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Can you discuss sex topics together? Can you gently get them to tell something about their sexuality? If yes, then you can go further into more intimate topics. Otherwise if you try to push it or force the conversation, that’s when you become creepy.
But in general I wouldn’t be too worried. If you’re both adults, it’s ok to express your intentions.
if you’re good friends and you can openly and comfortably talk about sex, you can steer the conversation toward the topic. last time you had sex, your preferences and what you enjoy, things like that. if they go along and reciprocate the enthusiasm, and what they’re saying matches up with what you’re saying,
then it’s just about timing well the “what if we fucked”
From (painful) experience, and observing others:
Being in social proximity and always being “nice”, tells a woman absolutely nothing about your intentions. That is you actively removing yourself from contention.
Asking someone out on a date doesn’t have to be nerve-wracking at all, because the answer shouldn’t affect you at all. Generally speaking, you should ask a woman out as soon as you know that you’re interested. The longer you wait, the more your imaginary future with her grows, upping the stakes, making it vitally important that you don’t fuck this up by being awkward when you do and maybe just maybe she will….. until it feels too risky to ask.
Expect and understand rejection as a part of the process. Discover interest, ask, find out, proceed. If you get turned down, you accept it and move on. No pressure on her to say yes, and no hostility or refusal to accept a no. Rhetorically, what kind of reputation would you like regarding how you act when rejected?
Whenever I try to smile for a picture, I look like I’m contorting my face. In pictures of me that were taken when I’m not aware of the camera, I’m handsome as fuck. Use this metaphor when trying to cobble something useful out of advice like “just be yourself “. Think of “Just be confident” as presenting yourself as you actually are, instead of trying to put on some sort of “picking up chicks” affectation.
Get out there and socialize. Talk with groups, talk with men, talk with women. Be exactly the same guy in all scenarios.