According to About.com, Swift described this song at a concert she gave at Gold Country Casino as being about the best first date that she has yet to have.
Taylor Swift explained to That's Country: "This is a song about the fearlessness of falling in love. No matter how many break up songs you write, no matter how many times you get hurt, you will always fall in love again. When I wrote 'Fearless,' I wasn't dating anyone. I wasn't even in the beginning stages of dating anybody. I really was all by myself out on tour and I got this idea for a song about the best first date. I think sometimes when you're writing love songs, you don't write them about what you're going through at the moment, you write about what you wish you had. So, this song is about the best first date I haven't had yet."
One of the themes on the Fearless album is kissing. For instance on this song Swift describes the first kiss as "flawless", whilst on "That's The Way I Loved You", she sings about kissing in the rain. Swift admitted to CMT Radio that she is fascinated by the "theme of love and kissing and breaking up and fairy tales and boys." She added: "That's what I love to write songs about. It's funny how you can mention one thing, like kissing, and have it be completely different in each song and have it mean a different thing."
Swift got this song off the ground with her frequent songwriting partner, Liz Rose. She then called on songwriter Hillary Lindsey, who is best known for Carrie Underwood's hit,"Jesus, Take The Wheel
," to complete it.
Fearless was #1 on The Billboard 200 for 11 weeks, making it the longest-running #1 album since Santana's Supernatural reigned for 12 weeks in 1999-2000. It was the first LP by a female Country singer to spend over five weeks on top of the album tally and the longest-running #1 album by a solo female artist since Alanis Morissette ruled for 12 weeks with Jagged Little Pill in 1995.
Fearless spent its first 19 weeks in the Top 10 of the Billboard 200. It was the first album to do this since the Black Eyed Peas' Monkey Business dropped out of the Top 10 in its 24th week in 2005.
Fearless won the prize for Best Album of the Year at the 44th Academy of Country Music Awards. In her acceptance speech, Swift said about her autobiographical writing style: "I think a lot of people who know me know that if I talk to you for more than five minutes, I'm probably going to write a song about you, so, that being said, I'd like to thank all the characters in my songs: Abigail, Hey Stephen, Tim McGraw and Romeo." Swift added backstage to reporters that she that she "obsessed" over making the album. She said: "I labored over this album for two years. The fact that you can write songs in your bedroom about your feelings and boys and can win album of the year at the ACMs. I just didn't think that was possible."
In May 2009, this re-entered the Hot 100 at #95. Coincidentally one place below was a song by Lily Allen titled "The Fear
According to Billboard this was the best-selling album of 2009 in the US.
This won the Album of the Year award at the 2010 Grammys. For once the Album of the Year award for Swift's best selling LP of 2009 mirrored the taste of the record buying public. The 20-year-old chanteuse was the youngest artist ever to receive the award.
When this became the fifth track from Fearless to reach the country chart top 10, Swift became the first solo female to collect five top 10s on the chart from each of her first two albums. The only previous acts to achieve this feat were Brooks & Dunn and Dixie Chicks.
In August 2019, Swift announced her intention to re-record her first six studio albums following the sale of her master recordings to American businessman Scooter Braun without her permission. The first re-recorded record to see the light of day was Fearless, which Republic Records released on April 9, 2021.
So why did she drop Fearless first? One theory is the album turns 13 in 2021, and 13 is famously Swift's lucky number. She frequently sneaks in references to the number in her music and doesn't disappoint her with this release:
Swift first announced the release of Fearless (Taylor's Version) on February 11 (2 + 11 = 13).
She dropped Fearless (Taylor's Version) on April 9 (4 + 9 = 13).
The album has 26 tracks (26 = 13 + 13).
Fearless (Taylor's Version) reached #1 on the UK albums chart. It was Swift's third chart-topping album in 259 days, following Folklore and Evermore, meaning Swift broke the record for the fastest accumulation of three #1 albums. The Beatles previously held the record when their LPs Help!, Rubber Soul and Revolver all reached the summit in 364 days between 1965-1966.