• Share
  • Tweet
  • Share

Jennifer Lopez has certainly been through the ringer when it comes to relationships.

The 47-year-old singer and Casper Smart, 29, called it quits in August after nearly five years together. Now, E! News can confirm J.Lo broke up with him after discovering he had cheated on her...for the second time in their relationship.

People was the first to report the story on Monday, as an insider told the publication, "She kicked him out because he cheated on her and he got caught. It happened two years ago, and he promised he would never do it again and once he did, she was done."

While this news is surprising for many reasons—how could anyone ever cheat in Jennifer Lopez?!—it's not the first obstacle she's faced in her love life. The gorgeous singer has had a bit of a rocky relationship history. She's been married and divorced three times, maintained several long-term relationships that never made it the distance and dealt with her fair share of mental and emotional trauma, which she's been the first to admit affected her deeply.

Still, despite the heartbreak, Lopez has not once given up on love.

Jennifer Lopez, Casper Smart, GLAAD

Jason Merritt/Getty Images for GLAAD

For example, her split from Marc Anthony was one of the most difficult "personal failures" (as she called it) of her life. And yet she still maintains hope.

"With personal failures, I have thought, 'This is too hard,'" she told W magazine in April. "When my marriage [to Marc] ended, it was not easy to find forgiveness. It wasn't the dream that I had hoped for."

However, she admitted, "I still think about getting married and having that long life with someone. I love the movie The Notebook. A dream of mine is to grow old with someone."

Jennifer Lopez, Marc Anthony

Ethan Miller/Getty Images

That's something she's reiterated while doing Carpool Karaoke with James Corden, too, even poking fun of herself for it. "I'm a relationship kind of girl," she told the host in March, laughing. "I'm so monogamous, it's ridiculous."

When he asked about the most romantic moments she's ever experienced, the mother-of-two revealed she's been proposed to five (yes, five) times, being forced to turn down a couple of them.

"I've had some amazing proposals. You know, I've been married a couple times," she admitted to Corden. "I'm still trying to get it right. There's some that asked me to marry them, but it just didn't feel right. So I said no."

Jennifer Lopez, Ben Affleck

Gus Ruelas/LADN/WireImage.com

That kind of honesty is something Lopez has always maintained, never being too proud to admit she truly cared about many of her former flings.

For instance, even though she and Ben Affleckcalled off their wedding just one day before walking down the aisle, the singer has never denied their connection. "I think different time, different thing, who knows what could've happened, but there was a genuine love there," she reflected in an interview with People earlier this year.

Jennifer Lopez, Sean Combs

FAMEFLYNET PICTURES

Eventually, Lopez learned how to use heartbreak to her benefit, taking the good from her previous relationships and looking for better partners in the future.

"I have my own high standards for what I want in a partner and how I want to be treated," she told Cosmopolitan in 2013. "I bring a lot to the table. I'm not talking about material things but what I have to offer as a person – love and loyalty and all the things that make a good relationship."

Through it all, Jenny from the block hasn't stopped believing that true love still exists.

"I remain an eternal optimist about love," she previous revealed to On the Red Carpet. "Sometimes it doesn't work, and that's sad. But I believe in love."