Hey guys, I've got a challenge in front of me with one of my INFp friends. Put simply, he's probably one of the most socially awkward people I know, so I've made an ongoing commitment with an ESTp and an ENFj to get him out of his socially awkward shell. One of the reasons for this is that he could probably get a ton of ass if he could just get over himself already! For example, if we're all out and doing normal things that teenagers do on a weekend, INFp is always very concerned that people he doesn't know are looking down on him specifically, when he's the by far the least obnoxious / suspicious-looking person in the group at the time. He also appears to have a hard time mingling with new people, which is problematic for obvious reasons, lol.
So what we (Me, ENFj girl, ESTp guy) tried doing yesterday was to bring him everywhere with us. We ended up dragging him into two lingerie stores, the tampon and condom section of the drugstore, the softcore porno section of the bookstore, etc. The ENFj ended up flashing him like 357645646337693 times throughout the day, and he got that sheepish grin on his face while looking away, every time. A few other times, we had this ESFp guy act all flamboyant with him, which ended up being quite funny to watch. Basically, we're trying to expose him to things that stretch his comfort zone so that he stops being concerned with every little opinion that random people might possibly have of him. Are we taking the wrong approach here?
Any suggestions as for how to help him become more comfortable? I really want to see him get less awkward, but I don't want to accidentally make it even worse. Thanks for the suggestions!