The Demented Courtship of Charlie and the Waitress on ‘Always Sunny’


Crack out the milk steak and jelly beans, Charlie and the Waitress finally did the deed on ‘Always Sunny’! But we’ve traveled a long and weird road to get here. Let’s review.

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Charlie and the Waitress. It finally happened. We never thought it would ever happen. Actually, in the words of the Waitress, we never ever ever ever thought it would happen, but here we are. Wow.

In over a decade of Always Sunny, Charlie has always been chasing the Waitress like Wile E. Coyote chases the Road Runner. It always seemed to be a futile pursuit. The Waitress thought Charlie was gross and creepy (yep), and the more the Waitress rejected Charlie, the grosser and weirder he got.

One of the most hilarious bits of info about the relationship between Charlie and the Waitress is that the two are actually married in real life. Actors Charlie Day and Mary Elizabeth Ellis have been married since 2006, and they even have a young son together. Soooo, basically the opposite of the relationship between Charlie and the Waitress, but much closer to the version of their relationship that Charlie’s glue-addled brain knows to be true.

In a pretty shocking twist in the Season 12 finale, Charlie was finally able to break the Waitress down into sleeping with him, and even consider having a baby with him. It’s still kind of hard to believe. Did someone slip us some lead paint chips? But, when we looked back at the history between these two, it’s kind of all been leading up to this.

So, in honor of this momentous and completely unexpected occasion, let’s take a look back at the weird and demented courtship of Charlie and the Waitress on Always Sunny.

Charlie Has Cancer (Season 1, Episode 4)

While we learned that Charlie had a certifiable issue stalking the Waitress in the very first episode of the show, he never really made any serious moves on her. That job fell to Mac (Rob McElhenney) and Dennis (Glenn Howerton). When the gang thinks Charlie has cancer, they want to avoid any guilt associated with his diagnosis. So naturally they try to pay the Waitress to bang the sadness out of him. Of course Charlie doesn’t have cancer, and the Waitress doesn’t sleep with him.


Mac Bangs Dennis’ Mom (Season 2, Episode 4)

Disturbing on a whole bunch of levels, this Season 2 episode is one of the most emotional moments for Charlie throughout the entirety of the series. After Dennis threatens to sleep with the Waitress, Charlie and Dee (Kaitlin Olson) cook up an elaborate scheme. It involves Dennis attempting to sleep with both Charlie and Mac’s moms, and the Waitress gets fed up. As retaliation, she impulsively has sex with Frank (Danny DeVito), and then storms into the bar to tearfully rant about it.

Charlie, who had been waiting for a date with the Waitress, stands in horror, heart smashed to smithereens. Just wait it out, buddy. It gets better.


The Gang Gives Back (Season 2, Episode 6)

When the gang is ordered to do community service and attend AA after a legal snafu, Charlie lands at his first meeting. He sees the Waitress there, and tries to strike up a conversation. While she’s not willing to date Charlie, the Waitress does agree to sponsor him until he gets comfortable with the program. Was this a sign that she was warming to Charlie all along? Probably not. Especially because the whole episode ends with the Waitress’ admission that she was just using Charlie to get to Dennis all along.

The Nightman Cometh (Season 4, Episode 13)

One of the best Sunny episodes of all time, “The Nightman Cometh” marked Charlie’s boldest and most uniquely weird attempt at getting the Waitress to be with him. At the conclusion of a deeply erotic and upsetting musical, Charlie literally flies down from the ceiling and proposes to the Waitress in an original song. He definitely gets points for creativity, but alas, he doesn’t win the girl.

The Gang  Goes to the Jersey Shore (Season 7, Episode 2)

In an odd turn of events, the Waitress happens to be tripping hard when she encounters Charlie on the Jersey shore. The two have a magical night together, collecting shells, cuddling puppies, and jumping through the ocean waves. Seeing as the Jersey shore is kind of far from Philly, it’s almost as if fate brought them together… until the drugs wear off and the Waitress snaps back to reality.

Later that season, Charlie almost gets to bang the Waitress after the gang totally embarrasses themselves at their high school reunion, but misses out last minute when Schmitty (Jason Sudekis) swoops in and introduces himself first. Charlie just can’t catch a break.

Charlie and Dee Find Love (Season 8, Episode 4)

In Season 8, Charlie met a lovely rich girl and seemed to be having a great time hanging out with her. However, the entire relationship was just a ruse to get to the Waitress. And, in an interesting twist, it works. Due to some weird and unrelated scheming by Frank and Dennis, the Waitress pleads with Charlie to come back into her life and make all the insanity stop. Looks like that was Charlie’s plan all along.

Since the Waitress openly invited Charlie back to meddle in her life again, things have been relatively quiet on the Waitress front. Frank set up a lunch for the two of them in Season 9 episode “Flowers for Charlie”, but aside from that there have been few interactions solely between Charlie and the Waitress.

Until now.

The Waitress hadn’t appeared at all in Season 12. And for good reason. When she finally pops back up, looking at crude flow charts in Charlie’s apartment, we’re definitely supposed to think that this is just another failed attempt in a string in Charlie Kelly’s oddball schemes to get the Waitress to be with him. But it’s not. Instead of begging, he tries negging, and it works. Considering the fact that this woman has crazy low self esteem, the whole endeavor actually makes sense.

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Of course, once Charlie gets what he wants from the Waitress, he no longer has much of an interest in her. Could it be possible that we’ll see a role reversal and the Waitress will start stalking Charlie in Season 13? Charlie would probably welcome the attention, so probably not. But if there’s a baby on the way, all bets are off. If those fertility moves worked, we could certainly be seeing a “Charlie Wants An Abortion” redux in the near future.

‘It’s Always Sunny in Philadelphia’ Seasons 1 – 11 are currently available on Netflix. Season 12 is available on FX NOW.