While the characters on 30 Rock were often preoccupied with keeping their ridiculous sketch comedy show going, the show would occasionally allow them to look for love. As in many television comedies, a lot of love interests popped up throughout the series, but only a few that stuck around long enough to develop a real relationship.
Most of the characters on 30 Rock seem like they would be terrible to live with, but despite that, there have been a few relationships that have worked. On the other hand, there have also been a few failed relationships that never should have gotten off the ground.
Best: Liz And Floyd
Liz Lemon has probably had the worst luck on the show when it comes to love. She is constantly either getting stuck in a relationship with a terrible person, or finding the right guy at the wrong time. The latter was originally true with Floyd, who was married when he met Liz. While that relationship fell apart, Floyd and Liz eventually came together to make an adorable couple.
He was sweet and understood her quirks while also forming a strong bond with Jack, which cannot be said of most of Liz’s boyfriends. In the end, long distance ended things, but it was fun while it lasted.
Worst: Jack And Phoebe
Despite Jack Donaghy’s apparent professionalism and intelligence, he does make bad relationship choices. One of his earliest ill-advised romances was a whirlwind courtship with Phoebe.
Jack met Phoebe while on the rebound from another relationship. In his damaged state, he proposed to her almost immediately. They quickly realized they have nothing in common, and her Avian Bone Syndrome makes it almost impossible for Jack to embrace her. To add to that, it is revealed that she is a gold digger and the whole affair gives Jack a heart attack. Certainly not a very successful romance.
Best: Jenna and Paul
It’s hard to imagine a person who could deal with being Jenna Marony’s partner. Then again, it’s hard to imagine there is someone like Paul in the world. The fact that Paul is a drag impersonator of Jenna probably helps to explain the relationship a lot, since it lets Jenna fulfill her dream of dating herself.
It’s very lucky these two found each other ,as they seem like the only two people who share the same fantasies. This mutual bizarreness helped them form a strong and loving relationship.
Worst: Kenneth And Hazel
Kenneth is not a character who has much experience with romance, nor does he seem overly interested in pursuing it. His only real dalliance with a relationship comes when it is forced upon him from the new NBC page, Hazel Wassername.
Hazel worms her way in with the TGS crew. She forms an unhealthy obsession with Liz, tries to kill Jenna and tricks Kenneth into a relationship. Poor naïve Kenneth doesn’t realize he’s being duped even after she leaves him, but he’s certainly better off being alone than with her.
Best: Liz And Chris
After dating a lot of stinkers, Liz finally found her perfect guy in Chris and settled down with him. Part of Chris’ charm is that his life seems to be as big a mess as Liz’s, but he doesn’t let it bother him.
In this relationship, we finally see Liz becoming comfortable with romance and being happy with another person. This leads to Liz and Chris eventually marrying and adopting two kids together, giving Liz the happy ending she deserves.
Worst: Liz And Duffy
Duffy is the first boyfriend we see Liz have in the show, and he is by far the worst. It’s hard to say how these two decided they would be a good match and what kept them together. By Liz’s own admission, all her best memories with Duffy are food related.
Liz and Duffy breakup early in the series, but he still manages to crop up in her life again and again. He even almost convinces her to take him back, before she finds out he was featured on To Catch a Predator.
Best: Jack And Nancy
Jack is a man of class and style, always willing to flaunt his enormous wealth. When it comes to his relationship with Nancy Donovan, however, he lets his guard down and embraces a little of his poor upbringing.
Nancy was Jack’s high school crush, who rekindles things with Jack when her marriage hits a rocky patch. The complication of her marriage means the two put their romance on hold, and when they finally come together, Nancy insists Jack stay with Avery instead. Sadly, it was not meant to be.
Worst: Jack And Diane
Jack, like many rich businessmen, has a penchant for dating women far young than himself. When he began showing chemistry with Diane Jessup, it was refreshing to see him with someone his own age. Unfortunately, it was still very uncomfortable, seeing as she was his wife’s mother.
While the two did seem to be a good match and Avery did eventually leave Jack for another man, there’s no getting around how disturbing that relationship is. Sometimes good chemistry isn’t a good enough reason for a relationship.
Best: Tracy And Angie
Though he has heavy competition, Tracy Jordan is probably the show’s most off-the-wall character. His free-spirited hijinks, his oblivious nature and his unpredictability means that he needs a very strong partner to keep him in check.
Luckily for Tracy, he has Angie, who is the stability that he lacks in every other aspect of his life. While she sometimes has to be more of a manager than a wife to him, they do love each other deeply. Despite the persona Tracy presents, he remains completely faithful to Angie.
Worst: Liz And Wesley
You know those romantic comedies where two people meet by happenstance and form an instant connection? The relationship between Liz Lemon and Wesley Snipes (his actual name) is the realistic version of that.
After their cute meeting, Liz and Wesley quickly find they have nothing in common and actually genuinely dislike each other. As the universe keeps pushing them back together, they keep trying to make it work and end up hating each other even more. To each their own, but we believe hatred isn’t a good quality in a romantic relationship (funnily enough).
