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I have a lot of unsolicited advice here and it should be taken as such. I'm not trying to persuade but trying to say things I wish someone would have told me when I was younger. I've only lurked on LW up to now. Please, someone tell me, if I'm breaking any rules.

I haven't been on any dates since 2015-ish (I'm old and very happily married, now). So, this advice may be a bit outdated. But that is beauty of unsolicited advice; you can keep what fits your priors and throw the rest away.

  • The SNR of PUA stuff is too low to be useful. Ignore it all. If you can't help yourself and just have to read some of it. Mark Manson's book, models, is the best thing to come out of the terribleness.
  • I never had any success meeting women while volunteering. Most of the people you meet while volunteering are going to be older and retired. So unless you're trying to break into that septuagenarian dating market; volunteer because you want to help people and not to meet women.
  • On hobbies and sports: IFF, you can find a hobby that you truly enjoy and is predominately made up of women will you have success. If you're only doing it to meet potential partners everyone will be able to tell that you're just a tourist. If you want to meet someone in a hobby based setting you're going to need to invest a lot of time into that activity. So make sure it is something you enjoy. I got really into social dancing for a while and I had several great longer term relationships with members of that community. But I had been working on my dancing for several years before I ended up dating any dancers. I found that I enjoyed dancing because it was something artistic yet very algorithmic. The relationships end up being the icing on the cake.
  • TW: Weight and body issues. Disclaimer: I'm really only going to talk about my experience here. Everyone's body is different. Please don't take my N of 1 as gospel. In retrospect I really wish someone would have told me I needed to lose some weight. When I finally realized it, I was about 60 lbs overweight. Yes, I still had some moderate success dating around that time. But I was playing the game on hard mode! Playing the game on easy mode is way more fun! The best diet is the diet you can stick to. For me that was logging calories and daily weight measurements. I didn't obsess about getting the exact right number of calories. I just made sure I logged everything I ate and drank and that the calorie count was first order correct. When I first started logging I found out I was eating around 3500 calories a day. I bumped that down to 2500 and my weight started going down. After 4 months or so I stopped losing weight. So I had to go down to 1800 calories a day to keep the smoothed derivative of my weight negative. After about a year I got to around 15% body fat and decided to stop cutting. I moved my calories back to around 2k a day and my weight leveled off.
  • I found obsessing about fashion and tends to be a waste of time. Wear whatever you feel most comfortable in. How the clothes make you feel is more important than how they look. I found a nice uniform of dress shoes, jeans, and a collared shirt. I don't wear cologne. Seems to try hard to me. But maybe it is more popular on the east coast.
  • Others will disagree but apps gave me the best time-invested to dates-went-on ratio of anything I tried.
  • Learn how to game the apps. Never try to game people but being a bit Machiavellian to game the algorithm is justifiable. Get great pictures! A/B test them! You'll be surprised what people swipe on. Borrow a friends puppy and get girls to swipe on you just because of the puppy. The more engagement you generate the more the algorithm will put you in front of people. Unfortunately the apps are a numbers game. You will only match with a subset of people that see your profile. You will only go on a date with a subset of the people that you match with. You will only go a second date with a subset of people you go on first date with. You will only be in a relationship with a subset of the people you went on a second date with. Increasing the number of people that see your profile and the number of matches you get has a large effect on the number of dates you go on/relationships you are in.
  • I always swiped left on everyone and filtered later because I wanted to see who was interested in me. But I think the apps punish you for this behavior now. Still, try quantify who is matching with you. See if you can make a model of who is matching with you and what variables change your matches.
  • Don't chat forever on the app. You want to get off the app ASAP. If they want a chat partner, move on. Make the first date low risk. Think coffee, tea or beer. Dinner can be agonizingly long for both of you, if it isn't a good match.
  • Be ethical. If you want a short term thing, own it and be honest about it! Know that this will be a deal breaker for some women. If that is what you want, your job is to find the women that want that too. You need to talk about this before anyone's clothes are off but you shouldn't open the date with it either. Follow Dan Savage's campsite rule. "Leave people better, than you found them."
  • Try dating outside of your typical "type." I had a great May December f-buddy thing for while. I probably wouldn't have pursued that option when I was your age. Don't be dumb like me.
  • When hooking up use Dan Savage's magic words of "What are you into?" and listen to what they say. Basically, just go listen to a lot of Dan Savage's podcasts. Figure out how to sexy conversations about consent.
  • Use protection. Get tested.

I could go on but it is getting late and I need to go make dinner with my wife. :)