Dear Miss Emily, 

I have a guy friend, I'll call him "Jay," who I think may be obsessed. I'm in a long-term relationship and my boyfriend and I are very happy. "Jay" was a mutual friend and everything seemed kosher until he caught wind a few months ago that there was some trouble between me and my guy. He came to me and literally gushed that he had always been in love with me and that I was perfect for him. He said how he didn't feel his day was complete until he got to see me or talk to me. I told him that all I saw of him was a friend and tried to laugh off what had happened because I didn't want it to get complicated. He became sad and declared that he didn't want to but now he had to put me in the "friend zone". Why wasn't I there in the first place? That angered me but I let it go and treated him like I normally did. My guy and I were fine (it wasn't any end relationship issue anyways), and we happily hung out with our friends including "Jay." He would insist on hanging out and that he was fine but the moment he saw me and my guy together he would get depressed and ruin the event by being dramatic. He would lie about stuff to get pity. At one point, he called me pretending to have a drug overdose (according to him he took a single white pill) and was slurring. I informed him that I was calling 911 and hung up on him. He immediately texted me begging for me not to and suddenly he was magically sober. It would anger me he would lie and stir up that kind of stuff to make me feel guilty I rejected him. He would constantly message me about how he should have asked me to date him before my guy did and how he regrets it. He would try to make me feel guilty by displaying cryptic messages about being alone and life and death on his facebook wall. When I stopped reacting to him he started barraging me with compliments and would say "I love you" to me and claim how sexy I am. I stopped talking to him after that. My guy and I stopped all communication with him and two months later he randomly popped up with a new girlfriend. I was happy for him not just the sigh of relief that I don't have to deal with that crap anymore but also I hoped he learned something and actually found happiness. Unfortunately that wasn't the case because a week later the compliments started again, and so did the "I love yous". I told him that he needed to stop because out of respect for his girlfriend he shouldn't be doing that. It would stop, but then start back up. I stopped talking to him again but then he started posting songs and messages on my wall about breaking up with s/o and when my guy would right something Jay would try to make a passive aggressive comment. I deleted him from my friends list and then he started sending me texts calling me sexy and stating "I'm sorry I just realized how much I should have talked to you. I know we are friends but we could have been more once!  I should get to sleep or something before I regret saying something that I want" I told him flat out I saw you as a friend nothing more now I just want you to leave me a lone. My phone blew up with calls from him so I blocked him number. I'm just worried it will progress to something else. My guy hates him now and had told him to leave us a lone. In the beginning I tried to be a friend but he wouldn't stop. A lot of things have happened and I dislike him now. I dislike him more for the fact that he doesn't respect me as a person and thinks that he can force his "love" on me to make me want to be with him. I found out recently he had been taken to the psyche ward in the past for suicide attempts and was also arrested for assaulting his Mom. I don't know if I'm overreacting, or if I should I consider this with more caution? I haven't spoken to him since I blocked his number so I hope maybe he lost interest? What is your opinion on this? Thank you.

----------------------------Miss Emily's advice----------------------

Of course you're not overreacting! You're not reacting strongly enough! You've given him a great deal of understanding and patience, when another person would have cut him out of her life completely. But he is not only obsessive, he is emotionally disturbed and you, in a sense, are his victim. You are right to be concerned. With his history, you can't be sure you're safe from anything he might do. He's displayed the behavior of an extremely volatile, and troubled man and appears to have a history of mental illness. This is a delicate situation because you don't want to trigger anything that will set him off. It's a sort of "damned if you do, and damned if you don't" problem. But I wonder if you are getting close to filing a police report against him based on harassment. And do keep records of phone messages and texts. That may seem overboard to you, but after reading your letter, there's no telling what he's capable of doing. You didn't mention your ages, but if he lives at home, perhaps his parents should be told. These are all possibilities on how to handle this, because I don't think he's going to stop harassing you. If he does, great, but please do not hang around him, or answer any of his calls. As well, make sure you are extremely careful in terms of locking doors, and be on the alert -- and maybe that even means carrying pepper spray. You seem like an extremely sweet girl, but don't be naive to what he's capable of doing. He is obsessed, and you should address this problem as a threat and not just from someone who is harmless, but whack. I am sure I have frightened you, and that is not my intent. But I would be remiss if I didn't want you to see that this is no small matter.