Jennifer Lopez and Alex Rodriguez’s Relationship Timeline: A Look Back

Jennifer Lopez and Alex Rodriguez got engaged in 2019 but separated in 2021 before marrying.

Unlike the trajectory of traditional Hollywood romances, cultural icon Jennifer Lopez and former MLB star Alex Rodriguez’s relationship was written in the stars from the very start. Their love story began when J.Lo signed an autograph for the young baseball pro in 1999. They crossed paths again in 2005 at a Yankees Game, but both were married at the time. Cut to 12 years later, and J-Rod officially became an item.

Despite their non-traditional beginnings, J.Lo and A-Rod’s relationship was full of milestone moments, from their red carpet debut at the Met Gala to that fairytale engagement. It was no secret that these two were crazy about each other. On their one-year anniversary, the singer publicly declared her love before performing “Us” at a concert. 

“I don’t want to get all mushy or anything, but baby, this song’s for you. I love you,” she said during AT&T’s Super Saturday Concert in 2018, per iHeart. 

The former shortstop returned the favor on their two-year anniversary, posting the sweetest tribute on Instagram to his S.O. However, the couple wasn’t without issues; in 2021, Lopez and Rodriguez broke up.

Here’s a look back at Jennifer Lopez and Alex Rodriguez’s relationship.

October 1999: Jennifer Lopez and Alex Rodriguez first meet

Rodriguez revealed that he first met Lopez when he asked for her autograph in 1999. 

“#TBT to almost 20 years ago when a big time global pop superstar signed a pic for a young ball player,” he captioned a shot of the keepsake on Instagram in 2018, adding the hashtags #lifecanbeafunnythingsometimes #pictureperfect.

May 21, 2005: Jennifer Lopez takes a picture with Alex Rodriguez and then-husband Marc Anthony

Six years after their initial meeting, J.Lo attended a Yankees baseball game at Shea Stadium in Queens, New York, with her then-husband Marc Anthony. Before the first pitch, Lopez and Rodriguez shook hands — a moment the singer described to Sports Illustrated as “this weird electricity, for, like, three seconds.”

“Three to five seconds of looking at somebody right in their eyes and getting stuck,” she added. 

February 2017: Jennifer Lopez is first spotted with Alex Rodriguez
The two reconnected again after bumping into each other at a restaurant in Los Angeles, with J.Lo making the first move. 

“I was having lunch somewhere, and I saw him as he passed by,” Lopez said, according to Entertainment Tonight. “Afterwards, I went outside, and, for some reason, I felt like tapping him on the shoulder.”

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Later, A-Rod asked her on a dinner date, and sparks flew. 

“He texted me, said, ‘Let’s go out to dinner,’ and I said, ‘OK,'” Lopez recalled. “We had a nice dinner.”

April 8, 2017: Jennifer Lopez and Alex Rodriguez go Instagram official
J-Rod took their romance to Instagram and posted their first couple’s photo (which has since been deleted). The following month, the pair made their red carpet debut at the Met Gala. Inside the venue, J.Lo proved she was absolutely smitten with her new beau by blowing him a kiss across the dinner table.

June 2017: Jennifer Lopez and Alex Rodriguez vacation together

Coining the term “baecation,” J.Lo and A-Rod took their first couple’s trip together to none other than Paris, France — aka the City of Love.

That August, J-Rod crossed off another romantic milestone when they attended their first wedding as a couple.

October 31, 2017: Jennifer Lopez and Alex Rodriguez appear on the cover of Vanity Fair

Lopez and Rodriguez reached power couple status after gracing the cover of Vanity Fair together. In their first-ever joint interview, the twosome revealed why they’re an ideal match. 

“We are very much twins,” Rodriguez told the magazine. “We’re both Leos, we’re both from New York, we’re both Latino … and about 20 other things.”

March 9, 2019: Jennifer Lopez and Alex Rodriguez get engaged

Rodriguez announced on Instagram that he popped the question to Lopez with an enormous diamond ring while the couple was vacationing in the Bahamas — and he went to extreme measures to make sure it was a picture-perfect moment. During an appearance on The Tonight Show, A-Rod revealed that he prepared the proposal months in advance.

“I planned it for about six months,” Rodriguez told host Jimmy Fallon. “[And] the three days prior to me going down on one knee and getting engaged, I rehearsed for three days in a row. Because I wanted the sunset to be perfect.”
He even calculated the timing of when the sun went down over the ocean. 

“One day, the sunset was at 6:27, the next day it was at 6:29, and then the third day it was raining!” he recalled. “So I kind of [decided on] 6:29, and I said, ‘This is the time that I’m gonna do it.’ And it worked out well.”

September 28, 2019: Jennifer Lopez and Alex Rodriguez throw an engagement party

Six months after getting engaged, Lopez and Rodriguez celebrated their upcoming wedding with a lavish party at singer Carole Bayer Sager’s home in Bel Air. Following the bash, the couple shared photos of themselves looking head over heels in love on social media.

…to be continued