When thinking of television’s greatest romances, It’s Always Sunny in Philadelphia is not a show that would immediately come to mind. The series about the group of deranged friends who own a Philadelphia bar is more interested in exploring hate than love. The main characters in the show, while hilarious, are very unlikeable people so it’s hard to imagine that they would even find love.
But while romance is not usually seen in the series, it does have some compelling relationships. Some of these relationships work mostly due to how outrageous they are, while others are just too much to handle. Here are some of the relationships in It’s Always Sunny that fans have gotten behind and some they rejected.
Accepted: Frank And Artemis
Frank Reynolds is an incredibly disgusting human being. As the series goes on, he just seems to sink deeper into depravity. It’s off-putting to imagine him with anyone but he did seem to find a soulmate of sorts with Artemis.
Artemis is Dee’s uninhabited and dramatic friend who, like Frank, is capable of some truly gross stuff. Seeing these two together was not what you would call pleasant, but they do make a compatible match and a thriving sex life together.
Rejected: Frank And Gail
At a certain point in the series, Frank just decides to fully embrace his insanity. He realizes he isn’t getting any younger, so he sets out to get “real weird” with his remaining years. He quickly achieves that with this horrific romance with Gail the Snail.
Gail is Dennis and Dee’s grotesque and annoying cousin, which makes Frank her former uncle by marriage. If that isn’t enough to explain what’s wrong with this relationship, Gail is a disgusting human being herself. Their entire relationship will make you sick.
Accepted: Dennis And Jackie Dernardo
Though he sees himself as a seductive and attractive ladies’ man, Dennis Reynolds has revealed himself to be a complete psychopath. From his crazy temper to his disturbing system for luring women, Dennis is not someone capable of a healthy relationship. However, when it comes to Jackie Denardo, Dennis is surprisingly vulnerable.
Jackie is the local weather newscaster who Dennis becomes infatuated with. In person, she seems as thoughtless as most people on the show, but Dennis is just not himself around her. His confidence disappears and he becomes an awkward fool which is a good change for him.
Rejected: Dennis And Maureen
As Dennis the final step to the D.E.N.N.I.S. System proves, Dennis is not interested in a long-term relationship. So when he decides to marry Maureen Ponderosa, it’s clear that the whole thing is heading for disaster.
Maureen was a former high school girlfriend of Dennis and he finds himself oddly drawn back to her time and time again. But each time, Dennis quickly remembers her annoying quirks, off-putting habits and strange obsession with cats. Though it’s funny to watch Dennis making the same mistake over and over, it’s just uncomfortable seeing them together.
Accepted: Dee And Ben
Even though she is the only female of the Paddy’s Pub gang, Dee is as manipulative and selfish with her relationship as the guys are. That is most certainly the case with her sometimes-boyfriend Ben.
Ben is one of the few nice people who have appeared on the show. He is a kind-hearted army veteran and Dee walks all over him. While that might seem like a hard relationship to cheer for, the fact that Ben always ends up fine and Dee gets what’s coming to her makes it one of the more satisfying relationships on the show.
Rejected: Dee And Cricket
No character on the show has had a bigger fall from grace than Matthew “Rickety Cricket” Mara. He was introduced on the show as a well-respected priest and is now a drug-addicted, heavily-scarred degenerate living on the street. And it is pretty much all because of Dee.
Cricket was in love with Dee when they were younger but she was only interested in manipulating him. As adults, Dee continues to toy with his emotions and each time he slides deeper into a pit of disgust. Every time we see Dee show him even a little warmth, we know something bad is coming for poor Cricket.
Accepted: Charlie And The Waitress
Charlie’s romance with the Waitress is the longest romance seen on the show. Of course, for most of the series, the relationship has consisted of Charlie stalking her. For the most part, she wants nothing to do with him which is very understandable, yet their relationship just won’t seem to die.
Part of what makes the relationship easy to cheer for despite Charlie’s creepiness about it is that he seems to genuinely care for her. The Waitress has a lot of issues and Charlie looks past that and remains devoted to her, eventually getting together with her, albeit briefly.
Rejected: Dennis And The Waitress
The sad reality for Charlie is that the one woman he is always obsessed with is also obsessed with Dennis. When Charlie tells everyone that he has cancer, the Waitress sleeps with Dennis to comfort him instead of Charlie. It’s that heartbreaking betrayal that makes this relationship so hard to watch.
Just as the Waitress has no interest in Charlie, Dennis is completely annoyed with the Waitress. No matter how mean and disrespectful Dennis, she still jumps at the chance to be with him and it never happens. Her desperation makes her dismissal of Charlie all the more hurtful.
Accepted: Mac And Dennis
At this point, we can accept that the relationship between Mac and Dennis has evolved beyond friendship. Though they were best buddies for a long time, over the years we have seen Mac develop a more intimate aspect of his relationship with Dennis. Although Dennis isn’t interested, he also doesn’t seem to mind the attention.
Given that these two live together, bought a house in the suburbs together, and have broken up with each other, they are more like a married couple than a pair of friends. They might bring out the worst in each other but they are a lot of fun to watch.
Rejected: Charlie And Dee
So many shows have hit a wall when forcing two of their main characters into a pointless romance. Thankfully, It’s Always Sunny is the opposite of every other sitcom around and have avoid such tired tropes. However, in one episode, they did tease viewers with the potential for one of these forced romances.
After the group decides to split up and try their own separate things for a while, Charlie and Dee begin bonding over being the most put-upon members of the group. This eventually leads to them sleeping together. But as much as fans didn’t want to see these two get together, the show realizes that and has them immediately regret the whole thing and pretend it never happened.
