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Kyle Cooke and Craig Conover’s Loverboy Drama Explained

Kyle Cooke Breaks Down Craig Conover and Loverboy Investment Drama Timeline
Kyle Cooke, Craig Conover. Bravo (2)

Kyle Cooke and Craig Conover have been friends for years — but that hasn’t stopped them from feuding over Loverboy and loyalty.

Cooke launched his alcohol brand, Loverboy, in 2018, with his now-wife, Amanda Batula, and friend Carl Radke by his side. Five years later, the canned cocktails landscape had grown even bigger and pal Conover jumped on the bandwagon.

When Conover announced in April 2024 that he was an investor in Spritz Society, Cooke claimed there was “no bad blood” between them. However, Cooke confessed during a May 2024 appearance on Watch What Happens Live With Andy Cohen that it “rubbed me the wrong way” how Conover told him he was working with a competitor.

“First and foremost, all my friends that I’ve filmed with know that I’ve raised money,” Cooke later claimed during a June 2024 episode of the “Trading Secrets” podcast. “The only person that ever expressed interest was Carl.”

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Cooke, who has known Conover since 2018, alleged, “Craig never expressed interest. He never once asked to invest in Loverboy.”

Scroll down for a complete timeline of Cooke and Conover’s drama surrounding Loverboy — and see where they stand now:

The Initial Announcement

“I’m so excited to announce that I am now an investor in @spritz! I first found out about Spritz last summer when me and Paige [DeSorbo] were on our way to @taylorswift at Metlife and the party bus was stocked with these delicious wine spritzers,” Conover wrote in a lengthy Instagram post in April 2024. “One sip was all it took for me to realize they were onto something and I needed to learn more about the brand — I loved the concept of a refreshing wine based drink & how they brought everyone together.”

He gushed, “I’m so excited to be in the Spritz Society family and for y’all to see the amazing projects we’ve got in the works.”

Craig Breaks Down His Spritz Choice

Kyle Cooke and Craig Conover Break Down Loverboy Investment Spritz Society Drama
Bravo

“Obviously I’ve always had respect for Austen [Kroll] and Kyle and all of them but being in the liquor business or wine liquor business now, I’m like, ‘Oh my gosh. This is a new territory,’” Conover told Page Six in May 2024, referring to Kroll’s Trop Hop beer and Cooke’s Loverboy alcohol brand.

Conover noted that he has “always respected Kyle’s hustle,” but he also “didn’t understand it at times” until he got involved in the industry. “I understand why he’s had to work so hard, because the grind in the alcohol business is extreme,” he added.

Conover alleged that prior to the Spritz Society investment, he “offered to buy into” Kroll’s beer company but Kroll declined his offer. Conover also claimed he “would have loved to invest” in Loverboy, but “that wasn’t an option.”

Kyle Goes on ‘Watch What Happens Live’

Cooke initially told Andy Cohen on a May 2024 episode of Watch What Happens Live With Andy Cohen that there was “no bad blood” between him and Conover over Spritz Society. “I think this is being blown out of proportion,” he explained. “I don’t really think there was an investment, and it seems like all the press is referencing me.”

Cooke later said, “Look, I wish him the best, but the way he handled it, and we don’t have time to get into it, really rubbed me the wrong way, and I’m just trying to take the high road.” He alleged Conover “has a reputation of lying and he lied to me.”

The Investor Issue

Kyle Cooke Breaks Down Craig Conover and Loverboy Investment Drama Timeline
Courtesy of Kyle Cooke/Instagram

After Spritz Society founder Ben Soffer’s wife, Claudia Oshry, claimed during a May 2024 episode of “The Toast” podcast that Cooke denied Conover the ability to invest in Loverboy — and alleged that Loverboy has no investors — Cooke addressed the drama.

“I don’t know what got lost in translation. Loverboy has investors, we’ve had investors since 2019,” Cooke said on Jason Tartick’s “Trading Secrets” podcast in June 2024. “I value them immensely. I’ve had lots of them texting me saying, ‘What in the heck is going on?’ I could not have done it without them.”

Cooke claimed that Conover was well aware that he was looking for investors and fundraising opportunities when they were in Vermont for Winter House in March 2022.

“I am not a sole owner. I wanna make that very clear,” Cooke said on the podcast. “We were actually fundraising — I was very vocal about this with my close friends, Craig included, during Winter House [season 2]. I was busy raising a round of financing. It’s like, this is not a secret.”

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Kyle’s Spritz Society Conversation

Nearly two years after Cooke was fundraising in early 2022, he crossed paths with Soffer, Spritz Society’s founder, in New York City. “He had DMed me when we were both at an industry conference in January. And per the timeline his wife laid out, he was already in talks with Craig,” Cooke explained in June 2024 as to how he first connected with Soffer, noting the pair agreed to go to dinner the following month.

“This dinner ended up taking place about two weeks before Craig and I got drinks. We’re talking like receipts and timelines these days [so] dinner was February 7th,” Cooke confirmed. “I really enjoyed the conversation.”

The Summer House star recalled Soffer eventually saying, “‘Hey, maybe we could collab and like throw a party, kind of cross pollinate our audiences.’” While Cooke was entertaining the idea, he learned that Soffer was with Conover the following day and Soffer “never mentioned” it.

“I didn’t know at this time that him and Craig were talking about a collab,” Cooke said, noting, “He knows Craig and I are friends. … I just wish he was a little more transparent with his intentions.”

Cooke confessed that found it “extremely odd” that Soffer didn’t tell him or Conover that he’d been spending time with the other person all while working on an investment deal with Conover.

How Craig Told Kyle About His Spritz Society Situation

Kyle Cooke Breaks Down Craig Conover and Loverboy Investment Drama Timeline
Courtesy of Kyle Cooke/Instagram

Shortly after Cooke met with Soffer in NYC, Conover reached out to go to get drinks in the Big Apple. “It all kind of unfolded in early February, Craig and I got drinks,” Cooke said during the June 2024 podcast episode. “I thought it was just to catch up.”

Cooke claimed that “10 minutes before” their friend Tom Schwartz showed up at the bar, Conover “sprung” his Spritz Society deal on him.

“It sounded very much like the offer on the table was [that] he was being given equity and then boom, he actually left [the bar] early and that was it,” Cooke recalled. “The next day I texted him like, ‘Hey man, I’ve been giving a lot of thought to what you said about this opportunity you have, and please, like, hold off from signing anything. I’d love to put an offer on the table to kind of counter it.’”

Cooke alleged that after some “back and forth” Conover told him it was “too late” for Cooke to counter with a Loverboy offer.

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“I just figured he’d at least give me an opportunity to [be] like, ‘Hear me out,’” Cooke continued. “To be honest, I kind of feared that this would impact our friendship because this has been my blood sweat and tears for the last five years.”

Cooke admitted he is “sensitive” about his company, revealing that while he doesn’t need Conover involved in Loverboy he was surprised by the move to go with Spritz Society.

“I just didn’t think one of my good friends would go hop in bed with a competitor,” he said. “You know, that’s it. That was the extent of our conversation.”

‘Watch What Happens Live’ Debacle

Kyle Cooke and Craig Conover Break Down Loverboy Investment Spritz Society Drama
Charles Sykes/Bravo

Cooke revealed that after his chat with Conover in February 2024, he chose to keep it to himself and not bring up the news publicly. However, that changed when Cohen asked him about their Loverboy quarrel on WWHL in May 2024.

“You’re in the hot seat. … I’ll be honest, like, he caught me off guard, Andy Cohen,” Cooke recalled during the June 2024 podcast, referring to the talk show appearance. “I was ready to talk about Summer House, and I hadn’t thought about this in a while. And I let my emotions get the best of me.”

The reality star continued, “Up until then, I had very consciously decided not to comment via the various press requests about Craig’s involvement in this competitor. I was very much focused on keeping this a private matter.”

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Cooke said that it was not his intention to bring it up when he did. He noted that he is not only friends with Conover but he’s close with the Southern Charm star’s then-girlfriend, DeSorbo, as well. (Conover and DeSorbo split in November 2024 after three years of dating.)

“The last thing I’m trying to do is make it awkward for any of us,” Cooke shared, adding that he wishes he “wasn’t so reactionary” on WWHL. (Cooke claimed at the time that Conover “has a reputation of lying and he lied to me.”)

Cooke stands by what he said to Cohen about Conover but confessed he “could have handled it better.” He added: “Sometimes I’m right, but it’s my delivery and it’s my tone and my temper [that] make me dead wrong.”

A Hopeful Future

Kyle Cooke Breaks Down Craig Conover and Loverboy Investment Drama Timeline
Courtesy of Kyle Cooke/Instagram

“I’m pretty bummed with how everything went down,” Cooke told Tartick in June 2024, explaining that the “only choice” now is to “hopefully” not let the career decision “interfere with our friendship.”

Cooked continued: “In all seriousness, I hope to have a chance to talk with Craig. I wanna squash the beef. Like, what’s done is done. I tell ’em straight up like, ‘I’m sorry for being reactionary and Watch What Happens.’”

He concluded, “The irony here is it’s really not about two startups competing against one another. It’s trying to stay relevant in an industry that is really good at keeping the startups small.”

His Instagram Comment

Following Cooke’s appearance on Tartick’s podcast, he doubled down on claims that Conover “never” expressed interest in investing with an Instagram comment.

“The more I think about it, the more I think Craig was intentionally or unintentionally trying to justify things and misled Claudia and Ben as to what we discussed,” Cooke wrote in a comment left on Tartick’s June 2024 Instagram post. “Craig NEVER asked me to invest and never offered to reconsider anything.”

Craig’s Rep Weighs In

“Craig is deeply disappointed and saddened by Kyle’s abrupt accusations,” a rep for Conover told Page Six in June 2024 after Cooke’s appearance on the “Trading Secrets” podcast. “The truth only hurts one person in this instance, and it’s not Craig. Therefore, he will not comment further on this matter nor be drawn into an unprofessional arena.”

The statement continued: “Craig has learned to blame himself and not others for everything that happens in his life, including the success of his products and companies. He looks forward to continuing to share his life with everyone and thanks all his friends and supporters, whom he views as family.”

The Cameras Were Rolling

Kyle Cooke and Craig Conover Break Down Loverboy Investment Spritz Society Drama
Courtesy of Kyle Cooke/Instagram

Conover exclusively told Us Weekly in September 2024 that his feud with Cooke was captured by the Summer House cameras. “Unfortunately for you, we did film it,” he teased, confirming season 9 highlights their issues. “That has to carry the tag of you have to wait and watch that.”

Despite their tension during summer 2024, Conover explained they had moved forward. “I love Kyle and we have a really fun history and relationship and he’s one of my favorite people on the network,” he revealed. “I’m glad I was able to go out there and you’ll get to see how that all went.”

The Fences Are Mended

“Andy [Cohen] caught me off guard,” Cooke exclusively told Us at Us Weekly + Pluto TV Reality Stars of the Year Party in October 2024, reflecting on his and Conover’s drama.

Cooke explained, “Ultimately, I cherish friendship above everything else and I think that’s why I was hurt. But [Craig and I are] good. We’re good.”

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