While Charlie may tirelessly falter in one harebrained attempt after another at winning the love of The Waitress, and Dennis routinely employs the D-E-N-N-I-S system to much success, it’s Dee who’s had the most turbulent love life on It’s Always Sunny In Philadelphia. With Valentine’s Day here, I thought it would be fun to look back at the ups and downs — but really all downs, if we’re being honest — in the romantic escapades of Deandra Reynolds. Dee doesn’t so much date, but more drunkenly stumbles from one embarrassing lover to the next, never gaining any wisdom from the perils of her shallow and manipulative ways.
There are lessons to be learned from the dating missteps of Sweet Dee, so take from her heartache what you will. In no particular order, here’s a roster of Dee’s many suitors and the misfortune that crossing paths with her brings.
Bill Ponderosa is a man of little willpower, and when he encounters Dennis and Dee with his sister Maureen, his life quickly spirals down the shame drain. Bill might not have given Dee the time of day in high school, but putting on some extra weight has knocked him down to her league. At first, Dee is repulsed by Bill and rejects him, but she later hooks-up with Bill and convinces him to buy her a car. When we see Bill in seasons eight and nine, it’s apparent that he’s become a shell of the man he once was and is now a sex and drug-addicted deadbeat who let the most vile of all vices destroy his life: the siren’s call of Deandra Reynolds.
Despite Dennis’ convincing argument, and the revelation that Lil’ Kev has the legendary strength of a retarded person, Dee continues to see the aspiring Philly rapper. She begins to think that maybe Lil’ Kev just might be retarded after noticing his shirt’s on inside out and witnessing his manic laughter while watching cartoons. It’s understandable that Dee would have qualms with Kev upon learning this, but she goes back to him once Dennis reveals that he never rode the short bus. It’s too late, though, and Lil’ Kev calls Dee out in a rap like the “broke-ass b*tch” that she is.
Technically, Trevor was never one of Dee’s partners, but a puppet master who played her for his own amusement. While Charlie somehow convinced Ruby Taft to fall for him, Dee is merely a pawn that Trevor toys with to show his buddies what a leg-humping loser he had found.
Snyder may not have all of his teeth, but he’s got all of his skin and as Dee sees it, is the man who can help her achieve stand-up stardom. Except, he can’t because the entire thing was a sham by the guys to trick Dee into thinking she really was funny. Sleeping with Snyder was certainly a low point for Dee, and it was likely a piece of karma handed down for her romantic crimes committed against Rickety Cricket.
Right away, there is something off about Colin. He’s good-looking, charming, and generally cooler than the rest of the gang, which all translates to: too good for Dee. I would say that Colin is a master con man, but you probably don’t have to be that cunning to con Dee, and a romantic dinner and trip to the firing range is all it takes to put her under his spell. It turns out that Colin seduces female bartenders and then robs them, and being that Dee is about as easy to play as a kazoo, Colin manages to rob Paddy’s twice.
Sweet, gullible Ben. The guy serves his country fighting in Iraq and returns home to a hero’s welcome that probably rivaled the horrors of war — dating Sweet Dee. Dee lures Ben in with her online alias, Desert Rose, but abandons him when she sees that he’s in a wheelchair. It’s only after pushing Artemis on him and learning that his legs do work that Dee decides Ben is worthy of her affections. Foolishly, Ben actually sticks around with Dee longer than any other man — a testament that he’s not the smartest guy — despite being locked in a car on a hot summer’s day and watching her flirt with a carny right in front of him. Even when they do split, we learn at Charlie and Frank’s party that Dee still calls him up and harasses him until he sleeps with her. No veteran should be subjected to that kind of emotional abuse.
Dee first encounters Rex when he shows Dennis up at Frank’s modeling competition by being the fastest cockroach eater, among other things. Similar to Ben’s encounters with Dee, Rex tells Frank and Charlie that Dee occasionally calls him up and belittles him until he agrees to sleep with her. It’s a cruel and psychologically abusive practice, but it seems to yield successful results for Dee.
Poor Rickety Cricket, a once respectable man of the cloth who falls under Dee’s spell and slowly transforms into a Freddy Kruger doppelgänger. As we’ve documented before, the gang often employs Dee to use her charms on Cricket to do their bidding, whether it’ eating a turd or taking the fall for scamming the mob. It’s only in the episode “Mac’s Big Break” that Cricket realizes that Dee may just be his own personal Satan.
Trey, the high school kid
As the gang points out many times over the series, Dee was incredibly unpopular in high school due to the back brace she wore for her scoliosis, landing her the nickname, the Aluminum Monster. It’s this desire to reshape her high school memories that leads Dee to fall for underage cool guy Trey when the gang opens up Paddy’s to high school kids. It soon becomes evident that Trey is merely using Dee to make his girlfriend Tammy jealous. And while hooking up with a high school kid is certainly a low point for Dee, hooking up with Dee is an equally — if not more so — low point for Trey.
The toothless Korean busboy
Harboring a strong fear and disgust for the elderly, it’s surprising that Dee would have gone so far as to sleep with the busboy. While taking this toothless lover to bed likely had Dee crying in the shower in a desperate attempt to wash off his old man musk, I imagine sleeping with her was probably a high-point in his year.