Jack’s interest in a new social networking site unexpectedly reconnects him with a high school crush. Kenneth tries to organize a Secret Santa Fun Swap, but not without resistance from some of the staff members. Meanwhile, Liz battles the task of buying a gift that’s good enough for Jack, and Jenna is horrified at the prospect of sharing her annual Christmas solo.

Hoping to boost staffers' spirits, Liz takes TGS on the road, but Jack takes over for his own reasons, and the staff find reasons to blame Liz for all that's wrong in their lives.

Liz Lemon starts making an effort to date by attending singles events with Jenna Maroney, and Jack Donaghy feels forced to choose between childhood love, Nancy Donovan and news anchor Avery Jessup. Meanwhile, a racist comment sparks an office-wide debate on affirmative action and leaves Toofer with a big decision to make regarding his future at TGS.

Jack becomes even more entangled in his love triangle between Avery Jessup and Nancy Donovan, and he turns for advice to Liz, who is focusing on her own romantic problems. When Liz can't find a date to Floyd's wedding, she revisits her old boyfriends in hope that a spark will reignite. Meanwhile, Tracy continues his journey to earn his egot.

Liz questions fate when she meets the man of her dreams, while Jack's love triangle between high school love, Nancy Donovan, and CNBC anchor, Avery Jessup, comes to a head. Meanwhile, Jenna's boyfriend is confronted with a similar dilemma when his desire for another woman threatens to ruin their relationship, and Kenneth, with the help of Tracy, tries to avoid a promotion that would land him in LA.

Liz has trouble adjusting to being a stay-at-home mother. Jack takes stock of his life, and Tracy struggles to get on without Kenneth.