Insecure

S5 E1 • 31m • 18

Pulling up to her ten-year college reunion in style as an alumni panelist, Issa's self-doubt surfaces, while Molly-still reeling from her breakup - struggles to get out of her own head.

S5 E2 • 27m • 18

Despite her now thriving business, Issa struggles to find her footing and turns to an old friend for support. Meanwhile, Molly contemplates jumping back into the dating pool.

S5 E3 • 26m • 18

Still adjusting to newfound responsibilities, one of Issa's exes finds himself torn between two places, while an important woman in his life remains wary of his ability to be fully present.

S5 E4 • 27m • 18

Issa and her new man tread awkward waters at a work-related social event. Meanwhile, Molly juggles multiple suitors, and Issa plays defense against online attacks about her business.

S5 E5 • 24m • 18

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.

S5 E6 • 25m • 18

A distracted Issa mulls over work and love as she stumbles through the consequences of her falling out with a colleague.

S5 E7 • 27m • 18

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

S5 E8 • 27m • 18

At a crossroads in her career, Issa weighs the pros and cons of two viable paths while simultaneously contemplating an important personal next step.

S5 E9 • 27m • 18

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.

S5 E10 • 39m • 18

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.