‘She’s gonna hate you’: Jason Kelce admits the dating move he regrets before meeting the love of his life, Kylie

Before Kylie Kelce ever watched him fall asleep in a bar on their first Tinder date, Jason Kelce was busy making what he now calls his “crucial flaw” in dating.On a Feb. 27 hotline episode of the brothers’ “New Heights” podcast, the retired Philadelphia Eagles center told a caller that trying to perform for women instead of acting like himself backfired long before he married Kylie in 2018.

Jason Kelce says trying too hard was his ‘crucial flaw’ before Kylie Kelce

Asked how to ask a girl out, Jason did not sugarcoat what went wrong for him earlier in his dating life. “Don’t try and make her like you because then she’s gonna hate you,” he told the caller. “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 approach led to plenty of rejection and overthinking instead of a real connection.

According to Jason, forcing a version of yourself you think women want usually does the opposite of what you intend.The 38-year-old also reminded listeners he is not pretending to be some smooth operator now just because his marriage is public. “I still don’t really know how to talk to women. I’m a f**ing Neanderthal,”* he joked. “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.”That lines up with how the couple has talked about their origin story. Jason first met Kylie on Tinder in 2014, and he has said 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 message now is simple: stop trying to script every move. Take the “no” if it comes, move on, and let the right person like you for who you actually are.

Travis Kelce’s rule for guys who overthink asking someone out

Travis Kelce, who announced his engagement to Taylor Swift in August 2025, backed his brother and went straight at men who talk themselves out of even starting the conversation. “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 told the caller.His blueprint was basic on purpose. First, figure out what you genuinely like about her. Then say it. He laid it out as a step-by-step:“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 like how kind she is?” Once you know that, he said, you compliment that one thing and read her reaction to see if there is any interest.From there, both brothers ended up at the same rule: stop circling and just ask. Jason cut the whole thing down to one line: “Here’s what you do, you ask her out.” Travis agreed. “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?”Coming from a guy whose failed friendship-bracelet bit on “New Heights” in 2023 turned into a relationship, and later an engagement, with Swift, that attitude is not theory.

Swift herself told Time that “this all started when Travis very adorably put me on blast on his podcast, which I thought was metal as hell,” before they quietly started dating that summer.Put together, the Kelce brothers’ hotline segment was not some polished dating seminar. It was two Super Bowl champions telling guys who listen to their show the same thing they learned the hard way: be yourself, stop running plays in your head, and ask the question out loud.