There's a lot of data and research on what makes people successful at online dating, but I don't know anyone who actually tried to wholeheartedly apply this to themselves. I decided to be that person: I implemented lessons from data, economics, game theory and of course rationality in my profile and strategy and OkCupid. Shockingly, it worked! I got a lot of great dates, learned a ton and found the love of my life. I didn't expect dating to be my "rationalist win", but it happened.

Here's the first part of the story, I hope you'll find some useful tips and maybe a dollop of inspiration among all the silly jokes.

P.S.

Does anyone know who curates the "Latest on rationality blogs" toolbar? What are the requirements to be included?

 

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67 comments, sorted by Click to highlight new comments since: Today at 10:49 AM
[-][anonymous]8y140

"Why are people seduced by the pernicious meme that finding love requires no deliberate effort?"

Possibly because relaxing about their dating prospects makes them more attractive. For people whose effort looks like desperation, they may have better results if they stop trying so hard.

EDIT: I think I just did the thing that has been annoying people. I searched for the contrarian statement I could make, rather than any other type of commentary or response. I'm sorry.

I think we may mean different things by "effort".

I referred as effort to the invisible things you do behind the scenes to maximize your odds, like spending hours reading profiles, crafting strong messages and analyzing your matches. I broadly agree that when you get to the visible part, i.e. going on the actual date, you probably shouldn't treat it as intense labor and relax into who you actually are - more on that in Part 2.

[-][anonymous]8y60

That's a good distinction, and obvious in retrospect. Thank you!

I'm interested in Part 2; I'll keep my eye out.

For people whose effort looks like desperation, they may have better results if they stop trying so hard.

Wow, you really hit the nail on the head!

No, I think it's reasonable. This is good advice for correcting the particular failure mode most people engage in, but it lacks sufficient... specificity, and results in a different mode if applied without discernment (which Jacobian's response does, quite usefully). So your comment furthered the debate, and added information.

I think you're misunderstanding. "Deliberate" need not be "desperate". There is a big difference.

[-][anonymous]8y40

"For people whose effort looks like desperation."

I think we're having an inferential gap issue here. There is "High effort, no skill" and "Desperate." These look very similar. Then there's "Low effort, low skill," and "no desperation," which also look similar. These often result in a massive improvement over "High effort, no skill." I'd bet on many people seeing that improvement and thinking it's enough; maybe they're satisfied with their results, or maybe they don't realize that better results could be had. Hence, the proliferation of the meme.

Then, of course, there's deliberate effort, which requires actual skill. "High effort, high skill" probably delivers better results than "no effort, low skill," and this article seems to be a good example of that.

I'd love to see the results of a large survey on how successfuly married people found their partner. Is the "love finds you" meme based in anything real? The most common anecdote that I've heard is of the form "I really wanted this person and I pursued them persistently until they settled for me".

[-][anonymous]8y90

My SO and I did not pursue each other relentlessly. Granted, the conditions of the area meant that I was under even less pressure than women normally are to be the pursuer. The area had very few women between the ages of 18 and 30. He didn't have to pursue me that much, either, but I am not sure if there were reasons beyond my personality.

I had just ended a relationship, he and I befriended each other, we expressed interest. We started dating officially a few months later, I moved in with him, and we got married 1.5 years later. We're coming up on our fourth anniversary and the relationship has been successful by all meaningful metrics. :)

The most common anecdote that I've heard is of the form "I really wanted this person and I pursued them persistently until they settled for me"

My fiance might describe it that way; she's more or less stated that she feels I'm out of her league. I'd define it less (which is to say, not) as "settling" and more "noticing that this relationship is emotionally healthy for me".

The whole concept of "settling" is... wrong. The goal of dating isn't to find the "best", by some criteria, person you can find, which is unfortunately how many people tend to see it. The goal of dating should be to find your complement; somebody who enhances you (and ideally, who you enhance as well).

[Edited: Typographical error corrected]

The goal of dating should be to find your compliment

Sorry if this comes across as needlessly pedantic, but the correct word should be 'complement', not 'compliment'.

I am not trying to put you down; I just thought it might be something you'd like to know.

Fixed, thanks!

What signs do you look for to identify a person who would compliment or enhance you in the way you describe? (i.e. How would you identify a person like this?)

Note: I agree with you and do very similar things for friendships. I'm curious about other people's methods to improve my own.

My minimal requirements were:

  • she doesn't mind that I have nerdy hobbies (programming, math...)
  • she also has some hobbies, so she doesn't require constant "babysitting" from me
  • if there is a problem to be solved, I can rely on her cooperation
  • she wants to have children in reasonable time horizon

This is probably better explained in negative, as an experience of traits that ruined my previous relationships. At some moment I became able to impress girls, even those I previously thought were "out of my league", by being smart and witty, a good dancer, and having a few interesting stories and impressing achievements in the past. The problem is, it probably created wrong expectations.

I like to go out and dance, once in a while, but I also love to spend a lot of time with my computer or debating "nerdy topics". I can be funny, but I also have some problems that I need to solve (such as procrastination, not being satisfied with my career, etc.). I do achieve quite impressive things once in a while, but my typical day is completely unimpressive (I go to work, come back tired, read some web, and go to sleep). So I guess the things that helped me seduce the girls seemed like false advertisement afterwards.

Seemed to me that the girls I seduced by fun and dancing often expected the whole life to be "fun and dancing". They probably expected the whole life to be just like at the college; at the beginning it seemed like I could provide such life to them, and when I disappointed them, they moved to someone else who seemed he could fulfill the promise better.

For a stable relationship, I need someone who doesn't expect the whole life to be like a college. Someone who can help me solve problems when they appear (and of course I provide the same in return). Someone who can spend their time with their hobbies, while I spend my time with my hobbies.

I got all this, and more. My wife enjoys reading SSC, and we can discuss that kind of topics. We also have similar ideas about upbringing children.

Unfortunately - I'm not sure. It took me two or three months to figure it out in that case, and while I remember the revelation that "This is a healthy relationship", I don't remember anything in particular sparking it.

If this relationship ends, I still don't know what criteria I'd use to identify what I'm looking for. (She messaged me on OkC, actually; perhaps the only woman to do so who wasn't threatening me or who hadn't read my profile at all, although I fixed the latter by making my profile picture deliberately off-putting to the sort of person who wouldn't read a profile in the first place.)

I agree vehemently and should have probably used a different phrasing. What I was really getting at is that in most anecdotes that I've heard - one person is significantly more enthusiastic to start off with (and I don't think this is necessarily a problem).

The "love finds you" meme would match up to lots of things. It matches up to "I didn't use a dating service or website to find someone and found someone anyway" and "I didn't make any effort at all to date and eventually ran into someone". I think that an eligible, decent-looking young person will find someone eventually (especially as the dating pool decreases as they get older and remain in demand), but just because a strategy can barely scrape by doesn't mean you should ignore much better options that are available.

If you want to find the best person you can and want to date people sooner rather than 'eventually', then Jacobian's ideas sound like a much much better strategy.

"I really wanted this person and I pursued them persistently until they settled for me"

Yuck.

I think the yuck-ness is pianoforte611's point.

Not exactly, see my response to OrphanWilde.

I decided to learn from and apply okcupid and related insights and had some minor success but there are confounders and it is still not on first position in my priorities list (which obviously is a serious impediment).

Does anyone know who curates the "Latest on rationality blogs" toolbar? What are the requirements to be included?

I suggest adding "customizable blogroll" to a suitable comment on the recent http://lesswrong.com/r/discussion/lw/n9b/upcoming_lw_changes/

I've enjoyed the article, and I look forward for the parts, though it required me three/fourth re-reads to dig out the actual tips, they are scattered and sort-of buried amidst jokes and story.

I get what you're saying.

My approach is that I'm a blog writer and not a dating consultant. My main goal is for my readers to enjoy what they are reading even if the topic isn't at the top of their interests. People who know nothing at all about soccer (like Scott Alexander) and certainly don't work in soccer development seemed to enjoy the Tails of Great Soccer Players series.

I see your comment as actually encouraging my style: people who care about the advice will dig a bit to isolate the tips, people who don't care about it will spend a fun 5 minutes and have a few chuckles. Do you think the writing would be better if it was more structured (i.e. adding an intro and conclusion with a clear list of tips)?

P.S. The day I start writing listicles, take me behind the shed a put a bullet in me.

Join https://www.reddit.com/r/SneerClub/

I certainly don't write well enough to be considered "porn" :)

It's true that my blog doesn't have a terminal value outside itself, although I will occasionally write about Effective Altruism topics.My goal is to have a popular blog with a lively discussion, my blog will be popular if people enjoy my writing. That's the goal in itself, I am not planning to turn it into a source of income or anything like that.

Different people enjoy vastly different things: I am getting overwhelmingly positive response on LessWrong, and overwhelmingly negative response on Reddit. That's a good thing: like a dating profile my goal is to find my specific audience and not write universal clickbait, and LW is definitely the audience I aspire to have.

To apply to a LW audience, I'm trying to:

  • Come up with genuine insights based on analysis rather than repeat common wisdom that's based on sounding plausible.

  • Be always willing to learn and be corrected, including offering a reward for people finding major errors in my posts. One person has deserved it so far for pointing out a serious factual mistake that I fell for because of confirmation bias.

  • Show my math. If you don't want to see me calculate the influence of outliers on a regression slope, the blog isn't for you ;) If I can't do the math myself, I won't take someone else's word for it.

  • Puns.

The above list is very different from what would apply to 90% of my Facebook friends, for example, and I'm OK with it. If I wanted 100,000 shares, I would write "27 ways how Bernie is actually a lot like Batman and Trump is like Lex Luthor".

True glory consists in doing what deserves to be written; in writing what deserves to be read

Pliny the Elder (via Civilization IV)

Do you think the writing would be better if it was more structured

Not really, but I think I would have enjoyed more technical details. I understand that this would have made your writing less universally appealing, it's just that the topic is quite dear to me and I can't seem to read enough stuff on the subject.

I'm not in the market for a date, but your post was interesting enough to get me to subscribe to your RSS feed, so kudos to you!

Two Questions:

  • I. One of the options on OKCupid is to message a person whose inbox is already full by paying $1. Have you used this option and what were the overall results?

On one hand I have a knee-jerk reaction to paying extra money to message someone specific who may not message me back. Also, any person who has their inbox full has had a lot of attention and already hasn't found someone. There are easily a handful of explanations for why that may not have happened (guys message too often, she's very approachable, she had a long conversation with one or two people who didn't work out, she's very picky, she has had the profile a long time and left the site but doesn't update her relationship status on there, or some other option)

On the other hand, any person who has their inbox full is unlikely to be recieving a lot of messages in the recent past. That distinguishes the person who pays the extra $1 to message them since the person being messaged will be in a situation that resembles being in low demand (recieving messages rarely). This places you in a smaller pool of competition than normal.

  • II. What are your thoughts on the usefulness of paying for the site's subscription service?

I can see the draw of joining a dating service that requires you to pay for access to it since a paywall instantly filters for a lot of things (though OKCupid seems like it might be good enough for the task). However, I'm on the fence about the benefits of the A-List subscription service for OKCupid. Have you tried it out at all?

"There are 729,500 single women my age in New York City. My picture and profile successfully filtered out 729,499 of them and left me with the one I was looking for."

I know this is sort of meant as a joke, but I feel like one of the more interesting questions that could be addressed in an analysis like this is what percentage of the women in the dating pool could you actually have had a successful relationship with. How strong is your filter and how strong does it need to be? There's a tension between trying to find/obtain the best of many possible good options, and trying to find the one of a handful of good options in a haystack of bad ones.

I'm somewhat amazed that you looked at 300 profiles, read 60 of them, and liked 20 of them enough to send them messages. Only 1 in 5 potential matches met your standards for appearance, but 1 in 3 met your standards based on what they wrote, and that's not even taking into account the difference in difficulty between reading a profile and composing a message.

You make a big deal about the number of people available online, but in your previous article on soccer players you implied that the average had a much larger effect on the tails than the average did. If you're really looking for mates in the tails of the distribution, and 1 in 729,500 is about 4.5 sigma event, then being involved in organizations whose members are much more like your ideal mate on average may be a better strategy than online dating.

leplen, thanks for the feedback. Here are my thoughts.

  1. ChristianKI is correct that I looked at match percentage, but mostly I felt that I would learn about someone more from a quick chat than from their profile so I wasn't limited to "perfectly written" profiles. Attractiveness is ultimately less important, but easier to judge.

  2. I didn't think of the "average vs. total" point, but I liked it. Let's do the math: 1/729,500 is 4.68 sigma. If I was picking from a group that was a whole SD better, I would need to only meet a 3.68 sigma girl, that's 1 in 8,900. I don't know if I could think of a group that large and that much better in my life right now, the only thing that comes to mind is the student body of a large and excellent university. Your point would apply to a 20-year old undergrad at Columbia or NYU: they should look at other students before the rest of New York City.

Only 1 in 5 potential matches met your standards for appearance, but 1 in 3 met your standards based on what they wrote,

Not really as he likely prefiltered them by match percentage. The 300 profiles at which he looked are likely woman with a high match percentage and the match percentage more likely signals that they written values are the same as it signals meeting standards for appearance.

I started making use of the suggestions to make things slightly silly on my profile and to message people about the stranger things that we had in common (especially odd movies and non-mainstream authors). I sent out around 20 messages on Monday and got back 5 responses. One of those is going to be a date next Tuesday.

For the time being, I primarily attribute this to slightly increased desperation around Valentine's Day and fixing flaws in my profile that were likely too bland before. However, it's a substantial improvement over how I was doing when I attempted actions on OKCupid several months back and had a less friendly profile and overly serious picture. My rate back then was about 1 in 10.

If you are in a relationship lasting greater than 2 years that you consider successful, how did you meet your SO? [pollid:1100]

The poll is screwed up because it lacks a "just show the answers field". Additionally the dichomy of being in a relationship lasting greater than 2 years and I'm not in a relationship lacks cases that exist in reality.

I was going to redo the poll a few hours after I made it, but I didn't think this was a big deal. Just choose I'm not in a relationship or other - neither is an interesting field anyway.

The problem is that you don't know how different people who take the survey make their choices. Some people who are in a relationship that's shorten then 2 years will answer one of the other options. That makes the whole data set difficult to interpret because you don't know a a particular person made their decision.

Alright full disclosure - if you had just said "You should probably have included a "show me the answers" option", I would had agreed and moved on. But instead your tone of ~Bah, everything is ruined!~ I found quite jarring*, especially since I had already gained some useful and surprising information off of despite its limitations. This isn't a particularly scientific poll for many reasons, I don't know how to tease apart strategies that are popular with strategies that lead to long term success which is what the qualifier was for - if I figure out a way to do this some day, I'll be more careful in its implementation.

*I'm not sure why, this LessWrong after all.

I think that LW is about furthering high epistemic standards, especieally when it comes to applied rationality. Applied rationality is at least as important than the specific subject matter.

Additionally I think voicing this criticism this way increases the chances that people who read the criticising to future polls at higher standards.

[-][anonymous]8y00

Effective Altruists guide to choosing between sperm donation, adoption, intercountry adoption and having kids, please!

How many children can you adopt? How many sperms can you donate? Seems like the answer is obvious.

"Find something in the profile to comment on" sounds like it's trival to say, but I'm not sure how to write good messages that way. Could you go into more detail (examples would also be good)?

Lots of good information. The part I liked the most though were the ideas related to the Stable Marriage Problem. OKCupid looks like it could provide a much better environment for finding the best match for yourself rather than just finding a decent or acceptable match. This is an area I haven't seen properly breached often enough.

Additionally, were there any specific resources you used to get better information on the basics of OKCupid culture and presentation when you started?

[-][anonymous]8y00

If you are in a relationship lasting greater than 2 years that you consider successful, how did you meet your SO? [pollid:1099]

[This comment is no longer endorsed by its author]Reply

What would you say about facebook? I have an inactive account I always wanted to rejuvenate but didn't know how to. To me it's mainly a list of (freaky at your pleasure) "girls I always wanted but never got to know in HS" and being the stereotypical unpopular guy that's quite a bit of girls. (Strangely enough, I thought none of them except maybe the ones in the same grade would remember me. Last week I've approached a girl I didn't remember and she said she remembered me, and the only time we saw each other is when passing by on school breaks)

[-][anonymous]8y00

(Anecdotal evidence warning)

Facebook seems variable enough that it would depend on your social circle. I think Jacobian's points about standing out are relevant, though, if you want to give it a try. Do you dance? The friends in my "dancing" group seem particularly responsive to flirting and dating behaviors through Facebook, provided that they're not constant or aggressive.

I would probably not be very successful if I used Facebook as a means to find a partner, given the culture of most of my Facebook friends.

Do you dance? The friends in my "dancing" group seem particularly responsive to flirting and dating behaviors through Facebook, provided that they're not constant or aggressive.

As having danced a lot of Salsa myself in the case of dancing I think facebook is seldom the first contact. It's a useful medium for communicating and other regulars generally accept friend requests from other dancers but I would be doubtful about it's value for a first cold contact.

[-][anonymous]8y00

I've seen a lot of "Dances together, but one party makes the first move through Facebook." I appreciate the alternate perspective, though, I don't have a wide range of groups to compare.

I've seen a lot of "Dances together, but one party makes the first move through Facebook." I appreciate the alternate perspective, though, I don't have a wide range of groups to compare.

Yes, I can see that but "first move after having danced together" feels to me substantially different than "first move with a person I have never seen in person".

Facebook friends are a non-think button press or in other words, pretty much nothing (unless you keep in contact, and in that case they're just friends)

My idea for the next incidentgate is (and seems kinda silly when typing it) "Hi I remember you from HS and always thought you were kinda cute but I was too shy to talk, would you like to meet up sometime?"

PEDANT EDIT: There's also a few girls from middle school before I moved, (Same city, different school)

I would replace "thought you were kinda cute" with "thought you were really cool/interesting", OkCupid's data shows that women respond negatively to physical compliments.

I've never really tried using Facebook even though I have an active account with a good variety of people. I guess I don't think that "we went to the same middle school together" is a better criterion for a match than "your profile shows we have a ton of things in common". Also, if someone's on a dating site you know that they're actively looking, and the pool is much bigger.

If you are reaching out on FB to someone you're really into, I would recommend again writing about a unique interest ('Hey, I saw your dancing picture, is that Argentinian Tango?') and not appearance. I assume that good looking women on FB get unsolicited messages a lot, you always want to start a conversation and show that you looked at more than their pretty face.

I might be overextending here but what would you say if I think OKC stuff is specific to OKC (and online dating sites specifically) and could not apply to other places?

Also, does OKC define "physical compliments" more precisely? My real life experience says otherwise, and there's also the question of why women wouldn't like their appearance to be appreciated despite spending a non-minor amount of their time on it.

Here's the data.

As for reasons, I can only offer some speculation since I'm 0/2 on being hot and/or a woman. First of all, I also spend a non-negligible amount of time on my appearance and I like people who are into my humor/intellect/interests/personality and not my looks. Commenting on appearance can also seem vulgar or indicate that you're only looking for sex. Finally, good looking women get complimented on their looks a lot, and not very beautiful women may be insecure about their appearance and question the sincerity of your compliments. I think this applies not just on OkCupid but in most online and offline situations.

Again, just speculating.

I don't give out a lot of compliments in general. But when I do, I've had better luck complimenting people on appearance when it's stuff they obviously chose and put effort into: a haircut; tattoos; choice in clothing. Few people like to be complimented on stuff they didn't do anything for; many people like to be complimented on stuff they did.

(If you try clothing, though, be aware that "nice top" is likely to be read as "nice breasts".)

There's a difference: on OKC you can filter people based on whatever, in non-OKC situations you don't have that information available to you. I only have the woman's looks (and the women have a perv-o-meter) to notice.

Re-reading your article I think a better way to describe this is "approaches with comparative advantages" and "approaches without comparative advantages".

You have context. If you meet a woman at a bar, she's probably the kind of person that hangs out at bars. At an Iron Maiden concert, she's probably a metalhead. At a climbing gym, she's probably athletic and at least a little outdoorsey. Even if you just ran into her in a Starbucks, it's still one Starbucks in one neighborhood, and she was there and not somewhere else for a reason. You're filtering, but you're filtering less on what she wrote in one of the little boxes and more on what you both bothered to show up for -- which can actually end up being a stronger filter.

And if you talk to her for a couple minutes, you have more than that. That's true on OKCupid, too, but striking up a conversation there is a stronger indicator of interest than it is in person, so people might be more reluctant to indulge it.

I think I referred as "comparative advantage" to something different from what you mean. I was speaking to the advantages of the person hitting on someone: all else being equal you should focus on fora where your skills come to play. If that forum is large enough (like OkCupid), I think it makes sense to focus on that exclusively. In any situation where you meet potential dates specific skills matter and some people are better than others.

For example, I'm at a strong comparative disadvantage when hitting on people on the subway because I have a really goofy accent that people don't expect from my appearance and it lconfuses them. Someone who looks hot and has a great voice will do well on the subway without needing any context or background info on the person they are talking to.

My real life experience says otherwise, and there's also the question of why women wouldn't like their appearance to be appreciated despite spending a non-minor amount of their time on it.

The point isn't that woman don't like their appearance getting appreciated, it's:
(1) Opening a conversation that way signals a focus on physicality instead of getting to know them as a person. It signals only wanting sex.
(2) If you wouldn't find a girl "kinda cute" you wouldn't ask her out. There no additional information communicated.

(1) Opening a conversation that way signals a focus on physicality instead of getting to know them as a person. It signals only wanting sex.

I'm using Mark Manson's methodology* and I'll just be lazy and quote him

At MarkManson.net, I encourage men to pursue women with honesty and authenticity because this screens for women who are honest, authentic and conscientious themselves, making for far better relationships.

In other words, telling a woman that she's pretty and I'd like to get to know her is both about honesty and self-expression AND the woman herself.

Something feels quite wrong about the second statement though. It's common knowledge that men want sex. Is there any harm in expressing yourself about it?

(2) If you wouldn't find a girl "kinda cute" you wouldn't ask her out. There no additional information communicated.

That's quite general (if girl X didn't Y then nothing) but I'll break it down as I see it.

First of all, it implies at least one side believes there might be compatibility (far fetched, because there's plenty of pretty women or I just have low standards) which is the first step toward anything. Surely nobody would do something they wouldn't like, so we now have a minimal start. And compatibility aside it also satisfies the man = assertive thing that seems to be recommended by seemingly all dating advice (for men).

Second of all is to filter (perhaps harshly) women who aren't comfortable with themselves. Now I think this will make people feel somewhat bad and disincluded but at some point in life you just have to take responsibility. This means putting some effort into yourself (and others in extent) and unless she's really pretty it's going to be difficult and annoying being reminded of how much of a pervert you or the book says you shouldn't or (INF x possibilities). It's understandable that not everyone will be comfortable with everything but it's a change for the better in yourself. (So there's no reason not to)

And third (coming from the second) is that it raises the question of WHEN should you express yourself? It gives the woman a (possibly unjust) ultimatum to decide about you. I personally don't like this but the alternative - the wait-then doesn't seem like a better idea.

(also upvoted, can't see why that's at -1)

Something feels quite wrong about the second statement though. It's common knowledge that men want sex. Is there any harm in expressing yourself about it?

The question isn't so much whether the man wants sex but whether he wants more than just sex. Whether he also wants an emotional relationship in addition to sex.

First of all, it implies at least one side believes there might be compatibility (far fetched, because there's plenty of pretty women or I just have low standards) which is the first step toward anything.

The basic act for asking a woman out states that you believe there's compatiblity.

In other words, telling a woman that she's pretty and I'd like to get to know her is both about honesty and self-expression AND the woman herself.

It doesn't express anything about you that's different from other guys that approach her. It doesn't express anything about her that makes her special as you are saying the same thing to plenty of woman.

A woman on a dating website get's a lot of messages and if you are just like the other stereotypical man who want sex with her because you find her pretty.

Yes, you might only express that she's exchangable and you don't care about her in particular and any number of other pretty girls would be just as good as her, but that's not what she wants to hear.

A first message thus should present you in a light that doesn't make you seem like all the other guys who message her.

And third (coming from the second) is that it raises the question of WHEN should you express yourself?

In person good self expression is often about being in touch with the moment and expressing what you feel exactly when you feel it strongly.

Alright. I give up. I'm now convinced my methodology was bad. I should read a book.

Upvoted for updating my beliefs.

I agree with what Christian is saying, but that doesn't make Manson wrong either.

The difference is in the context. There's a lot of nuance to it, but one big piece that hasn't been mentioned yet is that saying things in person allows you use nonverbal communication to signal things you cannot signal in text.

A message like "You're cute. I'd like to get to know you" opens you up to rejection, and a willingness to face this unafraid is attractive because it's a fairly credible way of showing that you must have reason think you're worthy of her - stuff like that. Online, anyone can shoot off a "You're cute. I'd like to get to know you" without having to be able to back it up. Even if you can't say with a straight face that you're good enough, you can hit ctrl-v and send on the hope that she bites anyway - which is why the line won't have the same oomph behind it as it can in person.

[-][anonymous]8y00

Also, I might want to have a short introductory conversation before that message. Don't feel like this should be copied word for word, but something like this:

You: "Hey, how's it going?"

Her: "Hello! It's going well!"

You: "I saw [recent mention or post about something relevant to both your interests, non-sexual]. [Comment on thing, keep it positive]."

Her: "[response]."

THEN maybe the high school message. Again: autism. So don't take my advice as the pinnacle of social skills. :)

It looks like a conversation with a person I haven't talked to in something that isn't either long enough for them to forget about me or someone close I haven't talked to in some time.

But let's be pedantic and you'll probably like this or the autism stereotypes aren't true, here's a few scenarios:

  1. Girl I know to a good degree, will probably recall me if I say hi
  2. Girl I barely interacted with but might recall me
  3. Girl I only saw at school breaks, might not remember me

Your example will probably work on category 1. Category 2 MIGHT go along, although a simple hi is rather generic and therefore is more of a lottery bet than a sure bet. I can't tell how category 3 will respond, but probably not better than category 2.

Consider how you'd feel about the introductory messages if you were from each of those scenarios.

We could also dive into sub-scenarios, tailored to specific optimisations or lack of them. Such as my fashion choices, how I live, people I hang out with, etc. Although it's dubious how much they matter since all of this is my unresearched model in my head about online messaging.

[-][anonymous]8y00

You are correct, (some of) the autism stereotypes are true in my case!

  1. I would respond very positively.
  2. Maybe
  3. I would respond positively, but would first inquire about who you are.
[-][anonymous]8y00

Were I single, and did not have memories of you being a horrible person, I would respond positively to that message.

On the other hand, I AM on the autism spectrum and am told that I'm not a representative example of the group "Human Females."

It would be effective on most people, I think, regardless of gender. The "you were kinda cute" part flatters the ego, while being weak/soft enough a compliment to avoid making somebody suspicious that that is what you are doing. The "I was too shy to talk" suggests self-improvement and self-awareness, which are attractive qualities on their own; and then the message itself conveys confidence, which paired with that self-awareness and self-improvement, implies that the confidence is both genuine and earned, avoiding arrogance and hubris both.