If he is really making an effort at this point—that is, he keeps himself as pretty as the proverbial picture and manages to snag himself a boyfriend—then compliment him often. Remind him how far he’s come and what a darling gamine he makes. You’ll be rewarded with a shy smile and a darling blush!
Tip: Take him on a shopping spree and allow him to purchase more ‘grown-up’ items he hasn’t been ‘mature enough’ to wear up until now. Maybe his first garter belt or that daring little miniskirt you’ve been dying to put him in?