If you were scrolling through Twitter—back when it was actually called Twitter—at 5:00 a.m. on May 10, 2011, you might have seen one of the most effective "thirst tweets" in internet history. Drake, who was already a massive star but hadn't yet reached his current "final boss" status, decided to shoot his shot with 2 Broke Girls star Kat Dennings.
The tweet was simple: "Kat Dennings I just woke up out of bed to let you know you were a dime on Conan tonight. XO."
It worked. Sorta.
People still talk about the Kat Dennings and Drake "relationship," but calling it a relationship is a huge stretch. It was more like a singular, deeply awkward blip in pop culture history that left Kat terrified of the rapper’s fan base. Honestly, looking back on it from 2026, it feels like a fever dream from a different era of celebrity interaction.
The Sushi Date and the "Black SUV" Energy
When they finally met up for dinner, it wasn't exactly a casual "Netflix and chill" vibe. Drake doesn't really do casual.
🔗 Read more: The Fifth Wheel Kim Kardashian: What Really Happened with the Netflix Comedy
Kat eventually opened up about the experience during an interview with Chelsea Handler on Chelsea Lately. She described a scene that sounds more like a high-stakes witness protection relocation than a first date. They went for sushi, which sounds normal enough, but they were being tailed by a massive black SUV full of security.
Imagine trying to eat a spicy tuna roll while a team of professional bodyguards watches your every move from a nearby vehicle. It's not exactly the recipe for a romantic spark. Kat basically called it a "non-date" because the sheer scale of Drake’s entourage made it impossible to just, you know, talk.
Why Kat Dennings Got "Scared" of Drake Fans
The most intense part of this whole saga wasn't even the date itself. It was the aftermath.
Kat told Chelsea Handler that after the news of their "hangout" broke, she went home to find her social media absolutely blowing up. And not in a good way. She suddenly had 50,000 new followers, but most of them weren't there to congratulate her on her sitcom success.
💡 You might also like: Erik Menendez Height: What Most People Get Wrong
Instead, she was greeted with a wave of "F you, Kat Dennings" and "You can't take Drake from me."
"I'm like, 'I'm literally not trying to take Drake from you,'" she joked during the interview.
She admitted the experience was so overwhelming that she felt like she would "die" if she actually tried to date him seriously. The intensity of "Stan" culture in 2011 was already peaking, and Kat, who has always projected a more low-key, indie-cool vibe, clearly wasn't looking for that kind of heat.
Drake's Version: The Ellen Interview
Drake didn't stay silent about his crush, either. In 2013, he sat down with Ellen DeGeneres for one of those classic "Who has Drake dated?" segments. When Kat's picture popped up on the screen, he didn't hold back.
📖 Related: Old pics of Lady Gaga: Why we’re still obsessed with Stefani Germanotta
"I just always had a huge crush on Kat Dennings," he told Ellen. He confirmed they went out for dinner once but followed it up with a self-deprecating joke: "They don't call me back after one date, according to this."
It’s actually kind of refreshing to hear a global superstar admit he got ghosted—or at least didn't get a second date—by the girl from Nick and Norah's Infinite Playlist.
Where Are They Now?
A lot has changed since that sushi dinner. Kat Dennings found her "forever" in a way that couldn't be further from the Drake aesthetic. In 2021, she announced her engagement to rock legend Andrew W.K., and the two later married. Her life now seems to involve a lot of knitting, gardening, and leaning into her "witchy" aesthetic, which is pretty much the opposite of the "Champagne Papi" lifestyle.
Drake, meanwhile, went on to have high-profile flings and "situationships" with everyone from Rihanna to Jennifer Lopez. The Kat Dennings era was just a small chapter in a very long book of "Drizzy" romances.
Lessons from the Kat/Drake Era
- The "Thirst Tweet" can work, but have a plan. Drake proved that a public compliment can get you in the door, but you still have to close the deal once the security SUVs are parked.
- Security is a vibe killer. If you’re a billionaire rapper, maybe leave the fifth bodyguard at home for the first date if you want a second one.
- Fanbases are terrifying. Kat Dennings is a tough, smart woman, and even she was rattled by the sheer volume of Drake fans coming for her neck.
In the end, this wasn't a tragic heartbreak or a "the one that got away" story. It was just two people from very different worlds realizing over some expensive fish that they probably didn't belong in the same room.
Next Steps for Pop Culture Historians: If you're still curious about Kat's dating history, you should check out her long-term relationship with Josh Groban, which lasted from 2014 to 2016. It's another example of her penchant for dating talented, slightly eccentric men who aren't necessarily in the "rapper" category. You can also find her 2013 interview on Chelsea Lately on YouTube to see her tell the Drake story in her own words—her facial expressions when describing the security detail are worth the watch alone.