Hi Everyone,
I am a 31F here to ask about how to handle my relationship with my friend (31M), who I'm going to call "Henry".
Henry and I met through graduate school, and we were part of a bigger friend group throughout the entirety of graduate school. We all graduated in May, and I'm the closest of Henry's friends still left in the area. Everyone else has moved away and they've been busy starting their new jobs. I'm still here because I'm still looking for a job and staying in this city is cheap.
We went from a class group of 200 to 20, and I understand Henry has been dealing with how hard it's been with everyone moving, but because I'm his closest friend in the area he is always texting me to hang out. Every day to every other day. I believe he got used to how many people/how often he was able to see people and has been really struggling to adjust. When we were in school, he was used to being able to text a group of people and someone always being down to come over and watch a movie or go out to dinner. Now it's pretty much just me and it's starting to make me go insane when I spend an evening with him and then get another text the next day asking if I want to come over and hang out.
Henry does some stuff with his free time, he signed up for an arts class, and works hybrid, but generally he mostly just sits at home and watches movies or shows, then texts to see if anyone wants to come to his place and watch movies.
I also want to bring up another incident that made me more upset/frustrated with him.
This past Friday, my fiancé went out with him and a few other friends to a bar. I stayed home because I was hungover because we all went out on Thursday, and I didn't want to go out two nights in a row. During this time, my fiancé and Henry got dinner together, had some drinks, and then other friends met up and they kept drinking. Towards the end of the night, Henry bought my fiancé them both a shot before they left the bar, but thought it would be funny to tell the bartender, "can you give me the most disgusting tasting liquor you have for a shot", then brought it to my fiancé who assumed him and Henry were drinking together (they weren't) and took the shot and had an immediate visceral reaction.
Basically my fiancé left right after this and spent the next few hours at home puking and being absolutely miserable. He kept telling me he'd never had something so disgusting that made him sneeze, cough, and stuffed up his nose–like this was so bad he genuinely thought he may have been drugged (he's okay now).
I was already getting irritated with my friend, but now I'm pretty frustrated. My fiancé wants nothing to do with Henry; if he sees him he'll be fine and nice, but he's not interested in any more one-on-one time or going over to his place.
How do I talk to Henry about this? I know he's lonely, I know he needs more friends, but also, I don't want to handhold him to make new friends. I've suggested and sent enough links for him to go do other things (festivals, meetups, group sports), but he is seriously stubborn about doing things about himself (I know it's hard, but I'm dealing with my own sh*t, I can't dedicate the time or money to help him go make new friends–job hunting is really tough and my savings is dwindling).
I don't want to end this friendship, but I'm becoming seriously avoidant and frustrated. I can tell he's going through loneliness and depression (he's on medication and has a therapist), but I just can't be the main source of his social life. What can I do? What should I do?
Tl;dr my friend from graduate school has no other friends left in the area except me, and his behavior is making it so no one wants to hang out with him.