Switch up date
Tell someone like Ehren that you set then up with someone hot. But in order to go out with her he has to get a makeover. Tell him she is a playmate. If he doesn't believe you give him a picture of a playmate. If he still doesn't believe you then call her up and have her talk to him. (It can either be the actual playmate or someone posing as her). Give him the playmate's turn on and offs. So when he agrees take him to get the make over. Makeover example: Get a really jacked up hair cut and dye it, Get him a spray on tan, Wax everything and I mean every thing, and get rally stupid clothing, When the makeover is over take him to his favorite place to eat and make him wait there. Have some ugly man or woman go over to him and claim he/she is the playmate from years ago or from playgirl or a gay guy that had a sex change.