Jennifer Aniston & John Mayer

Mayer’s dating history is like no other. From Katy Perry, Taylor Swift, Jessica Simpson, to Jennifer Aniston. According to The List, Aniston and he met at the 2008 Oscar Party. Since then, the two began a romantic relationship. However, the two reportedly split later that year. In an interview with People, the Friends actress opened up that she is still very much in love with him, and that “It’s painful.” Despite the break-up, the two remained good friends, and “There is definitely no weirdness between them” US Weekly’s source revealed.

After their breakup, John was under the sheets of a handful of celebrities, while Jen also dated a number of stunning men like Bradley Cooper, Gerard Butler, and even tied the knot with Justin Theroux in August 2015. However, the two eventually called their lawyers to void the marriage after three years of being together. In 2021, Aniston floored her fans with the release of the special Friends: The Reunion, while Mayer also put out his album Sob Rock.