The Truth About Jennifer Lopez And P. Diddy's Former Relationship

The year was 1999, the world was bracing itself for Y2K, and splashed across nearly every tabloid was a headline about Jennifer Lopez, P. Diddy (then nicknamed Puff Daddy), or both. Lopez rose to fame in 1997 when she starred in "Selena," followed up by other blockbusters such as "Out of Sight," "Anaconda," and "U Turn." Two years later, she released her first album, "On the 6," launching her music career.

Diddy was already a bona fide rapper by 1999. He released his second solo album that year on his label Bad Boy Entertainment, according to AllMusic. He also made headlines after he was hit with felony assault charges for attacking Interscope executive Steve Stout (per MTV News).

Lopez, the charming Latin pop star, and Diddy, the bad boy rapper, may have seemed like an unlikely pair, but they officially kicked off a romantic relationship in '99. Though the singer and rapper were madly in love, scandals and behind-the-scenes chaos would eventually get between them.

Jennifer Lopez and P. Diddy worked together before dating

Jennifer Lopez and P. Diddy both had roots in the Bronx, a commonality that Lopez would later tell CBS News helped the two bond. However, their paths first crossed while working in the music industry together. Lopez appeared as a princess in Diddy's 1997 music video "Been Around the World." Soon after, Diddy worked with Lopez as a producer on her debut album. Newsweek reports that the two got closer after working together on Lopez's music video for her single "If You Had My Love," which sparked their romance.

In archived interviews, Diddy says it was love at first sight, though Lopez's initial impression wasn't so positive. The singer said that her first impression of the Bad Boy CEO was that he wasn't as family oriented as she was. After becoming friends, Lopez explained, "we developed this bond. We both understood where we were at that time in our lives and we both knew nobody else understood exactly how we felt." From there, a romantic connection blossomed, making the pair one of the most powerful couples in entertainment at the time.

P. Diddy and Jennifer Lopez got arrested early in their relationship

In December 1999, still early in their relationship, Jennifer Lopez and P. Diddy were arrested after a night at a NYC club turned dangerous. The New York Daily News reported that Lopez and Diddy had been having fun mingling with fans until Diddy got into an altercation with a man. The rapper then ruffled feathers when he threw cash around the club, prompting security guards to interfere. During the commotion, a rapper signed to Diddy's label fired a gun, injuring three in the club.

Lopez and Diddy fled the scene in a car that was later stopped by police. Law enforcement then found a stolen handgun under a front seat near Lopez's feet, leading to both her and Diddy's arrest.

After a short stint in custody, the singer-actress was released and charges were dropped, though Diddy would have to take his case to trial before eventually being acquitted (per InStyle). Despite the chaos so early in their courtship, Lopez stayed by Diddy's side.

Jennifer Lopez felt she was 'going nuts' with P. Diddy

Jennifer Lopez's loyalty to P. Diddy following their 1999 arrest wasn't enough to maintain a strong relationship. The celeb couple seemed to be totally in love when walking red carpets together (remember when Lopez walked alongside Diddy in that green dress?), but their private life was much more tumultuous. When looking back on her "Puffy era," Lopez described it as a "crazy, heightened time in my life" in an interview with CBS News.

In a 2003 issue of "Vibe" magazine, Lopez revealed she was constantly crying and "going nuts" when dating Diddy. Sources said that the rapper would go missing, prompting Lopez to go knocking on hotel room doors trying to find him. Diddy also recognized how turbulent their romance was, comparing him and Lopez to Frank Sinatra and Ava Gardner, who were known for their intense marriage that eventually ended in divorce (via ABC News).

Infidelity broke up Jennifer Lopez and P. Diddy

Despite being one of the most talked-about couples of the early aughts, Jennifer Lopez and P. Diddy's relationship couldn't survive their hardships. The two finally split in 2001, announcing their breakup on Valentine's Day (per Newsweek). Several issues created a wedge between the two, including infidelity. Lopez opened up to Vibe (via PopSugar) about Diddy's unfaithfulness, saying, "I never caught him but I just knew. He'd say he was going to a club for a couple of hours and then never come back that night."

Rumor had it that Diddy was also still in love with his ex, Kim Porter, which he later confirmed on "True Hollywood Story": "Jennifer, she definitely a bad chick, but I was still in love with Kim ... so I couldn't marry Jennifer." Still, he wasn't ready to let go of Lopez easily. The rap mogul tried to win the singer back by sending her 100 white doves (per Entertainment Weekly). For Lopez, the gesture didn't make a difference, and the breakup was final.

P. Diddy and Jennifer Lopez remain on friendly terms

Jennifer Lopez and P. Diddy (who now uses the name "Love") have mostly grown apart since their relationship ended. Lopez has carried on a legendary love life, most recently reigniting a relationship with Ben Affleck. According to Capital Xtra, Diddy may have dated model Naomi Campbell before returning to his ex Kim Porter in 2003. He later dated singer Cassie and had several other rumored flings.

Though Lopez and Diddy will likely never be an item again, they still share a connection — though it seems to be strictly platonic. In 2018, they were seen chatting and hugging after Lopez performed in Las Vegas (per Us Weekly). Then in 2020, the two hopped on an Instagram Live together for a charity dance-a-thon, according to Elle. During Diddy's dance, Lopez joked, "I probably taught you that!"

More recently, the rapper made things a little awkward by posting a throwback photo on Instagram of him and Lopez, right as rumors swirled of Lopez and Affleck getting back together. He later commented on the now-deleted photo in Vanity Fair" saying that he meant no harm and that Lopez is just his friend.