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Insecure Season 5 Episode 1 Recap “Reunited, Okay?!”

Don’t miss Celebrity Myxer’s recap of Insecure Season 5 Episode 1 premiere “Reunited, Okay?!” Pulling up to her ten-year college reunion in style as an alumni panelist, Issa’s self-doubt quickly surfaces, while Molly — still reeling from her breakup — struggles to get out of her own head. As the crew takes the opportunity to reflect, old wounds remain tender. Here’s what you missed!

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Watch Insecure Season 5 Episode 1 “Reunited, Okay?!”

On the Insecure Season 5 Episode 1 premiere, two months after the events of the fourth season finale, the gang heads back to Stanford for their 10-year reunion. Tiff, Derek, and Molly are celebratory, but coming back to her alma matter has an unexpected effect on Issa, and Kelli is frustrated at the reception she receives.

Issa and Molly on Insecure Season 5 Episode 1

Issa and Molly on Insecure Season 5 Episode 1

When we left them, Issa and Molly were finally sitting down for a real talk after all the drama and distance between them last season came to a head. Big changes are happening in both of their lives, Molly is single again after her relationship with Andrew burned out, and Issa is dealing with a new career and a boyfriend with a baby mama. With so much history behind them, and a changing future in front of them, in this episode, Molly asks Issa the question we all want the answer to, “Are we gonna be ok?”

Stanford Reunion

Kelli, Molly, Issa, Tiff, and Derek on Insecure Season 5 Episode 1

Kelli, Molly, Issa, Tiff, and Derek on Insecure Season 5 Episode 1

On the way to Stanford, Tiffany, Derek, and Kelli discuss Molly’s not-so-subtle Instagram posts about her breakup with Andrew and agree to overlook all drama this weekend in honor of celebrating their ten-year reunion. Arriving in San Francisco, Issa meets everyone at Stanford and it’s clear things are still awkward between her and Molly, even though they’re twinning. As a panelist for the event, Issa is feeling very “officish,” and the group hypes her up about her new business, the B.L.O.C.C. even though she can’t quite recall what it stands for.

Molly’s therapist, Dr. Rhonda, has encouraged her to “be in the present moment”, and “disconnect” two things Molly is pretty sure she doesn’t know how to do. When she finds out Omari, (her old FWB from college) is divorced and interested in seeing her again, she immediately begins to overthink it.

Kelli, at first annoyed, that she isn’t registered for the event, is shocked to find out it’s because Stanford thinks she’s dead.

Molly gets real with Kelli about her and Issa’s friendship, asking her how long it took for Tiff and Kelli to get back after they had a falling out. Kelli, in her own roundabout way, tells Molly to give it time and to just support Issa when she needs it. This comes in handy when Issa’s panel doesn’t go to plan.

Issa's pep talk to herself on Insecure Season 5 Episode 1

Issa’s pep talk to herself on Insecure Season 5 Episode 1

After talking to her college self in the mirror, Issa starts to think about her path in life and her relationships with her friends and family. At the panel, when asked questions about B.L.O.C.C. and knowing she’s on the right path, Issa is awkward and admits she doesn’t know for sure, that all of this could be a waste of time. Molly reassures her and reminds Issa to be proud of herself and her company, and the two bond over their college days.

Robbed

After fake smiling and hello-ing lots of classmates, she can’t actually remember, Issa and the group run into Cheyenne, a party-girl who was in a rap group with Molly and Issa in college. Later that night, the girls head to Oakland to party with Cheyenne and on the way Kelli blows up, frustrated that her friends only see her as a joke and that Stanford barely memorialized her.

At the liquor store, Cheyenne, Molly, and Issa go inside while Tiffany and Kelli wait in the car. After buying the drinks all three girls are robbed at gunpoint, and Cheyenne starts to freak out before the gunman calls her by name, and she admits that she set them up. After stealing Molly’s shoes, the liquor, and their purses, Cheyenne takes off and Molly and Issa head back to the car.

Issa and Lawrence Break Up

Kelli and Tiffany are shocked to hear that Cheyenne robbed them, but Issa and Molly crack up over it. In a diner, the group has a fake memorial for Kelli and all the women say wonderful things about her, especially Tiffany. Molly asks Issa for advice about Omari, both women say they want to move forward, and back in LA, we get our first glance at Lawrence and Issa’s relationship (and possibly our last) as he picks her up from the airport.

When they reach her place, Issa comes clean and tells him she’s had time to think about everything, to which Lawrence says “I know.” It looks like Issa and Lawrence are done, again, this time because he’s having a baby with Condola.

What did you think of Insecure  Season 5 Episode 1? Let’s talk about Insecure in the comments below! Stay right here, stay myxed in for next week’s episode “Growth, Okay?!”

Air Date: October 24, 2021

Insecure Main Cast

  • Issa Rae as Issa Dee
  • Yvonne Orji as Molly Carter
  • Jay Ellis as Martin Lawrence Walker
  • Lisa Joyce as Frieda
  • Natasha Rothwell as Kelli Prenny
  • Amanda Seales as Tiffany DuBois
  • Y’lan Noel as Daniel King
  • Alexander Hodge as Andrew
  • Kendrick Sampson as Nathan Campbell
  • Wade Allain-Marcus as Derek DuBois

Watch a new episode each week on HBO Max, check out the listings dates below. Stay right here, stay mixed in because Insecure Season 5, Episode 2, Molly contemplated jumping back into the dating pool, while Issa – struggling to find her footing at work leans on an old friend! Drop your email to get insights into your inbox…

News Updates

Will there be a season 6 of insecure? Find out the truth here!

Insecure Season 5: Release Date, Plot, News, Trailer & More

Insecure Season 5 Episode Guide

Season Episode Title Air Date
5 10

Everything Gonna Be, Okay?!” Insecure Season & Series Finale

As she and her friends try to make time for each other no matter what, Issa looks back on all it took to get to where she is today.

December 26, 2021
5 9

Out, Okay?!

At a friend’s going away party, Issa navigates unresolved feelings. After spending the day letting loose with her new man, Molly opens up about her fears.

December 19, 2021
5 8

Choices, Okay?!

At a crossroads in her career, Issa weighs the pros and cons of two viable paths while simultaneously contemplating an important personal next step. Meanwhile, with help from Kelli, Molly spends an overwhelming day getting her parents’ estate plan in order.

December 12, 2021
5 7

Chillin’, Okay?!

A long overdue girls’ night filled with self-reflection and real talk puts things into perspective for Issa and her friends.

December 5, 2021
5 6

Tired, Okay?!

A distracted Issa mulls over work and love as she stumbles through the consequences of her falling out with a colleague. Meanwhile, Molly — still struggling to cope with family matters — finds comfort in an unlikely source.

November 28, 2021
5 5

Surviving, Okay?!

A family emergency finds Molly stretched thin between taking care of loved ones, staying on top of work, and zeroing in on her own perceived shortcomings. As a hectic day unfolds, Issa and her new man grow closer than ever.

November 21, 2021
5 4

Faulty, Okay?!

Issa treads awkward waters with her new man and plays defense against online attacks, while Molly juggles multiple suitors.

November 14, 2021
5 3

Pressure, Okay?!

Eager to embrace newfound responsibilities, one of Issa's exes finds himself torn between two places.

November 7, 2021
5 2

Growth, Okay?!

Molly contemplated jumping back into the dating pool, while Issa - struggling to find her footing at work leans on an old friend.

October 31, 2021
5 1

Reunited, Okay?!” Insecure Season 5 Premiere

At her ten-year college reunion, Issa’s self-doubt quickly surfaces, while Molly struggles to get out of her own head.

October 24, 2021

Photo credit: HBO/Warner Bros.

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Halla Warner is a Content Writer for Celebrity Myxer.

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