Jen took a shot with another musician, this time with singer-songwriter John Mayer. The two met in 2008 at an Oscars after-party. Although Mayer was eight years Jen’s junior, the two clicked…for a time.
The relationship started to disintegrate later that year. Unfortunately for Jen, it was a highly publicized breakup and Mayer took little issue with sharing his side of the story with the media. Reportedly, it was Mayer who broke up with her but, in later interviews, the singer hints at regretting his decision. Despite the initial awkwardness after the breakup, the two are still friends.
Vince Vaughn — On Good Terms
Dating an A-lister like Jen was definitely not in the best interest of Vince's secretive side. Even though they broke up, Jen and Vince stayed on good terms. The two still chatted afterward and Vince even went to one of Jen’s birthday parties.
She confessed that Vaughn was her “defibrillator” after her painful divorce and that he had come into her life at just the right time. They laughed, they had fun together, but they decided that they were just not good as a couple, especially under the pressure of the spotlight and the paparazzi.
Many may not remember this very brief fling of Jen’s. The actress was seen with Paul Sculfor, a British model, after calling it quits with Vaughn. This “relationship” might have been classified as more of a “fling” as it didn’t last more than a few months.
According to those close to Jen, it was primarily because of Paul’s demanding modeling commitments that the two couldn’t take their relationship further leading to its dissolution. However, the pair did manage to avoid the paparazzi for the few months that they were together - a major win for anyone in the public eye!
John Mayer — Bye, Bye Drama
John Mayer hasn’t been known for his great diplomacy and decorum. The singer-songwriter has been known to stick his foot in his mouth and then some when it comes to the press. He definitely threw out a verbal faux pas when it came to his breakup with Jen.
In speaking about the pain of the experience, Mayer said that when the couple broke up he “burned the American flag” and that he had “murdered an ideal”. Yikes. The controversial remarks gave him nothing but public scolding. Reportedly, Jen was also “really, really upset”.
Josh Hopkins — Maybe?
Reports spread that Jen briefly and casually dated actor Josh Hopkins in 2010 after the two were introduced by Courtney Cox. It was soon after reported that the two had broken up and that Hopkins hadn’t treated her well. Specifically, that she had wanted a real relationship and he just wanted to date casually.
But, according to Hopkins, the two simply had a friendly dinner and that the rumors “spread like wildfire.” After denying the rumors and calling them “weird” and “hurtful” he confirmed that he and the actress were “just friends”.