Okay, so my friends GF put up some pics, and she had her friend in a few of her pics, and she was strikingly attractive, I PMed my friends GF asking about her, I soon found out that her friend was right there reading everything I said. Luckily I didn't say anything like "oh I think she's hott" or whatever. My friends GF suggested I add her and talk to her and whatever. So I messaged her......

ME: So were you really right there reading everything I said?
HER: lol yes...
ME: so like how much of it did you see?
HER: everything until sep told you i was sitting right by her.
ME: HA, awesome, well if you are still curious, I was just going to say that you have an attractive smile.
HER: lol aw well thank you.

I left it at that, I just added her after I received that last message.

Can I get any pointers?

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Dont Light The Dynamite, Then Get Mad At The EXPLOSION.....what did you expect?

You pretty much did say "I think she's hot" by telling her that she has an attractive smile. That's a pretty generic compliment.

I would have probably complimented her on her style or on some of her pictures (where she's been, etc). You could still do this, but I'm sure you already know that you don't want to over-compliment her before she shows any interest in you.

Next time your friend and his GF go out, ask if you can join (without telling your target that you asked them). Then send the target an invite and say "well, I'm supposed to go out with so and so tonight, but I really don't want to be the third wheel. You should come with. I was really looking forward to it cause it sounds fun, but I don't want to be the odd man out, and it would be more enjoyable with a 4th person".

That way you've set up a date, AND she'll feel comfortable because she'd be around her friends as well. It's far less threatening and you don't come off as needy by doing this.

Does it really sound like I said she's hott by saying she had an attractive smile?
GEEZ....I mean the only pic I had to go off of was the one I saw....
AND I SERIOUSLY DOUBT that they will let me tag along ANY WERE with them.....they are loners mostly, if they arent with each other they aremost likley by themselves.

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Dont Light The Dynamite, Then Get Mad At The EXPLOSION.....what did you expect?

Relax man.
I was just trying to help.
No need to get hostile.

whoah, If I came off hostile I apologize, I yell comically in real life, and try to type it out as such. So once again sorry.

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Dont Light The Dynamite, Then Get Mad At The EXPLOSION.....what did you expect?

Ask her if she want's to meet up....that's it..

Yep.

No doubt your mutual friend told her all about you, and probably showed her photos.

You then msg'd and struck up a bit of a rapport.

She would have checked you out on FB by now.

Just ask to meet up sometime.

It wouldnt have got this far if she wasnt interested.