Hey BHW, I'm having a serious dilemma. A quick background: The guy I'm talking about, we'll call him Bill. He's my best friend, well he was.. he's been my friend since we were 10 or 11. I'm 24 years old so you can imagine there's some history there. Well recently, he started acting a tad weird (like 1 year ago) so about 6 months ago, I figured to myself. "Ok, I gotta see what this guy does online, he always jokes about sick/disturbing/weird stuff" and viola.. his Gmail and Facebook passwords were saved... oh boy but was the joke on me. So I read through his entire facebook clear to the beginning of when he had it, I read through the gmail e-mails and still do to this day. It's like an addicting fucked up show I can't stop watching but I know i should do something. It's like "what's he going to do next, what does he do next?!" It's addicting but at the same time I know he needs professional mental help or to be in an institutionalization. I've known he was bisexual for a long time (he always joked about it for a long period of time) He finally came out years after constantly joking about it. Well now a days, he keeps joking about children, philipino boys, having sex with them and how hot it would be to have them. He's also typing in "How to conceive a boy" in his search results on Chrome. You know, I appreciate fucked up jokes but I don't think he's joking. Additionally, he's continuously joking about having sex with his mom. he even sent a fake email to her (more on that later). His girlfriend to day said "I'm not your mother, you can do it yourself" he said "Can you pretend to be" She obviously thought he was joking. She's been his girlfriend for 9 months to give you more insight on this. Now for a list of all the creepy shit - Apparently he let a guy drill him from behind while wearing his sister's clothing when he was 16. (More specifically her skirt) - He tried to sleep with his sister.. and naturally she declined and moved out without telling anyone until years later. She told her brother which eventually got around. He always jokes about incest and has a TON of "Incest Porn" on his Chrome History... - He messages everyone possible if he sees they're "bisexual" and tries to get "stories" from them all. "So what did u do with her" "so what do u do with girls" I'm sorry no, it's not normal. - he messages everyone asking "is it cheating if it's with a guy".. he literally brings up this and the above in nearly 100% of his convos. - He poses as a woman on Craigslist (not e-whoring or for making money) but to try to score legit pictures or stories from the girls. When guys reply, he goes "are u bi hun i know a guy". - He posed as a woman and sent a message to his family members saying "hey I found your e-mail on a website, are you bi? I hope i got the right email id love to talk to you and share stories with you" He sent this to his mom.. his 70 year old aunt/grandma (I forget who she is) and another 50 year old woman that works with his grandma. - He's constantly posting in Craigslist looking for bi-sexual discreet hookups and again posing as a woman to earn "stories" of people. When do you finally confront the guy and say "yeah.. dude.. you're a complete fucking creep, and you have a girlfriend of 9 months." When do you finally do something about it?