Insecure, Chillin', Okay?!

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.

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.

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.

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.

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.

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