Liz Lemon’s Love Interests on ‘30 Rock,’ Ranked

Is there any man in the world who can top Astronaut Mike Dexter?
Liz Lemon’s Love Interests on ‘30 Rock,’ Ranked

Across seven seasons of 30 Rock, Liz Lemon (Tina Fey), creator of the fictional NBC sketch show TGS, handled problems at work, problems with her family and a lot of problems in her love life. Is her body count as high as her network neighbors Jerry Seinfeld or Frasier Crane? No. But she did date a fair number of people — certainly enough for us to count them down from her worst romantic partner to her very best.

Conan O’Brien (Conan O’Brien)

We can only technically count Conan, since his entanglement with Liz occurred offscreen, before the events of the series. The most we see of their interaction comes in the Season One episode “Tracy Does Conan”: Liz has to convince Conan to re-book her new TGS star Tracy (Tracy Morgan) as a guest on Late Night, despite an earlier appearance in which a “confused” Tracy nearly stabbed Conan. Things don’t seem to have ended well between them, as Conan icily calls Liz “Elizabeth” when she asks about his wife; later, he claims that since he and Liz didn’t lose their virginity to one another, as planned, while they were together, he will never lose his. (“Didn’t Conan have children by this point?” you may be asking. The Conan in our reality did, but surely we must take this one at his word.)

Astronaut Mike Dexter (John Anderson)

Some might rank Astronaut Mike Dexter higher on this list, since he is quite literally Liz’s ideal man (meaning: he’s just an idea she had and not a real, corporeal person). And given what we learn about Liz, a figment of her imagination who only wants to kiss and discuss reality TV is a better match than a lot of flesh-and-blood dudes who pass through her life. Still, it’s impossible not to dock him points for not being real.

Brad Halster (Roger Bart) & Thad Warmald (Steve Little)

Canonically, Liz has not particularly cared about sex, which is why her interactions with both these guys are especially unsettling: “Dating” for transactional reasons is not her vibe!

Liz meets Brad in the Season Three episode “Cutbacks.” As the title suggests, TGS’ budget is at risk, but Liz thinks she might get herself a reprieve by fooling around with Brad, a consultant brought in to cut costs. It doesn’t work, on top of which Brad feels betrayed when he finds out about Liz’s ruse and reports her for sexual harassment, getting her suspended for two weeks, and setting up the absolutely legendary episode “Jacki Jormp-Jomp,” in which Liz falls in with the women of leisure in her apartment building and learns the dark secret of how they really spend their time.

We meet Thad in “Leap Day,” but he’s been well known to both Liz and Jenna (Jane Krakowski) for years before that: When they all did theater together in college, he was “Sad Thad the Skin Tag Lad,” who nursed a helpless crush on Liz. Since then, he’s become a tech billionaire, which is why Jenna wants to attend his Leap Day party, but it’s Liz who may actually benefit from his new wealth — he offers her $20 million to be his first-ever sex partner. By this point, Liz is in a relationship — more on that partner later — but even he urges her to do it. Unfortunately, she waits too long to accept his indecent proposal, and gets snaked by a cadre of supermodels. But it’s just as well — a few years after this, nothing will have been more embarrassing than having boned a tech bro.

Wesley Snipes (Michael Sheen)

An oral surgeon’s recovery room is a dangerous place to fall in love, because everyone in it is high as hell. But that didn’t stop Liz from entering one dude from her dentist’s office in her contacts as “Future Husband” — only to discover when they meet while sober that they’re both basically disgusted by one another. Still, at their age, is that reason enough to rule one another out as “settling soulmates”? Eventually, Liz decides it isn’t, but maybe only because she met a better person just in time.

Steven Black (Wayne Brady)

30 Rock has been critiqued for its portrayal of race over the years, but this storyline isn’t one that gets dinged. Liz isn’t interested in Steven, Tracy’s new business manager, because his personality is annoying and they have nothing in common, but because he is Black, she agrees to multiple dates with him rather than risk being perceived as racist. That things come to a head at The Source Awards is unlucky for Liz and any point she might be trying to make.

Gavin Volure (Steve Martin)

Gavin, a friend of Liz’s boss Jack (Alec Baldwin) seems to offer Liz everything she could want in a partner — his many phobias prevent him from leaving the house or being physically intimate; he’s very wealthy; and he’s happy to have her favorite cupcakes delivered to his estate. Except, just kidding, he’s not agoraphobic; he’s under house arrest for multiple crimes. Maybe it could have still worked if he hadn’t evaded his confinement.

Dennis Duffy (Dean Winters)

The most tenacious of Liz’s many exes, and arguably the funniest, the one-time Beeper King first ensorcelled Liz by chance when they both sneeringly agreed that The Hours should have been called The Weeks. A coarse jerk who brings out the coarse jerk in Liz, Dennis nearly hooks her again by bullying her staff and plying her with food, but always spectacularly screws up in the end; it’s hard to imagine anyone else on this list getting nabbed by To Catch A Predator and nearly pushing Liz onto subway tracks to get credit as the “hero” who rescued her.

Stewart LaGrange (Peter Dinklage)

Remember how Liz dated Steven to save face when she worries that she’ll seem racist? The same kind of thing happens in “Señor Macho Solo.” Liz, deep in a baby fever phase, tousles the hair of what she thinks is a random child on the street, only it’s not a child, it’s Stewart, an adult with dwarfism. Liz pretends she was just being romantically aggressive, and Stewart’s into it. On their date, he is fun and cool, and maybe they could have worked out if Liz could be cool; sadly, we know she cannot. 

Anders (Eion Bailey)

A breakup with a long-term boyfriend leads Liz to declare she is so done with love that she’s adopted a cat and named her Emily Dickinson. Behavior this annoying cannot possibly stand, so Jenna insists on taking Liz out to prove there are other people worthy of her attention — like Anders, an attractive stranger whose preferences and views align so exactly with Liz’s that she can’t help being suspicious. It’s almost like Astronaut Mike Dexter came to life! 

James Franco (James Franco)

Initially, Franco is set up to date Jenna on a quasi-professional level. Stories have started to circulate about his “relationship” to Kimiko, a Japanese body pillow printed with an illustration of an anime woman. But Jenna ends things when she starts to have real feelings for him, so when Liz later runs into him at a club, he’s officially single, and they’re free to go wherever the night may take them.

It’s rare for Liz to be this impulsive, or this horny, but it’s still a little difficult to enjoy this episode as much as when it first aired, now that we know about the credible sexual misconduct allegations against Franco.

Gretchen Thomas (Stephanie March)

Early in their acquaintance, Jack decides Liz needs his help with her personal life, and sets her up on a blind date with a friend of his, Thomas. What it never occurs to Liz to ask is whether “Thomas” is her date’s first name, and surprise! It’s actually Gretchen’s last name. For someone as famously sex-averse as Liz, “dating” a woman actually suits her great; however, Gretchen prefers partners who do want to fool around with her, and it doesn’t work out. (Why did Jack think Liz was queer? “Those shoes are definitely bi-curious.”) 

Gray (Peter Hermann)

“The Head and the Hair” revolves around the titular MSNBC staffers Liz and Jenna keep running into at work, and are so nicknamed since one (Brian McCann) is balding and the other (Hermann) has a great coif. Liz lets Jenna and Pete (Scott Adsit) talk her into asking out The Head, who seems like he’s in her league, but The Hair — whose real name is Gray — stops her by asking her out himself. 

Liz and Gray have great chemistry: Other men might be embarrassed when Liz makes a scene over a bodega cashier’s refusal to break her hundred-dollar bill, but Gray immediately takes her side. When Gray and Liz find out it’s possible to have too much in common with a prospective partner, it’s a shame. Hermann, who happens to be Mariska Hargitay’s real-life husband, later goes on to fulfill his destiny as a romantic lead in the sitcom Younger.

Drew Baird (Jon Hamm)

After opening a new doctor neighbor’s mail and convincing herself they’re destined to be together, Liz manufactures a meet-cute and sets up a date — only belatedly realizing she’s scheduled it for Valentine’s Day. Things with Drew go downhill from there.

Somehow, Drew and Liz push through and continue seeing each other, but this is apparently Liz’s first experience with dating a partner who is, you know, as attractive as Jon Hamm. Jack — who was treated in his handsome youth as Drew is now — urges Liz to enjoy The Bubble while she’s in it, but she tires of him before long.

In later appearances, we learn Drew may have spent his entire life skating through school on his good looks, and should have possibly been under full-time care by a qualified professional and not treating patients. 

Danny Baker (Cheyenne Jackson)

Danny starts out as a street performer who paints himself silver and poses as a robot, and gets his big break when he bravely shakes hands with a bedbug-afflicted Jack, who hires him on the spot to join the cast of TGS. Several episodes into his tenure, Liz apparently notices that he is extremely hot, and starts dating him in secret — in the process lowering his worth with Jack. Later, in an effort to convince Jenna to accept her age and take a guest shot as a teen’s dying mother on Gossip Girl, Liz lets her mustache grow in, and Danny decides he’s not that interested in her after all.

Floyd DeBarber (Jason Sudeikis)

Liz thinks she has a secret admirer when a floral bouquet is delivered to her, only to learn that Floyd, an NBC lawyer who works in the building, intended for them to go to his girlfriend, Liz Lemler (Anna Chlumsky). Liz can’t stop nursing her crush, following him into a church and pretending she, like him, is there for an AA meeting. But eventually, her persistence pays off. They don’t just get together — enjoying all the goofs she did with Dennis, without any of the toxicity — but stay together even when Floyd takes a job in Cleveland and they try dating long-distance. Ultimately, though, Floyd decides he wants something different — specifically, a much younger fitness model who doesn’t have so much bitterness about life or rules about weeknight sex.

Carol Burnett (Matt Damon)

As mentioned earlier, Carol is the exciting new man Liz meets while seeing Wesley, convincing her that it’s not time for her to settle down with a settling soulmate. An airline pilot, Carol can whisk Liz away to exciting second-tier locations for stays in commuter hotels. He’s even the partner Liz is dating when Jack helps her figure out where her lifelong issues with sex come from. But they’re not meant to be, as they learn during a delay in their flight to Nags Head. They break up, and one assumes Damon took the lessons learned from playing this doomed trip to his work on The Martian.

Warren “Grizz” Grizzwold (Grizz Chapman)

With Dot Com (Kevin Dotcom Brown), Grizz is one of the two mainstays in Tracy’s entourage, and by far the more taciturn. What he had with Liz was not exactly a relationship, but we do see them fool around at a party thrown by Kenneth (Jack McBrayer) that gets wildly out-of-hand.

Whatever else happens between Grizz and Liz offscreen, it seems to have been very healthy: He maintains the intimacy of calling her “Beth,” as no one else in her life does; he asks her to participate in his wedding to his fiancée, Feyoncé (Susan Heyward); and when TGS finally ends, we see that Liz has created a sitcom vehicle, Grizz & Hers, for him to star in.

Criss Chros (James Marsden)

Criss doesn’t seem like Liz’s kind of guy at first glance. Yes, his job operating an unlicensed hot dog stand isn’t as high-status as some of her other partners’ professions, but she does love hot dogs. Sure, she doesn’t read as someone who would enjoy having original songs sung at her, but anyone would make an exception when the song is coming out of a face that attractive. Criss supports Liz’s career ambitions, joins her in her desire to raise a family and fits perfectly into her life. Plus, he was fine with her sleeping with Thad to earn $20 million. What more could anyone ask for in a partner? After all the weirdos and duds we’ve seen her date over the years, Liz definitely earns her happy ending with Criss.

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