Single mom Jami Rhodes "wins" a romantic getaway with her ideal match. Only the contest is a publicity sham to launch her friend Sierra's Internet matchmaking service, CupidKey, and the "match" is Sierra's brother-in-law, Grant Carrington. Miffed for being railroaded, Jami drags along her mischievous little boy, Toby. As if Toby isn't enough trouble, Grant gets stuck with the infamous Carrington Cupid charm. A clash of wills ensues, proving love sometimes needs a bit of magic.