Why Jennifer Aniston Reportedly Misses Her John Mayer Romance

Actor Jennifer Aniston has had her share of high profile relationships over the years. The "Friends" star dated Vince Vaughn, was previously married to Brad Pitt, and later wed Justin Theroux. But while those relationships made the headlines, it's the one with musician John Mayer that she perhaps misses the most.

In a 2024 Life & Style article, a source revealed that Aniston's 2008/2009 relationship with Mayer was unlike anything she had before. This was due to the fact that Mayer wasn't competing with Aniston, since the two were in separate industries. 

The List consulted exclusively with Susan Winter, Relationship Expert and bestselling author of "Breakup Triage: The Cure for Heartache," and she believes this separation is important. "When two people share the same profession, competition and jealousy have a fertile breeding ground — especially when one's success outpaces the other's." In contrast, Winter highlighted the positive aspects of a couple who work in different arenas. "Having a partner in an unrelated industry puts an additional barrier between the urge to compare or compete."

"The Morning Show" star Jennifer Aniston has been romantically linked with some of Hollywood's top stars over the years, and while those high profile relationships were with men competing with her for mainstream attention, her time with musician John Mayer was different. Relationship Expert Susan Winter pointed out the contrast in The List's exclusive interview. "With no direct competition, each partner is able to run their own race. This offers a greater likelihood of mutual support."

Aniston and Mayer dated off and on from 2008 to 2009, and during their relationship, Aniston had nothing but kind words to say about her ex. "We care about each other," Aniston said to Vogue after their first breakup in 2008. "It's funny when you hit a place in a relationship and you both realize, We maybe need to do something else, but you still really, really love each other. It's painful."

Aniston's words came after Mayer told reporters that he was the one who ended their relationship. Instead of contradicting him, Aniston defended her ex. "Trust me, you'll never see that happen again from that man." In a 2010 interview with Playboy, Mayer regretted that things didn't work out with Aniston. "I would be sitting here saying, 'What I have when I go home is the thing I've always wanted.'"