Fifth Time's the Charm: Why Jennifer Lopez's Engagement to Alex Rodriguez Could Only Happen at This Point in Her Life

Star announced her engagement to the former MLB pro on Saturday, March 9.

By Billy Nilles Aug 16, 2019 10:00 AMTags
Watch: Jennifer Lopez & Alex Rodriguez Are Engaged!

"I wish you were my first love/'Cause if you were first/Baby there would've have been/No second, third or fourth love."

When Jennifer Lopez sat down to discuss relationships with pop music impressarios Max Martin and Savan Kotecha while working on her last album, 2014's A.K.A., it's hard to imagine she could've known what was coming her way. She'd been separated from ex-husband Marc Anthony—her third—since July 2011 and was in the throes of an off-on situation with dancer Casper Smart that seemed, at least to those watching from afar, destined to go nowhere. The prospect of a world-rocking relationship with Alex Rodriguez was merely a twinkle in her eye. And yet, the track that came out of that convo—the dreamy "First Love"—with its chorus that so perfectly applies itself to the habitually unlucky-in-love star's current situation, seems to have been a little bit of art predicting life.

Jennifer Lopez & Alex Rodriguez's Road to Engagement

In case you haven't heard, the multi-hyphenate received quite the thrill over the weekend when Rodriguez, her beau of two years, did the damn thing and popped the question during a romantic getaway in Bakers Bay. As she accepted the stunning ring estimated to be worth more than $1 million, she officially became engaged for the fifth time in her life. And while there's no doubt that the lyrics of "First Love" have been running through Lopez's mind as she's fallen deeper and deeper for her retired MLB hunk—truly, despite however gauche it may be to play your own music at your wedding, this track could/should used for their first dance, that's how perfect a fit it is—if you were to ask the World of Dance star whether she'd want to start back at zero and find Rodriguez first, sparing herself from all those false starts and repeated broken hearts, she'd probably tell you no.

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"I understand him in a way that I don't think anyone else could, and he understands me in a way that no one else could ever," Lopez told Vanity Fair of the relationship back in December 2017, a few months shy of their first anniversary. "In his 20s, he came into big success with the biggest baseball contract [at the time]. I had a No. 1 movie and a No. 1 album and made history. We both had ups and downs and challenges in our 30s, and by our 40s we'd both been through so much. And more importantly than anything, we had both done a lot of work on ourselves."

In fact, it's that last bit that stands as the only piece of evidence the Second Act star needs to prove that she and Rodriguez are exactly where they need to be at exactly when it ought to have happened. "We had to grow and discover ourselves first," she told the magazine.

Jennifer Lopez Is Engaged to Alex Rodriguez

And over the years, through the course of four very public engagements (three of which actually made it to the altar), Lopez has been afforded the opportunities to learn and do the work necessary to ready herself for Rodriguez. "It was about me figuring out me," she admitted in the February 2019 issue of Harper's Bazaar. "Until you learn to love yourself, you can't completely love [someone else] in a way that is pure and true. Once you do that, you can have relationships that are based on love and respect, that are supportive and nourishing. There's an evolution there that had to happen for me. I feel like I'm in a better place now."

While Lopez was learning to love herself, she was also learning a few other lessons thanks to the men who found their way to one knee in her life pre-Rodriguez.

The first one, taught over 20 years ago, came courtesy of first husband, Cuban waiter Ojani Noa, whom Lopez married in 1997 after meeting him at a restaurant in Miami Beach. Marrying a month before Selena hit theaters, propelling Lopez into a new, upper echelon of the fame game, the two would split in January, a month shy of their one-year anniversary. While the break-up was said to be an amicable one, the ways in which Noa has attempted to cash in on his ex-wife's superstardom over the years, leading Lopez to institute a confidentiality agreement between the two of them in 2004. (It didn't stop Noa from shopping a tell-all book in 2007 or a honeymoon video in 2009—both of with were successfully blocked by Lopez in court.) The lesson here? Choose your men wisely.

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After a turbulent relationship with rap icon Sean "Puff Daddy" Combs that began in 1999, included a dark post-Christmas run-in with the law that saw the two briefly taken into custody after gunfire broke out at Club New York, saw her rebrand herself as J.Lo, and ended in 2001 while Combs was on trial for weapons charges—he was found not guilty on all counts—Lopez ran headfirst into the arms of dancer Cris Judd. After meeting him in late 2000 when he was hired to direct her "Love Don't Cost a Thing" music video, the couple went public at an Oscars after-party shortly after she and Combs split and were married on Sept. 29, 2001.

"Coming out of a torrid relationship, I meet this sweet person who's so refreshing," Lopez told Vibe in 2003, after revealing that her relationship with Combs was the first in which she'd ever been with someone who was unfaithful. "But marriage is not just about love. I thought I had learned that in my first marriage...I loved Cris, still love him, he's one of the best people. This wasn't an easy thing to walk away from, but we didn't have what it takes to make a marriage work. Cris knows the last thing I ever wanted in this f--king world was to hurt him."

So, not only did she learn that a marriage must be built on more than love alone, but she was shown that maybe, just maybe, it's good to take things slow. However, it would take a few more classes on that particular topic for the message to really stick.

Inside Jennifer Lopez and Alex Rodriguez's Early Fame & Roller Coaster Relationships: Riding Parallel Tracks Headed to the Same Station

By June 2002, Lopez would split with Judd and, by November, find herself engaged yet again—this time to Ben Affleck, who popped the question with a massive pink diamond. For the singer, it was an opportunity to finally have something her two previous engagements had failed to yield. "I've been married twice but I haven't had a marriage yet," she told ABC News' Diane Sawyer that year. "This is not to take anything away from Cris or Ojani, who are wonderful people and who I loved very much—but I think it more had to do with me...being in such a crazy life and needing a sense of security."

Sadly, though, it wouldn't come to pass. Not this time, at least. Despite planning a September 2003 wedding, Lopez and Affleck—or as they were more infamously known, Bennifer—would postpone their nuptials at the last moment following the dismal returns for Gigli, their big screen stinker that bombed in August. By October, the coupling would be no more. And it's here that Lopez learned her next lesson: Know when to call it quits. 

"I have such a respect for the institution of marriage that I don't believe people should spend their lives together if they're not going to be totally happy," she told Vibe of the breakup. "Do we spend time now trying to make it work and wasting precious moments of our lives, or do we remedy the situation and move on?"

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Always quick on the rebound, Lopez saw herself through her self-described "first big heartbreak" with Affleck by dating musician Marc Anthony, who'd been a friend for years. And on June 5, 2004, she was walking down the aisle for the third time in her life, after surprising guests at her Beverly Hills home who'd arrived thinking they were attending a garden party. Despite the arrival of twins Max and Emme in 2008 and a union that lasted seven years, she'd later admit that she'd forgotten the lesson Affleck taught her. "I hung in there for seven years," she admitted to W in 2016. "I knew very quickly that it wasn't the right thing."

But as is always the case, from the bad came something good and another lesson was, indeed learned: to know when to forgive and to always trust in your own worth. 

"When my marriage ended, it was not easy to find forgiveness," she told W, leading one to wonder if perhaps Anthony had joined Combs on Lopez's Unfaithful Partners list. "It wasn't the dream that I had hoped for, and it would have been easier to fan the flames of resentment, disappointment and anger. But Marc is the father of my children, and that's never going away. So I have to work to make things right. And that is, by far, the hardest work I do."

Jennifer Lopez's 6 Engagement Rings

Not all lessons learned from Anthony were born out of heartbreak, though. Speaking with Today's Willie Geist in December 2018, she admitted, "When I was married to Marc, he really helped me with my confidence. When he saw where I suffered he was like, 'You're a great singer. Don't ever let anybody tell you you're not a great singer.' And I respected him so much because I consider him one of the best singers of all time."

The pair would separate in 2011, with their divorce finalized in 2014.

After her split from Anthony, the on-off dalliance with Smart saw her through until, after a run-in with Drake that's merely a blip on this relationship radar, the addicted-to-love Lopez decided she ought to give being single a try. You know, just to see if she could conquer her fear of being alone. And then along came Rodriguez. 

After a chance encounter at a restaurant in Beverly Hills in the winter of 2017 led to a swoon-worthy first date a few weeks later and, very quickly, to a melding of families—Rodriguez has two daughters, Natasha and Ella, from his first marriage to Cynthia Scurtis—Lopez and her new beau took their time before taking things to the next level despite however much it seemed like their respective journeys had been preparing one for the other.

"She's definitely older and wiser. She knows herself better than she ever has before. She's a different person from the Jennifer in her 30s," a source close to Lopez, who turns 50 this summer, told E! News. "She has a better understanding of what goes into a marriage and being a partner. She feels ready to make a different commitment than she has ever made."

According to the insider, their shared family values are what makes this union such a perfect match. "They aren't trying to date or have a relationship outside of their kids. The kids are just as much a part of it as they are," the source told us. "Alex has cared so much about her kids from the start and is a great dad himself. The kids are best friends and love being together. It just works. It was never a struggle or painful. She has never doubted his love for a second."

What to Know About Jennifer Lopez's $1 Million Engagement Ring From Alex Rodriguez

And it's because of this new blended family that the powerhouse businesswoman who always seems to be constantly juggling four projects at once, while making each one look so easy, is taking a new approach to her work-life balance as she moves forward as a soon-to-be wed woman, a second source told us. "Jennifer has learned from previous relationships that quality time is very important, but stepping away from career responsibilities has often been a challenge for someone as driven as Jennifer is," the insider said. "It's something Jennifer is consciously aware of and it's the primary reason why she is making changes to how she handles doing business this year. She is making family time a priority and although she will continue to work at her various businesses, she is focused on maintaining a happy work-family life balance that so that Alex and their children always have quality time together."

According to the source, Lopez and her beau are even planning to collaborate together on "several new business ventures and financial that even while they're working, they'll be working together."

It all plays into Lopez's feelings that Rodriguez is the one she's been waiting for all along, the one worth making changes for. "Jennifer feels Alex is her soulmate and her true life partner," the source continued. "She feels their similar backgrounds, with both of them having career success in multiple industries, previous marriages and children, [have] enabled them to have a deeper understanding of where they're currently at in life and they can appreciate each other's pasts.  They're true equals."

And it doesn't hurt that he's so good with Max and Emme. "Alex has so many great qualities that Jennifer adores, but the one she loves most is how loving and giving he is with her children," our insider added. "Jennifer feels Alex loves her kids as though they were his own and she falls for him all over again whenever she sees them interacting."

As for the lessons from her past, while she's definitely learned, she's not paying them too much mind. Not anymore. "Jennifer doesn't dwell too much on her previous relationships," the source said, "and is focused on her amazing future with Alex."

First love? Not quite. Lasting love? Sure sounds like it.

(This story was originally published on March 14, 2019 at 3 a.m. PT.)

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