The Cheesy Way Kylie Kelce Pursued Jason: How The Couple Hit It Off
With his goofy antics and soft, girl-dad side, and with her authenticity and wit, Jason and Kylie Kelce quickly became one of the sports world's most beloved couples The odd-ball couple has been together since 2015, tying the knot in 2018. Their fairytale love story is one for the books, but when you get the inside scoop on how they met, you might think differently.
The couple were initially connected via Tinder, and Kylie has expressed how none of Jason's profile alerted her to him being an NFL player. Thinking this was just some Joe Shmo, she decided to cheekily drop some of her best pickup lines. She told Alex Cooper on "Call Her Daddy" in February 2025 that when "I need Life Alert. I've fallen, and I can't get up," didn't work, she tried, "If I told you I worked for UPS, would you let me handle your package?" To which he finally responded.
The List asked relationship expert Susan Winter, creator of the "Love À La Carte Method," for her opinion on opening dialogue with quippy satire, and she advised to steer clear of the red flag if one's in search of a meaningful connection. "Cheesy, overused, and run-of-the-mill pick up lines are not going to create a connection in online dating. Trite pickup lines signal minimal effort and a lack of creativity. It's not a far leap to imagine you'll be lazy, boring, and superficial in real life," she said. She added, however: "Naughty pick up lines 'could' work if the recipient is looking for a casual dating situation. But even the naughty lines have to be clever and show originality or they'll simply appear as lewd." As she mentioned on the podcast, that's exactly what Kylie and Jason were looking for.
Their first in-person meeting should've been the end of their story
Despite having a turbulent take off, when Kylie and Jason Kelce first met in-person, believe it or not, it was worse. Jason had invited Kylie out to a bar one night, and the rest, as they say, is history, mostly because Jason doesn't remember it. What he does remember, though, was his first impression of Kylie. During an episode of his "New Heights" podcast from September 2023, he recounted: "I was sober enough to know it was the most beautiful woman I had ever seen in my life. It was love at first sight." Kylie joked that he didn't believe in such a thing until he had met her.
Meeting her was all that happened, though, as Jason fell asleep on the bar 45 minutes later, which he admitted was "not a good first date." No kidding. We asked Susan Winter about the importance of having meaningful conversation as the foundation for a healthy relationship. "Conversations that have depth will always serve you well," she said. "Not only do they prove there's more to you than looks, but they serve as connection points. The more topics of conversation at hand, the greater the odds your online match will feel drawn to you via mutual interest."
The Kelces finally got it right on their second date
During the Valentine's Day episode of Kylie's podcast, "Not Gonna Lie," in 2025, the couple told the story of their second meeting, an ice skating date. "We went ice skating at Penn's Landing where I farted tying my skates when I bent down," Jason joked. "I couldn't even play it off because it was so audible. There was no way to get out of it." Poor guy. Good thing Kylie has a sense of humor, "The issue was that at that moment I was like, 'You cannot be crying laughing when this man picks his head up.'"
Despite the gaffe, the couple was able to come out the other side, with Kylie admitting on "Call her Daddy" that she was falling in love with Jason after two months of dating. "At the very beginning, we would sit and talk for hours — it was insane how long these conversations would go on," and it's a good thing they did.
Susan Winter shared with The List that these kinds of chats are crucial for building a strong relationship. "This skill set and foundational framework is necessary for a healthy relationship. Relationships bring challenges as well as joy. If you're comfortable with deep conversations in the beginning, you'll both be more comfortable when the topic is challenging." She continued to reveal the detriment that comes from avoiding the sometimes difficult task. "This process also gives you valuable information about your prospective mate. Are they rational? Are they able to disagree but find a way to listen and value your opinion? Or are they hotheaded, dogmatic, and judgmental? Knowing these things upfront saves you time and energy on a relationship that would decompose at the first disagreement."