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I am so upset right now I don't even know what to do. One of my closest friends has just entered the dating market. Her parents were always really overprotective, so when she started university this year it was also the first time she started dating. She's dated a few guys in the past couple of months, but they're decent guys and once they realize how inexperienced she is, they all back off because they don't want to fuck up and end up hurting her.



Another friend of mine is an unintentional womanizer. He doesn't mean to, but he goes through women like an alcoholic at an open bar. And it always ends badly. He's looking for a specific kind of girl, and he always thinks 'she's the one' but once he gets to know her and realizes she isn't it, he just stops caring. He just keeps up the facade while the girl gets more and more attached to him, until he just can't take it anymore or he finds a good excuse to break it off.



What's worse is that no matter how many times I explain it to him he just doesn't understand why doing that is wrong. He's passive aggressive, so he avoids conflicts such as sitting a girl down and explaining to her that he doesn't feel the same way and doesn't think it will work out. He'd rather avoid the issue and pretend everything is okay, meanwhile becoming an increasing bad boyfriend who ignores her phone calls, lies about things, and 'never has time' to get together with her.



He also hasn't had a girlfriend in a couple of months. He doesn't really go out anywhere anymore, he always hangs out with the same people, the girls he knows are either in relationships or just not interested, and no one introduces him to girls anymore. He's been going on and on for months about how he misses being in a relationship, and how hard it is to find a girlfriend, and so on.



I'm sure you can see where this is going. I suppose it's my own fault for trusting him. The two of them didn't know eachother, but there was a big get-together on Halloween for all of my friends and I wanted to invite both of them. Before it happened, I made him promise me he'd stay away from her romantically. Every time I mentioned her it came with the follow-up, "But seriously, don't touch her. Don't even look at her the wrong way. I mean it."



I absolutely forbid him from flirting with her, hitting on her, dancing with her, or in any way suggesting, encouraging, or allowing any kind of romantic attachment to her. After they met he told me he kind of liked her and I flipped on him. I told him flat-out, that he was to stay the fuck away from her, and under no circumstance was he to pursue anything with her whatsoever. I then reminded him of his promise, of his previous track record, and of the fact that she was my close friend. He agreed not to do anything, and I thought that was the end of it.



Today he called me on his lunch break to say that "Oh, by the way, I was over at her house last night and she said she'd like to do something with me. I was just calling to give you a heads up, and see what you'd say before I call her back and let her know. Is everything cool?" I'm sure you can imagine my reaction.



Altogether, I think I've spent over an hour and a half on the phone with him trying to talk to him and explain to him, literally crying with frustration and fear that he's going to do to her what he's done to every other girl that he's ever been with, while he keeps insisting that this time is somehow going to be different. Absolutely nothing I said has made any kind of a difference in his mind. Basically, the only way he is willing to stop is if continuing with her means the end of my friendship with him.



We've been close friends for almost six years and know eachother for even longer, and he's met her twice. This is what it takes to put a dent in his reasoning. As far as he's concerned, I have no right and no reason to keep him away from her, and the only thing stopping him is six years of friendship on the line.



I honestly don't know what to do. I haven't been able to get ahold of her, I just left her a message saying that we need to talk. I don't know how she's going to feel about this. The last thing she wants is yet another person being overprotective of her, but she also knows I'm her friend and I want her to be happy. I just want her to find a decent guy who isn't going to fuck her over in the end.



He is my friend, and in every other way he is a great guy. But when it come to things like this, he is a complete fucking douchebag. And she has no idea. I trusted him to stay away from her, so I never told her. And now I'm waiting for her phone call so I can explain to her that I've been interfering in her relationship, and if he decides to say no that it's because of me. I have to tell her all the things I never told her about him, and what he does to the girls he's with.



I have to tell her all that, knowing that she's probably going to blow it off thinking he's a decent guy and that he wouldn't do that to her. She's probably going to be mad at me for going behind her back and not telling her. She'll probably forgive me because she knows I just want to protect her like I do with all my friends. But I can't protect her from everything. And if she gets hurt, it will be all my fault for trusting him in the first place, for not warning her in the first place, for thinking I could take care of it on my own and she'd never have to worry about it.



And I will have to live with myself knowing that not only could I not protect my friend, but that it's my fault she was even in danger in the first place.



My friendship with her will never be the same, because I wasn't honest with her about this guy and what I was doing. And my friendship with him will never be the same because I trusted him with something deeply important to me and he knowingly betrayed that trust without a second thought. Writing this all out has helped a bit, but in all honesty this has been one of the worst days of my life. And it isn't even over yet.