In 2005, The Weepies recorded a second album, Say I Am You, in the bedroom of their home in Pasadena, California; the occasional motorist can be heard passing by in the background of some of the tracks.

[2] In May 2005, after a sold-out show at The Living Room in New York City, The Weepies were approached by Nettwerk Records and signed by the label later that year.

Released in April 2008, it sold 14,000 copies in its first week and was the band's first entrance on the Billboard Top 200, charting at number 31.

The Weepies' fourth full-length album, Be My Thrill, was released in August 2010, and featured Colbie Caillat in back-up vocals on the track "I Was Made for Sunny Days."

On December 16, 2013, it was announced on the band's Facebook page that Deb Talan had been diagnosed with stage 3 breast cancer.

[9] Many songs by The Weepies have been licensed for use in films, television shows, and advertisements, including the films Sex and the City,[10] Morning Glory,[11] Adam, and Prom, as well as episodes of Grey's Anatomy,[12] Everwood,[13] One Tree Hill,[14] Scrubs, Pretty Little Liars, The Riches,[15] How I Met Your Mother,[16] Gossip Girl,[17] Kyle XY, Life Unexpected,[18] Up All Night,[19] The Fosters[20] and Sense8.

[22] Talan and Tannen have at various times been supported in recording and touring by Meghan Toohey, Catie Curtis, Brad Gordon, Jonny Flaugher, and Frank Lenz.