Author's Summary: When Blaine Anderson gets a fresh start at McKinley High in 1997 thanks to his best friend Rachel Berry, her parents, Emma Pillsbury, and the group of misfits that would become the New Directions, the last thing he expects to gain from playing it straight and dating Quinn Fabray is a daughter at the age of sixteen. Fast forward to present day, where Blaine is raising Sugar as a single dad in the same sleepy town of Lima he grew up in. When Sugar is recruited at the beginning of her sophomore year by Will Schuester to join New Directions and falls deeply in love at first sight with one of the co-captains, Blaine isn’t sure what to think, especially since Kurt Hummel is quite out of her league, being three and a half years older and, well, gay.