Of course, I’d have to include the self-titled single at some point on this list. To me, there is no better embodiment of this era than “Fearless.” While the song is more about falling in love and not being afraid to fall, it also could be interpreted as a metaphor for growing up or any type of big life change.
On the whole, though, I feel like this is such a sweet and fun song. It’s all about puppy love and finding that person you’ll be “fearless” with. As this album still remains one of Taylor’s popular, I must say that I wish this song got more love because it really doesn’t seem to. It gets overshadowed by others on the album, but I feel like “Fearless” is so sweet and fun that it was an easy middle-of-the-road pick.
3. “You Belong With Me”
Moving onto #3, this was where things got even tougher because I was trying to decide between a few songs. However, I ended up going with “You Belong With Me” here because it doesn’t seem to have the same staying power as the top two. Regardless, this song is so fun as it feels like the perfect intersection of country and pop with major crossover appeal.
Coupled with the fact that it touches a lot on unrequited love, it’s perfect for teens and adults alike. Teens tend to relate to this while most adults have gone through this at some point in their life. Let’s not even mention the fact that Taylor features Lucas Till in the music video and the iconic “I love you” notes at the end. Catch me, I’m swooning but all in all, this is a fun song and is one that can get anyone hyped upon hearing the first few lines.