Sociability - Dating (for men) - Finding a Partner
Increase your chances numerically, don't fear your own sexuality
Working on your physical and social attractiveness, and working on trimming the unattractive elements (or at least understanding which ones can be removed and which are simply aspects of your personality that shift your audience) will help you maximize each opportunity you get, but it doesn't actually get you into a relationship.
Getting into a relationship requires meeting women, following through on your interest, and getting interest in return. Staying in a relationship requires building partnership. I talk about partnership elsewhere - , so we'll focus on finding a partner to build that partnership with.
Meeting Women
The most common question that I see - more than how to become more attractive, which is a (relatively) solved problem - is how to meet women. Honestly, I'm not particularly good at answering this because I heavily leveraged OKCupid (successfully) and that particular route really isn't open to people anymore in the way it was for me - but I can do my best.
First - online dating. There are different apps, obviously, and those apps all have their own markets that vary wildly geographically. If Tinder works for you, great. I've never cracked it, but that's probably because I'm 5'7". I know a gentleman who is 6'7 or so and gets a hundred matches every time he passes near an urban area. OKCupid might also still work for some people, but I can't really recommend it anywhere beyond Tinder. I've heard (relatively) good things about Bumble and Hinge, but never experienced them myself.
There's social media, of course. I had 2-3 dates off reddit's r4r (back in '14), and that was decent. Twitter can be great if you post a lot and have a social crew. This is really just an extension of social groups, though, and not necessarily a great way to meet people you don't have some kind of connection to. The same for the various discords and other platform groupchats that spun out of metatribe communities. And, moreover, it gives you the demographic problems I discussed at the top of this section.
Okay, great. What about if not that?
Pick up a hobby that has a decent balance of women. I don't have a list for you. Anime is better than gaming if you dearly want to stay in your comfort zone, but there's lots of stuff out there. Hiking, book clubs, whatever. The balance of course is that it's very possible your favorite hobbies don't have women in them, and faking a hobby isn't very fun. Gardening is a decent option that has a lot of ladies in it, and you can still nerd out over the technical aspects.
You can definitely try new things! That's a great way to learn more about your tastes in general, pick up some interesting stories (as I discussed above), and meet people...but it's just as likely you won't necessarily like them. I don't have a silver bullet here.
If you're religious, I'm under the impression there's a lot more young women than men attending services in many places. Look for a church of your denomination that has a good gender balance.
Dance is great. Go to social dance nights. I have lots of thoughts on dance outside of the discussion of dating. More than a lot of hobbies, though, it's directly related to interaction with the opposite sex, and is also something that is a light form of cultural participation, so it shouldn't grate on you too much as a skill to pick up (though I am a dancer, so that's definitely my bias speaking).
I would also like to say that dancing is one of the best ways to develop social skills around the opposite sex that don't require you to _already_ have social skills around the opposite sex. These definitely vary, but simply regularly engaging in conversation, touching them (I don't mean this in a concerning way, but just holding a dance frame and moving), and in some cases even broadcasting the body language of flirtation ('characteristic of dance', which varies dance to dance) can definitely help you become more comfortable with women in general.
If you've been working on becoming more attractive, physically and socially, then you'll have a better chance when you meet the girls as well!
If you meet taken girls, never fear! In many cases, especially in places where the gender balance isn't so far off, they'll know single girls! Meeting couples is a good way to meet single girls (* again, in better gender balanced groups -- unfortunately many of the women who come to my social events with their husbands also don't know many other women!).
Finally, it is possible you may temporarily want to move to a place that's just higher population density in general. This isn't a cureall though - you should understand what you're getting from a higher population and pick a place that fits your needs. College towns, certain densities of different cultures/ethnicities, religions, these can all figure into improving your chances. Simply being around more people like you will help a lot.
Masculinity
I have an eclectic audience. Most of you, by virtue of having found my content in the first place, are nerdy guys. This doesn't necessarily mean you fulfill a nerd stereotype, but you are the type to deeply indulge in 'the life of the mind'.
A lot of you will fulfill that stereotype, however, and if you're especially focused on this part of the book on dating, then there's also a decent chance this next section applies to you, so please pay attention.
If you are a nerdy, 'cisheteronormative' dude - and not a musician or artist or whatever - you absolutely need to become comfortable with your masculinity.
Do not be Untitled (https://slatestarcodex.com/2015/01/01/untitled/). Do not be 'entitled'. Be titled. Be a king.
You neither deserve a relationship by virtue of existing, nor do you deserve to be alone. Most men are worthy of a relationship (by which I mean - most men will bring fulfillment to a partner in such a way as to leave their lives better by virtue of that continued partnership). Most of us also have some bad memes, and some of the worst ones are the ones that stop you from being able to pursue that partnership.
The entire scope of masculinity is a discussion far beyond this essay, and I'm going to have to add it to the long list of stuff that this book covers, but it is essential to drive one point home, and it's one that might get me in trouble:
Do not be afraid of considering women as sexual beings. Do not be afraid of feeling sexually attracted to them for physical and non-physical reasons. Simply make yourself worth being objectified in return. Make the facet of yourself that they desire for sexual purposes have a larger surface area, more obvious, more desirable.
Asymmetric Interest and Friendship
Rejection sucks, but you need to be prepared for it.
Be prepared to get rejected.
Be prepared to get rejected a lot.
That said, you're going to be dealing with a lot lower of a rejection rate in person than online -- there's much less of an ability for the woman to feel like she's picking from a menu, rather than actually engaging with you directly.
It's not just about accepting the fact you will be rejected, though. If you become attractive, there's a very good chance you're going to have to deal with the other side of things as well. Sometimes people's emotions are asymmetric in ways that can be painful.
Be aware that women will become attracted and attached to you, it won't always be a person you want to - or perhaps you do, but there's reasons it won't work out. If you cannot understand how attached someone can get TO YOU, when you break their heart it will be a surprise. I've been that guy. Try to avoid being that guy.
Don't lead them on. Be prepared to REJECT.
On the other hand, if there is a girl you're interested in, it's both fine to ask her out immediately and also to get to know her a little bit. Do you want to pursue things further? However, don't just 'wait and see what happens'. Nut up and ask her out.
Might your relationship change if she says no, or you break up later? Absolutely. Are you going to very run into various dramas and weird issues regardless if you just become closer and closer as friends? I wouldn't say it's unlikely.
You need to be decisive, though. Sometimes that decisiveness itself is the thing that will push her over the edge to a yes, rather than a hinting 'will he or won't he'. Sometimes a lack of decisiveness - even if it comes from a fear of losing your friendship - comes across as a lack of seriousness, or a lack of commitment to the relationship (or the potential relationship).
You also need to realize that when there is an asymmetry in interest - either before a relationship, or tragically after they end as well - your friendship probably will change. It might be a unpopular view in some circles, but: It's not impossible to have cross gender friendships, but once you start adding ingredients like 'single', 'attractive', 'crush', you start creating a recipe.
A recipe of what? PAIN and MADNESS and MR BRIGHTSIDE THE WORST SONG EVER...ahem.
As a potential side note: Lesbians can make great wingmen, but don't count on them being purely homosexual and don't count on not getting a crush on them, or vice versa (speaking from experience!). They are not totally exempt from the dangers mentioned. That said, they're quite a bit safer in this way. Make sure that there’s no cultural clash here.
I know this is a weirdly specific side note but it does come up as a thing quite a bit in ‘queer adjacent’ spaces that are often found in nerdy hobbies.
Communicating Interest
I think that there are escalating levels of communicating interest when you're building a relationship. As always, this is a guideline from my own experiences, more than an absolute, and it's symmetric. Also, I'm operating within the western dynamic of romantic relationships building on top of something that resembles friendship, even if they're not necessarily your best friend.
You need first to communicate your like for a person - elements of them that appeal to you, that make you want to be near them, makes you want to be friends with them.
Symmetrically, make yourself likeable. I've talked about sociability, social attractiveness, communication skills, etc. This is a lot of where these come into play. Make them enjoy being around you! These are many of the same skills that you need to make friends in general.
Once you've made a friend (at whatever level) you need to realize it's not simply going to take care of itself. There is a friend trap, and in some cases it's your fault (not always!). You need to communicate your desire. Oftentimes this is as simple as a confession, or asking out on a date. Whatever your method is, don't beat around the bush more than you have to (and I will totally acknowledge there are elements of dancing around, plausible deniability, that sometimes seem inevitable). Make it clear that you are romantically interested in them. Leave them an out, don't pressure them, but also don't undercut yourself.
Don't say 'If it's not too much trouble, would you like to go out on a date? Maybe? Doesn't need to be a big thing'. Just ask them out - 'Would you like to go on a coffee date with me on Saturday?'.
Hopefully, you've worked on making yourself desirable as well. They may not necessarily actively desire you yet - they may not have seriously considered you int hat light - but you've worked on making yourself someone they can desire. Physically, interpersonally, whatever. You've worked on the parts of yourself that you found tractable, and they match the interests of your potential partner.
Finally, if you move from liking to loving them...tell them.
There's a lyric from a Jason Mraz song that often comes back to me: "It takes no time to fall in love, but it takes years to know what love is." I think I know what love is - but feel free to fill in your own definition, for now.
Tell people how you feel. You can't always tell someone - even a successful long term partner - everything about how you feel. Sometimes there are things that saying it will make things worse (talking about insecurities!). But work on communicating.
Some people say to not overuse 'I love you'. I prefer to throw it on everything.
Hopefully if you've made yourself likeable and desirable, you have also made yourself lovable in the process. There's a bit more to it, though, beyond making yourself physically and socially desirable. It might play into any of the stages, but I think it's necessary to make someone want to be your partner.
You need to provide a mix of long term emotional stability and indications of being appropriate to build a family with.
Dates
Whether you met someone explicitly for romantic purposes, or you knew them already and have asked them out on the prospect of converting your relationship to a romantic one, you will probably go on a date!
As I mentioned above, don't try to undercut yourself. If it's a date, it's a date. If you think she may not be sure - this is especially the case with existing friendships! - make sure you say when you ask them out 'a date to a play' or 'a date to the aquarium'. I have a friend who asked a girl to a play, who had mutual friends, and she thought it was a group thing. Mistake!
My favorite first date is coffee. It can easily transition into lunch if you're enjoying each other, there's no reliance on substances or loud music (generally), you can get a nice relaxed feel for the other person. It lets you do a bit more planning than, say, seeing a movie (which I've never comprehended as a first date). There's other options, obviously, but coffee is fun.
Don't press too hard. Don't go into sensitive topics the first time you're out (religion, money, politics, sex). Don't expect it to turn into anything, but don't be afraid to indicate your interest in it turning into something. Get to know the person!
Mirroring body language is great. If she leans in, lean in a little bit more. If she leans in a little bit more, and so on. Hard closes or whatever the fuck it is PUAs call it are a filtering mechanism.
The purpose of a date isn't to show off. It's to experience things together. Don't drag her around if she's not having fun (often but not always indicated by laughter, conversational engagement, and so on). Find out if she'd rather do something else, or see if perhaps the chemistry simply isn't there and wish her a lovely day instead.
Conclusion
There's no overarching message I'm trying to drive in this section of the book. There are certainly expanded elements I hope you learn from, but I'm not building towards any conclusions - more a series of thoughts on the practice around finding a partner.
Optimize what you can about yourself, emphasize the good, avoid the bad. If someone is interested in you, lean into it. Don't qualify yourself out.
And as I've said elsewhere - love yourself. Respect that they like you, that they may love you, instead of blowing off their taste and perspective.
Good luck. I believe in you.