‘I Tried Way Too Hard’ — Jason Kelce Admits His Biggest Dating Mistake Before Meeting Wife Kylie

Before the fairytale marriage… there was a lot of awkward trial and error.

Jason Kelce has candidly revealed the crucial flaw that nearly derailed his dating life long before he met his wife Kylie Kelce — and his honesty is striking a chord with fans everywhere.

The retired NFL star, 38, opened up during a special hotline episode of the New Heights, which he co-hosts with his younger brother Travis Kelce, as the pair answered listeners’ questions about romance, confidence, and what not to do when asking someone out.

💬 “Don’t Try to Make Her Like You”

Jason didn’t sugarcoat it when reflecting on his pre-Kylie dating days.

“Don’t try and make her like you — because then she’s gonna hate you,” he admitted bluntly.

Looking back, Jason said his biggest mistake was constantly trying to impress women instead of just being himself.

“This was my crucial flaw with talking to females,” he explained.
“I was always thinking, ‘How do I impress them? How should I talk differently?’”

The result? Overthinking everything — and missing the point entirely.

💡 Travis: “Who You Are Is Enough”

Travis, now engaged to Taylor Swift, was quick to jump in with reassurance — both for the caller and for his brother.

“Who you are is good enough, bud,” Travis said.
“You’re doing too much. Just be you. The right person will appreciate that.”

It was a rare moment of quiet sincerity between the brothers — and a message fans immediately praised for its simplicity.

😅 Rejection Happens — And That’s OK

Jason also admitted he spent far too much time chasing unrealistic expectations, joking about the number of times he’d heard the word no.

“Do you know how many times I was told ‘No’?” he laughed.
“It’s gonna be fine.”

According to Jason, rejection isn’t failure — it’s part of the process.

🎯 Keep It Simple

While Travis suggested opening with a compliment and a conversation starter, Jason boiled dating down to its most basic truth.

“Here’s what you do,” he said.
“You ask her out.”

Travis fully agreed:

“You gotta own it. You gotta have some cojones.
What’s the worst she’s gonna say — no?”

🤣 “I’m a Neanderthal”

Despite the heartfelt advice, Jason couldn’t resist poking fun at himself — admitting he still doesn’t consider himself an expert.

“I still don’t really know how to talk to women,” he joked.
“I’m a f—ing Neanderthal.”

He added that his wife Kylie reminds him of that fact daily — but insisted the formula is still simple:

“You ask her out. You go on a date. Then you go from there.”

💍 The Woman Who ‘Channeled the Bear’

Travis later appeared on Kylie’s Not Gonna Lie, where the couple discussed Jason’s limited dating history before meeting his future wife.

Travis joked:

“I had never seen him be so into someone — but I’d also never seen someone able to control the bear.”

Kylie quickly corrected him:

“Channel it.”

Travis laughed and agreed:

“Channel it — that’s a great way to put it.”

🏡 A Family Built on Authenticity

Jason and Kylie married in 2018 and now share four daughters — Wyatt (6), Elliotte (4), Bennett (3), and baby Finn (11 months).

Looking back, Jason’s biggest takeaway is clear:
Trying to be someone else never works.

Being yourself?
That’s what got him everything he didn’t even know he needed.

👇 READ MORE — inside the Kelce brothers’ most honest dating confessions yet 👇