It all started going downhill once he got a decent paying job. He really lucked out, and got a job making 40k/yr with no education past a high school diploma. He started getting really cocky after that.

I was still in college, and was working at Walmart, while trying to graduate with a CS degree in 4 years. I wasn't jealous, but he loved flaunting his ability to start buying whatever he wanted. He loved criticizing whatever "inferior" product I had, and compared them to his. He got an almost brand new Chevy Camaro, built a $2500+ gaming PC, and some ridiculously overpriced home theater system. He lived on his parents' property, so pretty much every dollar he made, he could spend it towards whatever he wanted.

With all of this cockiness from money, he felt that women were now obligated to start liking him. He got REALLY into the whole meninist thing, and turned into a full-blown reddit Nice Guy™.

I started talking to him less and less. Every conversation we had was just about whatever new item he bought, followed promptly by him complaining about not having a girlfriend.

All of this leads up until one night. One night, my wife's (girlfriend at the time) roommate "hacked" her FaceBook, and changed her relationship status to 'Single' as a joke. This was promptly followed by her roommate setting the relationship status as 'In an Open Relationship with (her roommate's profile).

In the short window of time that it was set to 'Single,' this guy messages my wife telling me how shitty of a person I am, how I constantly check out other girls when we'd hang out (false), attempted cheating on her with my ex (super false), how I told him that I only dated her because her parents have a lot of money (they do have a lot of money, but very false), how he will always be there for her to comfort her, proclaimed his love for her, and finished it with saying some lame shit about how he'd "treat her like a princess."

I called him immediately, he pretended to be all concerned, then I told him what happened, how we didn't even break up, and told him to go to hell. He told me what he told my wife was a joke too, and I told him to try to fuck someone else's girlfriend.