I have a very very close male friend, who is 23 years old. We’ve been friends for nearly 6 years now, and I’ve seen him at his highs and his lows. Like your friend, my friend has never been with a woman (or had a girlfriend, been kissed in his adult years, etc.) Until recently he’s lived at home, and his family life was downright toxic. He tried to maintain jobs, but he just couldn’t. Partly because he relied on his dad to drive him to work, and when dad didn’t feel like it, there was no going to work (he didn’t have a DL) and partly because he’s struggled with depression and sometimes couldn’t even get himself out of bed.
My friend does things that I wouldn’t do online (sex chats, live cams, etc.) but it is not my place to approve or disapprove of his actions. He has needs and he satisfies them how he choses.
Anyway, recently he really really really needed a friend there for him. He became downright miserable to talk to, and boy were his mood swings crazy. He would say hurtful things, then apologize a while later, and yes, it got old, but you know what? I know for a fact that if I were ever like that, he would be there for me, no matter how miserable I was being. So I sucked it up and I was there for him. I offered my advice, and after a while of him not listening I told him that I was trying to help, but if he wouldn’t let me, then that was fine. He could still vent to me, but he needed to be aware that I wasn’t going to offer up any more suggestions or try to be helpful. A few weeks later he called me up and told me that he was “finally doing it” (meaning finally moving out of his family’s house to live with his aunt and uncle in another state) and already had a few job interviews lined up. I was proud of him, and I am still there for him even when he’s ready to throw in the towel and move back home. He is happier and he now has a DL and SPENDING MONEY!
My point is, sometimes friends can be irritating and hurtful, but if it is someone you truly care about, and someone whom you believe would do the same for you, you’ve just got to suck it up and let them be human. Yes, there are times you have to draw the line, and you’ll know when it is reasonable, but sometimes when people are so far down in the dumps, they really need some unconditional love and tolerance.