Kyle Cooke breaks down Craig Conover investment drama timeline after ‘WWHL’ shade

Kyle Cooke breaks down what happened when Craig Conover invested in a competing alcohol brand to his Loverboy. Jason Tartick/Youtube

Loverboy founder Kyle Cooke admits he “let [his] emotions get the best of [him]” amid Craig Conover’s decision to invest in a competing alcohol brand.

“Craig never expressed interest [to invest in Loverboy]. He never once asked to invest in Loverboy,” the “Southern Charm” star said on Monday’s episode of Jason Tartick’s “Trading Secrets” podcast.

Instead, Conover became an investor in sparkling wine company Spritz Society.

The “Summer House” star said Conover “never once asked to invest in Loverboy” before investing in Spritz Society. Instagram/@drinkloverboy Cooke said he and Conover talked about the investment for the first time in February. Blake Shorter/Spritz Society

Cooke, 41, went on to share that in “early February,” Conover, 36, was in New York City and asked him to grab drinks, where his co-star “sprung this collaboration” idea on him to initially invest in Spritz Society.

“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 [with Spritz Society] and please hold off from signing anything. I’d love to put an offer on the table to kinda counter it [with Loverboy],’” Cooke claimed.

The two had a brief “back and forth” before “Craig essentially said it was too late.”

Cooke claimed that he tried to give Conover an investment opportunity for Loverboy, but “it was too late.” Instagram/@drinkloverboy ”Was I disappointed? Absolutely,” Cooke admitted on Monday’s episode of the “Trading Secrets” podcast. Instagram/@drinkloverboy

“Was I disappointed? Absolutely,” he admitted. “Like, here’s a good friend of mine. I just figured he’d at least give me an opportunity to hear me out. And, 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 also addressed Spritz Society co-founder Claudia Oshry’s claim that Conover told Cooke he would “invest in you if you don’t want me to do Spritz,” but Cooke “said no.”

“Someone said Craig gave me the offer to reconsider, because I had not given him an opportunity to invest in Loverboy, which is not true. He just never asked. I would have loved for him to do exactly that…that just never happened,” Cooke claimed.

Cooke said he “would have loved” for Conover to invest with him. Blake Shorter/Spritz Society “I just figured he’d at least give me an opportunity to hear me out,” Cooke said. Jude Domski/Bravo

Cooke also denied Oshry’s claim that he doesn’t offer equity. He said he has “had investors since 2019,” is “not a sole owner” of Loverboy and was filming Season 2 of “Winter House” with Conover when Cooke was “very vocal” about fundraising.

The “Traitors” alum went on to discuss his dinner with Oshry’s husband, Spritz co-founder Ben Soffer, which took place on Feb. 7 – “about two weeks before” Conover told him about his opportunity with Spritz.

At the time, Cooke said he actually “really enjoyed the conversation” with Soffer. However, he found it “odd” that the businessman spent time with Conover just one day later and wasn’t “transparent” about their meeting.

The “Traitors” alum also went into detail over his dinner with Spritz Society co-founder Ben Soffer. Sara Feigin/Page Six Cooke said he actually “really enjoyed the conversation” with Soffer. Instagram/@drinkloverboy

“If Ben was spending three hours with me and three hours with Craig in a 24 hour period, he didn’t tell me that he was talking to Craig, and he didn’t tell Craig he had dinner with me, and I just found that odd,” Cooke said. “I just wish he was a little more transparent with his intentions.”

Cooke clarified that more than anything else, he was just “bummed” about how everything transpired with Conover, because he “thought [they] were good friends.”

“I just didn’t think one of my good friends would go hop in bed with a competitor, and so that’s it,” he said.

Cooke clarified that more than anything else, he was “bummed” about Conover not considering their friendship more. Instagram/@drinkloverboy “I just didn’t think one of my good friends would go hop in bed with a competitor, and so that’s it,” he said. Blake Shorter/Spritz Society

However, Cooke did confess that he has been “beating [himself] up for letting [his] emotions get the best of [him]” when he went off on Conover’s “wack” investment on “WWHL” two weeks ago.

“I wish I wasn’t so reactionary, [but] at the end of the day, I don’t really think anything I said was not true, but I could’ve handled it better,” he said.

Cooke said he hasn’t chatted with Conover since the episode aired, but “hopes to have a chance” to “squash the beef” and “tell him straight up, ‘I’m sorry for being reactionary.’”

Cooke also addressed his “reactionary” comments on “Watch What Happens Live” two weeks ago. Charles Sykes/Bravo “I don’t really think anything I said was not true, but I could’ve handled it better,” he said. Charles Sykes/Bravo

“I’m not gonna let this hopefully interfere with our friendship. I just wish the friendship was taken into a little more consideration, or maybe I have a different interpretation of our friendship,” Cooke concluded.

Cooke made headlines for his appearance on “WWHL” last month when host Andy Cohen pointed out how “upset” he looked after asking him about Conover’s investment with Spritz.

“Look, I wish him the best, but the way he handled it … it really rubbed me the wrong way, and I’m just trying to take the high road,” he said on the May 23 episode.

“I just wish the friendship was taken into a little more consideration,” Cooke concluded. Instagram/@drinkloverboy The “Southern Charm” star has not responded to Cooke’s comments. Blake Shorter/Spritz Society

Cooke further claimed that Conover “lied” to him about investing in the “copycat” company and called the entire ordeal “shady.”

Conover has yet to respond to any of Cooke’s claims. Oshry addressed all of Cooke’s “WWHL” comments on a May 25 episode of her podcast, “The Toast.”

After claiming that Conover offered to invest in Loverboy instead of Spritz, Oshry went on to call Cooke a “liar,” told him to “eat my ass” and shut down his claim that Soffer “milked him” for information.