Like I have nothing interesting to say, I don’t know what they want from me, I just draw blanks. There’s this one girl I keep having these flirty moments with when we’re both drunk but I can never seem to pull it together when it counts. We’ve kissed twice now. First time she brushed it off with the whole “I was so drunk I barely remember” thing. Second time was actually amazing, we were both hammered but I was on fire, she was all over me, grabbed me, we were vibing hard. Then at the next bar she jumped on my back for a piggyback ride and I completely ate shit, face first, blood everywhere, had to go home early. So that was that. Sometimes it feels like she hates me but I don’t think that’s actually true. I just want to hit it off with her again without making it weird. There’s a lot of mutual friend overlap so I don’t want to go all in and scare her off, but she’s genuinely so pretty and I feel like we could actually have something if we just gave it a real shot. I think I just need to be patient and not force it since I know I’ll keep seeing her. A few days ago I got a last minute invite to hang with a group she was in. Showed up two hours late, stayed maybe an hour, then everyone went to grab food and I went home. Haven’t stopped thinking about all the ways I should’ve done it differently. The frustrating part is I know I’m not a social outcast. People invite me places, I have friends, coworkers like me. But I feel like I’m not actually contributing anything when I’m around people. Just kind of there. Boring. Forgettable. What really gets me is I used to be naturally confident around women. Not perfect, but I wasn’t in my head about every little thing. Now I’m running some mental checklist mid-conversation and it’s exhausting. Can’t tell if I’ve actually lost something or if I’m just rusty and overthinking. Has anyone gone through this? Where you used to just naturally be good with people and then one day it kind of stopped? What helped? submitted by /u/tonystarkthefourth
Originally posted by u/tonystarkthefourth on r/AskMen

I feel like there is a lot to unpack here but I’ll try and field things I feel like I have a useful opinion on.
First, the root problem you have brought up in “what are they looking for” or “how to hold a conversation with a woman”. In my experience, they want the same thing you want. If you like laughing and being weird/silly then the woman you’re looking for matches that. If you prefer dry humor and lean more to a serious nature then the woman you’re looking for will want that. Essentially, be yourself and the other shit falls away. I’m old (or consider myself to be old) and can remember a slew of women that things never ended up clicking with that I thought were the smartest, funniest, most beautiful, fun to be around types and if they would just give me a chance we’d be so happy yada yada yada. Thing is, in the end, they weren’t what would have worked out for me.
I didn’t meet my wife until I was thirty. The woman I dated and married made every woman I met before her seem drab and boring. Those women weren’t actually drab and boring they just wouldn’t have clicked the way my wife and I did. There was no weird stress about keeping the conversation up or if she found me interesting. Those things just organically happened. If you’re dwelling on that with someone you hope to date be it male, female, or others then maybe that person isn’t what will work for you? Why waste time trying to make something work that won’t?
Let’s think of this in reverse for arguments sake. Would you be happy with a woman that changed who she was just to get your attention because she was smitten with you? Would you be happy months or years down the line when you find out this person doesn’t actually enjoy the same things you do and is no longer fun to be around? Changing yourself to get a person’s attention will not work out well.
Be yourself. Enjoy the things you enjoy and invite others to enjoy them with you. You don’t have to work at a conversation on a topic you’re really into and in the long run the person you want to spend your life with will be just as enthusiastic about it.