'30 Rock': Liz Lemon's Most Disastrous Relationships

In August, all seven seasons of the NBC comedy 30 Rock returned to Netflix. The show offers viewers a look behind the scenes of a flailing sketch show, TGS, and the lives of its writers. At the center of it all is the showrunner, Liz Lemon (Tina Fey). Liz’s love life — or lack thereof — is a frequent source of humor throughout the series. Here are some of her messiest attempts at finding love.

Dennis Duffy, played by Dean Winters

Dennis Duffy is the ex who Liz can’t shake. Liz gets back together with him early in 30 Rock‘s first season, but they break up after three episodes. Despite this, he makes appearances on the show through the fifth season. He comes back every time she tries to throw him out of her life, at one point even trying to claim squatter’s rights in her home. 

Dennis is always crude, often ludicrous, and sometimes downright dangerous — he tries to throw Liz in front of a train to be hailed as the “Subway Hero.” While she holds some fond, food-based memories of him, he’s mostly a nuisance in her life.

Dr. Drew Baird, played by Jon Hamm

Dr. Drew appears to be Liz’s dream man. He’s a handsome pediatrician who shares nearly all of her interests. Even better, he takes her back after she admits to going through his mail and lying about losing her dog. It all works out, even though Liz was “making assumptions about him based on [his stolen mail],” as Fey told EW.

When they begin dating, though, Liz realizes that Drew might be too good-looking. He’s not actually good at anything; people just treat him differently because of his looks. She tries to look past it, but this becomes impossible. At one point, Liz is choking, and he tries to shake it loose or push it further down, knowing nothing about the Heimlich maneuver (he’s a doctor).

Wesley Snipes, played by Michael Sheen

The other Wesley Snipes, that is. Wesley is another in a line of 30 Rock characters who share a name with a more famous counterpart. After an addling experience on nitrous oxide, Liz wakes up with Wesley’s phone number saved as “Future Husband.” When the two meet up, however, they can’t stand one another. 

Though they attempt to make things work, it’s clear that they have nothing in common. Wesley wants them to settle and marry each other so that neither ends up alone. While Liz considers it, she snaps to her senses, realizing she cannot spend the rest of her life with this man.

Gavin Volure, played by Steve Martin

Though not technically a boyfriend, Liz is drawn to the reclusive Gavin Volure. Due to his agoraphobia, the wealthy Gavin does not leave his home. This trait appeals to Liz, who would prefer a more distant relationship.

As it turns out, however, he’s not entirely truthful with her. Gavin is under house arrest for tax fraud and arson. He manages to escape and tries to convince her to flee to Canada with him, which she refuses.

Carol Burnett, played by Matt Damon

For much of their relationship on 30 Rock‘s fifth season, Liz and Carol get along well. They bond over the fact that his favorite show is TGS and their personalities are incredibly similar. The only problem is that his schedule as a pilot means they see each other infrequently, but Liz prefers this informality. 

When Carol pushes for them to spend more time together, the relationship shows its deep cracks. After a plane Carol is flying stays grounded for hours, Liz leads a passenger protest against him. The interaction grows so heated that both take hostages, and Carol pulls a gun, invoking Sky Law. 

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