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.

In searching for tuxedo shoes for her disastrous date Wesley (returning guest star Michael Sheen) in preparation for Cerie‘s wedding, Liz Lemon found another potential soulmate - this time, in the form of the dashing pilot Carol (played by the consummate Matt Damon). As she confesses her faith in Carol as her one true lover to Wesley in order to end their tenuous relationship for good, Liz reveals a couple of less than satisfactory secrets about herself. In overhearing this, Carol is shocked and leaves at first, but returns to find Liz at the set of TGS (where Grizz and Feyonce‘s wedding is taking place) and offers to give their relationship a shot.
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