The entire record had already been written and the band was preparing to enter the studio to record it when manager Rick DeVoe informed the trio he felt it lacked a catchy, "feel-good" song. DeLonge and Hoppus each went home that night, with the two emerging with what would become the two biggest singles from the album, "First Date" and "The Rock Show". "First Date" was inspired by DeLonge and wife Jennifer Jenkins' first date at Sea World in San Diego. "I was about 21 at the time and it was an excuse for me to take her somewhere because I wanted to hang out with her," said DeLonge. The track was written as a summary of neurotic teen angst and awkwardness.
The video features the band in mid-1970s attire, suggestive of bands such as the Bee Gees. The end of the video has spoof titles as to what band members are doing now, similar to the end of the 1978 film National Lampoon's Animal House.
There are two versions of this music video, the longer version includes two band members talking in the beginning. At the start of the longer version, before the band begins playing, Tom DeLonge tells Mark Hoppus how he ended up kissing his brother. Hoppus replies, "You know what they say: 'Like Father, Like Son.'" Tom DeLonge says, "You said it best, brother." It also includes an interruption where in the video a baseball bat flies out of the hands of Chad Gilbert of New Found Glory and ends up in the front tire of a girl's bicycle, causing her to flip forward over the handlebars. Her headgear scrapes the road. This happens after the line, "I'm probably gonna miss."