One more thing... if this friend is female, hold off a little on the complete makeover.
As we all know, women love shopping! Another thing that they have ingrained in them from childhood is playing "Barbie and Ken." Use this to your advantage. And slip this into your conversation during your date: "Say F, I've decided I need a complete makeover. I'm going shopping on Saturday for a new me. I'd really appreciate if you could come with me and share your opinion." Girls love this stuff. I swear!
Advantages: 1) You have a fun filled day with a friend 2) You get a woman's opinion on what makes you look hot. 3) You get a boost in self-esteem.
Oh... and later... IF your WAW mentions anything. e.g. "I see you got a new shirt." (sniffing snootily...) You have a wonderful opportunity to drop a hint. "Oh yes, "I" like it. You should see all the stuff my friend helped me pick out for myself." .... if she says, "Who?" ... Answer: "Oh, no one you know." and keep it evasive. She doesn't deserve to know what's going on in your life.
M:11 | T:12 | Status: Married 4C's of WAS communication: Cool, Calm, Collected and CONFIDENT