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10 Celeb Friends Who Dated The SAME PERSON

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Ten pairs of famous best friends have all shared the same ex, and Hollywood’s dating pool is smaller than you’d think.

TheThings Celebrity’s countdown “10 Celeb Friends Who Dated The SAME PERSON” digs into a phenomenon anyone who follows tabloid coverage already suspects: the A-list dating scene is really just a handful of interlocking circles. Co-stars, tour mates, and industry friends keep ending up with the same exes, sometimes years apart, sometimes practically overlapping. The video runs through the most notable overlaps, from teen-pop love triangles to grown-up divorces, and asks whether sharing a boyfriend actually blows up friendships or just gets absorbed as the cost of doing business in a town this small.

• Selena Gomez dated Taylor Lautner in early 2009 while filming in Vancouver, and her close friend Taylor Swift dated him later that same year after they filmed Valentine’s Day together.
• Taylor Swift dated John Mayer from late 2009 into 2010 — a relationship that inspired her track “Dear John” — and her friend-turned-rival Katy Perry dated Mayer on-and-off from 2012 to 2014.
• Cameron Diaz and Kate Hudson both crossed paths romantically with Yankees slugger Alex Rodriguez and pop star Justin Timberlake during the late 2000s and early 2010s.

The Taylor Lautner Handoff

The Selena-to-Taylor pipeline is the cleanest example in the countdown. Gomez and Lautner were linked during production in Vancouver in early 2009, well before Swift and Lautner became a couple that fall after wrapping Valentine’s Day together. Gomez and Swift’s friendship survived the overlap in plain sight — they’ve been photographed as a unit at award shows and each other’s shows for years — which the video uses as its first proof point that a shared ex doesn’t automatically end a friendship in this industry.

John Mayer, Serial Crosser Of Girl-Group Lines

Mayer’s dating résumé does a lot of the heavy lifting in this list. Swift’s relationship with him ran from late 2009 through 2010 and became famous mostly because of what she wrote about it afterward. Katy Perry then dated Mayer on-and-off between 2012 and 2014, years after the Swift-Mayer breakup had already cooled into public record. The video frames the Swift-Perry fallout — well documented elsewhere as one of pop’s longest-running friendship-turned-feud stories — as at least partly downstream of the overlapping Mayer timeline, even though the two have pointed to other flashpoints, like dueling backup dancers, as the real trigger.

Two pop stars, one guitarist, one very public “Dear John” — the timeline barely needed a decoder ring.

Diaz, Hudson, And The Same Two Guys

Long before either was doing press together, Cameron Diaz and Kate Hudson each spent time linked to Alex Rodriguez and to Justin Timberlake across the late 2000s and early 2010s. The video treats this pairing as evidence that the overlap habit isn’t limited to twentysomething pop stars — it runs straight through veteran A-listers who’ve spent two decades in the same tabloid orbit, dating across sports and music with the same handful of names recurring.

The Aniston-Cox-Mayer-Pitt Web

The countdown also traces a wider circle inside the Aniston-Cox social set: John Mayer dated Jennifer Aniston from 2008 to 2009, years after Aniston’s marriage to Brad Pitt had already made Pitt’s own dating history — including his past ties to other high-profile actresses — permanent tabloid furniture. Cox and Aniston’s decades-long friendship, well outside any of these overlaps, has stayed intact through it all, a point the video uses to argue that shared exes matter less than shared history. That same durability shows up off-screen too, in stories like David Arquette’s account of working alongside Cox years after their own relationship ended.

Young Hollywood’s Small Dating Pool

The final stretch of the countdown zooms in on younger stars — Alex Pettyfer, Dianna Agron, and Emma Roberts among them — to show the pattern isn’t generational. Teen and twenty-something actors tend to date within the same co-star and press-tour circuit, which means the same names keep resurfacing on each other’s relationship timelines. The video’s closing argument is simple: in a business this insular, dating an ex’s ex isn’t scandal, it’s math.

None of the pairings in the video triggered a lasting public war — Gomez and Swift, Aniston and Cox, even Diaz and Hudson all stayed visibly friendly well after the overlaps became public. The one exception the video flags is Swift and Perry, where the Mayer timeline sits alongside other grievances in a feud that, as of this countdown’s release, had gone unresolved for years.