Jason Kelce's Honest Confession About His Dating Mistakes
Before Kylie Kelce ever witnessed her future husband doze off in a bar during their first Tinder date, Jason Kelce was busy making what he now openly describes as his "crucial flaw" in the dating world. On a recent February 27 hotline episode of the popular "New Heights" podcast he hosts with his brother Travis, the retired Philadelphia Eagles center offered blunt advice to a caller, reflecting on his own pre-marriage missteps.
The Problem With Trying Too Hard
When asked how to approach asking a woman out, Jason did not hold back in analyzing what went wrong for him before he married Kylie in 2018. "Don't try and make her like you because then she's gonna hate you," he told the caller candidly. "This was my crucial flaw with talking to females. I was like, 'Okay, how do I impress them? Or how I would think that I need to talk any differently?'"
He admitted that this performative approach led to numerous rejections and excessive overthinking, rather than fostering genuine connections. According to Jason, forcing a version of yourself that you believe women desire typically backfires, achieving the opposite of your intentions.
Embracing Authenticity Over Performance
The 38-year-old Super Bowl champion was quick to clarify that he is not presenting himself as a dating expert now, despite his public marriage. "I still don't really know how to talk to women. I'm a f**ing Neanderthal," he joked self-deprecatingly. "My wife, Kylie, reminds me every single day. But I think you just ask her out and then you go on a date and then you go from there. I wouldn't worry too much about it, bud."
This perspective aligns perfectly with how the couple has recounted their own love story. Jason first connected with Kylie on Tinder back in 2014, and he has famously stated in his "Kelce" documentary that "right away, when she walks in the door, the most beautiful woman I've ever seen. Very much like love at first sight."
His core message today is refreshingly straightforward: cease attempting to script every interaction. Accept a "no" if it comes, move forward, and allow the right person to appreciate you for your true self.
Travis Kelce's Supportive Brotherly Advice
Travis Kelce, who announced his engagement to global music icon Taylor Swift in August 2025, strongly supported his brother's viewpoint and directly addressed men who overthink initiating conversations. "Who you are is good enough, bud. No, you're doing too much. That's what Jason's [saying]. Just be you, man, who you are is enough for the right person," Travis emphatically told the caller.
His proposed method was intentionally simple and practical:
- First, identify what you genuinely admire about her.
- Then, express that compliment sincerely.
- Observe her reaction to gauge mutual interest.
"I think first you gotta figure out what do you like about her? You like the way she looks? She likes the way she dresses? You like how funny she is? You like how kind she is?" Travis elaborated. From that point, both brothers converged on the same fundamental rule: stop hesitating and simply ask. Jason distilled it into one powerful line: "Here's what you do, you ask her out." Travis concurred wholeheartedly. "Yeah, there's no other way around it other than you just gotta just gotta do it, man. You just gotta own it. You gotta have some cojones. What's the worst she's gonna say? No?"
Real-World Proof From High-Profile Relationships
This advice carries significant weight coming from Travis, whose own failed friendship-bracelet segment on "New Heights" in 2023 unexpectedly blossomed into a relationship, and ultimately an engagement, with Taylor Swift. Swift herself confirmed to Time magazine that "this all started when Travis very adorably put me on blast on his podcast, which I thought was metal as hell," before they discreetly began dating that summer.
Collectively, the Kelce brothers' hotline segment was far from a polished, corporate dating seminar. It was two accomplished athletes sharing hard-earned wisdom with their audience: embrace authenticity, halt the mental rehearsals, and courageously voice the question.
