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Notes -
Part two:
Simple example: I dated a woman who revealed - after we'd been together for several months - that she had serious financial problems and that they were a major source of anxiety for her. If she'd told me this on our first or second date, it would have been a huge red flag for me. As it was, by the time she revealed this to me she'd already demonstrated many really impressive virtues, as well as displaying good sense in realising this was quite a personal piece of information, so it was no longer a deal breaker.
(5) Don't be (too) spontaneous. Romantic comedies play up spontaneity and we associate it with romance. That's why it's important to be able to fake it. Glib one-liners aside, you should try to be prepared for different eventualities so you can embrace spontaneity when it comes. This means simple stuff like ensuring your apartment/house is clean and presentable and doesn't look like the abode of a serial killer (seriously, have some decorative objects/stuff on the walls). It means having a trashcan with a lid in the bathroom (if it's not obvious why this is something you should have if you're expecting female company, think about it). It also involves having options to cover various contingencies. If you meet your date for happy hour drinks and tells you she's getting hungry, you should know a few good restaurants nearby. If the initial bar you picked to meet is crowded and noisy, have some decent alternatives in walking distance. The rule against spontaneity also extends to responding to messages. While the whole 'three day rule' is bullshit, I think it's a good idea not to respond to a date's messages too quickly. It can be super awkward when you write someone a message saying "hey that was fun last night, HMU next week if you want to do it again" and they respond immediately, basically forcing a conversation you weren't prepared for. Give yourself some time to think about your response and don't pressure communication.
(6) Don't be too open with your feelings too quickly. Again, Hollywood has a lot to answer for here. We rarely see romantic leads downplaying their affections, but it can be really important early on in a relationship not to come over too strong. Two simple reasons for this. Firstly, it can again show a lack of judgment. There are lots of emotionally unstable people out there (men and women) who express their undying love for someone after a couple of dates, and most people are aware (if only implicitly) that this kind of behaviour typically bespeaks someone with a cluster of personality disorders. Displaying good judgment means showing that you're a smart cautious person who doesn't rush into things or make themselves vulnerable unless they've had clear indicators of interest from their partner. Second, there is a balance of power issue here. I don't want to overstate this, but thinking back to the investor metaphor, if you're too eager, too soon, it can make you look like a dodgy salesman trying to offload an inferior product as quickly as possible. By being sensibly restrained and responsive to what your new romantic partner says and does, you show that you recognise your own value: you have something important to bring to the table, and you're not going to risk giving it away too quickly to an unsuitable partner. In special conditions - an intense and rapid holiday romance for example - the above advice may be temporarily waived, but again, pay attention to cues and respond appropriately.
(7) Don't expect instant results (and don't get bitter). Finding a lifelong romantic partner is one of the most important and challenging things people do. While some people get lucky and stumble on a suitable partner early on, it's increasingly common for people to have to go on a lot of dates before they find someone they can happily date for a few months, let alone the rest of their life. I suggest leaning into the experience and learning to enjoy the process of dating itself rather than just focusing on outcomes. Dating offers an unparalleled way to hone social skills in an emotionally complex environment, as well as a unique opportunity to meet people from varied backgrounds and learn about them and their lives. This is true even if they don't go home with you at the end of the night. Indeed, you should absolutely expect to be rejected repeatedly. Rejection burns, but it's a little less intense each time, and if you've been on the dating market for a while then it'll probably become incrementally less painful. If you are rejected, try to be gracious and smooth about it, and I'd generally recommend not asking the person why they ended things (or didn't want them to start). While you might get lucky and hear some useful advice, you're far more likely to get a delicate platitude about things just not working out.
In fact, most people have lots of implicit criteria for romantic partners that they may not even be fully aware of themselves. Maybe you weren't tall enough, maybe they didn't like your accent, maybe you reminded them too much of a bad ex. Closure is something we do for ourselves, and if you rely on other people to provide it for you then nine times out of ten you'll be left hanging. Moreover, just because a date doesn't result in romance doesn't mean it's pointless. In addition to providing good life experience, it can provide other opportunities. Two of my best friends today are women I went on dates with where there didn't turn out to be much chemistry. Both of these women subsequently set me up with friends of theirs, complete with a letter of recommendation stating that I was a good and decent guy. Above all, for god's sake don't get bitter and starting coming up with theories about how women are stupid, silly, or evil. Dating is a nightmare for women too, and while the problems they face are often different from those experienced by men, almost no-one has it easy. And on a more practical note, bitterness will not help make your more attractive or enhance your dating prospects - in fact, quite the opposite.
(8) Don't think you're above following the rules. "This is all bullshit. Two of my best friends got together on a first date where they bonded over their love of anime and MT:G and they were immediately open about their kinks and are now married with ten children." There are absolutely people who find love via pathways quite different from those discussed here, and I don't pretend any of the suggestions I'm giving are absolute. However, they represent my considered advice as to how to make dating more productive and less mysterious for straight men, and if you're feeling frustrated or despondent, I think they're a solid starting point. But the internet is full of people giving romantic advice, some of which is quite different from my own, and I don't take myself to be some inspired oracle dispensing eternal truths. Nonetheless, if what you're doing isn't working, or is making you unhappy, you should try something else.
I didn't start dating until 26. I'm now 33 so I have some experience and have learned a lot, much of it the hard way. I find it's hard to recognize good advice when in the position of needing it, so I just want to say that this is all excellent advice, and one of the things that makes it good is it offers explanations and reasons to trust it over competing ideas that are out there (e.g. Holywood).
I grew up a bit sheltered and rarely talked about dating with the few friends I had. Starting around 23, I sought advice online and while some of it is good, most of it I now know is terrible.
I wonder: do those that do not date (because they're asexual) have worse social skills?
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