Liz schedules a root canal to avoid feeling lonely on Valentine's Day; Jack woos an attractive and successful TV host; Jenna's stalker loses interest.

Liz searches for a man she met in her dentist's waiting room. Jack fears for the future when he learns a cable company may have its sights on NBC. Jenna helps Tracy try to get a Tony award.

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.

Liz Lemon meets her mother's old flame, while Jack Donaghy's mother, Colleen, gets tangled in his relationships with Avery Jessup and high school love, Nancy Donovan. Jenna's mother, Verna returns, while Tracy learns a lesson from his "mom".

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 uses her newfound confidence to solve Pete's problem with a difficult editor (Paul Giamatti); Jack tries to cheat mortality; Tracy vows to be present when his wife gives birth.

Avery Jessup becomes suspicious of the relationship her fiancé Jack Donaghy has with his employee and friend Liz Lemon, so she orders Jack to set boundaries in their friendship. This proves a problem for Liz when her father, Dick Lemon arrives in town on a break from his marriage. Meanwhile, actor Tracy Jordan is upset when he discovers that his pre-recorded NBC obituary shows him to have done nothing worthwhile in his life, whilst Jenna Maroney learns of the video obituaries, she decides to make a video of her own.

Liz and Avery try to persuade Jack to disclose two secrets he's been hiding from his mother, who visits for the holidays. Then, Liz tries to repair Jenna's relationship with Paul; and Tracy tries to block his film's release because it undermines his newly invented serious persona.

As Jack tries to cozy up to the owner of Kabletown, Liz fakes being pregnant to help Avery gain advantage over a competitive colleague. Elsewhere, Tracy and Jenna clash when trying to share a gift from their new bosses.

Jack and a very pregnant Avery take a romantic break in Canada. When Avery goes into labor, the power couple desperately scramble to not give birth to a Canadian. Meanwhile, Liz's getaway with Carol gets grounded, literally, when their plane collects dust on the tarmac. And Tracy is an EGOT winner, but with that comes overwhelming demands.

Liz tries to turn her personal life from drab to fab by revamping her dream apartment. Meanwhile, Avery is held hostage, and Tracy discovers that Kenneth, Dot Com and Grizz have forged a solid bond while he was away.

Avery finally returns home from her kidnapping ordeal in North Korea, yet Jack grows uncertain of her fidelity while she was away. Elsewhere, Criss is crossed due to Liz's role as top wage earner, and Jenna seeks a sponsor for her approaching nuptials.

Determined to prove his marriage has survived Avery's kidnapping unscathed, Jack asks Liz to officiate their vow renewal. Meanwhile, Criss (Marsden) tries to convince Liz that he's worth sticking around for. Tracy meets with Cornel West to discuss his influence as a black celebrity.