Jennifer Lopez's dating history: From 'nightmare' marriage to Ben Affleck, a 'fling' with Drake, to a romance with a dancer 18 years her junior - as she reignites dating rumours with Brett Goldstein

She has never shied away from being open about her quest for love.

From A-list actors to big-time ballplayers, Jennifer Lopez has famously romanced some of the world's most celebrated bachelors.

Some of her relationships led to marriages (three of them), whilst others were flirtatious flings.

But behind the fairytale romances, her journey through love has had its fair share of heartbreak and second chances.

The singer and actress, 57, famously married fellow Hollywood star Ben Affleck, 54, in 2022, almost 20 years after they were originally an item. 

But in 2024, she filed for a divorce from the actor after reports that she was 'done waiting' for him to show commitment to repairing the marriage after months of living separate lives.

Now, after being single since her second heartbreaking split from the actor, insiders have claimed that Jennifer is now 'casually' dating Brett Goldstein, 46, after they met filming the Netflix movie Office Romance, where they played a couple.

As her new 'romance' heats up, here's a look back at JLo's dating history and the loves that shaped her story.

David Cruz: 1984-1994

Jennifer met David Cruz at an early age, while one of his friends was dating hers.

She was only 15 when they first began dating, but their relationship fizzled after a decade. 

 A source previously told PEOPLE that David was truly head over heels for the singer throughout their years-long romance and was very supportive of her rise to fame.

'They were high school sweethearts,' the source said. 'He was soft-spoken and kind and he would do anything for Jennifer.

'You could see her trajectory early on and at the time he didn't mind seeing her take the lead. He was completely content with that. He just loved her.'

In 2004, Jennifer said of David: 'He's a friend, and he probably knows me better than anyone else.'

Tragically, in 2020, he passed away at the age of 51 from heart disease.

Ojani Noa: 1997-1998 

Jennifer and producer Ojani Noa, tied the knot in 1997 after the former couple first crossed paths when he was a waiter at a restaurant in Miami.

However, after only 11 months of marriage, the pair divorced in January 1998.

The songstress and Noa appeared to be on good terms following the split when she hired her ex to help manage a Cuban restaurant she opened in L.A., per Harper's Bazaar.

Six months later, she fired Ojani – causing him to sue the star for breach of contract.

He was later forbidden by a permanent injunction issued by the court from 'criticizing, denigrating, casting in a negative light or otherwise disparaging' Lopez.

Noa was sued by Jennifer in 2006 when he pitched a book based on their brief marriage, and three years later, sent him a cease-and-desist letter to put an end to a mockumentary called How I Married Jennifer Lopez: The J.Lo and Ojani Noa Story.

After the performer tied the knot with Ben in July 2022 at a chapel in Las Vegas, Ojani shared his thoughts on her fourth marriage while talking to DailyMail.com.

'I wish her and Ben the best, but I'm not convinced it will last,' he said at the time. 'Jen loves being in love but she's been engaged six times. Ben is husband number four.'

'I was husband number one and she told me I was the love of her life. When we lay in bed on our wedding night, she said we would be together for ever.'

The personal trainer later added: 'I'm happy she has gone back to Ben but I have a feeling this won't last.'

'I think she's someone who will be married seven or eight times. I can't see her ever settling down with one person.'

Ojani explained: 'She pushes herself to constantly go forward in her professional life, which is why she's had a three-decade career, but she also moves on in her private life.'

Sean 'Diddy' Combs: 1999-2001

Although Jennifer and rapper Diddy were never engaged or married, the pair notably had a high-profile romance.

The two first met on set of her music video in 1999 for the track, If You Had My Love.

In 2000, the former couple made an appearance at the Grammy Awards in Los Angeles, where Jennifer donned the iconic, green Versace dress with a plunging neckline.

Of the look, Diddy – who has been embroiled in legal woes and sexual assault lawsuits – told Entertainment Tonight in 2017: 'We were just stepping up our game as far as what we were wearing and how we were gonna use fashion.'

'I thought it was gonna really change the game as far as for her and fashion. I didn't know how big it was gonna be, but it was a great moment for her. She deserved it. She is one of the fliest out there..'

However, after two years of dating, the pair split.

In 2003, during her interview with Vibe, the songstress claimed that the separation took place due to the music artist not being 'faithful' to her.

She explained to the outlet: 'I never caught him [cheating] but I just knew. He'd say he was going to a club for a couple of hours and then never came back that night.'

'I had to think, do I want to be home with kids in 10 years wondering where somebody is at three in the morning?'

Cris Judd: 2001-2003

Jennifer later said 'I do' to dancer Cris Judd in 2001 after the two met on set of her music video for Love Don't Cost A Thing.

But the marriage was also short-lived when the pair filed for divorce nine months later in July 2002.

The following year in 2003, the divorce was officially finalised.

In 2014, Cris opened up during a candid interview with Us Weekly about his past relationship and marriage to the On The Floor songstress.

'You know it's very tough. Your privacy is breached. You're no longer a normal person,' he stated at the time.

'[Our wedding] was a circus. I think several people got arrested trying to climb up a mountain… trying to sneak in. We actually rented the airspace.'

He admitted that being in the spotlight was 'tough' but expressed, 'You kind of sign up for that, you know? You kind of have to take it and accept it and embrace it.'

'Once you stop fighting it, it smoothes itself over. If you try to keep that privacy, it drives you nuts and that's why people break,' Cris said.

In regard to the reason behind their split, he simply added: 'Unfortunately, it just didn't work out.'

Jennifer also previously discussed the end of her second marriage during a past interview with Vibe in 2003, per Entertainment Weekly. 'Coming out of a torrid relationship, I meet this sweet person who's so refreshing.'

'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.'

The Selena actress continued, 'This wasn't an easy thing to walk away from, but we didn't have what it takes to make a marriage work.'

Marc Anthony: 2004-2014

Jennifer and Anthony first crossed paths in 1998 when he was performing in the Broadway musical titled The Capeman.

The pair soon developed a close friendship and later tied the knot in 2004 during a private ceremony – shortly after her first engagement to Ben Affleck came to an end.

Four years later in 2008, the former couple welcomed twins Max and Emme. However, the two split in 2011 – with the divorce being officially finalised in 2014.

During an interview with W Magazine in 2016, per Us Weekly, Lopez reflected on her third marriage. 'When my marriage ended, it was not easy to find forgiveness.'

'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.'

The star added, '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.'

'I hung in there for seven years. I knew very quickly that it wasn't the right thing,' she revealed to the outlet.

Despite the split, the exes have still remained on good terms and also continued to work together in the entertainment industry.

The two notably performed together at the 2016 Latin Grammy Awards and sang, Olvídame y Pega la Vuelta.'

While talking to Extra in 2017, per People, the Rain Over Me hitmaker said, 'We've always been [in a good place] from day one, you know.'

'We met working - 20 something years ago we met, working. She's my goombah - that's my girl - for life. If you want to get along with a woman, just get divorced.'

Casper Smart: 2011-2016

After her marriage ended, Jennifer began dating her backup dancer Casper Smart, who was 18 years her junior.

They had an on-and-off relationship through 2016. 

Allegedly, the end of their relationship came when she got fed up with his infidelity.

'Whether there is any truth to what is being reported or not, it's irrelevant. Jennifer did not trust him,' a source told E!. 'The relationship had not been right for a while. Smart was never going to be the love of her life, but he was fun and a nice guy to be around. It stopped being fun once his friendships with other people started to come to light.' 

Drake: 2016

Jennifer and Drake never confirmed their romance, but rumours were flying in 2016 when the two met backstage at her All I Have show.

The pair even shared cuddly snaps on their social media pages, but nothing was made official.

They did, however, spend New Year's Eve and Day together.

The rapper added fuel to the fire on his track Diplomatic Immunity with the lyrics, '2017, I lost a JLo'.

Alex Rodriguez: 2017-2021

Jennifer later began to date New York Yankees baseball player, Alex Rodriguez, in 2017 and became engaged two years later in 2019.

However, the two had met on previous occasions before striking up a romance, such as in 1999 when they first crossed paths and the sports star asked her for an autograph.

And in 2005, the baseball player was seen taking a photo with Jennifer and her then-husband Marc Anthony.

Years later, they crossed paths once again before dating, and Jennifer reflected on the moment to Entertainment Tonight.

'I was having lunch somewhere, and I saw him as he passed by. Afterwards, I went outside, and, for some reason, I felt like tapping him on the shoulder.'

She then added, 'He texted me, said, 'Let's go out to dinner,' and I said, 'Okay.' We had a nice dinner.'

In 2019, Alex popped the big question, and opened up about the big milestone while on The Tonight Show With Jimmy Fallon. 'I planned it for about six months.'

'[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 added, 'One day, the sunset was at 6:27, the next day it was at 6:29, and then the third day it was raining. 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.'

Two years after becoming engaged, the pair announced their split in 2021 and released a statement at the time.

'We have realised we are better as friends and look forward to remaining so,' Jennifer and Alex expressed.

'We will continue to work together and support each other on our shared businesses and projects. We wish the best for each other and one another's children.'

'Out of respect for them, the only other comment we have is to say is thank you to everyone who has sent kind words and support.'

Ben Affleck: 2002-2004; 2021-2024

Jennifer and Ben first met in 2001 on set of the movie titled Gigli, and soon entered a romance which resulted in the pair becoming engaged in 2002.

The pair notably went public with their relationship after she split from her second husband, Cris.

The stars also appeared in another film together, Jersey Girl, in 2003 – although it was not a success in the box office. That same year, they were set to say 'I do' but opted to postpone the wedding due to 'excessive media attention'.

Months later, in January 2004, Jennifer and Ben ended their engagement. She soon married Marc, and Ben moved on with Jennifer Garner after they tied the knot in 2005.

Ben and Garner were married until 2018 – and also share three children: Violet, 20, Fin, 17 and Samuel, 14.

In 2021, Jennifer and Ben rekindled their romance and became engaged once again in April 2022.

A few months later, they said 'I do' at a chapel in Las Vegas in July, followed by a larger ceremony at his Georgia mansion on August 20, 2022.

Her relationship and marriage to Ben also inspired her album titled This Is Me... Now – which she opened up about while talking to Zane Lowe for Apple Music.

At one point, she stated, 'When he came back into my life, again the same thing happened where I felt so inspired and so overtaken with emotion that it was just pouring out of me.'

'When I feel good, I write music. And I wrote music and I got in the studio in I think May, and by August when we got married, it was done.'

However, earlier in May 2024, split rumours began to circulate and in August – their second wedding anniversary – Jennifer officially filed for divorce without an attorney.

The singer listed the date of separation as April 26, 2024, as per legal docs seen by DailyMail.com.

The couple did not sign a prenuptial agreement before tying the knot in July 2022.

The couple listed their $68million Beverly Hills marital home in May – one year after purchasing it for $60million. After failing to sell it off market, they publicly listed the sprawling property in June.

Days after Jennifer's 55th birthday in July, Ben closed escrow on a new $20.5million bachelor pad in the Pacific Palisades.

A source recently told Us Weekly that the star's decision to purchase the abode marked the 'closure of the relationship'.

But it reportedly felt like a 'stab to the heart' to Jennifer, who is still on the hunt for a new LA home.

A source close to the star told People that she is looking for a 'fresh start'.

Before the divorce filing, DailyMail.com exclusively revealed that documents had been 'finalised, but not yet turned in'.

The couple spent almost the entire summer apart – with Jennifer largely on the east coast while Ben remained at home in Los Angeles.

They even spent their actual wedding anniversary, which was on July 16, in different cities.

Ben was also notably absent from Jennifer's lavish Bridgerton-themed 55th birthday celebration in The Hamptons in late July.

In September 2026, Jennifer described her split from Ben was the 'best thing that ever happened' to her. 

While reflecting on their split over a year later, the actress admitted that their split 'changed' her and 'helped me grow in a way that I needed to grow'.

After their divorce was finalised earlier this year, she said she 'had so much fun'. 

On an episode of CBS News Sunday Morning, however, she told Lee Cowan about how she had a 'tough time' in the wake of their split.

When asked about how she handled the time when her personal life was 'not great,' she said she 'barely' could.

'It was a really tough time,' she confessed about working on the same project he was also working on in the wake of their split. 

She recalled working on her new movie, Kiss of the Spider Woman, which also had her ex serving as an executive producer on the film.

The movie premiered at the Sundance Film Festival in January earlier this year, the same month they finalised their divorce. 

She said working on the film helped her focus on something outside of her heartbreak. 

'It was hard not to think about stuff, but it was like the best and the worst of times, in a way. 

'Every moment on set, every moment I was doing this role, I was so happy,' she said. 'And then it was like, back home, it was not great.'

She added: 'And it was just like, 'How do I reconcile this?' But you get through it.'

The On the Floor hitmaker said she later realised their divorce was the 'best thing that ever happened to me' as it helped her 'grow'. 

She said their separation ultimately helped her 'become more self-aware'. 

'I'm a different person now than I was a year and a half ago,' she told Cowan.

And following their split, she said she was able to enjoy 'probably the best summer I've ever had' this year.

'I had so much fun. I'm able to enjoy things more and be great,' she said. 

She also spoke fondly of her ex when talking about his contribution to her film adaptation of the Broadway musical Kiss of the Spider Woman. 

'The movie wouldn't have been made if it wasn't for him and Artist Equity,' she said of her ex-husband and his production company. 

'I will always give him credit for that,' she said before explaining that it wasn't because he was always 'pushing' for the movie but rather because 'they financed it'.

'I told him this was the role I was born to play and I wanted to do it and he was like, 'Okay.' And he helped make it happen,' she recalled.  

Brett Goldstein: 2025 – present

Jennifer and her Office Romance co-star Brett are reportedly dating.

The Hustlers star and the Ted Lasso actor, 46, are said to be enjoying a 'casual' romance, a source told Page Six, following their cozy red carpet appearances and reports of 'undeniable' chemistry.

'The one thing they have in common is they both enjoy going out to parties and restaurants,' the source said, adding, 'Unlike her ex Ben who always had a scowl on his face when they were out.'

Jennifer – who previously raved about Brett being 'the best kisser' she has ever worked with – and the actor were recently seen arriving, and later leaving, a talent manager's party in Los Angeles on October 16.

The pair were reportedly in the same car, though they entered the party separately.

The Daily Mail has reached out to representatives for Lopez and Goldstein for comment.

It's not the first time the duo have sparked romance rumours, though they have previously denied dating.

In May, Jennifer was thrilled when Brett rated her kissing skills a '12 out of 10' at the premiere of their Netflix film, Office Romance, in Los Angeles.

Jennifer looked cozy with the actor amid rumors they have 'grown close' after filming, as they posed on the red carpet at the Egyptian Theatre in Hollywood, before answering questions about their onscreen kiss.

The star previously raved about Brett being 'the best kisser' she has ever worked with, and he returned the favor at the event, telling ET that her kiss was 'the best', which left her beaming.

The four-time divorcée giggled before she heard Brett's answer, while pointing out, 'Well, what is he going to say in front of me.'

Brett also said that when he heard how highly she rated him it felt 'better than winning an Emmy', though the singer joked that she was put 'on the spot' during the interview.

Jennifer made her flirty comments during an appearance on Watch What Happens Live in October 2025. 'I'm gonna say I just did a movie with Brett Goldstein, and I would say he was the best kisser,' she gushed.