The song, "Hey There Delilah" was inspired by Delilah DiCrescenzo, a Columbia University graduate, and steeplechase runner training for the 2008 Olympic trials.

There was never a relationship between Tom Higgenson and DiCrescenzo, but Tom was inspired to write a song about her soon after they were introduced by a mutual friend:

"There was never anything between us. It was kind of funny — kind of sad, actually. The story of my life... I thought she was the most beautiful girl I had ever seen. I told her, 'I have a song about you already.' Obviously, there was no song. But I thought it was smooth..." ”

It took over a year for Tom to write the song. However, the real life Delilah, who wasn't interested in Tom because she was already in a relationship, was not sure how to deal with the pressure of having a song written about her:
"It was so beautifully written", she says. "There was pressure to live up to this ideal. I didn't know how to be polite but, you know, ditch him."

DiCrescenzo also says of the song, "When I'm at the gym, it's playing; when I'm at the pool, it's playing. Part of me wants to scream at the top of my lungs that it's about me. Another part of me wants to cower and say it's not."

He says, "If we had lived happily ever after, then what would my next song be about?"