My Girlfriend's Not A Slut--She Just Dresses Like One

Q:How can I convince my girlfriend to dress better without hurting her feelings? I want her to dress more conservatively, but I don't know how to tell her. I met Jill a few months ago at my friend's barbecue, and she was dressed so normal: denim overalls and sneakers. Since then, we've been on six dates and each time she's dressed so slutty: too low-cut tight tops, short skirts and trampy high heels. We bumped into some of my buddies, and they joked that she dresses like a stripper. She's not "easy," and I really like her; so what should I say?

(Submitted by TT, summarized above)

A:AMY: Good God! Denim overalls and sneakers?? That's "normal" to you? Did this barbecue have a "Beverly Hillbillies" theme? A costume barbecue? How delightful!  So you're complaining that Jill's gone from "Hee Haw" (which you liked) to Hooker (which you don't) and now you want her to "dress more conservatively" so that your buddies won't assume she's a slut. Hmmm, it's a bit confusing, but I get it, and as usual, I'm here to help. Listen, rule #1: If you like the person, you can always change the clothes. A strong sense of style can be learned. Look at stupid celebrities. They need to employ stylists to choose their socks and underwear for them. It's pathetic. FACT: Jill needs a makeover ASAP. So begin this delicate process while watching TV/movies with her. Say, "Yuck, did you see those tacky short skirts, cleavage, and trashy high heels on that actress--that's gross." Then when you see a more tastefully dressed woman, say, "Now she looks perfect to me: classy, elegant, not to much skin showing--that's sexy." Hopefully Jill will connect the dots and you'll see some improvement.  

A:JOHN: I find Amy's plan rather ironic, seeing as how she has never once "connected the dots" after my repeated suggestions of how elegant I find it when a woman wears a string bikini, short shorts or a nurse's uniform. This is too subtle a tactic. Instead, just go out and buy Jill an outfit that you'd love her to wear. Then, go with her to the store to make the return (that's right, she's going to return whatever you pick out for her, right Amy?). Next, peruse the clothes at the store with her. Keep suggesting specific items that you think look appropriate and visibly display your anxiety about the trashy stuff she takes off the rack.  Make subtle comments like: "That material has kind of a cheap look about it;" or "Yeah definitely get that one... if you're going out whoring all night!!!" Hopefully, she'll get the hint.