TL;DR: the title and the last paragraph pretty much.

The title says it all, I'd like to read your advices about it.

It's something I've been realising lately, for a while I've been feeling like I'm either good or extremely bad with both women and men.

It's like I'm good in social situations such as parties or gatherings with people I already know, but with new people I want to meet, and women I want to approach, sometimes I suck and I end up talking about "bullshit" and I make the small talk too small.

2 examples:

Girl I met at a party, friend of my friends, after introducing we talk a little bit about everything. I end up making jokes with her and she kind of blushes. At some point we split and keep partying with our friends. Nothing happens but I don't care too much since she didn't look too much into me so I just move forward.

Next day I spot her sitting on a bench in a park nearby home, I decided to go there and say hello. The conversation straight up sucked, after the usual "oh wow so we live in the same neighborhood, you didn't tell me blablabla" I literally didn't know what else to say.

It's not like I was that interested in her but it kind of frustrated me how terrible I am and for sure I need to improve.

Other example: me and my roommate (guy around my age) are really good friends and we have had really good times going out or just chilling at home, but sometimes I feel like talking to him and maybe we are both at the kitchen and the only conversation I am capable of holding was "so... How was... Like... Work.. today?"

And then if I go to a party I end up talking to everyone and at some point I'm teaching 5 dudes how to say "I need to pee" in Spanish.

Yeah I know that night-time settings make it easier to socialise in general but I feel like I should be better , specially now that I'm getting older and I don't go out that much.