1) I feel like if they want to stay on the downlow then making up a secret identity and having it instantly rank up to A and do the more flashy and difficult quests is actually the best route. People will ask questions but nobody that doesn't know the MC's personality will know its him.
2) Valentine's day is so unnecessarily stressful in Japanese culture. Plus maybe it's just me being America, but I think it's a lot cuter when chocolate is the consolation prize and a personalized gift or amazing stuffed animal is the romantic gift.