I spend a lot of time on dating apps to no avail and am generally a bit down about having always been single.

Has anyone ever taken a rational approach to finding love? If so, what was it? Was there a particularly helpful resource such as a self-help book? Even if you didn't intentionally take a rational approach to love, did you find that a particular approach worked very well?

Any advice at all welcome.

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[-]mad96

I'm a straight woman who for whatever reason seems to date a lot of men who have never had a girlfriend before (as I get older it is happening less for obvious reasons) - but these include two men who had never been kissed in their mid-30s. I tend to mostly date "rationalist" type guys.

The other advice given here is useful as general advice, but I would advise you to ask for specific advice/feedback about yourself / your dating profile / etc. I'm happy to provide that if you want it, but an appropriate subreddit or facebook group would likely be better. 

You say you spend a lot of time on dating apps "to no avail" - where are you getting blocked? Are you getting no matches? Are you getting matches but the conversations don't lead to dates? Are you going on first dates but not getting second dates? 

Getting no matches implies your standards might be too high or your profile/photos might suck. 

No conversations implies that you might not be engaging women effectively or you might be engaging effectively but not want to seem pushy by asking for a date.

First dates but no second dates might imply anything from you smell bad to you come across weirdly to you're just not going on enough of them. 

You need to:

  • make yourself more attractive,
  • increase the chance of meeting the right person.

To make yourself more attractive:

  • fix the obvious problems,
  • improve yourself, generally,
  • do something special that will make you stand out of the crowd.

To increase the chance of meeting the right person:

  • figure out what kind of person you actually want to be with,
  • meet a lot of people,
  • especially at places where the-kind-of-person-you-want is more likely to be.

This is the outline. Maybe I forgot a few important things. A lot could be said about each point. And of course, all of that is easier said than done.

The part about problems depends a lot on what specific problems you have. The advice for getting fit is different from the advice for developing social skills, which is different from financial advice.

Your chance of success is P × N, where P is probability of success with one random person, and N is the number of people you meet. If your P is too close to zero, you have to work on that. But when it becomes sufficiently nonzero, your success becomes proportional to the number of people you meet. (Don't make the mistake of staying fixated on one specific person who rejected you. There are over 7 billion people on Earth.)

I joined the Optimized Dating discord server and got better photos. 

My advice would be this:

Trying to meet people for the sole purpose of dating them is a spiritually toxic endeavor, with online dating being particularly bad. I had a handful of girlfriends before meeting my wife, none of whom came to me through online dating or trying to get dates with people I didn't know.

I contend that the best path to a relationship is through community, broadly defined. What you want is to be around people with whom you can cultivate compatibility. The online dating/cold approach model relies on being able to quickly discern compatibility, which I think most people are kind of bad at.

My definition of community in this context is any circumstance that lets you repeatedly interact with people in a non-targeted way. For meeting my wife, that was a weekly bar trivia night. For past partners it was a mix of extracurricular activity groups and friends-of-friendgroups. These environments accomplish a handful of things at once; they establish shared background and positive memories, they let you display and observe positive traits that are difficult to signal on a dating profile or on a date (e.g. patience or thoughtfulness), and ideally they're intrinsically worth existing in for their own sake. That last one is important because, to use my first example, even if I hadn't met my wife playing that bar trivia game, I still would have had fun going and I made other friends along the way.

You can't just show up and expect things to fall in your lap, of course. You do want to be improving yourself and putting your best foot forwards. Not all communities are created equal so once in a while you need to step back and evaluate if you need new opportunities in your life. And obviously, you still have to be ready to actually ask someone out eventually.

It's not easy, necessarily, but it did work for me.

I disagree that that intentionally going on dates is "spiritually toxic". You don't really need to be able to discern compatibility quickly (you can always go on another date).

I approached dates as "doing something fun with a friend who thinks I'm hot", and even though I didn't end up seriously dating most of them, they were still fun experiences (having conversations at coffee shops and restaurants, hiking, paddlingboarding, etc.).

I do think dating people in your community is easier than online dating, but my experience is that finding a community is much harder than finding someone to date. Maybe this is a case of which one you're better at though.

For what it's worth, in my friend group, half of us are dating or married to people we met though online dating, and the other half are with people they met in college. I only know one person married to someone they met in other ways and their method isn't helpful (be so hot that people will hit on you at the gym).

I believe there are posts answering some of this in the Relationships tag.