Douglas agrees to babysit the kids on Valentine's Day, but when Graham finds himself in a Valentine's Day emergency and Big Red shows up unannounced, Douglas and Big Red band together to help Graham. Meanwhile, Will and Miggy celebrate "Palentine's Day" together - a day honoring the love of two friends - but when they run into Angie at her second job, they help her finish her deliveries so she can be with Owen on Valentine's Day.

In a magical encounter at the Bachelor mansion, Chris Harrison bestows his wisdom on a frustrated Poppy and Angie, attempting to restore their faith in love and happy endings. Meanwhile, Will saves one of the kids at school from playground injury; and Douglas insists Will capitalize on the glow from this heroic act by getting as much attention from women as possible within its 24-hour window.

Angie is sent into a tailspin when her long-absent ex-boyfriend Derek, Graham's father, suddenly appears on her doorstep. She asks Will and Miggy for help because, despite his faults, she can't resist Derek. Meanwhile, Douglas and Poppy try for a romantic second date.