Last night I was out with my wing around this shopping complex. We walked into a halloween store. I saw this cute girl looking for a costume. so I opened her, went something like this:

Me "so what are you going to be for halloween?"
Her "I have no idea, I'm doing a thing with my work and I can't be scary".
Me "Oh where do you work?"
Her "The YMCA"
Me "Oh cool, ya know.. I could see you dressing up as a clown"
she laughed .. and said "Well see"..
Me "I can pictue it: the white face two big red dots on your cheeks and everything".

then a sale guy came up in the isle and she turned and talked to him. I kinda gave up there, she turned to me quick and said. "sorry".. later my wing said I may have shown way too much interest up front and I was a bit "Too Mellow".. I realize what I did wrong.. just gotta keep on keeping on...

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"It's not who I'm underneath, but what I do that defines me"-SPAM Begins

I've had this problem too. Whenever I've been direct and showed genuine interest it just doesn't work. On the other hand, being aloof and being the prize has worked wonders. Kind of frustrating because I want to simply be genuine and interested in a girl! I am a very direct person and that's probably why indirectness seems to work for me so much better.

Maybe you weren't being "fun" enough when you were talking about her being a clown. If you were just being mellow, like you said, then it didn't grab her enough. Remember, the words you use are only 7% of communication, body language is 55% and tone is 38%.

Also, you want to make an image in her head that she can picture. So, you wanna be going on about the red polkadot suspenders and the giant red bow (with gestures to show how ridiculously huge it is and a look like you're picturing how ridiculous she would look) and the BIIIIG (more gestures) poofy orange hair. Maybe suggest that instead of wearing a wig "we" (not "you", because this makes her include you into what she's imagining) could dye her hair bright orange (wink or big grin). Make sure when you're doing your description, you start out by making the gestures at yourself and once you have her laughing and showing IOIs, that you start doing it on her, giving you the chance to initiate a bit of kino by maybe holding her hair up above her head, or brushing your hands down her upper arms lightly as you describe the red felt coat she'll be wearing.

Notice how just reading that you've already built this picture in your head of exactly the clown I'm talking about, whereas how you said it, it was just a white face with red marks (I would have said dimples to make a better connection to her imagination). Its a perfect example of the logic vs. emotional speak that you need to use with women.

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"The 'Brick Walls' are there to allow you to prove how badly you want something!" ~ Randy Pausch

~ Rye