I’ve been on both ends of the spectrum. I wouldn’t say either one is necessarily bad. I use to do CRAZY shit to get laid, no hesitation. Lately, I am more like you described. Leery, awkward, uncomfortable and sometimes to the point where I am unable to enjoy myself. I’ve had a handful of bad/embarrassing sexual situations. And a shit ton of missed opportunities and regrets. Don’t let it eat at you man. Your not alone, I’ve fucked up some awesome experiences in my life. And I still sabotage myself sometimes. But I get better at not beating myself up for it the older I get. Got to cut yourself some slack. Didn’t mean to sound preachy/coachy. I don’t know shit.