Alex Cooper's Romance with a Red Sox Player: What Really Happened

Alex Cooper's Red Sox player romance was truly one for the books. From late-night parties, penthouses, and champagne to heartbreak, letdowns, and a bittersweet end, here's everything the "Call Her Daddy" host revealed about her emotional and chaotic relationship with the Boston athlete.

Alex Cooper returned to her old stomping ground of Boston in June 2024 for a high-profile Red Sox appearance. The experience prompted her to reflect on the past, leading to a revealing episode in which she opened up about her whirlwind relationship with a Red Sox player.

What started with a chance meeting in a crowded bar spiraled into something much bigger. There were penthouses, steak dinners, spring training weekends, and dizzying highs that came with dating one of Boston's most recognizable athletes. But beneath the surface, cracks quickly formed.

Alex Cooper's Red Sox Player Romance

In June 2024, Cooper stood on the pitcher's mound at Fenway Park, throwing the ceremonial first pitch ahead of a Red Sox–Blue Jays game. The "Call Her Daddy" host was met with thunderous applause from the Boston crowd, a city where she spent her formative college years.

Her Instagram caption later summed up the moment, "College me used to sit in those stands cheering on a guy lol so throwing out the first pitch with thousands of women I love there to support me felt euphoric."

During an episode of her podcast, she revealed the Red Sox invited her after noticing her Unwell event. However, what began as a lighthearted anecdote quickly turned into a confession.

Their story began during Super Bowl weekend of her sophomore year.

Cooper proceeded to peel back the layers of a personal chapter involving a whirlwind romance with a high-profile Red Sox player during her time at Boston University.

The podcast host, who played Division I soccer at BU, admitted she'd dated several athletes during college — but none as unforgettable as Red Sox man. "To all my men in uniform, this one is for you," she said jokingly, before diving into the story.

It all started in 2013. Cooper recalled hearing the entire campus erupt when the Red Sox won the World Series. A year later, she found herself involved with one of those championship players.

Their story began during Super Bowl weekend of her sophomore year. Wanting to escape the college party scene, Cooper and her roommate headed to a downtown bar, West End Johnny's, where Bruins players were hanging out.

Cooper was making headway with a hockey player when a burly, bearded man cut in, "Oh my God, you're a smoke." She had no idea who he was. Then, a friend pulled up a photo — he was a Red Sox player making $16 million a year. Suddenly, Cooper's interest shifted. She revealed:

"In my head, I was like, 'Oh my god, this is gonna be a good night.'"

That night ended at his penthouse, surrounded by drinks, music, and a sweeping view of the Boston skyline. "I had never been in a penthouse in my life," she said. While nothing happened that night, the impression stuck.

The next morning, he called. "Get up. Get dressed. There's a car outside your dorm," he told her. That spontaneous invitation to his Super Bowl party marked the beginning of their romance. Cooper recalled, "This was the most exciting moment of our lives."

Then came a night that changed everything.

What followed was a full-blown once in a lifetime adventure. He sent car services to pick her up, flew her to spring training in Florida, and treated her to steak dinners and prime seats behind first base. "I was just a normal college girl experiencing his fame in such a wild way," she said.

For him, being 13 years her senior, it was routine as he had been in the MLB for a decade. The attention, the money, the photographers trailing him after games — it was all part of his world. For Cooper, it was intoxicating. "I definitely got swept up in all of it and felt excited by it," she admitted.

But what she saw as signs of affection — lavish dates, VIP access, and time spent together — were not what they seemed. "This was my first true athlete experience," she said. "I was so young and naïve and I was completely in over my head."

Some nights, she thought she'd get invited to a game — only to hear nothing. "I started to become obsessed," she confessed.

One weekend, she'd be in his bed. The next, he'd ghost her. Then came a night that changed everything. He told her he was staying in. Hours later, Cooper spotted him at a club — with other women. She said:

"This man walks into the club surrounded by his teammates and a bunch of girls, and I immediately wanted to throw up. I'm like, 'Oh my god. It must be, like, a miscommunication.'"

Fueled by alcohol and emotion, she followed him into the men's bathroom, and an embarrassing confrontation ensued. However, even after that moment, she kept going back.

Explaining how deeply tied she was to the romance, Cooper said, "This was my first real adult relationship." She further remarked, "Despite how inconsistent he was, I really thought we had something special in our alone moments."

However, after a year of emotional turbulence, she began dating others. Still, the Red Sox player had a hold on her. "Here's the thing. I think he started to pull away because he recognized how much more in love with him I was, and where I wanted things to go in the relationship," Cooper admitted.

Reflecting on it years later, Cooper didn't downplay the chaos.

"And he realized he couldn't give that to me. Like, we had a really consistent, great couple [of] months of just like, whirlwind. And then I think I naturally got invested. And he was, like, wanting to keep it where it was," she continued.

Their saga finally ended when her mother texted her an article — he'd been traded to a team across the country. She immediately called him.

"And he was quite emotional on the phone, and I was quite emotional on the phone, and he was like, 'I want you to come visit me. Like, this isn't the end,'" Cooper shared. However, the "Call Her Daddy" host knew it was, in fact, the end.

Before dropping the phone, the Red Sox player uttered the final words that stuck with her — "Alex, you listen to me. Boston is yours."

Reflecting on it years later, Cooper didn't downplay the chaos. From the highs of penthouse parties to the lows of public rejection, that era was more than a fun story to tell — it was also transformative. She stated:

"And, like, it oddly was such a perfect ending, because he was Boston. Like, I was living in his world and this man was just, like, basically saying, like, 'Here are the [...] keys to the city. Like, I trained you, I taught you all I [...] know. Now, go [...] take it."

And as she stood on the Fenway mound with her fans roaring, the moment felt full circle. Boston was hers now. However, that chapter of her love life — marked by the highs and lows of dating a Red Sox player — was long behind her.

Despite the chaos of her early love life, Cooper eventually found stability. She married film producer Matt Kaplan in April 2023, stepping into a new season far removed from the whirlwind that once defined her college years.

"We went on a few dinner dates in L.A. and sat in parking lots, pandemic-style, and there was no doubt in my mind after the first dinner that he would be the man I was going to spend the rest of my life with. I'm extremely picky, so this was big for me," she said.

Alex Cooper's whirlwind romance with a Red Sox player may have ended in heartbreak, but it shaped a woman who now owns her story — and the city that helped write it.