There is no mincing words on this one. 30 Rock's Liz Lemon had absolutely terrible taste in men. Even the good ones weren't great, though she did manage to get things right when she got together with Crisstopher Chros. But in the beginning, there was only the one-man horror show known as Dennis Duffy. Even stranger than their relationship was the fact that he turned into one of Liz's closest friends by the end of the series.
When 30 Rock started, Liz had recently broken off a long-term relationship with Dennis Duffy. Fans had yet to meet Dennis but they were hearing nothing but bad things about the guy. He finally appeared in Season 1, Episode 6 after he and Liz got back together. Not only was this the first time that fans were meeting him, but it was also the first time that Jack Donaghy met him. And he was not impressed.
Things didn't last long. By Season 1, Episode 8, Liz had dumped him yet again. The strange thing was that both Jenna Maroney and Jack had gone soft on the guy and started recommending that she get back together with him. She was considering giving Dennis a 30th chance when she saw him on a To Catch a Predator segment. This may have been the biggest red flag in the history of dating.
Over the next few seasons, Dennis continued to pop up. In one episode, she caught him trying to recreate the infamous Balloon Boy incident but with an actual kid in the weather balloon. In 30 Rock Season 5, Episodes 20 and 21, TGS with Tracy Jordan was preparing to celebrate its 100th episode when a gas leak broke out. Dennis took advantage of a gas woozy Liz and attempted to get her to sign a lease with him.
All of this seemed to indicate that Liz and Dennis were enemies but St. Patrick's Day changed the game. Dennis reappeared in 30 Rock Season 6, Episode 12 as Liz and Criss tried to hide from Liz's most hated holiday. Dennis revealed that he was now married to a woman named Megan, who was ostensibly the female equivalent of Dennis. And as hard as this is to believe, Dennis likely saved Criss and Liz's relationship in this episode.
Liz was sabotaging her relationship with Criss by being too emotionally guarded. Dennis pointed this out to Liz and helped her fix things with Criss. Even weirder is the fact that Dennis, Megan and Dennis Jr. were the ones who stepped up to help Liz pull off her dream wedding to Criss on incredibly short notice in Season 7, Episode 7. Dennis might have been the bane of Liz's existence for a long time but without him, she and Criss may never have worked out.
As a couple, Liz and Dennis were absolutely toxic. They just weren't meant to be together at all. But when they both found real relationships and moved on from each other, they managed to become friends. Dennis has been there for her during some of the biggest moments of her life. More than that, he has always believed in Liz. He just has a really terrible way of showing it sometimes.
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