Almost constantly beset by low self-esteem and a critical lack of decent single men her age living in Manhattan, Liz Lemon’s love life is a relatable story that’s always a great source of comedy throughout 30 Rock. It’s also a great excuse to feature some of the show’s best-ever guest stars.
On her quest to “have it all”, Liz encounters a wide variety of suitors and a mountain of incredibly awkward situations. From celebrities and millionaires to a guy so scummy that he actually appeared on To Catch a Predator while dating her, here’s our ranking of Liz’s love interests throughout all seven seasons of the show.
Dennis Duffy
Dennis Duffy is the epitome of that romantic partner that so many of us have had at some point in our lives. He’s a dirtbag, a huckster, possibly a psychopath and the perfect reflection of your own self-hatred. He’s like a demon that follows Liz Lemon around for most of the show to remind her of her own insecurities.
Dennis would actually almost feel more at home as a character on It’s Always Sunny in Philadelphia with the ludicrousness of his get-rich-quick schemes. He once describes his family heritage as being exiled from Ireland to America, exiled from America back to Ireland and then set adrift on a log.
Astronaut Mike Dexter
Astronaut Mike Dexter is a caring, compassionate and all-round perfect man who also happens to be the king of Monaco. His one minor drawback being that he isn't real but, instead, a figment of Liz’s imagination who appears in times of great need. The fact that he’s still higher on the list than Dennis Duffy, however, should give you some context for just how awful of a boyfriend Dennis is.
Liz relinquishes her fantasy over Mike Dexter after learning of the relationship between her mother and real-life astronaut Buzz Aldrin. Though Liz never gets her astronaut, she does get to share a nice moment with Buzz where they yell at the moon together.
Dr. Andrew “Drew” Baird
Dr. Drew appears, at first, to be Liz’s real-life Astronaut Mike Dexter. Not only is he Jon Hamm handsome, he’s a paediatrician who shares a number of Liz’s top interests. All of which kind of pales in comparison to looking like Jon Hamm but it’s an added bonus.
Drew’s unfortunate drawback, which is steadily realized by Liz after a number of odd situations, is that Drew is actually, literally, too good-looking. His handsomeness has resulted in no one ever telling him no, or even that he’s failed at something. The poor guy never really develops past the age of a child himself.
Wesley Snipes
A slightly more intellectually appropriate partner for Liz, Wesley Snipes is played by British actor Michael Sheen and he makes a pretty ironclad case for the name Wesley Snipes being more appropriate for a slightly-weaselly Englishman than it is for an American action movie hero.
Wesley’s major drawback is that both he and Liz find one another unbearable. But, after saving each other in their phones as “Future Wife” and "Future Husband” during a particularly wild nitrous oxide trip at the dentist’s office, the two attempt to settle for irritating stability at the expense of happiness. Liz, thankfully, finds her sense of hope and tries dating again.
James Franco
Playing himself in a moderately daring role, James Franco appears in 30 Rock due to his sham relationship with Liz’s old friend, and star, Jenna Maroney which has been orchestrated by Franco’s publicist. The relationship is designed to take the heat of bad press off of James and his relationship with his full-sized Dakimakura, or Japanese body/love pillow, who he names Kimiko.
In a moment of out-of-character adventurousness, Liz has a one-night-stand with Franco. But it’s quite clear that he would never, and probably could never, be anything more than just a beard for her – or any woman, for that matter.
Gavin Volure
Gavin is another very brief love interest of Liz’s, played by Steve Martin. He’s the owner of a successful company called Sunstream and she meets him at his vast Connecticut estate. Gavin tells Liz that he’s an agoraphobic and, as a result, can never leave his home. Something that seems hugely appealing to the somewhat sexually repressed Liz who’s in the market for a physically distant relationship at that time.
Things are not quite how they seem, however, and Gavin quickly reveals that he actually never leaves his home because he’d be arrested if he did as he’s under house arrest for a host of serious financial crimes. Finally succeeding in one of his escape attempts, he tracks Liz down and asks her to flee with him to Canada but she declines.
Stewart LaGrange
Stewart LaGrange is a diplomatic attaché at the United Nations played by Peter Dinklage. Due to his dwarfism, Liz mistakes him for a small child and tussles his hair. Whilst a hugely embarrassing mistake, it initiates a courtship between the two that’s always impeded by Liz’s patronizing instinct to view Stewart as a young child.
The two give it one last chance but, before they meet, Liz mistakes an actual child for Stewart and, after witnessing the mistake, Stewart ends the relationship on the spot. All things considered, it’s hard not to root for Stewart and think that he’s the one who can definitely do better.
Floyd DeBarber
Floyd, played by the always affable Jason Sudeikis, actually seems like a perfect fit for Liz. Not only does he stick around after Liz does a series of horrendous things to him like firing his girlfriend from her workplace and lying about being an alcoholic just to get closer to him, he’s forgiving and furthers the relationship.
Sadly, Liz has to ultimately choose between Floyd and another of her great loves - New York City. Floyd only returns to New York to get married but it’s just after his wedding that Liz meets another seemingly-perfect fit and the next entry on our list.
Carol Burnett
Played by Matt Damon, Carol is an airline pilot and a huge fan of Liz’s show. Initially, Carol’s drawback as a romantic partner seems to be the same as Floyd’s which is long distance. It’s not something that bothers Liz but Carol’s pushing for a more conventional relationship reveals their true problem.
Carol and Liz never work out because of a stand-off between the two characters that ends up with both of them taking actual hostages. It demonstrates that the pair are, in fact, too much alike. They're both too stubborn and strong-willed to ever be the one who backs down. They’re all yin and no yang.
Crisstopher “Criss” Chros
The obvious number one choice and Liz’s eventual husband. Criss is exactly the type of person who drives Liz’s boss, Jack Donaghy, mad and that only makes him seem more appealing to her. Played by James Marsden, Criss is the gentler energy to Liz’s chaotic life and a rock for her to depend on.
In a lot of ways, he’s actually kind of like a pure version of Dennis Duffy. Criss is full of harebrained, but well-intentioned, business schemes that seem doomed to failure and he’s more than willing to be a stay-at-home dad to their adopted kids, Janet and Terry.