AMAGAMI - SINCERELY YOURS

Amagami - Sincerely Yours summary:

Based on the visual novel by Enterbrain with the same name. A second-year high school boy finds himself uneasy during Christmas time due to an experience in the past. However, this year at Christmas, he gets his last chance to ask out a graduating female senior named Haruka Morishima or one of several other classmates. The story of the anime will be arranged in an omnibus format, with each heroine getting her own version of the story animated. Each heroine will sing her own version of the ending theme song.