Emboldened by the last remaining days of high school, senior Henry Samson writes a love letter to his neighbor, Claire. But, when he runs into her at school joking and laughing with her then boyfriend, he chickens out and never tells her how he feels. Fast forward ten years, Henry returns home to celebrate his mom's fiftieth birthday. When Claire volunteers to help Henry plan his mother's party, all his old feelings resurface. Will Henry find the courage to tell Claire how he feels? Will he finally give her the letter he wrote all those years ago? Or, will he chicken out again?