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Every Star Who Played Liz Lemon's Boyfriend on 30 Rock
Tina Fey's 30 Rock heroine had her share of dating misadventures. Behold, the hilarious actors (and one former NBC late night host) who guest-starred as Lemon's hot dates.
On any given episode of the seven-season comedy 30 Rock, Liz Lemon (Tina Fey) was deeply consumed by her demanding job as head writer for TGS, the series' Saturday Night Live-esque sketch show. Managing the demands of her staff, the needy stars of TGS (Tracy Morgan and Jane Krakwoski), and her highly-involved boss, Jack Donaghy (Alec Baldwin) didn't leave a ton of time for dating.
Occasionally, Lemon did find love—or, more often, a brief spark or two before a prospective match flamed out.
There was that time she clicked with a man that she considered too handsome (played by Mariska Hargitay's real-life husband, Peter Hermann), who turned out to be her cousin. Then there was Lemon's attempted romance with Wesley Snipes—no, not that one—who she connected with as the two were coming down from anesthesia at the dentist's office. And don't forget about Jamie (Val Emmich), the much younger guy whose preference for a 17-years-older woman becomes clear when Lemon meets his mom.
It's enough to drive anyone to make up their own fictional boyfriend named Astronaut Mike Dexter, as Lemon herself totally did. Luckily for 30 Rock fans, Liz Lemon's boyfriends, love interests, and eventual husband were played by an array of exciting (and handsome) celebrity guest stars.
Here's 9 stars who played Liz Lemon's boyfriend on 30 Rock, in order of appearance.
Dean Winters as Dennis Duffy
Dennis was Liz Lemon's on-again, off-again boyfriend, a loudmouthed beeper salesman who gained local fame as the "Subway Hero" after saving someone on the train tracks. He was played by Dean Winters, who also recurred as Detective Brian Cassidy on Law and Order: Special Victims Unit from 1999-2019.
Conan O'Brien as himself
As established in Season 1, Lemon dated Conan O'Brien for a year sometime prior to when we meet her on 30 Rock. O'Brien was the Host of NBC's Late Night with Conan O'Brien at the time (both on the show and in real life), and their brief interactions make it clear things didn't end well when O'Brien broke things off.
Jason Sudeikis as Floyd DeBarber
Lemon met lawyer Floyd DeBarber, who also worked in 30 Rock, through a name mix-up (flowers meant for his girlfriend, Liz Lemler, were delivered to Lemon). He seems perfect for Lemon, which makes it crushing when he moves to Cleveland for a job—and devastating again when he moves back to marry another woman in Season 4. DeBarber was portrayed by Fey's fellow SNL alum and Ted Lasso star Jason Sudeikis.
Peter Dinklage as Stewart LaGrange
Sadly, we only met Stewart Lagrange, played by Game of Thrones' Peter Dinklage, in one Season 3 episode. Lemon meets LeGrange, who works at the U.N., in a very awkward interaction. She asked him out to smooth things over, but things fell apart after just two dates.
Steve Martin as Gavin Volure
Fitting that Steve Martin made an appearance on a show that's based on SNL, given that the only person who's hosted that show more than he has (16 times) is 30 Rock star Alec Baldwin (17 times). In Season 3, Martin played Gavin Volure, a billionaire who never leaves his house due to his agoraphobia. He asks Lemon out and she's fascinated by his homey lifestyle—but then she learns he's actually under house arrest for tax evasion and arson. Awkward!
Jon Hamm as Dr. Drew Baird
Jon Hamm was very funny as Dr. Drew Baird, the handsome-yet-dim doctor who lives in Lemon's building. The Season 3 episode in which he and Lemon briefly date introduces the concept of "The Bubble," a skewed experience of life that only extremely attractive people like Baird have. Lemon can't deal with Baird's bubble and they break up. She bumps into him again in Season 4, to learn that he's lost both his hands in unrelated accidents.
Michael Sheen as Wesley Snipes
When Lemon finds an entry titled "Future Husband" in her phone, she learns that she and a man named Wesley Snipes (Welsh actor Michael Sheen) connected while under anesthesia from oral surgery. The two soon find that their sober selves can't stand each other, but they keep trying to make it work—even getting engaged at one point—and they're "settling sweethearts"...until Lemon meets Carol.
Matt Damon as Carol Burnett
Carol the pilot (or, "doorman to the sky") walks into Lemon's life by walking into Wesley Snipes' office, where he's trying to file a workman's comp claim. It turns out that Carol's a huge TGS fan, and the two date from the end of Season 4 through part of Season 5, when they realize they're way too alike. We'll always love Carol for introducing the concept of "sky law."
James Marsden as Crisstopher Chros
Liz Lemon got a happy ending in the final season: Underemployed hot dog vendor Criss Chros (James Marsden) became her husband, and father to their two adopted kids.