Jess invites Paul, a music teacher at her school on whom she always has had a crush, to the gang’s big Thanksgiving dinner at the loft, which naturally goes horribly awry.

When Jess decides to take her relationship with Paul to the next level, she consults with the guys for some sex advice. Meanwhile, Schmidt worms his way into his boss' baby shower to compete with his office female counterpart.

The gang attends Schmidt's holiday office party and Jess frets when she receives an expensive gift from Paul.

When Jess and Nick run into their exes Paul and Caroline, the gang fears they both may "backslide" into romantic relationships. Meanwhile, Schmidt desperately tries not to get aroused as he deals with a delicate medical issue, Winston suffers the consequences of a wild night out with his boss and Cece brings Schmidt to a nursing home to meet her grandmother.

After a night of partying at Bearclaw's, Jess and Cece make their way back to the loft and run into a familiar face. Meanwhile, Coach worries about bringing Nick and Winston around his sophisticated new girlfriend, May.