Just how many times has Jennifer Lopez been engaged and married? It seems like for the sexy bombshell, love doesn’t cost a thing —pun intended— but can she hold on to a man? Here, we take a look at her dating history to figure out just how much of a heartbreaker this sexy Latina is. The star from Maid in Manhattan dated men from sports, entertainment, and Hollywood and even took a few to the altar. But has that lasted? Let’s find out and see.

For J.Lo, love is a complicated issue. She’s very vocal about her relationships. And she’s had her ups and downs. But the one thing we know for sure is that this entertainment icon is more in love with herself than anything else! Over the course of the years, we’ve seen her jump from the arms of one lover to another. Who’s next? Let’s check it out!

How Many Times Has Jennifer Lopez Been Engaged ?

Jennifer Lopez has been engaged and married a total of seven times! No three times’ a charm for this one. She sure tried them all out. But hell, who are we to judge? The years keep passing, and the woman just remains gorgeous as ever. Let’s see some of the lucky gentlemen with who Jennifer has either tied the knot, put a ring on it, walked down the aisle, or all of the above!

Alex Rodriguez and Jennifer Lopez

Jennifer and the baseball player Alex Rodriguez began dating in March 2017. Both are Latin, both have strong ties to New York —She’s Jenny from the Bronx, and he’s a Bronx Bomber. A-Rod proposed, but things went sour when it turned out that A-Rod was caught having a romance with Madison LeCroy.

Drake & Jennifer Lopez

Drake and J.Lo had a small fling back in 2017. But it was all a ruse to sell some albums. Drake moved on, and so did Jennifer. After all, the age difference is there. But it did manage to hog all the tabloid’s attention.

Casper Smart & J.Lo

Jennifer dated Casper for almost three years. It’s worth noticing that Casper is seventeen years younger than J.Lo. What cradle robber that woman is! It turns out that Casper wasn’t into women. J.Lo caught the dude texting some tranny. And things went sour. Poor J.Lo, the dude had her fooled.

Marc Anthony & J.Lo

Marc Anthony and Jennifer Lopez got married in 2004 after a year-long engagement in 2003. They were married and happy. They had twins: Emme and Max. And they were later divorced in 2011.

Chris Judd & Jennifer Lopez

This was Jennifer’s second marriage to choreographer Chris Judd. Firstly, how did they meet? They met in Spain when they were filming the music video “Love don’t cost a thing”. They got married in 2011, and that lasted until 2002.

Ben Affleck and Jennifer Lopez

Remember Jennifer Lopez and Ben Affleck story ? When J.Lo was —still— married to Chris Judd and Ben Affleck started courting her, they dated while making that godawful movie “Gigli,” then Jennifer did that music video with Ben grabbing her butt. And later had a wedding —which included a pricey Vera Wang gown— that was called off two days before the wedding date because J.Lo got cold feet? Crazy times.

Sean Combs & J.Lo

Between 1999 and 2001, J.Lo dated Puff Daddy, and he cheated on her like hell! The whole relationship was marred by controversy and even dragged J.Lo to a courthouse to testify on Diddy’s behalf on a weapons charge over a drive-by shooting.

Ojani Noa & J.Lo

Ojani Noa was Jennifer’s first hubby. He’s Cuban and was a waiter. The two tied the knot back in 1997. But that marriage was short-lived, and it even had a controversy during the divorce process over an alleged stolen sex tape.