Minnesotan Chloe Radcliffe has a Comedy Central special. She wants her old crushes to notice.
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Comedian Chloe Radcliffe stood on a St. Paul rooftop last Friday, yelling about her unrequited crushes.
“Why won't you notice me?” she yelled, a few floors up from Black Coffee and Waffle Bar at the crossroads of Cretin and Marshall avenues.
Behind her is a billboard with a photo of her that says “Do you have a crush on me now, Tyler?” There are two more billboards just like this in Minneapolis, but they’re directed to “Matt” and “Seth.” Each has a Comedy Central logo in the corner.
“I guess there's no subtlety to it,” Radcliffe said, laughing. ”I'm really desperate that my old crushes finally notice me. They never paid attention to me when I was younger, and now I'm hoping that now that I have a Comedy Central special and a billboard in St. Paul, and two in Minneapolis, now they'll start noticing me.”
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Based in New York, the Prior Lake native has performed on “The Tonight Show with Jimmy Fallon” and appeared in Bradley Cooper’s 2025 film “Is This Thing on?” — a film about standup. She also recently taped her debut comedy special, “Eyes Down Here,” which premieres at 8 p.m.. CDT Oct. 27 on Comedy Central, the first full-length special the cable channel has released in more than five years.
Her friend comedian Patrick Susmilch, who produced the special, is preparing a drone to get a shot of the billboard.
“Chloe told me about the billboard. I was like, absolutely, we should do that. That’s insane,” said Susmilch, who is from White Bear Lake. “And now we see it, and yeah, it's insane like we thought, and that makes it hilarious.”
The billboards tie into the themes of the special — dating, self-esteem and “how the way that we see ourselves affects the way other people see us.”
Radcliffe didn’t reach out to her past Minnesota crushes to alert them about the marketing stunt, but she says, through the internet and “friends of friends of friends,” she figured out the general vicinity of where they lived and placed the billboards there.
Radcliffe said she knew the three men from high school, college and one of her first jobs at Target Corp.
“I spent so long feeling like the truly hot, truly cool, attractive people would never be into me because I am weird, but mostly look weird,” Radcliffe said, pointing to the birthmark on her face. “I have a huge thing on my face that has hair on it, like there's no getting around it, you know. I spent so many years feeling insecure about that.”
And does that insecurity linger now that she has a special coming out?
“People go, ‘Oh, you're killing it,’ and I'm like, ‘Am I?’” Radcliffe said. “I don't know. Currently, I'm in my hometown begging a man who never paid attention to me to like me.”
Regardless, there is something to learn from all this, Radcliffe said.
“The lesson is: Ask for what you want, and you might not actually get exactly that thing, but you might get something close.”
