Fifteen year old aspiring singer/songwriter Headly Henderson and her widowed mother René Henderson, co-owner of René & Lou's Bistro, have been the focus of each other's lives since René's husband/Headly's father Michael Henderson died suddenly in a tragic accident five years ago. The two do everything together. But as Headly is getting to the age where she may want some "boy" time of her own, especially as Bodie Miller, a childhood friend, has just reentered her life and shows interest, Headly wants her mother to find some love of her own again, which René has resisted if only because Michael was the love of her life. Unable to get René signed up to a dating website without a valid credit card, Headly and her more technologically adept friend Willis decide to create their own method of online dating with men of their choosing. After they come clean to the three men Headly approaches with the carrot of an "all about René" video, they tell them that they cannot tell René that it was them who set up the date, each date to evolve out of the men being regular customers at the Bistro. Of the three men, there is connection between René and only one of them: Andrew, a widowed single father. To get to a happy ending, René and Andrew both have many obstacles to overcome such as the memories of their respective first marriages, and what it means to be back in the dating pool after their relationship experiences, especially at their stage in life. Meanwhile, Headly herself may have a bumpy road to her first real romance, with she perhaps not being able to see past Bodie's good looks for the mismatch that they are, truly to see that her first real love may have been staring her in the face for years, if she can get over the geeky persona - including a bad haircut and not stylish eyeglasses - and friendship as the on the surface characteristics.