Alex Cooper has spent the better part of a decade telling millions of people exactly how to handle their "gluck gluck 9000" and when to ghost a guy. It’s kinda ironic, honestly. The woman who built an empire on being the ultimate single-girl-boss is now very much off the market. If you’ve followed the "Daddy Gang" since the early Barstool days, you know her romantic life used to be a messy, high-stakes game of professional athlete bingo.
But who has Alex Cooper dated, really?
It wasn’t all just "Mr. Sexy Zoom Man" and happily ever after. Before the $125 million SiriusXM deals and the Vogue-worthy wedding in Mexico, Alex’s dating history was a whirlwind of MLB pitchers, "psychotic" age-gap relationships, and at least one very famous YouTuber who couldn't keep his mouth shut.
The Pitchers, the Players, and the "Red Sox Man"
Long before she was a household name, Alex was a D1 soccer player at Boston University. This is where the "Red Sox Man" saga begins. If you go back to the early episodes of Call Her Daddy, she talks about this guy like he was the blueprint for what not to do.
He was 13 years her senior. He had just won a World Series. He had, as she put it, "f-ck you money." While Alex never officially named him, the internet detectives on Reddit have basically settled on Mike Napoli, given the timeline of his trade in 2015 and his legendary status in Boston at the time. Alex described the relationship as a "training camp" for toxic dynamics. She’s been open about how he "walked all over her," but also credits that heartbreak with giving her the edge she needed to start the podcast.
Then came "Slim Shady."
For a long time, Alex used this nickname to refer to her on-again, off-again boyfriend, who turned out to be former New York Mets pitcher Noah Syndergaard. They were spotted together at Knicks games back in 2017 and 2018, looking like the ultimate NYC power couple. But behind the scenes? Not so much.
Years later, Alex didn't hold back. In a 2023 episode with Alix Earle, she took some pretty heavy swipes at a "certain ex" who couldn't "get a f-king contract," which fans immediately clocked as a dig at Syndergaard’s free-agent struggles. It seems that relationship ended with a fair amount of "dark sh-t" and mutual resentment.
The Logan Paul Hookup
This one actually surprised people. On an episode of the BFFs podcast, Alex confirmed that she and Logan Paul had a "thing."
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She wasn't exactly thrilled that it became public knowledge. "He's telling people that we hooked up, and I thought we had this, like, a secret," she told Dave Portnoy and Josh Richards. Logan, being Logan, isn't exactly known for his discretion. While it wasn't a long-term relationship, it definitely adds a chaotic chapter to the history of who Alex Cooper has dated.
Transitioning from Chaos to "Mr. Sexy Zoom Man"
In 2020, everything changed. While the rest of the world was stuck at home in sweatpants, Alex was sitting on a work Zoom call that would end up being her last "first date" ever.
Enter Matt Kaplan.
At the time, she was extremely protective of his identity. She called him "Mr. Sexy Zoom Man" for years. Fans knew he was a producer, they knew he was successful, and they knew Alex was actually—dare we say—falling in love.
Matt isn't just some guy in the background; he’s a massive Hollywood player. He’s the CEO of Ace Entertainment and the producer behind Netflix hits like To All the Boys I’ve Loved Before. He also has his own high-profile dating history, having been previously married to actress Claire Holt and having dated Ashley Olsen back in the early 2000s.
Why Matt Kaplan Was Different
Honestly, it seems like Matt was the only person who could match Alex's intensity. They didn't just date; they built a business together. In 2023, they launched "Trending," a Gen-Z media company that became the parent for her podcast and his production house.
He proposed in March 2023 with a 1920s vintage oval-cut diamond after a literal scavenger hunt through their house. It was a far cry from the "toxic games" of her early 20s.
The 2024 Wedding and Life as a "Wife"
On April 6, 2024, Alex officially married Matt Kaplan in Riviera Maya, Mexico. It was an intimate beach ceremony where their dogs, Henry and Bruce, were the ring bearers.
She wore custom Danielle Frankel and vintage Alexander McQueen. For someone who spent years telling her audience that marriage was a scam, seeing her in a veil was a huge moment for the Daddy Gang. It signaled the end of an era. The girl who used to give advice on how to "get the bag" from a random athlete had successfully secured her own empire and a partner who actually supported it.
Lessons from the Alex Cooper Dating Playbook
Looking back at the timeline of who Alex Cooper has dated, there's a clear evolution that a lot of women can relate to—even if we don't have millions of dollars in the bank.
- The "Training Camp" Phase: Everyone has that one ex who treated them like garbage but taught them exactly what their boundaries are. For Alex, it was the Red Sox player.
- The High-Profile Mistake: Dating someone just because they’re "the guy" (like the MLB ace or the famous YouTuber) rarely works if the chemistry is "dark" or the communication is non-existent.
- The "Work-Life" Balance: Alex found her match in someone who understood her career. If you’re a "mogul" in the making, you can’t date someone who is intimidated by your success.
The most actionable takeaway here? Alex stopped looking for a "character" to talk about on her show and started looking for a partner. She moved from the "Slim Shadys" of the world to a man who was willing to stay in the shadows until she was ready to let him in.
If you're currently navigating the dating world, take a page out of the 2026 version of Alex Cooper. Be "picky as hell" (her words), keep your private life private until it’s solid, and never let a man—no matter how many World Series rings he has—make you feel small.
If you want to understand her current dynamic even better, listen to the "I HAVE A BOYFRIEND" episode from February 2021. It’s the exact moment she stops playing the game and starts playing for keeps.
Practical Steps for Your Own Dating Life
- Audit your "types": Are you dating people because they look good on paper (or Instagram), or because they actually make you feel safe?
- Set a "Privacy Period": Try keeping your next relationship off social media for the first six months. See how much better it feels when you aren't performing for an audience.
- Level up your circle: Alex met Matt through work. Sometimes the best "dating app" is actually just your own ambition and professional network.
The era of "Single Alex" is over, but the lessons from her messy, public, and eventually successful dating history are still very much alive. It’s not about finding a "Sexy Zoom Man"—it’s about finding someone who doesn't require you to play a character.
Next Step: Review your own dating "non-negotiables." If they haven't changed in three years, it might be time to update them based on the person you are becoming, not the person you used to be.