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(I'm new, so I'm not sure if this is Culture War.)
Does anyone have any modern dating advice?
I'm interested in finding out what are the "real" rules that people operate under when it comes to dating, which might be different from the rules they ought to have or the rules they claim to have or the rules that they believe that they have (but subconsciously they use different rules). And of course the word "people" is very broad and presumably various subgroups operate in different ways, so I'd be happy for clarification on that point too. (And then of course individuals differ from the norms of the subgroups they belong to). Ideally I'd like to see some objective evidence, but personal experiences/impressions still count for something.
I identify with the difficulties in Scott's classic posts "Untitled" and "Radicalizing the Romanceless". Generally I'm paranoid about approaching women, because I feel like maybe they think I'm a creep and they're just too polite to say so. My biggest concern isn't that they dislike me per se; it's that maybe I've hurt the woman without realizing it. I'm very sensitive about that.
I've done dating sites and speed dating but I can't seem to find any connections. I should note that I have low self-esteem, so rejection is hard on me, which in turn makes it difficult to put myself out there. (Here's a question: How much time per week does the average single straight guy spend on dating sites etc., assuming he's actively looking for a date?)
I'm not a misogynistic incel, but whenever I talk about my dating woes a good portion of people feel the need to tell me "Don't be an incel!" when I haven't said or done anything remotely misogynistic. I figure the Motte is probably a good place to find people who understand my perspective.
I've been looking for dating advice recently, but everything seems contradictory. You're supposed to treat all people equally regardless of gender (which is great!), but at the same time you're supposed to conform to gender stereotypes and you should expect that most women will do the same. People tell me it sucks and it's not fair, but I'm the man and that means I have to initiate contact and get rejected a lot. They also tell me to be persistent but in the same breath they tell me not to be too persistent and it's not clear where to draw the line.
They tell me to be authentic but they also tell me to "fake it till you make it" and act like I'm a cool guy who dates people all the time. They tell me to express my feelings but they also tell me that "women can smell fear" so I should act confident even if I don't feel confident. They tell me to be honest but I've also had a (female) therapist suggest that I should tell some white lies to make myself more attractive. This woman gave a TED talk about her wonderful relationship with her husband (who sadly passed away) and she admits that the relationship began with lies: He falsely claimed to be a Fullbright Scholar to get her attention. Months later she found out the truth, but she was only angry for a short time. Ultimately, his lie made their whole relationship possible!
People tell me that women like it when you express interest in them, but also they think it's creepy. People tell me I must never express interest in a girl at her place of work, but the only relationship I had in the last 10 years began with that exact scenario, and the girl was flattered! (We eventually broke up, and since then I've also approached a few female coworkers at my own workplace, without success.) People tell me that if I show interest in a girl early on then I'm "too easy" and there's no "intrigue", so the appropriate thing is to give little hints about my feelings so she can pursue me. (In which case, apparently I'm taking the female role and she's taking the male role? I'm not offended by that; I'm just confused.)
People say that they met the love of their life on a dating app, but they also say that dating apps are trash and nobody likes them. (But even though everybody hates dating apps, apparently nobody can think of anything better to do.) People tell me it's ok to wear t-shits with the name of my favorite show or whatever (it displays my personality), but also I should never do that and the only way to be attractive is to wear solid colors with the occasional stripe.
One commenter on the Motte wrote "running a 'playing hard to get' game on a woman seems suboptimal. If you are looking for someone with whom you are authentically drawn to/compatible with, why set up these hoops or create a culture of deception within the relationship?", but in the next breath that same person wrote "it is also a risk to be overly eager. It's unattractive". But if I'm very attracted and I act like I'm only mildly attracted, doesn't that create a culture of deception within the relationship??
Long story short, I'm lost.
(And it surely doesn't help that I've got a long history of mental illness and isolation and thus I missed out on a lot of opportunities for social learning.)
I am actually bi, but in practice it's rare for a guy to get my attention, so I'm mostly concerned about how to approach women.
"Radicalizing" was written in 2014, and the advice at the bottom leads me to essays from 2001. It occurs to me that this might be woefully out of date.
Does anyone have any modern advice for me?
Outside of work and places like that there's no issue expressing interest in a girl, in fact it's good to make it obvious by talking to her a lot and asking for her Instagram or telling her you want to take her out for a drink (after you've talked with her a while and noticed some chemistry). Best to set the tone early as it's hard to shift from the background of her mind to the foreground. Normal rules of confidence apply and you should talk to her directly, in fact talk to her friends and your friends and show that you can command people's attention for a while without shrinking away in fear. You mention being isolated, I think improving your normal conversational skills even with male friends will help a lot here. It's a good thing to pursue in general and I think much of dating despair is compounded by general social despair. Dating is just good conversation (which is a skill) + some well-timed moves that display your intentions for more.
As for being creepy.. while expressing interest is normal, there is an issue with prematurely expressing a desire for commitment with a girl, you should set constraints on this in your own mind and even explicitly (twice I have said let's just have one drink and if there's no chemistry we'll leave it there, those dates went well) and treat each date as something that's fun for its own sake with no harm done if it ends. Be ready to pursue a bit but if you're putting in all the effort just forget about her. Don't make the mistake of idealising her, it's fine to kick yourself for blowing your chance with that super hot girl for a bit or be excited about seeing her again but remind yourself that you barely know her. I will say the obvious and don't make any crude sexual comments either, I know some guys can make this work but you don't need to take that risk.
So about talking to girls, all the rules of normal good conversation apply and you can talk about history or whatever, the only difference is you're going to arrange for another meeting down the line (whether that's setting a date or you and her grabbing a drink right then and there). Dating advice which complicates things isn't usually useful in my opinion but keeping the simple roadmap in your head is helpful: set a date (you pick what, when and where or else it'll never happen), meet and talk, try get some physical chemistry going (can be as simple as sitting beside her rather than across from her), make some positive comments about her appearance (not crude but still direct, you show confidence by being direct about being attracted to her), then if she has responded positively to all of that take your shot and go in for the kiss. There will nearly always be some doubt about the right moment for the last bit but sometimes you'll get lucky and she'll say something like "when are you going to kiss me?".
On dating apps, don't spend too much time talking back and forth without setting a date. Unless the conversation is really enticing for both of you (which can happen, I've discussed books and sent excerpts before a successful date) it will fizzle out if you don't set a time and a place. If she cancels multiple times or doesn't respond she probably wasn't going to meet up with you in the first place.
On authenticity, I think there's reason for optimism here. I have honestly gotten my best success with dating when being authentic and specifically finding women I can talk to as an equal in conversation i.e. I don't have to dumb myself down and they surprise me with their wit. Authenticity is polarising, you'll narrow the set of people who you can attract but trade it for greatly deepening the attraction of those you do.
On hoops, there are hoops that you insert yourself (pointless in my opinion unless you suspect a red flag and want to test for it), and there are the hoops which are inherent to dating. The latter I think should just be accepted. Think of it like a dance, you might have a lot of wiggle room to do things your own way but the date isn't going anywhere unless you move on to the next step. The fact that there are traditional expectations on the male is something you should be grateful for as they line the complicated world of attraction with a few obvious signposts for what works.
Even in those, there's no ethical issue. I even know several real life examples where a supervisor dated and married a supervisee, to the benefit of all concerned.
There are logistic and legal considerations, so I'd be a bit more cautious than the usual case. But (aside from the supervisor/supervisee situation) even that consideration isn't likely to blow up in your face, and even less likely to be career ending.
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