When 'Girlfriends' Collide with 'Sistas' and 'Living Single': Exploring Hypothetical Romance Scenarios of Our Beloved Leading Ladies

From Regine and Gary to Khadijah and Rich, Max and Tony, and Joan's brief encounter with Aaron, dive into the what-ifs of these memorable characters navigating the complexities of relationships across different eras.

"Tyler Perry's Sistas" has introduced a new set of women, cementing their place in the ever-evolving landscape of pop culture girlfriend groups. A fresh crew emerges each decade, and the "Sistas" are the torchbearers for the 2020s. Reflecting on the iconic shows of the 90s, such as "Living Single" and "Girlfriends," it sparks curiosity about how those classic girlfriends might navigate the dating scenarios presented in "Sistas."

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Let's delve into the imagination and explore four hypothetical pairings, envisioning the dynamics between some "Sistas" men and our beloved leading ladies from the past.

Most Likely to Date a Gary 


That would be Regine from "Living Single." Gary presents like a sophisticated man who has it all together, and he has money, even if he likely got it illegally, but you already know that Regine loves a baller. However, while Regine is probably the type of woman who might put up with more drama than she should to have a rich man, she wouldn’t be as dumb about him as Andi has been. 

The Outcome: Regine would have cut Gary off the minute she learned he lied about having a wife and Maxine would have helped her figure out how to get that restraining order popping. 

Most Likely to Date a Rich 


It’s Khadijah from "Living Single." Rich is no Scooter; he’s a headstrong and reasonable entrepreneur like Khdadisha. All of the above would make them a good match. 

Outcome: It would work well for a while, but once Khadijah learns that he doesn’t want kids or to get remarried, she’d be out. Even though Khadiajah wasn’t fully sure if she wanted marriage and kids, she was the type to want the option or flexibility at least. 

Most Likely to Date a Tony 


That’s Max from Living Single. Tony is a boss; he’s confident and charming and knows how to handle a feisty woman like Max. As we saw on Sistas, he’s also persistent, which would be necessary for Max because the likelihood of her shutting him down at first would have been high.  

The Outcome: Max and Tony would have a lot of fun, but she’d break up with him as soon as he busts out with not one but two tweens. Max doesn’t do bonus mom. 


Most Likely to Date an Aaron 


Karen didn’t appreciate Aaron, but Joan from Girlfriends probably would —  at least for a while. Joan has dated various men, but she often got straight-laced men, so this seems like the most likely scenario. 

The Outcome: Joan would have fun for two seconds before getting bored and probably scared by the inevitable marriage and kids talk. It’s what Joan said she wanted in theory, but she often self-sabotaged when men got serious.

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