HN and tech spheres can tend to have more people (especially male) who struggle with socialising with others and romance on top of every other part of the human condition. To that end, I recommend (in order):

Robert Glover - No More Mr. Nice Guy Mark Manson - The Subtle Art of Not Giving a Fuck Mark Manson - Models

For those looking into reading into masculinity (to understand yourself or other masculine people:

David Deida - The Way of the Superior Man Moore & Gillette - King, Warrior, Magician, Lover Zan Perrion- The Alabaster Girl

Disclaimer: Some of these books I recommend are not going to be based on much research and science, or delve into more abstract forms of thought and draw inspiration from other sources (e.g. Eastern). Nevertheless I believe they are useful frameworks of thought that can provide value, and it's good to engage more "mythical" ideas at times.