Let's Walk Through Jennifer Lopez's Relationship Journeys

Jordan Claes
Jennifer Lopez selfie in purple shirt.
instagram | @jlo

Jennifer Lopez once famously sang "My Love Don't Cost A Thing." But if you examine the track record of her relationship history, you know that statement couldn't be further from the truth.

Recently, it was confirmed that JLo is indeed once again engaged to be married to her former flame, Ben Affleck. While we wish her good luck, it also seems that now is as good a time as ever to take a walk through the many relationship journeys of Jennifer Lopez.

By now, the majority of fans have heard the good news regarding JLo and Ben Affleck.

On Saturday, April 9th, 2022, JLo took to her social media feed to announce that she and former flame Ben Affleck are once again engaged to be married.

"So I have a really exciting and special story to share," Lopez said in a video posted to her social media accounts.

Jennifer Lopez sitting on the couch.
instagram | @jlo

Lopez then directed her fans to go to OnTheJLo.com, "It is my inner circle where I share my more personal things, and this one's definitely on the JLo."

In the video, JLo can be seen wearing and admiring a large green diamond ring, and heard whispering the words "You're perfect."

"Maybe you can remember a certain green dress," JLo began — a reference to the iconic Versace dress she wore to the Grammys back in 2000.

"I’ve realized there are many moments in my life where amazing things happened when I was wearing green," JLo continued.

David Duchovny and Jennifer Lopez in green dress.
Giphy

"It may be a coincidence, maybe not. But as I took a better look, I realized there are no coincidences," the Marry Me star concluded.

While this is undoubtedly wonderful news for Lopez, it's also far from the first time she's been involved in a high-profile romance.

Jennifer Lopez and Ojani Noa at premiere.
Getty Images | Getty Images | Steve Granitz

The first time that JLo said "I do" was all the way back in 1997. She was wed to producer Ojani Noa and the couple divorced after only 11 months together.

Two years later, JLo began dating hip-hop icon/founder of Bad Boy Records, Sean "Diddy" Combs.

Jennifer Lopez and Diddy at MTV Awards.
Getty Images | Getty Images | Jeff Kravitz

”It was the first time I was with someone who wasn’t faithful,” JLo told Vibe magazine. ”I was in this relationship with Puff (aka Diddy) where I was totally crying, crazy, and going nuts."

After the dust settled, JLo met back up dancer Cris Judd on the set of her "Love Don't Cost A Thing" music video.

Jennifer Lopez "Love Don't Cost A Thing" music video.
Giphy | Apple Music

JLO and Cris were married in September of 2001 and had already filed for divorce by the time June of 2002 came around.

2002 saw the birth of "Bennifer" — one of the most popular celebrity power couples of the new millennium.

Jennifer Lopez and Ben Affleck at 'Maid In Manhattan' premiere.
Getty Images | Getty Images | Evan Agostini

However, Ben and Jen decided to call off their wedding just four days before they were due to walk down the aisle.

"I lost my sense of self," Lopez later explained in an interview with 'Vanity Fair'.

Jennifer Lopez crying.
Giphy | NBC World Of Dance

JLo said that she "Questioned if I belonged in this business, thought maybe I did suck at everything. And my relationship self-destructed in front of the entire world."

In keeping with her two-year trend, Jennifer went on to marry singer Marc Anthony in 2004.

Jennifer Lopez and Marc Anthony.
Getty Images | Getty Images | KMazur

Even though JLo and Marc Antony remained married for seven years, she told W magazine that she knew very early on that their marriage wasn't meant to be. "It wasn’t the dream that I had hoped for," JLo said remorsefully.

Between the years 2011 and 2016, "Jenny From The Block" had an on-again/off-again relationship with backup dancer Beau Smart.

JLo and Beau Smart.
Getty Images | Getty images | Alo Ceballos

The couple eventually called it quits amid rumors that Smart had been exchanging sexually explicit photos with a transgender model. Despite the controversy, JLo and Smart reportedly hold no ill-will toward one another.

In early 2017, a source revealed to 'Us Weekly' that sparks had begun to fly between Lopez and Drake.

Drake caught pouring alcohol at basketball game.
Giphy | Truly.

Drizzy wound up sampling JLo's "If You Had My Love" on his 2017 mixtape titled More Life. Their relationship ultimately fizzled out, but not before Drake was able to rap about it on Scary Hours' "Diplomatic Immunity."

But when JLo and former New York Yankee Alex Rodriguez announced their engagement, everyone presumed that her fourth engagement would be her last.

JLo and A-Rod at SAG Awards.
Getty Images | Getty Images | Steve Granitz

However, the outbreak of COVID-19 and the rise of a global pandemic caused JLo to postpone her wedding to A-Rod not once, but twice.

Then, in March of 2021, news began to spread that JLo and A-Rod had called off their two-year-long engagement amid cheating rumors.

A-Rod and JLo at basketball game.
Giphy | NBA

Reports seemed to suggest that A-Rod had become entangled with Southern Charm star, Madison LeCroy. Thus proving the old adage of "Once a cheater, always a cheater."

Fast-forward to July of last year, when this spicy photo of Ben Affleck JLo began making the rounds.

Ben Affleck and JLo kissing.
instagram | @jlo

The couple had seemingly rekindled their romance in celebration of Lopez's 52nd birthday. Although there is no wedding date set as of now, fans are crossing their fingers and hoping that this engagement will be the one that sticks.