This song tells of an encounter between two high school classmates a decade later. The two friends bring each other up to date and share with each other the hard life lessons they've learnt along the way.
Pat Monahan trades vocals with the country singer-songwriter Ashley Monroe on this song. The songstress takes the part as a single mom whilst Train's frontman sings of maybe wanting to be more than friends with her after their chance encounter. Monroe is best known for being a member of the all-female trio Pistol Annies as well as co-penning several of Miranda Lambert's cuts.
The song is Pat Monahan's second hookup with a Nashville female vocalist following their collaboration on Martina McBride's version of "Marry Me."
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