- The story of a young businesswoman who tries to convince her uptight parents to accept her current boyfriend and instead finds herself falling for an old high school flame.
- Josie Mayfield, a no-nonsense businesswoman working at her father's prosperous cookware company, thinks her boyfriend Richard is the perfect man - handsome, successful and driven. The problem is that Josie's parents, Joseph and Claire, do not agree. When Josie meets up with Maxwell, an underachieving, old high school flame (who still has a crush on Josie), Richard dreams up a plan to make himself look good to Josie's parents: Maxwell will be Josie's date at Joseph and Claire's upcoming anniversary party. When Joseph and Claire see Josie with a "loser," they'll give anything to have Richard back in the picture. At least, that's the plan. Over the anniversary party weekend, Maxwell stays with Josie as a guest in the Mayfield home, horrifying Joseph and Claire with his unsophisticated ways. Though things are rough and rocky at first, Maxwell soon begins to win over Joseph and Clair and they start to appreciate his carefree and spontaneous lifestyle. Maxwell's presence even helps Josie's insecure younger sister Mindy finally stand up for herself and inspires Josie's grandfather (Conway) to pleasantly shock everyone by revealing a big secret. As Maxwell's visit loosens up the previously stiff and uptight Mayfield family, Josie starts to fall for him and realizes she hasn't been living her life for herself. When Richard shows up at the house, Josie must decide which direction her life - romantic and otherwise - is going to take.—The Hallmark Channel
- Gridley, the high school flame of Sophie; the elder daughter of the "Mayfields" the business family, springs a surprise on the Mayfield family. Gridley is on a mission to correct Sophie's perfectionist parents' opinion on Sophie's boyfriend Richard. Gridley shows how his genuineness transforms the Mayfield family.—Thejus Joseph Jose
- Josie Mayfield is a driven second generation executive at Mayfields, a successful kitchenware company founded by her father Joseph Mayfield thirty-eight years ago - he still the company president - and inspired by the immaculate kitchen of Joseph's wife/Josie's mother, Claire Mayfield. Astuteness in the kitchen is one trait of her mother's that Josie did not inherit. Joseph and Claire struggled financially before the company became a quick success. Everything they now do is solely to put forward a face of success and perfection. Of the men Josie has dated over the course of her adult life, none, including the current, Richard Wright, has been good enough in the eyes of her parents, despite most being carbon copies of Joseph and male versions of the professional side of Josie. Another knock they have against Richard, a corporate headhunter, is that he always seems to be making a pitch. As such, Joseph and Claire would prefer that Josie not bring Richard to their upcoming fortieth wedding anniversary party, which, fulfilling Claire's dream, will be featured in the Chronicle newspaper's Homes section. Knowing that Joseph and Claire do not approve of him as Josie's boyfriend, Richard comes up with a plan to raise his cachet in their eyes: Josie should take someone clearly inferior to him to the party, he posing as her boyfriend. The perfect person in Richard's eyes is Maxwell Gridley, an old friend of Josie's from high school with who she has just reconnected after not seeing since high school. Joseph and Claire have known and disliked Gridley since he was Josie's high school prom date. Gridley, a free spirit, has by choice moved from place to place every six months doing what has moved him, the current six months house-sitting for a mutual friend while he creates and sells driftwood art in the park. Good-hearted Gridley is happy enough to do this favor for his friend Josie. Beyond some mishaps at the Mayfields' house, Gridley does have the intended affect by being his sheer self. But Gridley's presence brings close to the surface other buried issues within the Mayfield family including: Josie's younger sister, Mindy, having difficulties in finding her place within the family and within life; and the reasons behind Claire's father's early onset dementia, which has rendered him speechless now for two years. Gridley's generally good heart may have some effect in bringing to light these and other issues the source of unhappiness, he hoping that heart being something that Josie can see and want as he starts to fall for her.—Huggo
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