There's been a ton of buzz around that Jessica Simpson and John Mayer are indeed back together. They broke up in 2007 after spending a year together. I never understood the connection, but they did look happy. Sadly, neither of them seem to be able to sustain a relationship in the long term. Maybe this time will be different. Maybe. John has dated everyone in Hollywood including Jennifer Aniston, Jessica most recently dated Tony Romo. This file is licensed under Creative CommonsAttribution 2.0 License.