Imho it’s just two tiered; being yourself and taking rejection with a grain of salt. High schools difficult at times to get it because it felt like so much was at stake if because of the social pressure. College? College was easy but also fake because it felt like everyone was going to give you a shot out of hormones and boredom, LOL.

It’s when I started dealing with WOMEN tho in my early 20’s to mid 20’s is when I felt like Herbie Mcgee. I had to learn it was more about being comfortable in my own skin(which id argue is probably at its lowest in your early 20’s because of that adulthood transition) then anything I had to say to them in the moment. Like Ambient1 said the key is to fail HARD and often, after a while you get used to it and when you get to that mentality of “I hope this shot goes in but if not, who cares” then it feels easy.

That said, even in my comfortable era I have had some spectacular fails. I remember having a bad day at work and getting LIT at a happy hour and ended up chatting up this lady on some small talk at bar. She said something sly about me helping her with something at her place when I expected nothing and Im like, damn, after that day at work this is karma hooking me up!

Every subsequent shot I took was an ugly air ball; my fav was when I cracked a small joke about 911 and she ended up being a survivor :( Her friend even tried to help me out but even at a certain point I saw her do this and walk away out of the corner of my eye.

https://media.giphy.com/media/Lsn6R0xjdstnG/giphy.gif

She was fine as all hell too, I was too drunk to make it happen. I swearing off alcohol for a week out of frustration with myself, lol.