A Look At Alex Cooper's Dating History

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.

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.'"

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. 

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!'"

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. 

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."

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.