If you spent any time watching MTV in the late 1990s, you remember the chaos. Carson Daly was basically the king of Times Square, standing in front of those TRL windows while screaming teenagers shook the glass. And Jennifer Love Hewitt? She was the undisputed "It Girl" of the era, fresh off I Know What You Did Last Summer and Party of Five.
When the news broke that they were dating, it felt like the ultimate crossover event. Two of the most famous people in the world, young and seemingly perfect. But the way it ended became a piece of Hollywood lore that’s still kinda hard to believe.
The Whirlwind Romance
They started dating in 1997. Honestly, it was a match made in teen-magazine heaven. For about a year, they were everywhere. Red carpets. Movie premieres. You’ve probably seen the grainy photos of them at the 1998 MTV Video Music Awards—Carson with his signature gelled hair and an oversized suit, Jennifer in that iconic black sparkly mini dress.
It wasn't just a casual fling either. Carson was so all-in that he actually got a tattoo of her name. Think about that for a second. Getting a permanent tribute to someone when you’re both in your early twenties and living under a microscope is a bold move.
Daly later admitted he used to fly to Los Angeles every single weekend just to see her for twenty-four hours before heading back to New York for his TRL duties. He was doing everything a guy is supposed to do to make a long-distance relationship work. Or so he thought.
The Breakup That Heard 'Round the Radio
Now, this is where things get weird. Very weird.
📖 Related: Jennifer Garner Kids: What Most People Get Wrong
Imagine waking up, turning on the radio, and hearing a shock jock tell you that your girlfriend has dumped you. That’s exactly what happened to Carson. In 2000, he told People magazine that he found out his relationship was over because he heard Howard Stern talking about it on the air.
"I woke up to Howard Stern telling me my relationship with Jennifer was over," Carson said.
Talk about a gut punch. If that wasn't enough, he then switched to E! and saw Steve Kmetko reporting that, according to the Associated Press, the couple had officially split. Jennifer’s publicist had apparently released a statement before she even bothered to tell the guy who had her name tattooed on his body.
He was publicly humiliated. Basically, the whole world knew he was single before he did.
What Most People Get Wrong
There’s a common misconception that there was some big, dramatic fight that led to this. According to Carson, there wasn't. He claimed he didn't even know anything was wrong. To him, the split wasn't "mutual," despite what the official PR statements said at the time.
🔗 Read more: Bad Celebrity Plastic Surgery: Why Hollywood’s Best Surgeons Still Get It Wrong
Jennifer, for her part, has been a bit more vague about the specifics over the years. When she appeared on Carson’s late-night show, Last Call with Carson Daly, in 2005, the tension was palpable but they were surprisingly civil. Carson didn't hold back, though. He told her straight to her face: "It ended a little weird, I got to be honest."
She didn't deny it. She just kinda shrugged it off, saying the "how" didn't really matter anymore.
The Aftermath and the Tattoo
What do you do with a "Jennifer" tattoo when you're dating someone else? You cover it up.
When Carson started dating Tara Reid a few years later, she (understandably) wasn't a huge fan of the ink. He ended up getting it covered with a design that looked like a crab claw coming out of a pocket knife. It’s a very 2000s solution to a very 1990s problem.
Surprisingly, there isn't much bad blood left. In 2018, Jennifer posted a throwback photo of the two of them on Instagram. She captioned it: "Wow that was a long time ago." She even had to jump into the comments to clarify that they were still on good terms because people started speculating that they were feuding.
Lessons from the TRL Era
Looking back, the Carson and Jennifer saga is a perfect example of how brutal celebrity culture was before social media. Today, stars can post a "we've decided to part ways" message on Instagram and control the narrative. In 1998, you were at the mercy of publicists and radio hosts.
If you’re wondering what to take away from this bit of nostalgia, it’s basically this:
- Communication is everything. Even if you’re a mega-star, don't let your publicist do your dirty work.
- Think twice about the ink. Tattoos are permanent; celebrity relationships usually aren't.
- Time heals. If Carson Daly and Jennifer Love Hewitt can laugh about a breakup that played out on Howard Stern, most of us can get over our awkward exes too.
Both have moved on to very different lives. Carson is a staple on the Today show and a father of four with his wife, Siri Pinter. Jennifer is married to Brian Hallisay and has her own family. The "weird" ending is just a footnote now, a relic of a time when MTV ruled the world and everyone was just trying to figure it out in front of the cameras.
If you want to revisit the era, go look up that 2005 Last Call interview. It’s a masterclass in "ex-etiquette" and a reminder that even the most public humiliations eventually just become a good story to tell at a dinner party.
To keep your own relationship history from becoming a tabloid headline, prioritize direct honesty over PR-style avoidance. If things are ending, make sure the person involved is the first to know—not the local DJ.