The 7 Most Embarrassing Freak-Outs by Celebrity Exes

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If you paddle in the dating pool for any length of time past the high school prom, you’re going to accumulate some exes. And if you’re on a journey of personal growth (and who isn’t? Onward and upward, sweetie!) then, chances are, those relationships ended for a reason and you are, as everyone likes to say, “in a better place now.”

But what, then, to do when an ex-‘s life is going in a so very different direction, somewhat publicly? You know they represent a part of your life and a piece of your past. But it’s also a piece that you consciously chose to leave behind—so how do you have compassion for that cringeworthy person without, well, cringing and worrying how their woes are going to cast a shadow over your life?

Take these celebrities as inspiration. We all have a few embarrassing exes in our closet—it doesn’t mean you can’t hold your head high and go on to better places.

1. The Wig Out

Here is the lovely Claire Danes. Happily married to Hugh Dancy, new baby, Emmy winner for her star turn in Homeland. Her first love, Ben Lee, a former Australian pop star. His new album is “Ahuyasca: Welcome to the Work,” a “meditative / sonic journey” “musical prayer cycle” ode to the Amazon tribal psychedelic drug. His “tour” includes yoga studios. This is that high school stoner boyfriend you run into who is still on the music festival circuit, still wearing dreadlocks, and still calls everyone “dude.”

2. Huh?

Sometimes the most embarrassing thing about exes is that you dated them at all. Natalie Portman broke up with “freak-folk” star Devendra Banhart in 2008, but not before starring as a mythic Indian princess in one of his music videos.

Since then, she’s married Benjamin Millepied, the choreographer from her Oscar-winning role in Black Swan, and had her first child. Banhart disappeared after a 2009 flop amid drug rumors and is now attempting a comeback.

3. The Baby Don’t Go

Justin Bieber and Selena Gomez were the teen power couple of the millennium, but everyone has to grow up sometime. Gomez is turning heads with her role in the critically acclaimed Spring Breakers, which plays with her Disney image in a daring way; Bieber, meanwhile, is making headlines in a less enviable way by fighting paparazzi, drug busts, and something to do with a monkey!?

4. The Ancient History

Justin Timberlake and Britney Spears are the Selena Gomez and Justin Bieber of their era. Timberlake has gone on to conquer film, music and comedy while Britney, despite her many top ten hits, will be best known for her contributions to the enrichment of Perez Hilton and the VH1: Behind The Music celebrity meltdown hall of fame.

5. The Bitter Pill

The gorgeous and superprolific Olivia Wilde has about twelve movies coming out this year and is engaged to SNL star Jason Sudeikis; her ex-husband is making a movie about the joys of non-monogamy.

6. The “What Are You Thinking, Girl?”

Four years ago, rapper Chris Brown pleaded guilty to felony assault of his girlfriend, one of the most successful pop stars in the world, Rihanna. Then they got back together. Now the world is sad and confused.

7. The Goes Around, Comes Around

“WINO FOREVER” reads the altered tattoo that Johnny Depp got back in the 90s to declare his undying love for America’s Grunge Sweetheart, the indie movie star of our hearts. Flash forward to the 2000s–Depp had three Oscar nominations and two children with French singer Vanessa Paradis, while Ryder faced the public humiliation of a shoplifting conviction. But today, in 2013, Depp is split up while Ryder is poised for a comeback with a role in the new film Iceman.