Thread: Clingy Friend Problem: break it off?

Quick warning: This is a story that is longer and more complicated than it should be. Only read if you've got time.

I'm a 3rd year undergrad, and back in summer 2008(I was a 2nd year), I got to be really close friends with a guy from a school club. We started talking through AIM a lot and found out we both shared taste in music, so we started having jam sessions (I sang, he played guitar) and got even closer as time went on. Then during the fall, he and his girlfriend of several years broke up (they were 4th years). I wasn't involved in any of it, but by then, I learned he was an emotional guy; I thought it might be a good idea to stop with the jam sessions because I know how powerful music can be in influencing emotions. I knew what rebounds were and didn't want him to wrongfully associate any catharsis from jam sessions with being with me. But then I thought I was being too paranoid and I should give him more credit than that. Not to mention, he could use a friend in a time like this. After all, he's the kind of person who does that for his friends.

So the jam sessions continued as normal, but I started feeling a bit uneasy at the way he was looking at me. Not a month later, he confessed to liking me. I figured it out as soon as he AIM'ed me a message that was loaded with hints. I was truthful with him and told him I didn't like him like that, but he asked me out anyway, insisting this wasn't a rebound and even his roommates confirmed this. Honestly though, I could see the potential and I'd never had any dating experience. We'd become really good friends and he was definitely one of the nicest guys I'd met, the kind who treats girls with a lot of respect. So I told him that even though I didn't like him at the time, if he wanted to go on one date to see if this could work at all, I'd agree to it. I made sure he knew this was just a trial, and that he shouldn't be surprised if nothing ever came of it.

Even today, my friends tell me it was extremely fair of me to give him a chance because not everyone would've done that. And now I wonder if it was a mistake.

After the "date" and a couple conversations I had with him after the date, I decided I couldn't be with him as anything more than friends. I had only gone out with him once and specified it as a "trial period" kind of thing, but from the conversations we had after that one date that he was too clingy for me. I told him the truth and he thanked me for giving him a chance at the least. I thought we could continue to be friends like before the date, but judging from his behavior, I wasn't sure he got the message.

Later on the next month, when I got into a relationship with another guy, I made sure he knew about it, and he confessed he was jealous but he didn't do anything rash. In fact, both guys knew each other from the sports club, and my guitar-playing friend also started dating someone else within that month, became friends with the guy I was dating and everything was going well.

But my guitar-playing friend stopped seeing the girl he was with, and although he was tactless with her, they are still friends today. Also, after six months, my ex and I broke up and he was one of the many friends who helped me through the breakup by just chatting with me and being there.

This past summer was the busiest time of my life, between studying for the DAT and also taking another summer school class. I barely had time to chat with anyone online, him included, but from that time, his behavior started to bug me a little. I talked about my high school friends a lot because I'm very close to them, and he kept insisting on meeting them. He'd already met my roommates because the jam sessions took place in dorm lounges when they were empty, but his wanting to meet people simply because I knew them and they shared a couple of interests bugged me a little. I shrugged off the paranoia and went ahead and let him swap numbers with one of my friends, more than anything because that high school friend insisted on it.

But the nagging feeling in my gut wouldn't go away. If I went online, the guy would message me within seconds. Usually, during school, he was always a lot slower about it, and he was slowest whenever he was interested in another girl. Also, I started getting random texts in the daytime, sometimes when I was trying to nap or was in class. Some of the things he said to me in person, online, or via text started resembling the way he talked back when he "liked" me, and in the meantime, he kept trying to be closer and closer friends with my roommates and high school friends. Needless to say, when I looked through my texts and AIM logs and found that I never had 24 hours without some form of contact from him, I was a bit freaked. Throw in the fact that he lives across the street (by chance, that was the apartment his roommate found and booked for this year) and that he studies in my apartment's downstair lounge. Add in that he drops by (sometimes at night) by coming in with other people who had keys and also told me he'd let himself in through a door he'd found had a busted lock if one of my roommates called him. Once he dropped by at 1 am unannounced because I had mentioned earlier in the day that I was borrowing my roommate's umbrella.

I got really freaked because he suddenly seemed everywhere. I blocked his phone number but texts still got through. I blocked him on AIM so at least I got peace on cyberspace, but by now he knew practically all those I was closest with and my roommmates. And as creepy as I found his behavior, everyone else just thought he was super friendly (although the 1am visit unnerved my roommates as well).

Adding to that feeling was the fact that he kept asking me personal questions even though I asked him to not press me if I told him I didn't feel like talking about some things (like religion for instance). He'd say things like, "I know you told me this is a personal issue, but can you tell me about it anyway? I *really* want to know."

Finally, I couldn't take it any more and I had to talk to him about giving me some space (more than 24 hours apart).

After those two weeks, he told me he liked me. Again. Exactly a year from the first time. My roommates and one of my high school friends confessed that night that he had told them that he liked me months ago.
Of course, I rejected him a second time, but his behavior was really bothering me by then. It creeped me out when the girl he had dated during the winter (one of my friends, incidentally) kept telling me she was really annoyed with how he perked up if I was mentioned in brief passing but generally didn't put her on the same "level" of friendship, even though I thought those two were still fairly close.

I was able to remain cordial to him for the most part, but it was getting really difficult to. It felt really strange to have a "friend" who knew all my closest friends (and tried to get to know those he hadn't met in person yet), tried to hang out with them (sometimes without me) and let himself in my apartment's lobby. Not to mention my roommates liked calling him in for random matters because they were friends too (but not extremely close), so he was in my apartment a lot. Him hanging out with my high school friends in my hometown made me feel like there really was no place I could be that he couldn't be (besides the women's bathroom).

So all that boils down to the current "problem." I'm trying to decide if I should break off the friendship.

He's a lot less polite to me and that conversations had become short and very cold on his end. He'd told me that it's because the 2-weeks' worth of not talking to me and the conversation I had wtih him about giving me some personal space had "hurt him deeply." More than anything else, simply not talking to me had wounded him. It's his last quarter here at undergrad (he's a fifth year now). He continues to be friends with my ex and keeps trying to talk to or hang out with my roommates or high school friends.

He was a really good friend to me in that last year and a half that I've known him, and helped me out a lot, but everyone around me observes that our relationship (at least on my end) has pretty much gone downhill from the time of the first confession. I really think I should drop the friendship, but it's going to be extremely awkward now that he's managed to be friends with all of my four roommates, my ex (who I don't talk to anymore), and my inner circle of high school friends. What should I do?