What Is Vanessa Carlton’s Dating History? Love Life Details

Everyone knows almost every lyric of “A Thousand Miles” by Vanessa Carlton, but she never revealed who it’s about. On Feb. 13, 2024, we celebrated the 22nd anniversary of the historic bop, which has one of the most iconic piano riffs of all time. But as Twitter celebrated Vanessa’s first major hit, some people theorized that Always Sunny star Glenn Howerton is the subject of Vanessa’s desire in the song.

In 2021, Vice shared a 20-minute interview with Vanessa in which she talked about the making of “A Thousand Miles” and revealed a bit about who it’s about. While she doesn’t name names, fans have come up with theories over the years and have even revisited her dating history to figure out if they’re right. So what’s Vanessa’s dating history and is “A Thousand Miles” about Glenn Howerton?

Before she got married in 2013, Vanessa had a public dating history as her pop music career developed. After looking through the history, one Redditor found that Vanessa had “a type” that could confirm the Glenn rumors.

John Mayer has seemingly dated every woman in the music industry, and Vanessa is no exception. Little is known about their relationship as the two rose to fame, but it allegedly lasted less than a year. Vanessa confirmed the relationship, according to the New York Daily News (via Bustle).

Vanessa continued dating musicians with Stephan Jenkins, the frontman of Third Eye Blind. In 2020, she said on the Music Is My Life podcast that she worked with Stephan on several of her records, including “White Houses.” She explained, “But I just ended up from one power control freakish guy to another one, which was then my boyfriend at the time, Stephan Jenkins.” Fans have even found a link between Vanessa’s “Come Undone” and TEB’s “Dao of St. Paul.”

Vanessa and John J. McCauley got married in 2013. The wedding was officiated by music legend Stevie Nicks just two months after Vanessa was diagnosed with an ectopic pregnancy and needed emergency surgery. John is known as the singer-songwriter for the alternative rock-folk band, Deer Tick. Now, John and Vanessa share their daughter, who was born in 2015, and they live together in Pawtuxet Village in Rhode Island.

Since 2002, fans have done their due diligence to find out who “A Thousand Miles” is really about. “The song is about a crush I had on a Juilliard student,” she giggled in her Vice interview. “I would never talk to this person. I was very shy. I was like, ‘There’s just no way on God’s creation that this would ever happen.'”

“So the idea of like, you have a better chance of falling up than ever having a relationship with this person. I can’t say that person’s name because they’re a famous actor and I don’t want to say.” She confirmed that they don’t know the song is about them, continuing to use non-gendered language.

For a short time, fans suspected that the song could be about a woman since Vanessa was careful about the language she used and came out as bisexual in 2010. But this was debunked by an earlier interview Vanessa gave to MTV in 2003. “I’ll never tell,” she said when asked who it’s about. “He never knew and never will. Actually, I don’t even crush him anymore.”