Living Single: A 90s Classic That Aged Like Fine Wine

The Jaleel White Interview That Got Me Thinking…

Recently, I was scrolling through Instagram when I saw a post from The Jasime Brand featuring a clip from an interview with Jaleel White (aka Steve Urkel from Family Matters). He was promoting his new book and, as expected, dropping a few attention-grabbing soundbites along the way.

In the interview, someone asked him why Family Matters isn’t seen as iconic as other Black sitcoms. His response? He said that in “family television,” his show gets recognition, but in “hood television,” it doesn’t—because it wasn’t “hood enough.” Then he gave Martin and Living Single as examples of hood shows.

And immediately, I was like… Excuse me?

Since when were Martin and Living Single considered hood shows? When I think of hood television, I think of something like South Central—a show that reflected the raw realities of life in a dangerous neighborhood. But Martin and Living Single? Nah. Those were adult sitcoms, pioneers in Black television, and cultural staples.

Funny enough, over the past few months, I’ve been rewatching Living Single on streaming platforms, and it’s been hitting way differently than it did when I first watched it as a nine-year-old little girl.

Back then, I loved it for the fashion, the friendships, and the fun. But as an adult? The humor lands differently. The career struggles feel real. The relationships make so much more sense. There are layers I completely missed as a child, and now, I find myself relating to these characters in ways I never expected.

Living Single isn’t just a nostalgic favorite anymore—it feels like a blueprint for Black women navigating adulthood. The friendships, the ambition, the financial struggles, the love lives—it’s all so much more relatable now.

So let’s break it down—how did my perspective on these iconic characters change from childhood to adulthood?

Khadijah James: The Blueprint for Black Women in Media & Entrepreneurship

Played by Queen Latifah

As a kid, I always loved Khadijah. She was the one that stood out to me the most—probably because I already knew Queen Latifah as a rapper first. Back then, I just thought Khadijah was cool, confident, and a natural leader.

But watching as an adult? Oh, I felt her struggles.

Khadijah wasn’t just a boss—she was an entrepreneur trying to keep her business afloat with limited resources. Now that I’ve run my own business, I understand:

✔ The pressure of managing people.

✔ Trying to meet deadlines while running a whole operation.

✔ Chasing a dream with passion but not always the budget to match it.

I know the stress of turning sugar into something profitable. I know what it’s like to have to make tough decisions to keep your dream alive.

And the wildest part? I had my own magazine too! iCandiland E-Magazine was my digital version of Flavor, and like Khadijah, I had writers, photographers, editors, and designers working with me. Watching Living Single now, I don’t just relate to Khadijah—I see myself in her.

Khadijah was the blueprint. She showed us what it meant to be a powerful Black woman in media—before it was even common.

Sinclaire James: The Underrated Late Bloomer

Played by Kim Coles

Growing up, Sinclaire was just the goofy one to me. She was quirky, she was funny, and she had a pure, good-girl innocence about her.

Now? I see how important her story was.

Not everyone knows exactly what they want in life right away. Sinclaire came to New York, working under her cousin, not really knowing what she wanted to do. But throughout the seasons, we saw her grow, evolve, and find herself.

She started pursuing acting, improv, and comedy—and that journey felt so real. Because let’s be honest—how many of us have shifted careers, discovered new passions, or had to figure it out along the way?

Sinclaire was a late bloomer, but she showed that taking your time is okay. And honestly? That’s a lesson some of us are still learning.

Regine Hunter: The Original Socialite & Influencer

Played by Kim Fields

As a kid, Regine was fabulous but extra. She was bougie, she had all the men, and she cared about fashion, brands, and status.

Now? Regine was ahead of her time.

Today, she would have been a socialite, a luxury influencer, and an Instagram fashion icon. She worked in fashion and branding, and she was strategic about her dating life.

People called her materialistic, but let’s be real—she just knew what she wanted and refused to settle. And there’s nothing wrong with that.

She wasn’t a gold digger—she was securing her lifestyle. And in today’s world? That’s called knowing your worth.

Maxine Shaw: The Alpha Female Who Needed an Equal

Played by Erika Alexander

Max was the hardest to connect with as a kid. She was sharp, witty, and successful—but she also seemed mean and aggressive.

As an adult, I now see that Max was simply a woman who had standards, boundaries, and confidence. She knew what she wanted in her career, in friendships, and in relationships.

She was also the definition of an alpha woman—and that’s why she needed a man who wasn’t intimidated by her.

Which brings me to…

Kyle & Max: The Love Story I Didn’t Understand as a Kid

Played by T.C. Carson & Erika Alexander

When I was younger, I didn’t get their back-and-forth, love-hate, chemistry-filled relationship. They insulted each other, hooked up, broke up, and repeated the cycle.

Now? I GET IT.

🔥 That tension? That slow burn? That “I can’t stand you, but you’re my person” energy? That’s grown folks’ love.

Kyle wasn’t just Max’s equal—he was the only man confident enough to handle her. He never tried to dim her fire. He could match her wit, her intelligence, and her drive. And at the end of the day, they made sense.

As a kid, I didn’t get why people loved them together.

As an adult, I’m like “Oh, that’s why.”

Would a Living Single Reboot Work Today?

• Living Single would have to be updated for today’s world.

• Regine as a socialite influencer.

• Khadijah running a digital media empire.

• Sinclaire as a content creator & comedian.

• Max in politics or running a law firm.

• Kyle as a business mogul.

But honestly? Maybe it doesn’t need a reboot. Maybe we just need to keep giving it the love it deserves.

Final Thoughts: This Show Still Hits in 2025

As a kid, I loved Living Single because it was fun—the fashion, the friendships, the jokes.

As an adult, I love it because it’s real—the struggles, the ambition, the relationships, the lessons.

It wasn’t just a sitcom. It was a blueprint for Black women navigating life, love, and career on their own terms. It showed us that:

Friendships matter. Your circle can be your greatest support system.

Success isn’t always easy. Chasing your dreams takes hard work, sacrifice, and resilience.

✔Love looks different for everyone. And sometimes, the best love stories aren’t perfect—they’re real.

The Moments That Hit Different As an Adult

One episode that felt completely different watching it now was when Regine got a breast reduction.

As a kid, that episode didn’t really stand out to me—I didn’t get why it was a big deal. But as a woman who has watched her body change over the years—especially after having children—I get it now.

Regine was used to a certain look, a certain size, a certain identity. Her sex appeal, her confidence—it was all wrapped up in her knowing exactly who she was. And when that changed, she had to rediscover herself.

I think so many of us as women can relate to looking at our bodies differently as we evolve. What once felt sexy might not feel sexy anymore. Or maybe we just don’t know how to feel sexy in this new body. Watching that episode as an adult, I saw Regine’s vulnerability in a way I never had before. And as someone who has considered getting a breast reduction myself? Whew, girl—I understand now.

The Storyline That Feels the Most Real as a Grown Woman

If I had to pick one journey that resonates the most now, it would be Sinclair’s.

Growing up, Sinclair was just the goofy one. She was fun, lighthearted, always bringing the laughs. I don’t think I ever really took her character seriously.

But now? A lot of us ARE Sinclair.

We’re still figuring ourselves out. We’re still evolving. We’re still trying to figure out what we want, where we belong, and how to fully step into ourselves. Watching Living Single now, I appreciate her journey of self-discovery so much more. She wasn’t lost—she was just growing. And aren’t we all?

I See Myself in All of Them

When I really think about it, I realize I see pieces of myself in all of these women.

✔ Khadijah? The strong friend. The one everyone goes to for advice. The entrepreneur constantly trying to budget, plan, and make things shake.

✔ Max? The foodie. And as I’ve gotten older, the blunt one. No sugarcoating. It is what it is.

✔ Sinclair? Always evolving, always finding herself, always discovering new parts of who she is.

✔ Regine? Listen—I get her now. Why should I lower my standards? I want a certain quality of life, and I’m working hard to create that for myself. So why wouldn’t I want a man who matches my fly? I get it, girl. I really do.

That’s what made Living Single so iconic. It was ahead of its time, and even today, it still holds up.

💬 What about you? Who do you relate to now that you’re grown? What’s a storyline that hits differently for you as an adult? Let’s talk in the comments!