All that ought to have some effect and it does, but it is a long-term project — months and years. If I knew of a faster or more effective approach, I'd one hundred percent be doing it. So far a fast approach has not appeared.

III.

So in summary, what seems maybe worth trying?

• To meet more women:
  • Habit seed/life changes: Go to bars.
  • One-time behavior: Find a drink I am not tempted to drink too much of.
    • This should be easy, as I understand it many drinks taste terrible.
  • One-time behavior: Ask a friend who goes to bars about bar norms, explaining that I'm literally autistic and never go to bars.
  • Habit seed: Remind myself that "I belong here" when entering a bar.
    • Thanks for the idea, Chatty G.
  • Habit seed/life changes: Go to dance events I wouldn't normally.
    • That is: Line dancing, HepCats, Latin parties, Louisville Let's Dance, other studios' parties, etc.
• To improve my "conversion rate":
  • Habit seed: Play the game. You idiot. Flirt, god damn it, flirt! Flirt like you're not just her dorky brother!
  • Habit seed: Proceed as if they already like me.
  • Habit seed: Frame appearance compliments as personal: "That [whatever] looks great on you."
  • Habit seed: Touch women I like on the arm, or (hard mode[, ETA: maybe most appropriate in a bar or club]) the small of the back.
  • Understand and implement body language changes
    • Habit seed: Mirror their body language a little.
    • Habit seed: Pace and lead.
    • Habit seed: Subtle head tilt.
    • Habit seed: Other shows of vulnerability.
    • Habit seed: Consciously do/hold an eyebrow flash when meeting a lady I'm interested in.
    • Habit seed: Smile better, more slowly.
    • Habit seed: Make longer eye contact.
    • Habit seed: Break off eye contact more slowly when I do.
  • One-time behavior: Analyze the Second Person post and write a plan (like this one) listing concrete ideas for how to apply its suggestions in my life.
  • Reminder: Sure would be nice if I could fit some strength training in somewhere.
• One-time behavior + habit seed: Shave my head
• One-time behavior: Get nicer everyday clothes — maybe some linen or flannel shirts, nicer casual shoes (chukkas?), maybe replace the pants, get a casual watch I like...

Okay, that's a pretty solid list. I think that's a comprehensive enough plan for now. It's not 100% of a plan, I still have to decide which of these I actually want to do in the near future, but it's a start. I should check back in a month or two and see how it's working for me. But these are all good ideas to try.

IV.

Oh right, this was supposed to be a post about overthinking my overthinking. Let's circle back to that real quick.

See, I think David MacIver's got it right when he suggests I'm not very good at it. Here's the problem: I worry about it but I fail to address my worries. I write about the feeling and maybe a solution but I overthink the solution — do I want to do it? — instead of writing down what it would be and contextualizing that against all the other worries competing for my attention under the broad-umbrella life concern I'm worrying about. What I need to do is write something like this post where I lay it all out in excruciating detail so I can get the whole picture at once and feel like I've adequately addressed all the things I'm worrying about at once.

Maybe. I mean, it seems like it helped tonight. Can't guarantee it will help forever or next time, but it seems plausible. Although this post took like three or four hours to write so it's not something I want to try every week.

What I worry most about these days is my love life. But now that I've written a detailed discussion of that and an actual plan for what I could change, maybe for a little while I can stop worrying about it. And maybe next time I can take this analysis as a starting point and it will go faster. Maybe I can worry productively.

What a thought.