For some background, I’m about to turn 18 and heading into my senior year of HS. I’d say i’m pretty good looking, but on the other hand I’ve always been really skinny/lanky. I’ve had a few hookups here and there, and i’ve done pretty much everything except sex (didn’t have a condom, she had to leave early, couldn’t get it up, i’ve had my share of fumbles) but my biggest issue is escalation. I do get pretty nervous sometimes, but in party situations and stuff pre-covid I could hold a conversation. Further than small talk and friendly banter is where I run out of stuff to say. When I do get a girl upstairs or ‘secure the bag’, it’s usually bc I didn’t really have to do anything and she was just really into me.

With the pandemic, I’ve noticed multiple girls who definitely show some interest over snapchat or something, but then I can’t escalate the relationship to where something actually happens and I sort of just watch them lose interest over time (ik it’s harder over text, but i’ve seen it in person too). Any advice for how to take things further? The best I can do are really basic compliments when she sends a hot selfie, and even then I always second guess myself. Whenever I think of something bold or confident to say, I always talk myself out of it thinking it’s corny and then just reply with nothing. Anything helps, especially examples.

First time posting on reddit, but i’ve been scrolling through this sub for awhile and seen some really good advice so thought I’d give it a shot.