Tagged friends to enemies

Chris and Alice have known each other for what seems like forever, best of friends and near inseparable. That is until Chris realizes he's fallen in love with Alice and asks her out. Sadly for him, she doesn't feel the same way and it makes things awkward. Even more sadly, he keeps asking and awkwardness becomes distance. He's finally ready accepts things for what they are, when he finds out she likes girls the same way he does. Seeing this as the missing piece, he enlists his roommate to help make him feminine enough to try again. What would you do to fix something precious, that you broke? How far would you go just to tell yourself you tried your best? What would you let be done you?