The Game gets real about his dating past: ‘You start feeling like you’re womanizing’

The Game reflects on his romantic history, the way he’s treated certain women, and the mistakes he regrets.

The Game, Den of Kings, The Game dating history, Black celebrity relationships, theGrio.com
The Game (Photo credit: Deng of Kings YouTube screenshot)

The Game regrets playing games with ladies’ hearts.

During an appearance on the latest episode of Kirk Franklin’s “Den of Kings” podcast, featuring Snoop Dogg, Big Boi, Matt Barnes, and Deon Cole, the 45-year-old rapper reflected on his past dating life and the mistakes he regrets.

“Sometimes, like when I was in my 20s and my 30s, it was just an exchange,” he said during the conversation. “It was, ‘Hey, hey, I’m giving you this. We’re having our moment and I’m going to get back to my life. You get back to yours.’ No emotions ’cause you’re young. Everybody’s got their whole life ahead of them.”

He continued, “When you get in your 40s, man, you start feeling like you’re womanizing, and I’m taking emotions home with me, or she’s taking emotions out the door with her if you are, you know, living that type of lifestyle.”

He noted how his level of accountability had shifted as he grew older.

“When you’re young and you’re dealing with a young woman, ain’t nobody tripping. It’s all good,” he explained. “But when you’re older and you know that that woman has trauma from her past relationship and all of that … dinner is cool, going out on the date is cool. But then once you start getting intimate with people and you know for sure that they are invested in you even a little bit, and you know you ain’t talking to this person after tomorrow…”

Born Jayceon Terrell Taylor, the rapper’s reflections come after a long and very public dating history in the spotlight. In the early 2000s, he was romantically linked to model Aleska Jordan, with whom he welcomed his first child, Harlem Taylor, in 2003. He later dated reality TV star Tiffany Cambridge from roughly 2006 to 2014; the pair were even engaged at one point and starred together on their VH1 reality series “Marrying The Game,” which chronicled their relationship and near-wedding. During their time together, they welcomed two children: son King Justice Taylor in 2007 and daughter California “Cali” Dream Taylor in 2010.

Most recently, he revealed that he was dating podcast host Sheinice Hairston and that they had welcomed a son together, Blaze Taylor, in December 2024, shortly before they appeared to part ways.

On a May episode of her podcast, “Drop the Lo,” Hairston publicly confirmed the breakup for the first time.

“I’m now a single mom, and my big thing now that I’m a mom, I think it was just such an insecurity of dating as a mom,” she said in a clip from the episode.

While The Game didn’t respond to her comments directly, just days later, he appeared to address the situation with a cryptic note on his Instagram Stories.

“It’s dark out here fellas… our options are: Deal with a KRAZZYYYY a— loyal chick or a SUPER kool h—,” he wrote at the time.

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