Kristy Martin is 20-something, single, and living it up in Chicago. She has a crew of close girlfriends to keep her social calendar active and is celebrating finally securing employment in her chosen field. While always free-spirited, Kristy is getting tired of the revolving door - or, more accurately, bed - of random guys and failed dates and comes up with a plan to get her act together when it comes to the opposite sex. That idea is quickly shot down by her bestie Breely Laver and replaced with a bet she can’t refuse.

Scarlett Walsh is 20-something, single, and lonely in Chicago. Still reeling from an unexpected breakup that left her broken-hearted, Scarlett relies heavily on her group of girlfriends to help heal and move forward. But her friendship with BFF and long-time roommate Tinsley Thompson has turned toxic, and Scarlett is on the brink of moving out - and causing more friction to the already rocky friendship. Wishing to avoid drama amongst their close group of girlfriends, Scarlett attempts to stay focused on her job as a vet tech and the excitement of being a first-time puppy mom.

Lauren Begay is 20-something, engaged, and miserable in Chicago. With her wedding to high school sweetheart Ben just months away, Lauren knows in her heart she can’t walk down the aisle. A proud workaholic and interior design assistant, she is chasing a promotion that will elevate her design career, preferring to study blueprints over wedding dresses. With her girlfriends eager to throw her bridal parties and a bachelorette bash, Lauren feels the pressure to put a stop to the wedding plans.

Breely Laver is 20-something, pregnant, and furious in Chicago. Breely never set out for motherhood, and is devastated when her birth control fails her. Her fitness career and helping women through her yoga practices is her top priority, while utilizing social media to create a life she truly loves is the most important thing to her. Not even her long-time boyfriend Jordan, who is thrilled at the idea of fatherhood, can get Breely excited for this sudden change in her life. Going from a travel-heavy career to being stuck in Chicago with a newborn is not what she had on her vision board.