Someone told me when I was younger, 'don't chase, be the chase.' What he meant was, to become so attractive, fit and well put together that you don't have to chase women anymore, instead they chase you. This method would work, and I believe on the phases of my life where I did in fact look decent, I did get some attention. Well, the one who told me that, he's a tall fit chiseled jaw looking handsome ass motherfucker who has a hairline that celebrities would envy. Of course, he'd get chased. For me to 'be the chase' would require 20 plastic surgeries, a hair transplant, two personal trainers and a personal fashion stylist - and in a decade maybe I'd have the frankenstein look that would garner enough attention that I could perhaps MAYBE leverage to intimacy.

I think that's fucking flawed if you're ugly like me. (no this isn't meant to be some cutesy 'oOoH I hAvE pOor SelF eStEeM' shit, I know what I look like and I'm working on it)

The real point here is, one that all the fucking weeaboo gamer nerds figured out.
Minimise your weaknesses, maximise your strengths. (or min/maxing)

I know I'm not super fucking handsome tall perfect chiseled jawline greek god material. I minimise the weakness by exercising enough to get some decent muscle mass, wear well fitting clothes - I'm not an absolute slob, my foot jammed in the door so I can let my strengths play out. My strengths are definitely my irl humor/charisma/conversation - I actively hone this by going out and just having as many conversations as possible, trying different tactics to get different outcomes constantly making mental notes of what works, what doesn't - perfecting shit down to an art.

Reverse this if you are a good looking motherfucker.

My mentality summarised became: 'have fun, live life, we're all going to die anyway',
We're all going to die anyway, so why do you fucking care so much what others think of you, why do you fear what someone might say. Wave a hello, slide in that dm, people are too self absorbed anyway. You are a mere speck in the floating continuum of social interactions, nobody really gives a shit. You and I we take a photo together and we look at the picture, you look at yourself first make sure you're looking okay looking fly. People are way too self concerned to care about you. Don't take shit too seriously.

We're all going to die anyway, so none of this would matter so fucking much - say that absurd shit you wanted to, paint your dick grey (non toxic ofcourse) put on some googly eyes above it and call it an elephant, have fun. You'll be genuinely surprised at how far you can take it.

Have fun, but establish your core beliefs. You want her to be your intimate sexual partner? Make it clear that you want it so - so she has the chance to politely decline you or play along. The odds of you starting out as a friend and making it to a lover are infinitely lower than if you had started out establishing yourself as someone who is the fucking MAN to her woman.