B.J. Novak Confesses to a ChatGPT 'Flirtation' Live on CNN

B.J. Novak admitted on live television to having a 'flirtation' with OpenAI's ChatGPT during CNN's New Year's Eve broadcast on 31 December.

Novak, an actor, writer, and comedian best known for playing Ryan Howard on The Office, appeared as a guest comedian alongside hosts Anderson Cooper and Andy Cohen on the network's annual countdown special from Times Square. The admission came during a game segment called 'Agree or Disagree,' in which the trio responded to a series of statements by holding up paddles, Mediaite reported.

The group was presented with the prompt: 'Have you ever had feelings towards a chatbot?'

Cooper flipped over his 'disagree' sign. Cohen did the same. Novak raised his green 'agree' paddle.

'You have?!' Cohen said, as both hosts turned quickly towards Novak.

Novak said he had experienced a 'flirtation' with a chatbot but did not go into detail. Cooper followed up by asking whether the AI in question was Claude, the chatbot developed by Anthropic, or a different platform altogether.

Novak called that a 'great question' and identified the chatbot as OpenAI's ChatGPT.

'Claude is all business,' he said.

Novak did not say more about the nature or duration of the interaction. Neither Cooper nor Cohen pressed him further on the subject before the segment moved on.

Chatbot Prompt Followed Cheeseburgers Debate on Air

The chatbot question came directly after another prompt in the same segment that had already produced an unpredictable moment. Cohen had read the statement: 'I would rather give up oral sex than cheeseburgers.'

Cooper refused to participate. 'I'm not participating,' he said, shrugging. 'I'm taking myself out.'

Cohen raised his 'agree' paddle. Novak, after a brief pause, held up 'disagree.' He joked that keeping kosher made the decision straightforward. He then turned to Cooper and said, 'Focus, Andy.'

The segment was one of several unscripted exchanges during the evening. Earlier in the broadcast, CNN correspondent Randi Kaye kissed a snake on air during a live report from a reptile-themed event, drawing laughter from Cooper and Cohen in the studio. Cohen also told viewers he had given his bed to Cooper and had 'black lighted' it before handing it over.

Novak's ChatGPT Remark Follows Year of AI Companion Coverage

OpenAI's ChatGPT now has more than 300 million weekly users worldwide. The platform expanded its voice mode features throughout 2025, making interactions with the software feel increasingly personal and conversational.

Reports throughout the past year documented multiple cases of users forming romantic or deeply personal attachments to AI chatbots.

In November 2025, a Japanese woman named Yurina Noguchi held a ceremony in Tokyo to 'marry' a ChatGPT-generated persona she had named Klaus, CNN reported. The union carried no legal standing in Japan.

Cooper's question about whether Novak's chatbot was Claude or ChatGPT reflected growing public familiarity with competing AI products. Anthropic's Claude and OpenAI's ChatGPT are the two most widely used consumer chatbots in the United States, and their commercial rivalry escalated sharply in early 2026 when Anthropic aired Super Bowl adverts criticising OpenAI's decision to introduce advertising into ChatGPT. OpenAI executives publicly pushed back against the adverts.

CNN's New Year's Eve special, now in its ninth consecutive year with Cooper and Cohen as co-hosts, aired live from Times Square beginning at 8:00 p.m. ET and ran until 12:30 a.m. ET on 1 January. The broadcast was also available on CNN's streaming subscription platform and its mobile app. Coverage then shifted to Austin, Texas, where Sara Sidner and Cari Champion took over for the central time zone countdown.

Performers on the broadcast included Shakira, Robyn from Times Square, Bryan Adams from Madison Square Garden, and Florence + The Machine. Other guests included Stephen Colbert, Amy Sedaris, Brandi Carlile, Patti LaBelle, Rebecca Romijn, Jerry O'Connell, and comedians Leanne Morgan and Sarah Sherman.

Novak has not commented further on his ChatGPT use since the broadcast.