So pretty new, maybe 2 weeks of reading around here, I had been thinking so many of the things I see on here prior to my stumbling on in. This was basically my first night out since coming here.

Sunday night get a txt from a ladyfriend to come out with a few people to play some pool, have some drinks and then head to the club. I should note that unbeknownst at this time, to her, come midnight I would be 30 years of ancient. She did figure this out before we went out mind you.

So we go to the pool hall, play a few games, have a few drinks. It is me, my hb5 friend, her hb8 friend and some dude who is so full of himself it is not even fit, we will just call him truck. He has a giant truck I hear, alot. Pool place is very sparsely populated and 90% what appears to be couples.

While admitedly I am sure I could have found someone to approach, likely they would not have been female, and I was only 1 beer in at this point. Managed to not let myself get run over by truck and kept up conversation well enough with my group. Went out for a few cigs where I interacted with whoever was out at the time, had a good laugh at some of the other guys who were tryin to guess my age (bday and all). Got a 19 once lol, nothing close to 30 though!

So around 12:30 the girls are complaining about the music in the pool hall, I think the comment was 'the cut your wrist soundtrack'. I am basically with them on that so we all head out to the only club open on Sunday (I live in a pretty smallish area). Place is DEAD, like bouncer barkeep and one dude. Girls seem skeptical but I am just like psh it is my bday someone buy me a drink. So we sit down. As time goes by a few people filter in, given it is Sunday I would assume mostly regulars. After a bit a pair of girls walk in, an hb5 and an hb7. They start playing pool with a couple of dudes who they definitely know. I make sure to check the hb7 out from across the bar and made some good eye contact. I stick to my table chatting with my lady friends (truck is gone), there are a few guys who sit down to chat and I have to stay in it to not get alpha'ed out.
At some point one of these guys who I am certain is not gay starts goin on with me and the girls about comparing dick sizes. For real. I try and play him off bein like uhh why exactly do you want to see my dick again, just ask these ladies about it in the morning ( which got giggles). Buddy just keeps on it, really weird- not sure at all what I should have done here, he was at my table eject would have been what he was aing for I am sure. So I whip out my cellphone and pull up a msg from a ladyfriend of mine (who was not trying to sleep with me at the time haha) telling me I am top 10 percentile in the male endowment category. This actually shuts him up, and my ladyfriends are fairly interested as well. Can't hurt to plant these kinda seeds right? Was this completely insane of me or?

Little bit later I catch the hb7 who is playing pool looking over at me. Give her a little smile amd eye contact, then minute later get up and vanish outside for a cig, making it pretty obvious that I was doing so, which I think she saw but could be wrong. Alone outside at first and then I am sure every guy in the damn place is outside with me smoking and chatting. Then the hb7 and hb5 stroll out. HB5 immediately runs off to sit away from the whole group of us, HB7 stands close to me. Me I just go for it, say hi whats your name, trade names etc. Now my big problem is, like many others I am sure, I just never find something to start a convo in the moment. I am great at keeping up convos on just about everything, starting, not so much. I think I babbled something about being old, intending to segue into the birthday thing, but just not hitting it right at all. We end up in the group conversation instead and then her friend drags her off away from the club and they are gone. So at least I made an approach, I am kinda laughing at myself but it is ok I am having a good time, and I would say this is one of very few times I have actually tried with a girl at a bar. So fast forward an hour or so, night is winding down, I am outside the bar with my hb8 friends and two random dudes and who strolls behind us but the hb7 from earlier. She looks me dead in the eye and says hi (but follows her friend back into the club). So I am dead confused at this time, figured that I had made a terrible impression. One of the guys that is with us is like, 'you should get on that'. So a minute later despite myself I head inside to use the washroom. I see hb7 and friend at a table, but like a right good fool go to the bathroom first. Not brilliant, by the time I am out a minute later they are talking to a group of guys who they leave with a minute later.

I am still kinda baffled as to why she was interested, maybe because I am not a regular and everyone else there was? Maybe because I was literally the only guy there who did not look he was on steroids? Maybe because despite my terrible fumbling with her when I did approach, that I think I really was independant of the outcome!
Any advice? Specifically on how to not freeze up when figuring out a conversation topic, or anything else really. Sorry for tldr i am not good at making things short.

Tldr; went out, approached, failed- sorta, don't care feel good!