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Travis Kelce’s 2016 Dating Dealbreakers Clip Spills Major Tea

Travis Kelce’s 2016 Dating Dealbreakers Clip Spills Major Tea
  • PublishedAugust 6, 2025

Greetings, joyous audience. I am Kai Montgomery, your resident grumpy guru who rolls eyes at the obvious before breaking it all down. Oh, fantastic. If Travis Kelce and Taylor Swift fans thought the superstar tight end had no skeletons in his romantic closet, a resurfaced 2016 clip from Watch What Happens Live proves otherwise.

In this long-buried clip, Kelce laid out his X-rated rules for budding relationships with guest Ramona Singer, who immediately gaped in stunned silence. As he recounted to host Andy Cohen, he expected to share the sheets by the third date or he was out. By the time he hit date number three, Kelce believed it was only fair that the “grand finale” unfold, especially after he’d treated her to fancy dinners and experiences on dates one and two.

Ramona’s shock prompted him to elaborate. If the spark didn’t turn into intimacy, he admitted, it felt like throwing money and effort into a void. “No hard feelings,” he said, “but if I’m spoiling you and we’re not getting intimate, I’m rethinking the whole thing.” He even declared that refusing oral sex ranked as a total dealbreaker. The kicker was his insistence on reciprocity—what goes around must come around according to Kelce’s old playbook.

That wasn’t all. In a move that had Ramona raising her eyebrows, he weighed in on cosmetic enhancements. Fake breasts were absolutely fine in his book provided the wearer carried them with confidence and flair. According to Kelce, an assured attitude makes any enhancement a power move rather than a turnoff.

This throwback moment arrives at a curious time when Kelce’s dating life is under a microscope thanks to his high-profile romance with Taylor Swift. Unlike his candid 2016 persona, he’s playing it much closer to the vest now, suggesting he’s swapped oversharing for strategic silence. Fans might wonder whether his old dealbreakers still apply or if love with Swift has rewritten his rules.

For context, Kelce appeared on Watch What Happens Live as part of a promotional circuit for his short-lived dating show, where oversharing was practically a requirement. Fast forward seven years and a multi-million-dollar NFL career, and it seems the gridiron legend has learned when to keep his dating advice under lock and key.

In conclusion, this resurfaced footage sheds light on the playbook that once defined Kelce’s approach to romance. Whether you judge him for setting such strict standards or praise his honesty, it makes you think twice before going on a third date unprepared. And that, dear reader, is why we can’t have nice things.

Sources: Celebrity Storm and TMZ
Attribution: Creative Commons Licensed

Written By
Kai Montgomery

Kai Montgomery is a trailblazing journalist with a talent for breaking down the latest celebrity news with a sharp and unique perspective. Their work blends boldness with authenticity, capturing the essence of Hollywood's most talked-about moments while never shying away from the hard truths. Known for their fearless reporting and eye for detail, Kai brings a fresh voice to entertainment journalism. Outside of writing, they’re an avid traveler, lover of street art, and passionate about fostering inclusivity in all aspects of media.