Fans Think Vanessa Carlton's Dating History Suggests She Had a Crush on Glenn Howerton

As fans celebrate the 22nd anniversary of Vanessa Carlton's hit “A Thousand Miles,” many questions come to mind. Who is the song about?

Jamie Lerner - Author

Feb. 15 2024, Published 12:56 p.m. ET

John McCauley and Vanessa Carlton perform during the All Hands On Deck! Tornado Relief Show at City Winery Nashville on March 10, 2020
Source: Getty Images

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.

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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?

Vanessa Carlton singing and playing piano
Source: Getty Images
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Vanessa Carlton’s dating history led people to believe “A Thousand Miles” could be 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.

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John Mayer (2002)

Vanessa Carlton and John Mayer onstage at the 45th GRAMMYs
Source: Getty Images

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).

Stephan Jenkins (2002–2007)

Stephan Jenkins and Vanessa Carlton at a Sundance event
Source: Getty Images

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.”

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John J. McCauley (2012–Now)

Vanessa Carlton, Skye Steele (L), Adam Landry, and Vanessa's husband John McCauley at The Sayers Club on Sept. 15, 2015
Source: Getty Images

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.

“A Thousand Miles” is about actor Wes Bentley, according to fans.

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.'"

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"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.

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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."

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Fans sleuthed on who was at Julliard around the same time Vanessa was studying ballet in New York City and several now-famous actors came up. Glenn Howerton was one of the most notable who seemed to fit into the timeline and Vanessa’s “type” based on her dating history. But one fan said on Reddit, “It's Wes Bentley. I'm part of a Vanessa Carlton Facebook fan group, and someone on there said that Vanessa actually confirmed it was Wes Bentley at a show several years ago.”

Glenn Howerton and Wes Bentley at separate events
Source: Getty Images

We can’t confirm or deny who the song is about without Vanessa’s recorded confirmation, but for now, we’ll have to take her fan’s word for it! For those who aren't familiar with Wes Bentley, he’s known most for his roles as Jamie Dutton in Yellowstone, Seneca Crane in The Hunger Games, and Doyle in Interstellar, among others. But now Vanessa is in a happy relationship with her husband, so VaWessa will just have to be the celeb couple that never was.

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