The 10 Worst Boyfriends Ever
The Guy Who Arranged For His Ex-GF's Rape
6 of 11
Ex-Marine Jebidiah James Stipe was angry that his ex-girlfriend broke up with him, so he impersonated her on Craigslist, placing an ad claiming she was looking to play out a "rape fantasy." The ad stated that she (Jebidiah) was looking for a "a real aggressive man with no concern for women." Ty Oliver McDowell responded and followed through with the request, forcibly entering the woman's home, tying her up and raping her at gunpoint. For his part in the crime, Stipe received 60 years to life in prison.