A Look Back at Jennifer Lopez and Alex Rodriguez's Famous Past Loves

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Wedding bells are chiming in the distance for Jennifer Lopez and Alex Rodriguez after the former New York Yankee popped the question over the weekend with a massive $1 million sparkler.

However, this isn't the first time at the wedding rodeo for either A-lister. In fact, when they eventually tie the knot, it will mark Lopez's fourth marriage and Rodriguez's second.

Throughout the course of their long, high-profile careers, both stars have found love -- and fleeting romances -- in the arms of both big-name celebs and regular, non-famous folk alike.

In celebration of the couple's engagement, let's look back at the relationships they've moved past and learned from on their journey to finding one another.

Jennifer Lopez's Steamy Romances

David Cruz (1984-1994)

David Cruz and Jennifer Lopez at the 'Money Train' premiere in 1995
Ron Galella, Ltd.

Cruz was Lopez's high school sweetheart and was by her side as she first started to gain fame. They began dating when she was 15, but eventually called it quits after a decade. Lopez would later say she and Cruz were still friends and that he "probably knows me better than anyone else."

 

Wesley Snipes (1994-1995)

Jennifer Lopez and Wesley Snopes in 1995
Ron Galella, Ltd.

Shortly after breaking things off with Cruz, Lopez found herself romantically linked in the press to her Money Train co-star, Snipes. This marked her first celebrity relationship -- and the film marked her first nude love scene -- but the fling was short-lived. Lopez later opened up about both Snipes and co-star Woody Harrelson's on-set flirting in an infamous 1998 interview with Movieline, and from her description, it didn't sound like she had a fun time.

 

Ojani Noa (1997-1998)

Ojani Noa and Jennifer Lopez
Ron Galella, Ltd.

Shortly before landing her breakthrough-starring role in Selena, Lopez fell hard for the handsome Cuban waiter, and they tied the knot in February 1997. Their marriage lasted less than a year, but the legal battles Lopez fought with Noa -- who attempted to shop a tell-all book about her and threatened to sell what he alleged was a compromising video from their honeymoon -- lasted for years.

 

Tommy Mottola (1998)

Jennifer Lopez and Tommy Mottola
Jeff Kravitz/FilmMagic

Lopez struck up a short-lived romance with the music executive shortly after her divorce from Noa, and just months after Mottola's high-profile divorce from Mariah Carey, after nearly four years of marriage. While Lopez and Mottola only dated briefly, it's believed by many that their romance was the catalyst for the long-running and highly salty feud between Carey and Lopez that has survived and thrived for nearly two decades.

 

Sean "Diddy" Combs (1999-2001)

Jennifer Lopez and Sean Combs
Scott Gries/ImageDirect

After working with Combs on her debut studio album, On the 6, the pair sparked a high-profile romance that seemed to have potential, but hit some turbulence when Lopez and Combs were both arrested by police in connection to a shooting at a nightclub in New York City. Lopez was released after questioning, but Combs stood trial on multiple weapons-related charges. He was ultimately acquitted on all counts, but it seems the legal drama took a toll on their romance. However, Combs was still her date to the 42nd Annual GRAMMY Awards, when Lopez wore the iconic green Versace gown, one of the most famous awards show dresses of all time.

 

Cris Judd (2001-2002)

Jennifer Lopez and Chris Judd
Ron Galella, Ltd.

Marriage number two came in September 2001 when she tied the knot with the former backup dancer -- the first of several backup dancers she would end up dating. They met the previous year on the set of the music video for Lopez's song, "Love Don’t Cost a Thing." Their union only lasted nine months, quickly withering under the intense glare of the tabloid spotlight. The pair would go on to call it quits in June 2002.

 

Ben Affleck (2002-2004)

Jennifer Lopez and Ben Affleck at the Gigli premiere in 2003
Jeff Kravitz/FilmMagic

Thanks to her relationship with Affleck, one of the most famous celebrity relationship names ever was coined: Bennifer. The pair met in 2002, while filming the romantic comedy Gigli, and were quickly swept up in a whirlwind romance that saw Affleck pop the question with a massive pink diamond ring. Their highly scrutinized engagement made headlines for months, and eventually, they put their wedding on hold in September 2003, one day before their ceremony was planned. In 2004, the couple called things off for good, citing the excess pressure from tabloids and paparazzi.

 

Marc Anthony (2004-2011)

Jennifer Lopez and Marc Anthony
Frazer Harrison/AMA2009/Getty Images

The two first met in 1998, and became fast friends but never really dated. Years later, they reconnected, shortly after Lopez called things off with Affleck. The pair ended up getting married after just months together -- and just days after Anthony's divorce from Dayanara Torres was finalized. While it seemed like they were taking things too fast, the couple ended up staying married for seven years and welcomed two children together -- son Max and daughter Emme. They filed for divorce citing irreconcilable differences in 2011, but have remained close friends and even collaborated on new music in 2016.

 

Beau Casper Smart (2011-2016)

Jennifer Lopez and Beau Casper Smart
Jason LaVeris/FilmMagic

Coming off her divorce, Lopez struck up a surprisingly long romance with another backup dancer and choreographer. Lopez and Smart, who is 18 years younger than the pop diva, drew a lot of initial criticism over their age difference, but then people realized that Lopez doesn't actually age like the rest of us, so the age gap soon seemed irrelevant. After a number of glamorous public appearances over the course of their on-again, off-again relationship, the pair went their separate ways for good in 2016. 

 

Drake (2016-2017)

Lopez reportedly had a fun, fleeting fling with the Canadian rapper for a few months, as he was spotted in the audience at her Las Vegas residency show twice and the pair shared flirty snapshots on Instagram several times. However, it seems that they never really got serious, and their rumored romance came to an end when she began dating her now-fiance.

 

Alex Rodriguez (2017-Now)

Alex Rodriguez and Jennifer Lopez
Mindy Small/FilmMagic

Rodriguez's relationship with Lopez began in early 2017, and the two were quick to confirm that they were dating. Since they were first photographed getting cozy while on vacation together, the couple has reveled in the high-profile nature of their love affair, and have spoken about their close connection time and time again. It came as little surprise that Rodriguez finally popped the question.

 

Alex Rodriguez's Famous Lady Loves

Cynthia Scurtis (2002-2008)

Alex Rodriguez and ex-wife Cynthia Scurtis
Arnaldo Magnani/Getty Images

Rodriguez and Scurtis met at a gym in Miami, Florida, and went on to tie the knot in 2002. The pair welcomed their first child, Natasha, in November 2004, and their second daughter, Ella, in  April 2008. Three months later, Scurtis filed for divorce, citing "emotional abandonment" and accusing Rodriguez of having extramarital affairs, which the baseball player denied. 

 

Madonna (2008)

Madonna
Dave Hogan/Getty Images

While the pop superstar got caught up in Rodrigeuz's messy divorce from Scurtis -- and was accused in tabloids and by the baseball star's ex-wife of stealing him away from her emotionally -- Madonna staunchly denied being romantically involved with him while he was married. However, their brief, high-profile fling after his divorce drew a lot of publicity and a lot of criticism at the time, and their connection quickly dissipated. 

 

Bethenny Frankel (2009)

The pair were a rumored item after his split with Madonna (and several other brief flings with various models) but things were never really hot and heavy between them. In 2017, while sitting down with Andy Cohen on Watch What Happens Live, Frankel finally confirmed that she'd gone on a couple of dates with the Yankee star, but it didn't really spark a love affair.

 

Kate Hudson (2009)

Kate Hudson and Alex Rodriguez Kiss at a Yankees Family Picnic Day in 2009
NY Daily News/Getty Images

Rodriguez and Hudson dated for several months in late 2009, and their romance made headlines every time the Oscar-nominated actress came out to support him at one of his games. In August 2009, she even brought out her mom, Goldie Hawn, and Hawn's longtime love, Kurt Russell, to watch him play in a late-season game. Things never progressed past dating.

 

Cameron Diaz (2010-2011)

Tom Cruise, Katie Holmes, Alex Rodriguez and Cameron Diaz
George Pimentel/Getty Images

Rodriguez dated the Charlie's Angels star beginning in May 2010 through September 2011. While their romance didn't prove to be as high-profile as several of his others, they were spotted spending time together quite often. The pinnacle of their tabloid fame came when Diaz was photographed playfully feeding Rodriguez popcorn at Super Bowl XLV.

 

Torrie Wilson (2011-2015)

Alex Rodriguez and Torrie Wilson
Matthew J. Lee/The Boston Globe via Getty Images

The WWE Diva and model sparked a real romance with Rodriguez in late 2011, but their relationship faced challenges in the form of public scrutiny and, according to Page Six, Rodriguez's close friendship with his ex-wife. Additionally, tabloid speculation claimed the baseball star was not ready to settle down again after his previous divorce. The pair remained together for over three years before eventually calling it quits in February 2015.

 

Anne Wojcicki (2015-2017)

Anne Wojcicki and Alex Rodriguez
C Flanigan/FilmMagic

A few months after he broke up with Wilson, Rodriguez sparked a high-powered romance with the tech mogul and 23andMe CEO, who'd just finalized her divorce from her husband, Google co-founder Sergey Brin, that June. The pair made their first public appearance as a couple at the 2016 Met Gala and ended up dating for a year and a half before splitting in February 2017.

 

Jennifer Lopez (2017-Now)

Jennifer Lopez and Alex Rodriguez at the 2018 Met Gala
HECTOR RETAMAL/AFP/Getty Images

A year after Rodriguez went public with Wojcicki at the Met Gala, he and Lopez returned to the high-profile, high-fashion event to make their first public appearance as well. While they had sparked romance rumors months earlier, it was after the Met Gala that they began gushing about each other constantly on social media and in countless interviews. Their connection was so strong, so quickly, that engagement rumors were swirling for over a year before he actually popped the question.

For more on Lopez and Rodriguez's recent engagement, and for a look at the singer's jaw-dropping new ring, check out the video below.

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