Jesse James and Kat Von D

The adage once a cheater, always a cheater fits the bill in this broken engagement. If you can cheat on Sandra Bullock, you can cheat on anyone. Tattoo artist and TV personality Kat Von D was a rebound relationship for Jesse James, Sandra’s ex-husband. Kat and Jesse began dating in 2010 and were engaged in January 2011. They split up in July 2011 but reconciled a month later. Another month went by and they split up again. Kat claims he cheated on her a record 19 times – with 19 different women!