Taylor Swift’s Newest Squad Member Is Best Friends with One of Her Famous Ex-Boyfriends

Taylor Swift
Photo: Axelle/Bauer-Griffin/FilmMagic.

In a twist of events, both Taylor Swift and Cazzie David have a John Mayer connection. Swift revealed that David is the newest member of her squad on Thursday when she posted an Instagram of the comedian at a wine night with her, Selena Gomez and HAIM. But as fans wondered how Swift and David knew each other and what the hell they were talking about last night (we have our theories later), we found another surprising connection: John Mayer.

As many know, Swift and Mayer dated for a couple months before breaking up in February 2010. Mayer, who is 12 years older than Swift, later became the inspiration for her 2010 song, “Dear John.” “It made me feel terrible,” Mayer told Rolling Stone of the song in 2012. “Because I didn’t deserve it. I’m pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do.”

That’s Swift’s connection with Mayer. But what about Mayer’s connection with David? Well, the daughter of Larry David appeared on Mayer’s Instagram live in October to ask him NSFW questions about his sex life, like if he’s ever masturbated to his own music or had sex with his songs in the background. (Spoiler alert: He used to do both when he was younger but not anymore.) Their friendship was so close that OK magazine reported a rumor that they were dating, which was later debunked by Gossip Cop.

This brings us to today, where Swift and David are new friends and David is still BFFs with Swift’s ex, John Mayer. It’s a messy situation, sure, but Swift’s friends have had connections to her exes before. (Squad member Gigi Hadid even dated one of Swift’s exes, Joe Jonas.) As for what David, Swift and Gomez talked about on their 20wineteen night? Well, their long list of famous exes is one (David dated Pete Davidson for two years, while Gomez was in relationships with both Justin Bieber and The Weeknd.) Their love of wine is another.

Who knows what their conversation was like but we sure as hell know we would’ve loved to be a fly on the wall.