A Look At Alex Cooper's Dating History

Best known as the host of the popular dating advice podcast "Call Her Daddy," which was acquired as a Spotify exclusive for a reported $60 million, per Variety, Alexandra "Alex" Cooper is on her way to becoming a household name in media. Cooper, who originally started the podcast at Barstool Sports with former co-host Sofia Franklyn, is now a solo player and landed Spotify's biggest deal for a women-led show.

On "Call Her Daddy," Cooper has divulged details about her relationships throughout the podcast's episodes while still providing the men some privacy. Although Cooper is open about discussing her sex life and dating tips for other women, she refers to the men under various code names — including "Slim Shady" and her current partner known as "Mr. Sexy Zoom Man."

Despite the nicknames, fans of the popular podcast have still managed to piece together parts of Cooper's past and present relationships. Here is a breakdown of that history.

Her first serious relationship was with a Red Sox player

In her sophomore year of college, Alex Cooper dated someone from the Boston Red Sox who was thirteen years her senior. As she shared on "Call Her Daddy," the pair hit it off at a bar after the Red Sox had won the World Series. On a February 2021 episode titled "I Have a Boyfriend" while in conversation with her best friend, Lauren McMullen, she revealed that crossing paths with the unnamed athlete would set a pace for the rest of Cooper's dating life. "It was dope ... I got to bring all my friends. We'd go to the games. Like, it was a cool lifestyle," she recalled. "This man was the epitome of making f***ing money, driving his f***ing Aston Martin. I'm in his penthouse after my f***ing last class the day before I go to practice."

Although she had VIP access to players' locker rooms as a girlfriend, Cooper had to come to terms with the fact that there was a sea of other women in the picture. She held onto the lifestyle for as long as she could, a task she described as emotionally taxing. "I was walked all over. I was treated like s***," she said. "He opened truly my eyes to some of the most psychotic, intense games that were possible to be played." Although Cooper has remained mum on the man's identity, internet sleuths have a strong suspicion that it might have been the Chicago Cubs first base coach Mike Napoli, who won the World Series with the Red Sox in 2013.

Alex Cooper says this athlete gave her career a boost

"Call Her Daddy" host Alex Cooper and former New York Mets baseball player Noah Syndergaard dated on and off throughout 2017, with their last public outing at a Knicks basketball game that December. Syndergaard appeared to confirm that his relationship with Cooper was officially over that same month, with a tweet stating, "Baseball is my significant other," along with an image of a single status change.

Cooper has seemingly discussed her relationship with ex Syndergaard under the nickname "Slim Shady," as listeners on Reddit pointed out. The podcast host confirmed to Bustle she began dating Syndergaard during her senior year at Boston University. She also revealed that dating him helped her get a foot in the door at a magazine called Gotham before "Call Her Daddy" took off. "I basically got that job because of him, and I have no shame saying that," Cooper said.

According to Cooper, the relationship with Syndergaard was glamorous on the outside and much more turbulent behind closed doors. "We loved walking in a room together," she shared on her "I Have a Boyfriend" episode. "We didn't like how we felt being in a room together ... That's some dark f***ing s***."

Milf Hunter gave NSFW advice to Alex Cooper

A relationship history recap wouldn't be complete without this piece of advice "Milf hunter" gave Cooper. Long before there was bad blood between Alex Cooper and "Milf Hunter," sometimes simply known as "Male X," he was a "Call Her Daddy" podcast staple. "Milf Hunter," suspected to be the ghostwriter Muj Fricke, had known Cooper since her mid-teens. Unlike Cooper and her co-hosts, however, "Milf Hunter" wasn't looking for fame and fortune. He had built a private life free from the spotlight and was content with working behind the scenes.

Things are about to get a bit NSFW, so fair warning. The Daddy Gang forever credits "Milf Hunter" with teaching Cooper about an oral sex technique dubbed the "Gluck Gluck 9000." In a 2018 episode fittingly called "The Gluck Gluck 9000," Cooper broke it all down, sharing the tips offered to her by "Milf Hunter." This was only the third episode of "Call Her Daddy," and the graphic conversation was one of the show's earliest defining moments. "I could feel the editors in the room, the producers with their cameras, and I remember being like, they're laughing, they're men in the room laughing, like, this s*** is funny," she recalled to Bustle in her 2021 interview. "We'd stop and they'd be like, 'No, keep going.'"

Alex Cooper and Paige DeSorbo have a lot in common

On another February 2021 episode of "Call Her Daddy," Alex Cooper and "Summer House" star Paige DeSorbo figured out that they had more in common than they initially realized. As DeSorbo went on to chronicle her experience with dating apps, one particular person — an unnamed actor from an NBC primetime series — caught Cooper's attention. "Wait! I wonder if we went on the same date with the same man," she interjected. The pair proceed to edit out the actor's name, but sure enough, DeSorbo and Cooper's dating histories overlapped, confirming they both dated him around 2018. 

So, who is the mystery actor? Of course, his name has not been confirmed, but Cooper's diehard fanbase believes it might've been "The Blacklist" actor Ryan Eggold, who portrayed the lead character Dr. Max Goodwin on NBC's "New Amsterdam." 

That, however, wasn't the only overlap. Cooper had previously matched with DeSorbo's ex-partner on a dating app, but all their plans to link up fizzled out. 

She talked about being 'interested in hooking up with girls'

On a January 2020 episode of "Call Her Daddy," Alex Cooper and her co-host at the time, Sofia Franklyn, discussed same-sex relations in depth. In classic "Call Her Daddy" style, they shared some details from their own lives. "We all love a little girl-on-girl," Franklyn declared. Cooper went on to say that she believes most straight women are not totally straight, adding, "We both have said that we'd be interested, we've been interested in hooking up with girls, how we've hooked up with girls." 

After getting into how straight men may or may not feel about their significant others hooking up with another woman, Cooper and Franklyn also recounted the time they ended up making out with a woman in the back of an Uber, only for that woman to film the interaction on their phone. According to Cooper and Franklyn, the woman took the video to send to her own boyfriend. "We were like, no, but oh, okay. So, yeah. And there we were," Franklyn said. 

She had a string of distasteful dates

As soon as Alex Cooper's brand began to rise, it was nearly impossible for her to date without the "Call Her Daddy" tag. "I didn't like meeting men for the first time as the 'Call Her Daddy' girl," she said on her "I Have a Boyfriend" episode, adding that some of her prospective suitors seemed only in it for a quick hookup. "I think it was just as strange as it sounds," she said. "I'm showing up and they're, like, staring at me like 'Am I gonna get the Gluck Gluck tonight?'" 

One man, for example, made a bet with his friends on how fast he could spend the night with Cooper. And on a possibly even more obnoxious note, a different love interest had a wedding coming up, and he approached Cooper with the intention of gauging her potential as a replacement for his then-fiancée, with whom he'd been together for six years. Cooper kept bumping into men who wanted to exploit her for their own gain, and it prompted her to go back to what was familiar.

Alex Cooper and Slim Shady had a second go at it

Alex Cooper and Noah Syndergaard's relationship took a different turn when they reconnected. Cooper had come into her own, having found a voice and a legion of fans who were rooting for her. What's more, Cooper felt that they had unfinished business. "I think closure ... There's something about when you have such a crazy, toxic relationship and it ended the way it did with us. We kinda both didn't even have a final say," she said in her "Call Her Daddy" conversation with Lauren McMullen.

For the second try, the pair chose to keep their relationship under wraps. As it turned out, however, Syndergaard had stayed the same. While Cooper had done a ton of work on herself since their first split, she felt he had barely scratched the surface of personal development. It was not long before his behavior prompted her to pull the plug on things yet again. "He, like, made up some lie, like why we couldn't hang out," she said. "And I like kinda laughed a little and was like, 'Oh my God, so classic.'... And I was like, 'I'm out!'"

Three of her suitors became quarantine buddies

At the height of the COVID-19 pandemic, Alex Cooper was seeing a man simply known as "The Canadian." However, things took a shocking turn when "The Canadian" sent her a photo that featured two other men she happened to be chatting with at the time. As far as she knew, the three guys didn't run in the same circles, and she couldn't make heads or tails of how they possibly all wound up quarantining together. "I just want you all to picture yourself ... You get a picture and three men that you are talking to that you didn't even know knew each other existed," Cooper shared on the "Seeking Arrangements: Our Story" episode of "Call Her Daddy."

Understandably, this threw a bit of a wrench in things with all three of the guys. "We're going to go ahead and put that s*** on hold," Cooper said. "I'm so aware that I can't be texting all of them while they're quarantined in the same house. No talking with the Canadian." As usual, the identities of the men in question were sealed, but word on the Daddy Gang streets is that "The Canadian" was a professional hockey player. 

Door No. 3 turned her life around

Alex Cooper's partner, referred to as "Door No. 3," arrived at her doorstep when she was dating one athlete after another. "Door No. 3," however, wasn't the sportsman she was accustomed to. Having been used to surface-level interactions with no flesh whatsoever, he tapped into a deep, vulnerable side of Cooper. "It was shocking at first," Cooper said of the relationship on the aforementioned February 2021 episode of "Call Her Daddy." "It was so different. It freaked me out because it opened a door that I never opened or explored. Hence why he's called 'Door No. 3.'"

"Door. No. 3" was also the one that got away. Although Cooper couldn't handle his intensity when they initially met, the timing was never quite right when she became more mature. Somehow, he lurked around when she was in between relationships. "Every time I was ready, then he wasn't ready and then when he was ready, I wasn't ready," Cooper recounted.

While this is, once again, extremely unconfirmed, some fans suspect "Door No. 3" was actually former New York Yankees pitcher Shane Greene. 

Her mom advised her to go out with someone from a prominent family

Prior to getting serious with "Mr. Sexy Zoom Man," Alex Cooper's exhilarating dating life was the glue that got her audience hooked to the "Call Her Daddy" podcast. One such affair involved one of America's prominent family members, thought to be the late president John F. Kennedy's only grandson, Jack Schlossberg. While she didn't drop his name, she did share some interesting breadcrumbs in a December 2020 episode.  

Alex had been going back and forth on whether or not she'd like to go out with this mystery guy, so she ran it by her mom. Her mom, who apparently has a real talent for finding any and all information about Alex's potential suitors, was adamant she go on the date. As Alex recalled, "Laurie Cooper does some hardcore research. She loves the guy's background. She loves specifically the family background." The podcaster also revealed that Laurie went on to show her a movie about the unnamed man's family. "In that moment I just flash forward and I'm like picturing myself on this date and I'm like, 'Oh my God. Yeah.' I'm like, 'Your aunt is so pretty,'" Alex said. While we may never know for certain if she went on a date with a Kennedy, we do know that her mother's intuition is a force to be reckoned with. 

Things got steamy between her and Logan Paul

When Alex Cooper made an appearance on the "BFFs" podcast, she corroborated the story that she and WWE signee Logan Paul had a secret rendezvous — except they hadn't gone all the way. "He's telling people that we hooked up and I thought we had this, like, secret that we were going to keep forever. Like, we weren't gonna tell anyone, we were going to keep it to ourselves," she said. "And Logan Paul is really bad at keeping a secret." According to Cooper, the hookup happened on a whim, and they didn't sleep together.

On an episode of the "Impaulsive" podcast, Paul confirmed that he enjoyed their time together but insisted that he had not broadcasted their encounter to all and sundry. He also shared that he reached out to Cooper after she went on "BFFs" and tried to plead his case. "I liken it to finding the Fountain of Youth and not telling anyone," he said. "I got it, I found it, and it was great."

Alex Cooper's new man

In February 2021, Alex Cooper confirmed on the "Call Her Daddy" podcast that she had been exclusively dating someone, referring to him under the nickname "Mr. Sexy Zoom Man." The nickname references her meeting him over Zoom for business (they later took their relationship to the next level during a trip to Los Angeles, where Cooper now lives). She hadn't identified the movie producer in question, because as she explained to Bustle in July 2021, "He was more like, [...] 'I fully respect and I support you and your podcast, but I have a job.'" 

It turns out that "Mr. Sexy Zoom Man" is Matt Kaplan, the CEO of Ace Entertainment, a film production company. His production credits include "To All the Boys I've Loved Before" and "The Lazarus Effect."

In many ways, Cooper was skeptical during the early stages of her relationship with Kaplan. Having grown an audience as a free-spirited, non-committed, carefree girl, a serious relationship was the exact opposite of her podcast persona. As she said on "Call Her Daddy," "I love this job. This show is my life. And so, I'm not gonna lie to everyone listening. Of course, it ran through my head. Like, are people not gonna love the narrative that I have a boyfriend? Are people going to think Alex Cooper went soft?"

Alex Cooper and Matt Kaplan got engaged

In another life, Alex Cooper may have kept her nonchalant persona going to stay true to her "Father Cooper" tag, but in this one, love came knocking at her doorstep, irresistibly. In April 2023, Cooper took to Instagram to relay the news that she was officially off the market.

In a conversation with W Magazine, Cooper revealed that she had reservations about marriage before, but choosing Kaplan was a no-brainer. "It immediately was obvious to me, once our relationship progressed to the point that it was time, that yes, I would love to marry him," she said. "We went to a date night at Giorgio Baldi in November, and I told him that he could propose whenever he wanted."

Propose he did, in a lush, green intimate candlelit setting at home with her fur babies as an audience. But not before he put his future wife through a romantic treasure hunt that chronicled their time together. Kaplan's choice of ring was an oval-cut 1920s rock. If Cooper's chat with W Magazine is taken into account, not only is a wedding in the works but sooner or later, mini Kaplans and Coopers will be part of the Daddy Gang family.