On a sunny afternoon, clad in hiking gear, John and Cassie prepare to repel off a cliff. Through all the years Cassie’s lived in Middleton, she’s never been to this hiking spot. John remarks that the trail is just one of the many surprises he’s discovered since moving to town. John feels an unseen force guided him to a rewarding teaching job, which has also given him the time to pursue an expedition to the Maldives. But while things are looking up for John, he’s got an important deadline that threatens to derail his upcoming dig. By the end of the week, John must name a field supervisor or lose the grant. With Cassie’s help, John’s poured over dozens of resumes and settled on two candidates. Since time is not on his side, John has decided to clear his head and spend the next few days camping. He hopes that the peace and quiet will help him come to a final decision about who will accompany him on the road ahead.
Emily (Faith Ford) misses her daughter Heather (Emma Lahana), who is attending college in Boston. Since her father died, Heather is sensitive to her mom’s dependence on long-standing holiday traditions. This Christmas, Heather has planned a trip to Phoenix with her boyfriend, but tells her mother she is staying on campus to study.
When commitment-phobe Rob Marino (Joey Lawrence) breaks up with his girlfriend before Thanksgiving, he is criticized by his big Italian family about his inability to keep a relationship through the holidays. Wanting to prove them wrong and fulfill his dying grandmother’s (Paula Shaw) wish to see him happy in love, Rob goes online and finds Julie (Emily Hampshire), another single New Yorker who’s meddling Jewish mom (Marilu Henner), has driven her to seek a temporary boyfriend. Rob and Julie agree to pose as a couple through the holidays to get their families off their backs. But things get complicated when Rob’s Catholic clan and Julie’s Jewish family get involved. With Christmas coming and Hanukkah around the corner, they double their efforts to keep the charade going, only to discover their fake feelings may be a little too real.
