1.
When he lied to Rachel about getting their marriage annulled.
2.
When he tried to kiss his cousin.
3.
When he dumped Bonnie after she shaved her hair off.
4.
When he was dismissive of Rachel's career.
5.
And convinced her to give up an amazing opportunity.
6.
When he filmed him and Rachel having sex, and kept the tape.
7.
When he dated his teenage student.
8.
His treatment of Mona.
9.
When he assumed that Rachel being naked in her apartment was an invitation for him to have sex with her.
10.
When he just refused to take the blame for his own actions.
11.
When he wouldn't give Joey his money back.
12.
When he fake outed Chandler on their school website for revenge.
13.
The whole "male nanny" debacle.
14.
When he freaked out over Joey and Rachel's relationship.
15.
When he slept with someone else.
16.
When he didn't want Ben to play with a doll.
17.
When he made out with what he thought was a drunk, semi-unconscious Rachel who turned out to actually be Monica.
18.
His jealousy over Mark and possessiveness of Rachel.
19.
When he tried to ban Rachel from seeing other people, even when they weren't together.
20.
When he just had to be right about everything.
21.
And finally, his homophobic comments.
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