Well, me and my mates have been talking about Neil Strauss The Game for about 1 year now and we all have wanted to "Sarge". Saturday was the day we all went out. First girl we saw was this tall Blond sitting on the seat of a resturant. Me and my mate Jon walked up to her and I asked her
" Does this hat make me look gay?"

and she replied

" No "

with my confusing on what to say next i turned to Jon and said

"see!"

and we walked off with a embarrased face as we walked away.
I really need to work on what i need to say next.
Any Tips would be fantastic!

I would not approach a single HB with my wing next to me. 2v1 is intimidating. Also,

You: Does this hat make me look gay?

I think that's a bit of an error. It's very direct and can be answered with a single word.

You: People say that I look gay in this hat.
HB: ~Really? I don't think it does.~
You: I like it because it keeps my ears warm when it's snowing.
HB: ~But it's the middle of summer~
You: How fickle of you! You're saying that just because it's not winter, I shouldn't like this hat anymore?! *Cheeky Grin*
HB: ~Haha, no I am saying that you don't have to wear it in the summer coz it won't snow~
You: Yeh, but if it suddenly does, then I'll be the best prepared guy in here. Then I'll have the last laugh...


And so on, and so on. I am not gonna make up a conversation, but you can see that the open ended style of this opener left room for some nice expansion into some light hearted discussion which would be likely to build attraction.

You could have said

"Cool, cause my friend over there said guys who wear *brimmed* hats are a bit on the funny side. And he wasn't talking "Haha" funny either."

Or you could have said

"Damn, I was really hoping to fit in at the Gay Pride parade later this week and I was trying to find an outfit that helped me look a bit more fruity. Stupid straightness, now I will never get that merit badge."

Or you could have said

"Thanks!" toss the hat over to your friend and say "Now you won't look like a fruit. You can thank this little lady over here for saving your manliness. Well... atleast helping it." Turn back to her "Got any more ideas? Cause from where I'm standing he is still on the prowl for the indian in the village people."

Anything.

EvoJ