The Gang in Always Sunny in Philadelphia definitely have their romantic ups and downs… and it’s usually more down than up!

It’s Always Sunny in Philadelphia stars Rob McElhenney, Glenn Howerton, Charlie Day, Danny DeVito and Kaitlin Olson as Mac, Dennis, Charlie, Frank, and Dee, respectively. This gang owns a bar, they are all pretty narcissistic, and each episode reveals them getting into some sort of trouble or being involved in some shenanigans.

Over the years, several of the plot points have centered around love lives, crushes, romances, and significant others. Based on their personalities, most of these moments did not go well and went too far (in the wrong direction). But there actually have been a couple of moves that were sort of smooth… kind of.


Too Far: Dennis’ Collection Of Recordings

As anyone who has seen even just a few episodes knows, Dennis thinks he is a literal god, meaning, in his mind, he should be appealing and attractive to anyone and everyone. That being said, he has spent a great amount of time luring in women (and yes, it is usually as creepy as it sounds and usually involves him using the D.E.N.N.I.S. system). He even has a collection of videos, which show off everything that has gone down in his bedroom, and he is quite proud of all of this. Too far, Dennis… too far.


Too Far: Mac Getting With Dennis & Dee’s Mom
Then there is Mac, who has had some interesting relationships over the years and who has finally come out of the closet. One of his worst moments in this category, though, was when he hooked up with Dennis and Dee’s mom, Barbara. Everyone knows that friends’ siblings and their exes are off limits, so that makes parents super not okay to go after! He proceeded made it even worse by admitting it was the best he ever had and by then hitting on Barbara’s sister, Donna (aunts are off limits, too, dude).



Sort Of Smooth: Frank’s Pretty Woman
As mentioned, Frank has been with many women over the years, including Roxy. He enjoyed spending time with her, he liked her unique sense of humor, and he decided to put a ring on it! When it came time for him to propose, though, she passed out and then passed away, due to too much of one of her extracurricular activities. Out of all of the women that Frank has hired to be with him, Roxy was his favorite (a big compliment), and who knows how things would be now, if they were married.


Too Far: Dennis’ Artwork
Despite how Dennis can be, he does have some good traits, including some creative abilities. However, on a couple of different occasions, when he has shown off his artwork, it has, well, gone too far; fans and his peers have seen animated-looking drawings of women with over-the-top features (and not just any features… only one set in particular).
Even if he does find certain aspects of the opposite sex more enticing than the rest, he does not have to have this outlook on bodies and appearances, nor subject people to all of this crude behavior!


Too Far: Frank Sharing TMI
Despite being the oldest and the parent of the group, Frank Reynolds sometimes gets into the most trouble on this show! He was once a successful businessman, but after spending some time with The Gang, he started picking up more and more bad habits. He has been with a whole slew of women, in a variety of different ways, and it almost always leads to not-so-great moments. He also seems to enjoy telling people what size of protection he wears (or what size he wishes he could wear, when it comes to alone time with a special someone).


Sort Of Smooth: Charlie & Ruby
While everyone else was busy getting around in interesting ways, Charlie actually did not get with anyone (like that) until season eight; during that time, though, he met Ruby Taft, an attractive and affluent woman who actually really liked Charlie. And one time, when The Waitress confronted him, he even called Ruby his girlfriend and kissed her. However, things went sideways when he told Ruby he was just using her to make The Waitress jealous. Before that moment, though, it was nice to see Charlie, well, have something nice!



Too Far: Dee Dating A Rapper
Speaking of women… Dee is not innocent, when it comes to this topic, and the most notable time she went too far was when she was dating Lil’ Kev. She bragged about being with a rapper, but the guys informed her that he had some problems. After observing Lil’ Kev more closely, she was convinced they were right, and she dumped him. In the end, everything blew up in her face, of course. As Lil’ Kev did not have problems… well, not like that (He did have a big problem with how Dee treated him, though).


Too Far: Dennis’ View On Love
All of these characters have some issues, and for Dennis, that involves not being able to express emotions, feeling empty and cutting down others to make himself feel/look better. In an episode called “CharDee MacDennis 2: Electric Boogaloo”, he said something that further proves that he is not totally okay (in general, when it comes to women and on the topic of love); he said that, in his opinion, the best way that he could think of to show that love exists would be to think about a woman’s head in a freezer. Again… too far.


Too Far: Mac’s Relationship With Carmen
Now, at one point in time, Mac was in a relationship with Carmen; he thought she was attractive, Dennis told him that she was a pre-op trans woman, but Mac did not care, because she complimented his muscular arms. Later, Mac said that he was just wasting time and waiting for her to have surgery, and after she did have it, she was done with Mac.
Yes, she ended up with Nick instead. And while Mac and Carmen may have had some actual good moments, he can’t say he was just putting in time and waiting for her to make a change, especially on such a sensitive subject.


Sort Of Smooth: Charlie’s Proposal
One of the most complex relationships on Always Sunny is the one that does/doesn’t exist between Charlie and The Waitress. She may not always like him or even tolerate him, and he may have tried to trick her or make her jealous, but there was a sort of smooth moment. Charlie, the guy who can’t read or write, created an entire musical called “The Nightman Cometh”, and one of the songs in it was Marry Me; he came down from the ceiling in a bright yellow suit, he performed this entire number in front of a live crowd, and he proposed to the love of his life. She said no, of course, but that was a pretty big and bold move!