Hollywood’s 7 Most Depressing Rebound Relationships

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6. Holly Madison and Criss Angel

We all know that Holly Madison really wanted to marry Hugh Hefner and have his children, but he couldn’t give her either of those things. As a result, she began looking for love elsewhere. Rumor has it that she began cheating on Hef with Criss Angel. When it looked like she had a future with the magician, she dumped the Playboy magnate and headed for Las Vegas to be with Angel.

Things got serious pretty quickly between these two. It wasn’t long before they were talking marriage and she also took him to meet her parents. While it was nice to see Madison dating someone who was more age appropriate and not legally married to another women, it seems pretty obvious that this relationship was a rebound. She left Hef to be with him and they then regaled the press with stories about how in love they were and then broke up after only four months. Sounds like a typical jump-off relationship.

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5. Kris Jenner and Corey Gamble

Since ending her marriage with Bruce Jenner, Kris Jenner has been shacking up with a much younger man – Corey Gamble. He’s reportedly only 33-years-old and works with Justin Bieber’s manager Scooter Braun. These two met at the designer Riccardo Tisci’s 40^th birthday party in Spain and then became a thing. While it is nice that Kris has met someone, why does he have to be young enough that he could be one of her children?

It seems obvious that she’s still reeling from her divorce from Bruce. He decided that he wanted to live his life as a woman and she couldn’t accept that, so their marriage came apart. It must be hard to hear that from a man she spent 25 years with. Gamble is so obviously a rebound – something to make her feel better. If Bruce had never decided that he wanted to transition, we bet she’d still be married to him and the whole Gamble thing would never have happened.

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4. Jessica Simpson and John Mayer

Jessica Simpson had a good thing with Nick Lachey, but she threw it away to live the single life. To be fair, she was pretty young when she married the former boy bander, so she obviously didn’t get to sow her wild oats. After leaving Lachey, Simpson made a series of really questionable romantic choices. One of them was John Mayer. He went through women the way that most men go through socks. He had romanced a bevy of beauties in Hollywood, but had an obvious aversion to settling down. In spite of this, the former reality star still got involved with him.

Most of us were really disappointed. While Lachey was on the marriage track with Vanessa Minnillo, Simpson was letting herself get toyed around by one of Hollywood’s most toxic bachelors. It took a year of going on and off like a light switch, but the “With You” finally learned her lesson and left Mayer for good.

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3. French Montana and Khloe Kardashian

Khloe Kardashian put up with a lot from Lamar Odom. He spent a good year of their marriage cheating on her and abusing drugs and alcohol. It took a lot for her to finally kick him to curb. Many of us were really saddened by the breakdown of their relationship. We really wanted them to work out – somehow.

When she immediately hooked up with rapper French Montana after filing for divorce from Odom, many of us weren’t impressed. He’s reportedly a deadbeat dad who abandoned his family a couple of years earlier and had to be taken to court to give the financial support they were entitled too. Thankfully, her heart was never actually in it. During one episode of “Kourtney and Khloe Take The Hamptons,” she admitted that she wished she was still with Odom. We think French knew this. He was just there to help her move on.

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1. Jennifer Lopez and Marc Anthony

Jennifer Lopez is a serial monogamist. She always goes from one man to the next – it is how she deals with a bad breakup. She’s been surprisingly open about most of her relationships. She has confessed that Ben Affleck was her first real heartbreak and that Marc Anthony was a rebound. “Ben and I split up at the moment when I thought we were committing to each other forever, it was my first real heartbreak, it felt like my heart had been torn out of my chest,” Lopez wrote in “True Love. “My way of anesthetizing the pain was different. I sought out comfort in another person, tried to find someone who could make me feel loved and wanted in my loneliest hour.”

Lopez went on to call Anthony a “Band-Aid,” which is what we all suspected. Surprisingly, their relationship lasted infinitely longer than all of her others and, when she and Anthony were dunzo, she jumped into another rebound relationship.

Cate

Cate has a B.A. and an M.A. in English Literature and has been the Managing Editor of Fame10 for more than 6 years. Despite having a love for the works of Thomas Hardy, Leo Tolstoy and Lord Byron, she also has an intense fascination with pop culture. When she isn’t writing for Fame10, she’s planning her next big adventure in Southeast Asia.