Ahead of the 'Insecure' Season 5 Premiere, Catch Up on Where We Left Off

We've built the ultimate Insecure refresher (with hints from the cast about the upcoming season) so you're ready to watch the fifth and final season when it returns to HBO on Oct. 24

About that cliffhanger ...

It's a bittersweet moment for Insecure fans when the Emmy-winning HBO series makes its return on Oct. 24 for its fifth season. The "bitter" part? This is Insecure's final season. The "sweet" part? We'll finally get all of our burning questions answered!

What will happen with Issa and Molly's friendship? What can we expect after Lawrence dropped that mega bombshell? Can Condola even handle an actual infant? The friendships, the relationships — and yes the (iconic) mirror raps — will continue with the 10-episode season, which is why we're here to remind you where we left off in season 4 (and drop some hints about what to expect next).

The comedy series follows the career journey of a young Black woman named Issa Dee (played by creator Issa Rae) and her uncomfortable experiences and racy tribulations. An adaptation of her popular web series Awkward Black Girl, Insecure was co-created by Larry Wilmore in 2016. Rae is also an executive producer on the series, alongside Prentice Penny.

HBO's Insecure Live Wine Down At Essence Festival

Rae told Deadline: "Prentice and I are so grateful that HBO believed in our show from the beginning and kept faith in us to see our vision through the end. We always planned to tell this story through five seasons, but we couldn't have made it this far without the tremendous support of our audience. I feel blessed beyond measure to bring our characters' stories to an end, on-screen at least."

Natasha Rothwell, Yvonne Orji, Issa Rae, Amanda Seales, Wade Allain-Marcus HBO Insecure Season 5
Raymond Liu

The core cast of characters consists of Issa Dee (Rae), Molly (Yvonne Orji), Lawrence (Jay Ellis), Kelli (Natasha Rothwell), Tiffany (Amanda Seales) and Nathan (Kendrick Sampson) — all of whom are returning for the final season.

Alexander Hodge, Yvonne Orji, Issa Rae, Prentice Penny, Elaine Welteroth and Jay Ellis
Michael Loccisano/Getty Images for HBO

In order for the characters to navigate their next steps in life, they must evaluate their past, present and future relationships. This is something fans can expect to see in the coming episodes. Actress and writer Rothwell shared in a brief teaser via Twitter, saying, "This season on the show is sort of the crescendo of four seasons of friendships and growth." She continued, "ya'll ain't ready!"

Rae revealed that the season starts with Issa and her career journey, explaining, "She's building off the success of The Blocc party." Orji added that Molly and Issa's friendship will continue to be explored, as it's "really the backbone of the show." She continued, "We're going to see a relationship that was fragile try and rebuild."

On Sept. 29, HBO released the season 5 trailer that opened with a sentimental scene of Issa talking to her younger (braces-on-teeth younger) self in the mirror. The clip continued with a mix of emotional and funny-filled moments of Issa and her friends; and even showed her and Molly at their alma mater, Stanford University.

KeKe Palmer will be joining the cast for the final season after she jokingly messaged Rae, expressing her enthusiasm for the show. After previously directing an episode in season 4, Kerry Washington will be returning to direct the fifth episode of season 5.

Before the season 5 premiere, here's a relationship refresher of the complicated character dynamics. (Spoilers ahead, So either keep reading, or stop and binge the first four seasons ASAP!)

Is this the end of Issa and Molly's friendship?

After weeks of high tensions and frustrating arguments, Issa and Molly sat down for a long-overdue conversation in the season 4 finale.

What's this conversation about? Between talking behind each other's backs and failed attempts to make amends, the entirety of the fourth season showed their friendship's slow and painful demise – which was even foreshadowed in the prologue of the season 4 premiere. (Remember when Issa told a mystery caller that she didn't "really f–k with Molly anymore?")

Rae told PEOPLE that she's "most excited for people to watch Molly's character development throughout the final season, but won't spoil any details."

Yvonne Orji, Issa Rae HBO Insecure
Merie W. Wallace/HBO

Fans can only hope that their friendship will be the same come season 5, but that unfortunately might not be the case. The writers "don't want them to go back to where they were," showrunner and director Penny told Entertainment Weekly about creating season 5.

He added, "They're going to be forever changed by this, forever humbled by this, and hopefully, forever close by this. I don't think it's about getting them back to where they were. I think we're always going to have a version of them having fun together because they're friends, but I think we want to explore what is that road back like and how is that road different."

Yvonne Orji, Issa Rae HBO Insecure
Merie W. Wallace/HBO

What's going on between Issa and her ex Lawrence?

Season 4 explored the rekindled relationship between Issa and her ex, after the two eventually decided to get back together. (But of course Insecure has to drop a bomb on anything that seems to be going "well.")

In the final episode of the season, Lawrence nervously admitted to Issa that he'd been offered his dream job in San Fransisco. Although he was worried about how she would react (since their relationship was finally in a good place), she was happy for him — even making plans to move together. Things were looking great for the couple.

Insecure ep 8 “Lowkey Happy” Jay Ellis, Issa Rae
Merie W. Wallace/HBO

Ready for bomb number two? Lawrence's ex-girlfriend Condola (Christina Elmore) told him that she's pregnant and keeping the baby. (If you're concerned about Issa, same.) Fortunately, Lawrence said that he's not getting back together with Condola, but the added challenge of being a father might be too much for Issa to handle.

But what about Issa and her beau Nathan?

Prior to Lawrence and Issa's restarted romance, Issa had been spending time with former lover Nathan (whom she thought ghosted her in season 3; she later discovered he was diagnosed as bipolar and was learning how to cope).

Insecure. Merie W. Wallace/HBO

We couldn't help but assume that there was going to be a season finale love triangle after Nathan expressed feelings for Issa, but she was quick to shoot that down when she committed to Lawrence instead. How did Nathan take it? He was surprisingly chill and accepting.

Are Molly and Andrew broken up?

The relationship between Molly and her music-industry boyfriend, Andrew, has been a struggle since the beginning of season 4, so it's no surprise that Andrew snapped by the end. Molly's inability to compromise was the basis of the couple's crumble.

Yvonne Orji, Alexander Hodge HBO Insecure
Merie W. Wallace/HBO

The breaking point for the two occured the night of Molly's work event. Andrew wanted to leave early, but Molly forced him to join in getting drinks afterward. When they finally went home, Molly freaked out on Andrew for attempting to watch Looking for LaToya without her.

Fed up, Andrew explained that he couldn't deal with accommodating her without any reciprocation, and asked Molly if what they had is what she really wanted. His question went unanswered.

Wait, did Tiffany run away from Derek?

Amanda Seales, Wade Allain-Marcus
Glen Wilson/HBO

After a night out alone, Tiffany went missing and her husband Derek (Wade Allain-Marcus) and their friends scoured the town to search for her. Issa and Molly are among those friends, which you would think would be a good enough reason for Issa and Tiffany to fix their friendship, right? Wrong.

Tiffany is a new mom and we found out that she's dealing with postpartum depression. Derek told the ladies, "I knew she wasn't happy, but I thought maybe time would help. I just didn't think it would get this bad. I can't believe I let this happen."

The group finally tracked her down at a nearby Sheraton using an Uber receipt, security camera and Issa's intuition.

Yvonne Orji, Alexander Hodge, Amanda Seales HBO Insecure
Merie W. Wallace/HBO

Season 5 of Insecure premieres Sunday, Oct. 24, at 10 p.m. ET/PT on HBO.

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