Meghan Cherry has the opposite problem. Reeling from a painful divorce, the techie with a desire to unleash her artistic side, can't figure out why her relationships end with nothing when she gives so much.

Attorney, Dawn Martin, is stuck somewhere in the middle. Waiting in purgatory for a marriage proposal that just won't come has molded her into a woman she swore she'd never be.

Against the backdrop of hot days and cool nights in Chicago and armed with red cups of Single Girl Sangria, Button, Meghan, and Dawn share stories, perspectives, and advice on everything from open relationships to open-toe shoes. They come together by chance, grow together as friends, and ultimately discover that for every girl, there's a season.