Help choose an appropriate subject
Boosting your boy's confidence is great, but keeping it real with him is just as crucial. Nothing will stifle his swagger like getting shot down by a girl you knew he had no shot with, or who appeared entirely uninterested.
If he aks that you chat up the model chick in VIP, and he's clearly over-extending himself, you must point him in the direction of a more suitable woman without hurting his pride. "Those VIP girls are always a headache. Plus, we'll end up dropping way too much cash on bottles. How about the cute blonde drinking the beer?"
Congrats, you just avoided watching your man walk into a land mine, and saved yourself the inevitable eye rolling from Mrs. Out-Of-His-League. Win!