High school sweethearts Maddie and Nate reconnect when Nate returns to their hometown to lecture at the hospital. Still hurt from their breakup, Maddie tries to avoid him. However, they eventually form a friendship, and Nate helps her as she secures funding to expand her cupcake shop. Just as Maddie and Nate rekindle their romance, Nate learns that a career opportunity awaits him in Boston. Devastated, Maddie returns the promise ring he gave her long ago and prepares for the grand reopening of her shop. Nate soon realizes how much he left behind, and must decide if his future lies in Boston with work or in his hometown with Maddie.
Looking for a fresh start, Robin, a recently divorced mother moves to a small town with her daughter, Sophie where she has purchased a fixer-upper. Needing help with the renovations on her new home, she hires a handyman, Henry her meddling guardian angel, who helps her with so much more.
Flower shop owner Poppy (Whelan), enters the annual holiday floral show for a chance to win the grand prize but standing in her way of victory is Garrett (Fisher), the underappreciated protégé of florist extraordinaire, Blair (Zuniga). While Poppy and Garrett’s rivalry heats up on the flower show floor, an undeniable romance begins amidst a whimsical holiday backdrop.