Since the divorce from her husband David, Maggie Delaney has partly moved on with her life in opening her own bakery, she and her business partner Devon who want to expand by opening a second location if only they could get more exposure. Maggie has to be all things to her two children, sixteen year old Emma and fourteen year old Gary, in David being a deadbeat father who doesn't have time for them despite his scheduled days with them which he never makes. Maggie comes to the realization that it is time for her to move on with the personal side of her life when her widowed mother Barb starts dating a man named Rick, Emma has her first crush on a classmate named Zack, but most importantly David announces that he is imminently getting remarried. Maggie entering the dating scene is easier said than done in not having gone on a date in twenty years. Widowed PR consultant Michael Taylor, Gary's best friend Will's father, and someone Maggie considers a friend herself, suggests that they, as friends, go on practice dates together to hone their dating skills in a comfortable setting. As Maggie watches both Barb and Emma go through their dating highs and lows, she, as she goes through her own dates with men that she largely meets online, may not be able to see that Michael would like a chance to be that next man in her life in being there for her in every important aspect of life, and not just in a practice sense.
