While ol' Liz Lemon did reasonably well for herself in the world of TV, she was never quite as capable when it came to romance. The funniest parts of 30 Rock were often the ongoing comedy of errors that constituted Lemon's love life. She was well known for making some truly terrible choices in the men she dated, which included accidentally dating her own cousin once.
None of them were worse than Dennis Duffy, possibly one of the most morally bankrupt people who has ever lived. Drew Baird, on the other hand, was a handsome, good, handsome person who was incredibly stupid and handsome.
DREW BAIRD: As Handsome As He Is Stupid
What initially attracted Liz Lemon to Drew was his mail, which was being mistakenly delivered to her apartment. When she finally took his mail back to him, she was taken aback by how attractive he was.
Drew Baird was so handsome that he could have worked as an advertising executive in the 1960s. The downside to that was Drew was one of the most shockingly stupid people Liz had ever met, making it impossible for her to date him.
DENNIS DUFFY: Doesn't Go Away
Dennis had a lot of terrifyingly bad qualities, both as a boyfriend and as a human being in general. Jenna Maroney was always happy to point these flaws out though it was eventually revealed that she had also slept with Dennis.
There is just something about the guy. One of the worst things was that Dennis would never, ever go away. He was like a tick who has burrowed his way into Liz Lemon's life and simply could not be removed.
DREW BAIRD: He's A Doctor, Somehow
Possibly the most unsettling fact about Drew was that he became a doctor. Somehow, beyond all reason, Drew Baird managed to become a legitimate, licensed doctor despite the fact that he did not know anything about the human body.
The only theory that explains how Drew made it all the way through medical school was that he was a classmate of Leo Spaceman at the Ho Chi Minh School of Medicine.
DENNIS DUFFY: To Catch A Predator
After dumping Dennis early in the series, Liz found herself actually missing the dummy. Despite the fact that he was prone to doing awful, stupid, and selfish things, he knew how to get to Liz's heart.
Mostly, it was through food. But the tipping point was when Dennis appeared on To Catch a Predator and Chris Hansen busted him trying to hook up with an underage girl. Yikes.
DREW BAIRD: Worst Tennis Player Ever
One of Drew's favorite hobbies was playing tennis. In fact, he seemed to believe that he could have gone pro and was even known to give lessons. The only problem was that he was a disturbingly bad tennis player.
Drew's inability to play the game was epic. This confused Liz to no end, who called him out and absolutely destroyed him. It was a confusing moment for everyone as Liz is not exactly an elite athlete.
DENNIS DUFFY: Tried To "Balloon Boy" A Kid
In 2009, worldwide media was gripped by the story of the "Balloon Boy." A family in Colorado was developing a new mode of transportation involving a helium-filled balloon that was in no way just a blimp.
They claimed the prototype accidentally took off with their son in it, which turned out to be a hoax. Not to be outdone, Dennis tried to replicate the incident for attention with an actual child inside. Liz dodged a bullet when she broke up with Dennis.
DREW BAIRD: Lost Both Hands (In Very Stupid Ways)
When Liz Lemon went to visit Drew to find out if she had missed out on a real relationship with him, she found out he was also missing something. Specifically, he was now missing both of his hands, which had been replaced with hooks.
One was lopped off by a helicopter blade when Drew waived at someone in Africa he mistakenly believed to be his old coach. The other was lost in a separate fireworks accident. So very, very stupid.
DENNIS DUFFY: Beeper King
While Dennis and Liz were in an on-again, off-again relationship for a much longer time than anyone would deem rational, fans first met the former when he was known as the Beeper King. Why? Because Dennis sold beepers and insanely believed that technology was cyclical.
It is, of course, not. Dennis's entrepreneurial efforts with beepers were never mentioned after season one, so it's safe to assume that his store went out of business.
DREW BAIRD: The Bubble
All of Drew's strange success can be attributed to what Jack Donaghy calls "The Bubble." Essentially, Drew was so handsome that he could literally do whatever he wanted.
This included becoming a doctor without knowing anything a physician should know or teaching tennis when he was incapable of playing the game. Had he been willing to live outside The Bubble, his relationship with Liz would have stood a better chance of making it.
DENNIS DUFFY: The Gas Leak
In his ongoing quest to win the heart of Liz Lemon, Dennis actually released a dangerous gas leak into the TGS studios. This caused the cast and crew to experience hallucinations. It also caused Tracy Jordan to try and shoot Kenneth to regain his old status as a lunatic.
Dennis was taken away by the police in the end, though Liz then caused another gas leak to save her show. Maybe they were more right for each other than she realized.