All the Times Taylor Swift Awkwardly Ran Into One of Her Exes

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Running into your ex can be rough. Maybe you saw your ex at the food store while you were in your sweats. Or you saw your former flame at a party where you showed up without a date. Dealing with these unexpected motions of fate are not always easy to handle… especially when you’re one of the world’s biggest pop stars, like Taylor Swift.

With most of her past loves in the same industry as she is, the 25-year-old “Blank Space” singer is bound to run into some of her ex-boyfriends (including the ones she’s written songs about, which just adds to the awkward factor). Although she’s proven to have made amends with Joe Jonas, going on double dates with him, current squeeze Calvin Harris and Joe’s rumored girlfriend, Gigi Hadid, she’s had plenty of uncomfortable reunions. Here are the best (re: worst) examples:

1. When she ran into… Harry Styles — Taylor’s most awkward run-in had to be the time she bumped into Harry in the lobby of the Sunset Marquis Hotel. While Taylor did have her girlfriends from Haim by her side, video footage from TMZ showed just how uncomfortable the usually confident star was once the One Direction singer walked in. She pulled out all the tricks: from super checking her phone even if there’s nothing to check to straight up walking away. It wasn’t one of Taylor’s best ex-boyfriend run-ins but, overall, she survived!

2. When she ran into… Jake Gyllenhaal — One of the biggest award season bashes has to be the Golden Globe Awards. Therefore, it only makes sense that Taylor Swift would attend. Meanwhile, her ex-boyfriend’s sister, Maggie Gyllenhaal, was nominated for one of the coveted awards of the night, allowing for Taylor and her ex, Jake, to be at the same after-party. Yikes!

However, like a true professional, the two were supposedly friendly with one another. So much so that they not only said hi and smiled, but they may have hugged as well. Taylor also had her best girlfriends by her side the whole time, so phew.

3. When she ran into… John Mayer — When you’re Taylor Swift, partying at Tower Bar in West Hollywood is what you do. However, that night it was also what this particular ex-boyfriend decided to do. The worst part? This awkward run-in occurred shortly after John told Rolling Stone magazine he wasn’t very happy about Taylor’s song, “Dear John,” which was obviously written about him.

New York Post reported that the encounter made Taylor uncomfortable and she demanded to be seated somewhere else. Meanwhile, GossipCop reported that everything seemed separate and fine. Overall, Taylor seems to have made sure she avoided direct confrontation with the singer. Not starting anything seemed like a safe move for Tay.



4. When she ran into… Taylor Lautner — What better way for your ex to see you than when you are at the top of your game? At the 2012 Video Music Awards, Taylor took the stage to perform her hit song, “We Are Never Ever Getting Back Together,” and confidently crowd-surfed in celebration. Meanwhile, her 2009 ex-boyfriend was caught on camera awkwardly smiling and clapping at the end of her performance. The best part? When the Twilight star realized he was on camera and quickly changed his face to look as if he was not amused. Ha.

5. When she ran into… Joe Jonas — They may be fine now, but it wasn’t always that way. In 2012, both T.Swift and Joe were scheduled to perform at the KIIS-FM Christmas Ball after splitting back in 2008. While the time difference may not seem like a big deal — it was four years later — this event was the first time they performed at the same place since they called it quits.

Fortunately, reports suggest that the run-in didn’t phase Taylor at all. She focused on her performance and rocked the stage. Like always.

6. When she ran into… John Mayer (again!) — It really seems like Taylor can’t avoid this guy. For the 2015 Grammy Awards, Us Weekly revealed that Grammy organizers were assuring that Taylor Swift, John Mayer and Taylor’s “Bad Blood” inspiration, Katy Perry, were sitting nowhere near each another. John even previously discussed his discomfort regarding possibly seeing her at the Grammys saying, “You can see me at the Grammys doing what I do best, being avoided by Taylor Swift,” on The Late Late Show. Taylor’s response to it all? It seems like she avoided all of the drama and just went on enjoying the show.

7. When she ran into… Conor Kennedy(‘s family) — What’s worse than bumping into your ex? Bumping into his family! Or, if you’re Taylor Swift, receiving an award from your ex-boyfriend’s family. Taylor attended a gala at the Robert F. Kennedy Center — shortly after her relationship with Conor came to an end — in order to receive the Ripple of Hope Humanitarian Award they were awarding her. While Conor was not in attendance, Taylor showed up proud and faced members of Conor’s immediate family, including his dad with whom presented her with the award. Now that is pure courage!

Just think, though, if Tay can ‘shake it off,’ so can you!

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