Kaitlin Olson’s First Impression of Rob McElhenney Has Us Second-Guessing Sweet Dee’s Stance on Tiny Baby Boys

Just to be clear, It's Always Sunny in Philadelphia star and Emmy-nominated Hacks actress Kaitlin Olson didn’t write the “Tiny Boy, Little Boy” song from The Nightman Cometh, but she did live it.

Last night, Olson and her husband and co-star Rob McElhenney attended the 76th Primetime Emmy Awards, one week after Olson’s performance as the chaotic faildaughter DJ on Hacks was honored at the Creative Arts Emmy Awards but ultimately lost out in the category of Outstanding Guest Actress in a Comedy Series to Jamie Lee Curtis’ work on The Bear. Together, Olson and McElhenney presented the award for Outstanding Supporting Actress in a Comedy Series, comedically riffing about the category with a touch of inappropriate humor after the orchestra welcomed them onstage with the It's Always Sunny in Philadelphia theme song.

Inappropriate onstage humor and musical numbers are a core part of Olson and McElhenney’s relationship, which they began around It's Always Sunny in Philadelphia Season Two, but Olson’s answer to a question about her sitcom romance during a red carpet interview with McElhenney makes us wonder what exactly her intentions were going into her relationship with McElhenney and whether any part of The Nightman Cometh might have been autobiographical:

So, while Sweet Dee swears that she’s not sexually interest in tiny little baby boys, Olson’s admission that, when she first met her future husband, “I thought he looked like a 14-year-old boy, and I was very confused when I started falling in love with him” throws the actress’ personal proclivities into some degree of doubt. 

This isn’t the first time Sweet Dee’s feelings toward teenagers has been a subject of an uncomfortable conversation, either. In the It's Always Sunny in Philadelphia Season One episode “Underage Drinking: A National Concern,” Dee starts a semi-relationship and even agrees to go to prom with a young buck named Trey, who is finishing up his senior year of high school. Of course, Dee never gets to go to prom with her barely-legal boy toy after Trey reconciles with his age-appropriate girlfriend, but the fact that, less than a year after “Underage Drinking: A National Concern,” Olson sparked up a romantic connection with the 14-year-old-looking boy in the main cast does feel like quite the coincidence.

Presumably, when the too-young-looking McElhenney finally put the moves on his future wife, he got plenty of gasps.