The following characters have (at some point during the show) been boyfriends of Liz.
Dennis Duffy (Dean Winters) was Liz's boyfriend for three episodes during the early part of the show's first season; he has also made appearances in each subsequent season. He is generally disliked by most of the characters (notably Jenna, and even Liz). Dennis claims to be the love of Liz's life (which she disputes). The few good memories she has of him are mostly food-related, but she admits he makes her laugh. His nickname for her is "Dummy."
Dennis is immature for a man his age, often exclaiming like a teenage boy. In one episode he sits on Liz's bed, playing Halo 3; then, he throws the controller down and yells that the controller is "defective" because "that grenade was right next to him!" He was the last remaining beeper salesman in New York City, and was known as the "Beeper King" (after the original Beeper King committed suicide). In the episode "100", it is revealed that his ancestors were kicked out of Ireland, then kicked out of America, sent back to Ireland, then sent adrift on a raft.
Floyd DeBarber (Jason Sudeikis) is an attorney working at 30 Rock. His name is a play on Floyd the Barber, a regular character on The Andy Griffith Show. Floyd's first appearance is when he accidentally sends flowers to Liz for Valentine's Day, which he actually intended to send to his girlfriend, Liz Lemler. Liz, who doesn't know his name, calls him "flower guy" and develops a crush on him. In "The Fighting Irish," Liz fires Liz Lemler and the rest of the accounting staff so that she can get closer to Floyd, with his girlfriend out of the building; however, Jack rehires the accountants and transfers Liz Lemler to a job at GE headquarters in Connecticut, thus breaking up Liz Lemler and Floyd. In "Fireworks," Liz follows Floyd to an AA meeting in order to get close to him and discovers that rules are important to him. When Liz lies about being an alcoholic so Floyd will confide in her, she discovers that members of the same AA group cannot date; therefore, she confesses she was never an alcoholic and merely had a crush on him. Floyd feels betrayed, but Liz makes it up to him by confiding in him and the two then begin dating. Jack becomes good friends with Floyd, calling him "the Floydster," much to Liz's dismay. Floyd eventually seems to want to spend more time with Jack than Liz. At the end of season one, Floyd decides that New York City is too much for him and decides to return to his hometown, Cleveland. Liz and Floyd go there on vacation; Floyd gets a job in Cleveland, and Liz returns to TGS in New York. Despite seeming perfect for each other, Floyd and Liz break up.
Dr. Drew Baird (Jon Hamm) is a pediatrician and Liz's neighbor. He first appears in season three, when Liz accidentally receives his mail. Reading it, she decides he is perfect for her and creates a false persona so he will like her. Liz's scheme unravels, and Drew is disappointed in her; however, he reads her mail and tells her he feels Liz would have been someone he would have wanted to know. Eventually, they agree upon a fresh start. He is recently divorced from Mandy and has one daughter from the marriage (Bethany, a rebellious teenager who drinks wine and starts fires). Liz and Drew's first date was on Valentine's Day 2009, during which Bethany ended up at Liz's apartment and Drew's mother died in the hospital. On her deathbed she told Liz that she was not Drew's mother; the person Drew thinks is his sister is, in fact, his mother. Liz reveals this to Drew later in the episode. In episode 15 of season three ("The Bubble"), Liz is concerned about Drew's behavior; handsome, he unintentionally manipulates the people around him. Liz tells him that this is "living in the bubble", asserting that this is not how normal people are treated. When Liz defeats him at tennis he is a "sore loser"; eventually he apologizes for his behavior, asking Liz if she wants to take a ride with him on his new motorcycle. Liz declines, as Drew careens incompetently down the street. Drew later reappears in a cameo in season five episode Live Show, having lost both his hands (one in a New Year's firework explosion and the other in a helicopter accident) Drew is portrayed as ignorant, lacking knowledge of the Heimlich Maneuver (although he is a doctor).
Wesley Snipes (Michael Sheen) met Liz in her oral surgeon's recovery room after her root canal, but does not remember the encounter; Liz discovers him on her phone, listed in her contacts as "Future Husband." After a few dates, Liz and Wesley realize they do not belong together. When talking, Wesley often uses misleading Britishisms which Liz recognizes as fake. He is displeased that the actor Wesley Snipes has his name, saying he (British Wesley) personifies the name better as a pasty, un-athletic British man. Wesley is rude to Liz, mocking her romantic history; he tries to leverage her desperation at being alone into helping him deal with his professional (and immigration) problems. He believes they are "settling soul mates" and sets the stage for another meeting during "sweeps" (alluding to the season finale), which he claims is the British version of spring cleaning. In the season-four finale Liz meets a pilot, Carol (Matt Damon), who seems to be her actual soul mate; she breaks up with Wesley.
Steven Black (Wayne Brady) was Tracy's manager during season one. He briefly dated Liz during "The Source Awards", but Liz realized that they were incompatible after one date. When she attempted to break things off, Steven claimed that she was racist. Liz continued to date Steven, hoping he would see their incompatibility for himself. At the Source Awards Liz accidentally fired Tracy Jordan's gun, hitting Steven in the upper thigh while he was trying to get his phone out of her purse. This brought their relationship to an end. Wayne Brady himself has been mentioned on the show, most notably in the season-one episode "Jack Meets Dennis" in which Liz remarks that Tracy stole a People's Choice Award from him).
Carol Burnett (Matt Damon) is a pilot who begins a relationship with Liz in the season four finale. His surname, identical to the comedienne's, is revealed by Kenneth in "Chain Reaction of Mental Anguish". In season five they differ about the seriousness of their relationship; Liz likes how casual they are (with Carol gone on flights most of the time), but Carol wants them to commit to one another. Despite this difference of opinion, they have similar quirks and character traits. This becomes a problem in "Double-Edged Sword", when Liz and Carol break up after a heated, public argument in a plane delayed on the tarmac.
Criss Chros (James Marsden) is an unemployed entrepreneur, and like Dot Com, attended Wesleyan University.
Astronaut Mike Dexter
Astronaut Mike Dexter (John Anderson) is Liz's fantasy boyfriend, to whom she compares all other men. She mentions him in several episodes, and he shows up in her fantasies in season four. In "Dealbreakers Talk Show #0001" he tells her he has to go back to space, but "enjoyed the kissing followed by his genuine interest in that TV dance competition". In "The Moms", Liz reveals that Astronaut Mike Dexter is also (secretly) king of Monaco. Liz meets a man named Mike (an attorney), who looks exactly like Astronaut Mike Dexter at Floyd's wedding in "Emanuelle Goes to Dinosaur Land"; this Mike describes himself as a "plushie" who enjoys having sex ("yiffing") with people in mascot costumes at state parks. Astronaut Mike Dexter also appears (although not by that name) in Jack's "porn for women" (featuring handsome men asking women about their day) in "Don Geiss, America and Hope" (which Liz buys).