'Insecure' returns

Updated 8:22 AM ET, Mon October 25, 2021
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10:37 p.m. ET, October 24, 2021

‘It ain’t nothing personal’

From CNN’s Lisa Respers France

Issa's smiling and so are we knowing there's a full season of "Insecure" ahead for us.
Issa's smiling and so are we knowing there's a full season of "Insecure" ahead for us.

I did NOT see Cheyenne robbing the girls coming!

So much for reconnecting with old and dear friends.

Also, is she not a successful background dancer after all? I mean, I know living in the Bay area can be expensive, but I have questions!!!

The whole gag about the reunion committee thinking Kelli was dead brought us the lovely scene of Issa, Molly and Tiffany “eulogizing” their homegurl and Kelli asking her podcast audience “If you knew the end was coming, how would you make the most of your time coming?”

Is this foreshadowing the death of Issa and Lawrence’s relationship?

It sure felt like that after a tearful Issa let Lawrence know she’s been thinking and…walked away from him.

At least she and Molly seem closer and like things are getting back to where they belong in their friendship.

What does it all mean?!?!?

Thank God we've got nine more episodes to find out.

Earlier Sunday, Rae posted a note on Instagram in which she said she was feeling emotional about the final season.

"This has been 'my' show for so long," Rae wrote. "But as we close out, I hope it lives on as 'your show.'” 

All the feels, Issa.

10:26 p.m. ET, October 24, 2021

This is the love we needed

From CNN’s Lisa Respers France

Issa and Molly's friendship is the true love story of "Insecure."
Issa and Molly's friendship is the true love story of "Insecure."

Seing Issa and Molly find their way back together is so heartwarming.

Reunions make us all sentimental and it’s a good time to remind us where we came from and where we are headed.

Seeing Molly turn to Issa with her insecurities (see what I did there) about relationships and boost Issa after her less than stellar performance on the panel is a reminder as to why their bff love story if the one we are truly rooting for. (Sorry, not sorry Lawrence.)

10:18 p.m. ET, October 24, 2021

Throwback Issa

From CNN’s Lisa Respers France

Issa Dee, master of self-affirming mirror talks.
Issa Dee, master of self-affirming mirror talks. Glen Wilson/HBO

Issa now talking to Issa from college is a hoot!

“I forgot how cute I looked with twists,” current Issa tells old Issa, who is also sporting braces.

Issa has been invited to speak on a panel about entrepreneurship. And while she’s not an attorney at a firm with Molly, she can at least tell the college version of herself that she’s a CEO.

If only we could go back to our former selves and let them know it’s all going to be ok -- and to be sure to invent Instagram so we could make a ton of loot.

10:16 p.m. ET, October 24, 2021

Those good ole days

From CNN’s Lisa Respers France

The Stanford alumni return to campus.
The Stanford alumni return to campus. Raymond Liu/HBO

So, Kelli, Molly, Tiffany, Derek and Issa are all Stanford alumni (hello Black excellence) and I love that the writers got them out of Los Angeles and took them north for this first episode.

Extra points to whichever one of the writers who suggested having a flutist accompany the DJ playing the Too Short classic, “Blow the Whistle.”

And Molly and Issa were in a rap group in college?! Of course they were.

10:15 p.m. ET, October 24, 2021

Why ‘Insecure’ matters

From CNN’s Kendall Trammell and Leah Asmelash

As creator, writer and star of "Insecure," Issa Rae has helped bring more nuanced portrayals of Black women to television.
As creator, writer and star of "Insecure," Issa Rae has helped bring more nuanced portrayals of Black women to television. Glen Wilson/HBO

If there’s one thing “Insecure” can be very secure about it’s the impact the show has had.

Below, CNN's senior producer Kendall Trammell and associate culture writer Leah Asmelash explain more about their personal connections to the show:

Trammell: “Insecure” filled a void for Black women TV rarely highlighted: the multi-dimensional Black woman. Yes, we loved the celebration and adoption of #BlackGirlMagic, but let’s not forget about the weight Black women have carried to be excellent 24/7, often putting their own needs -- their careers, their romantic desires, their mental health -- on the back burner. That’s why “Insecure” connected with so many Black women.

The show acknowledges our lives can be/will be/are messy. Even when it feels like the world doesn’t understand the plight of Black women, some of us can find refuge in our fellow Black women friends and know our imperfections will be embraced. Because they’re feeling it, too.

I know it firsthand having a handful of “Insecure” fans as friends who are also Black women. Before the pandemic, we knew we’d be together at someone’s house laughing, hollering and sometimes crying watching “Insecure.” So, the beginning of the end of this show is personal for me. Because as I matured in my 20s, Issa and her friends helped me realize how much I valued my own. And for that, I’m truly grateful. 

Asmelash: I agree, Kendall. There’s a moment in Season 2 of “Insecure” when, gathered around a dinner table, Issa and Co. lament over the Popeyes near her apartment transforming into a Pinkberry frozen yogurt shop. A few episodes later, we see Issa strolling down her rapidly gentrifying neighborhood, past the “Now Leasing” signs and the new coffee shop. In her hands is the signature white Pinkberry cup.

It’s an easily overlooked moment in the show, but it’s one I’ve returned to often for its clear display of something I had yet to see with Black women, or any women of color: nuance. That Issa can both mourn the turning demographics of her neighborhood while also casually partaking -- even enjoying -- some of the changes felt like a revelation.

For better or for worse, “Insecure” shows everything. Episodes casually mirror what, to me, feels like everyday life. Of course, the show makes me laugh, cry, and even groan. But more importantly, it makes me feel understood.

10:06 p.m. ET, October 24, 2021

“Reunited, Okay?!”

From CNN’s Lisa Respers France

Amanda Seales and Wade Allain-Marcus play loving couple Tiffany and Derek DuBois.
Amanda Seales and Wade Allain-Marcus play loving couple Tiffany and Derek DuBois. Glen Wilson/HBO

Welcome back, Issa and the gang!

Shout out to the music supervisor for “Insecure” because the tunes are always a vibe.

Episode one of Season 5 starts out with Kelli riding to their 10-year college reunion with Tiffany and Derek and I could legit watch a show with just the three of them traveling around talking about the rest of the characters.

First up to dish on: Molly and her Instagram account which shows some food, inspirational quotes and plenty of selfies with just a portion of her face. Ma’am…we need you to get it together.

Fingers crossed that Molly and Issa can get their relationship back on track this season.

10:07 p.m. ET, October 24, 2021

TV’s best female friendships

From CNN’s Sandra Gonzalez

Molly and Issa share a laugh.
Molly and Issa share a laugh. HBO

What a time to be alive! I mean, not really. The climate. The Covid. The Karens. But it is a great time to be watching TV.

If for nothing else, the fact that I get to enjoy watching female friendships like Issa and Molly’s and Rebecca and Keely’s and Rosa and Amy’s makes me proud of how far we’ve come from the days when people would tune into “Dynasty” to see women fight in shoulder pads.

That’s not to say the female friendships we see have to be perfect – Issa and Molly’s own tension has been an important plot point. Quite the opposite, in fact. As everyone blessed with meaningful friendships knows, it’s when people stop trying to be flawless that you learn to love them even more.

9:56 p.m. ET, October 24, 2021

What we want to see this season on ‘Insecure’

From CNN’s Kendall Trammell

Yvonne Orji as Molly Carter in "Insecure."
Yvonne Orji as Molly Carter in "Insecure." Raymond Liu/HBO

“Insecure” is coming to an end, and fans could use some resolutions. Here’s our wishlist for the final season:

  • Issa and Molly secure their friendship status. We love to see those TV female friendships.
  • Issa gets a love story we can all get behind. That means it’s time to end the Issa-Lawrence/Issa-Nathan web.
  • Molly embraces being an independent, single woman.
  • Tiffany finds the support she needs as she works through her postpartum depression.
  • Lawrence shows the makings of a great dad.
  • We get to the end of “Looking for LaToya,” the true-crime series highlighting the number of Black women who go missing.

For more pre-gaming, click here to read Lisa Respers France's conversation with Yvonne Orji.

And here's the trailer for the new season, in case you missed it.

9:32 p.m. ET, October 24, 2021

‘Insecure’: Where we left off

From CNN’s Kendall Trammell

Issa Rae as Issa Dee in the Season 5 premiere of "Insecure"
Issa Rae as Issa Dee in the Season 5 premiere of "Insecure" Merie Weismiller Wallace/HBO

The reunion we were all waiting for. An unexpected, pearl-clutching pregnancy. And a friend gone missing. Here’s a recap of what went down in last season’s finale. 

  • Molly and Issa finally talk. After a whole season of wishing for the two friends to make up, these gal pals got back together again over dinner at a restaurant.
  • Meanwhile, Molly’s steamy love life turned cold. She and her boo Andrew got into a huge fight about their evening plans, which led the couple to realize they’re not on the same page in this relationship. 
  • #TeamLawrence fans got what they wanted (sort of). Issa and Lawrence rekindled their love. Nothing a little Prosecco and whiskey can’t fix, right? Lawrence landed a job in San Francisco, but Issa doesn’t worry. She’s open to trying a long-distance relationship or even moving with him. Then comes the surprise — Lawrence has a baby on the way with Condola, his ex and Issa’s friend.
  • But there might be hope for #TeamNathan. Issa met up with her other ex Nathan who ghosted her for months. We learned he was dealing with mental health issues and needed time away from his love. Now he wants a second chance. Was he too late or right on time?
  • Tiffany went missing. As they work through their friendship drama, Issa and Molly put their differences aside to help find their friend who has been dealing with postpartum depression. Ultimately, they find her safe at a hotel and reconnect her with her loving husband Derek.