I started making use of the suggestions to make things slightly silly on my profile and to message people about the stranger things that we had in common (especially odd movies and non-mainstream authors). I sent out around 20 messages on Monday and got back 5 responses. One of those is going to be a date next Tuesday.
For the time being, I primarily attribute this to slightly increased desperation around Valentine's Day and fixing flaws in my profile that were likely too bland before. However, it's a substantial improvement over how I was doing when I attempted actions on OKCupid several months back and had a less friendly profile and overly serious picture. My rate back then was about 1 in 10.
There's a lot of data and research on what makes people successful at online dating, but I don't know anyone who actually tried to wholeheartedly apply this to themselves. I decided to be that person: I implemented lessons from data, economics, game theory and of course rationality in my profile and strategy and OkCupid. Shockingly, it worked! I got a lot of great dates, learned a ton and found the love of my life. I didn't expect dating to be my "rationalist win", but it happened.
Here's the first part of the story, I hope you'll find some useful tips and maybe a dollop of inspiration among all the silly jokes.
P.S.
Does anyone know who curates the "Latest on rationality blogs" toolbar? What are the requirements to be included?