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Hip Hop Squares is a lively new take on the classic Hollywood game show where celebrity contestants play tic-tac-toe for dough. It's been 20 years since Stevie J was last single. Now he's looking forward to the next 20 years and hitting reset in a major way. After his chaotic breakup with Joseline, Stevie is more than ready to focus on music, family and living the bachelor life to the fullest. But it's tough to get a train back on the tracks when life is one long train wreck, which is why he's determined to avoid repeating the mistakes of his past -- like mixing business with pleasure and getting involved with messy females.

It's easier said than done. A fresh start calls for fresh experiences, and Stevie thinks busting out of his comfort zone might be exactly what he needs. Along the way, Stevie resolves to forge deeper connections with his children who have suddenly grown into young adults with big mouths, big problems and strong opinions about everything.

As he re-evaluates his life, Stevie seeks the guidance of his longtime friend, collaborator, and confidante Faith Evans. Spending time with Faith will leave Stevie wondering whether the single life is overrated.

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