My buddy has been hanging out and messing around with this girl, who he thinks is cute, I don't, but she's cool enough so I meet up with them from time to time. Anyway, he invites me to hang out with them and says she has a friend (who actually turns out to be pretty hot - I'll call her "S") who wants to come, but doesn't want to third wheel so they wanted me to come too (I think the original girl told her friend I was cute so she wanted to meet me). I was busy that night but they hang out and I end up joining them the next night after work, we go back to his place and just hang out and watch TV.

Since it's only four of us all talking together, I felt really uncomfortable attempting to escalate, plus since they all had already met before I felt like the odd man out, which is bad for my social game and overall presence since I'm already not that outgoing to begin with. (All I could think to ask her is "where do you go to school, how do you guys know each other, what do you do," etc...I obviously need to work on not running out of things to say.) I sat there pissed at myself for being a pussy and not escalating, but I was also confused how to do it being sitting down together on a couch, no excuse to touch or anything, and as more time passes it obviously becomes even more awkward to begin kino. I even considered using the Cube, but I couldn't remember it well enough. Before last night I had felt like my game had been really improving, especially coming back from vacation where I went out approaching girls and ended up getting head from a girl off tinder.

As the conversation goes on the girls keep referencing how they're each other's only friends, they're ugly (even though the one I would consider to be a 7-8), etc. I begin to realize that they're pretty insecure, and they probably don't have much experience with guys being 18 in high school - I'm not that much older so I don't think it's that weird. It starts to make sense why playful neg type comments I made earlier seemed super unreceptive to her. I don't think even if she was into me she would've known how to give me signals, and coupled with me not being good at escalating/kino we went nowhere and the hangout had more of a friend vibe to it. At the beginning of the night I caught "S" giving me glances when I wasn't even talking to her, so I'm hoping she at least thought I was cute, but I'm worried by being boring and not escalating she got turned off. But she actually turned out to be smart and had cool hobbies so I would like to see her again. My only self reassurance is that since she's not totally socially acclimated to real world man/woman situations, she's used to going slow and that maybe if I had escalated quickly she would've been put off by it. Whatever, think on the bright side, right?

I'm just not sure how to go about conveying sexual interest with girls like this (I want to generalize this so the information is more useful than just this one girl). I'm really good at playfully negging more confident girls cause I can kind of be a funny dick sometimes, but this tends to work. On insecure girls, I feel like this would be counterproductive as it would just make them feel like shit. The opposite would be saying how cute they are, smart, etc. But I fear this sounds too needy, and also psychology states people don't like to have their own beliefs challenged, so telling a girl who doesn't think she's cute that she is would likely make her uncomfortable.

Not sure if this qualifies as a typical "FR," but it was a situation I found myself in and I'm racking my brain trying to analyze it and see how I can do better in the future. A lot of info on this sub is for hot girls with confidence, which is understandable, so I'm just wondering if you guys have any experience with this?