Cheesy, overused, and run-of-the-mill pick up lines don’t work… unless you’re Kylie Kelce. My feature in The List explains how she opened the door to love with Jason. #celebritynews #pickuplines #tinder #KylieKelce #JasonKelce
Jason and Kylie Kelce, known for their humor, charm, and genuine connection, have become one of sports’ favorite couples. Together since 2015 and married in 2018, their relationship seems like a fairytale—but their beginning was anything but typical.
They met on Tinder, and Kylie had no idea Jason played in the NFL. Thinking he was just a regular guy, she jokingly tested out her best pickup lines. When “I’ve fallen and I can’t get up” didn’t get a reply, her cheeky UPS line finally caught his attention with, “If I told you I worked for UPS, would you let me handle your package?” To which he finally responded.
Journalist Emily writes, “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
Though their first in-person meeting was rocky, the night Jason Kelce and Kylie first met at a bar turned out to be unforgettable—at least for Kylie. Jason admitted he couldn’t remember most of it, but one moment stood out clearly. On his “New Heights” podcast in September 2023, he recalled being sober enough to realize Kylie was the most beautiful woman he’d ever seen, calling it love at first sight. Kylie later teased that Jason didn’t believe in love at first sight—until he met her.
Emily continues, “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 right
On a 2025 Valentine’s Day episode of Kylie’s podcast, “Not Gonna Lie,” the couple recalled their second date—an ice skating trip to Penn’s Landing. Jason admitted to loudly farting while tying his skates, joking there was no way to play it off. Kylie, trying to hold in laughter, remembered thinking she couldn’t be crying from laughing when he looked up. Their story highlights the humor and comfort they share in their relationship.
Despite the rocky start, Kylie soon fell for Jason, saying, “At the very beginning, we would sit and talk for hours — it was insane how long these conversations would go on.”
Emily concludes, “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.”‘
