Haha, you may be right, devilman.

Look, your nickname says it all, shyguy.

There comes a time in every young man's life when he as to take a bold stand for something he wants. It's either that or resign yourself to a life of mediocrity, resignation and regret.

On your deathbed, years from now, I guarantee it won't be the things you tried and failed that you regret. It'll be the things you never attempted, the things you talked yourself out of, the things you were too afraid to try.

I know, ratbastid, I know. You've all answered my question and now it's up to me.

I just wanted to wish the poster luck.

I too am a shy guy and wish to rally for like-minded individuals.

Yeah---Good luck shyguy--

Although from everything you've said, I think she's just waiting for you to make the move.

Got my fingers crossed for you-

PB

Shyguy...you seem like a nice guy. I feel like I need to ask...how have you picked up girls in the past? Just a hunch, but I'm guessing you're generally not the kind to make the first move! I know it's kind of akward with your boss and other customers around, but if your boss is even halfway cool, he is going to understand - it's not like you're asking out every girl that walks in. It's just one girl, he should let that slide.

Maybe this sounds cheesy, but I would write my number along with "Next Coffee is on me - The coffee guy" on a napkin. Replace "The coffee guy" with your name if she knows it, I wasn't clear from your story if she did or not. Keep it in a safe place, when she comes in with her coffee give her the special napkin.

Of course just catching up with her after work and asking her if she would like to go out would be the direct preferred way.

Thanks for the words of encouragement. I had decided the next time I saw her I would talk to her. And I saw her about a half hour ago. She was with a guy friend and I chickened out. I really don't think they are a couple but I didn't know for sure. Damn.

Ya know this story sounds remarkably similar to the video for Keri Noble's video for "Talk to Me". Link

Be a little bold, and take a chance. At least then you'll know whether you have a chance or if it's time to move on to worring about how to ask out the next cute girl that crosses your path.

Wow, so yeah that video pretty much sums it up.

I can't make anything positive out of her bringing a guy friend around. Manipulative, insensitive, and/or oblivious...

Ask her out by the end of the week or go forward pretending you were just being nice to her because she was a customer.

I would agree with you except I was not working and never work that night. I "just happened" to be studying there. She always comes alone when I'm at work.

And us college kids get a 4 day weekend for Thanksgiving so I won't see her again until sometime next week.