Diddy was already a bona fide rapper by 1999.
He released his second solo album that year on his label Bad Boy Entertainment, according toAllMusic.
Though the singer and rapper were madly in love, scandals and behind-the-scenes chaos would eventually get between them.
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.”
After becoming friends, Lopez explained, “we developed this bond.
The rapper then ruffled feathers when he threw cash around the club, prompting security guards to interfere.
Lopez and Diddy fled the scene in a car that was later stopped by police.
Despite the chaos so early in their courtship, Lopez stayed by Diddy’s side.
), but their private life was much more tumultuous.
The two finally split in 2001, announcing their breakup on Valentine’s Day (perNewsweek).
Several issues created a wedge between the two, including infidelity.
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 (perEntertainment Weekly).
For Lopez, the gesture didn’t make a difference, and the breakup was final.
Lopez has carried on a legendary love life, most recentlyreigniting a relationship with Ben Affleck.
He later dated singer Cassie and had several other rumored flings.
In 2018, they were seen chatting and hugging after Lopez performed in Las Vegas (perUs Weekly).
Then in 2020, the two hopped on an Instagram Live together for a charity dance-a-thon, according toElle.
During Diddy’s dance, Lopez joked, “I probably taught you that!”
