I have a slightly diff take on it. Sure, obsess over it. Research. Experiment. Put things into practice. Just make sure what you’re getting into is rooted in reality.
Something I found helpful was romance novels and women’s magazines. Yeah, I know that’s paradoxical to what I just said. Romance books, rom/coms, women’s mags, Oprah, etc. TARGET the interests of a predominantly women’s audience. If they don’t appeal to women, they don’t make money. So pay attention to the magazines and media and who consumes them. Soap operas...I’m a HUGE fan of B&B. Ridge Forrester (Thorsten Kaye) is THE man. I mean, he’s a freakin dressmaker and he’s beating women off with a stick. He’s tough, passionate, and frequently at odds at keeping the moral high ground and succumbing to his weaknesses. He’s the archetypal “good guy.” He has a history as a womanizer, but his women have managed to tame him for brief periods of time.
Fictional characters like Ridge exist because women want the bad boy they can tame and make their own. They want to be THAT woman who settles him down.
On the other end of the spectrum is his rival Bill Spencer. Good looks, lots of money. Has a secret shrine to money in his office. But also fiercely protective of his family. Another bad boy that appeals to women who want that dangerous guy who will take control.
The point is not that you should be Bill or Ridge, or a character from a Nora Roberts novel. The point is you try to understand the kinds of fantasies women have that women’s media try to feed. Then you hook into that and try to fill women’s interests yourself. The real life version, not the fantasy. That could get you arrested. What kinds of things do these guys do that make women feel special? Is there a real-life equivalent?
Women’s media is great info on sex, too.
Mainly just be careful and try to filter out the bad stuff and keep the good stuff.
And just keep trying. Getting experience approaching and talking to women is always the best first move. Asking a girl out for a friendly cup of coffee is GOOD. Rejection is just part of it, so don’t sweat it. Keep trying.