It's been almost twenty years since Claire met her ex in high school, and now she finds herself thrust into the dating world for the first time as an adult, armed with little more than confusion and lack of experience. Not only is Ron the only man she's ever been with, she's also coping with the loss of her fertility, and if she goes on one more hideous blind date – possibly her mind.
Determined to avoid both online dating and meetup groups, she endures fix-ups with all sorts of memorable characters, such as weepy Pete, the drunk skunk, the cheap hot-dog eater, and let's not forget - the unholy speed dater.
As Claire becomes more depressed over her plight, her best friend Jane prompts her to redirect her maternal longings by adopting an adorable wiener dog puppy. Dixie is not a human baby, but hopefully she will provide her new Mommy with a diversion from the parade of loony men marching through her lonely nights – that's if Mommy's house and sanity survive the destructive cyclone that is an untrained three-pound ball of craziness!
Unfortunately, while Claire is trying to move on, Ron is trying to pull her back into the past, and his life. Determined to win back his wife's affections, he offers to help Claire with home repairs as he tries to implement 'Operation Friends' in an effort to persuade his wife into giving him another chance. However, Ron is struggling with his own adjustment to single life, and isn't finding it easy to ditch the Amazon woman, or his new 'mail order bride' dating site hobby, no matter how much he has convinced himself that he and Claire belong together.