[Bring_Back_Shantz]

Okay, you can ask most of my friends and they'll tell you that I'm a pretty straight forward guy. Hell on a recent road trip I used this little diddy "Hey my friends right there are trying to figure out how to get you girls to come to the bar with us, and they're being pussies about it, so we're going to this piano bar down the street, do you want to come?" It worked (ask Hulkrogan if you don't believe me, also, I'm still waiting for that thank you Hulk).

Of course the downside to this philosophy is that it lends itself to some pretty spectacular failures. In the above case, the worst it would have meant is a hearty no, and the posiblitly of 4 friends being upset that I killed the grass, but that was a chance I was willing to take.

In your case it could totally devestate the relationship in two ways:
1) She turns you down and thinks it's now akward and she buggers off
2) She turns you donw, but you get bitter and start being a jerk

Of course there are the better posiblitles:
3) She says yes and you're gold
4) She says no, but you're both mature enought to deal with it (this can be done, I know because I've done it)

Anyway, you've got to decide if the posiblity of any of these options is completely unacceptable to you and if it is, maybe keeping your mouth shut is the best option.

However, I'd say go for it, and don't skirt the issue.
Joking, and pretending to flirt, but actually being flirty are weak, she'll think you're either not interested, or don't have the guts to speak up. Thought words I know, but that's how I roll.
Tell her how you feel, but make sure she knows that your continued friendship is not contingent upon her saying yes, and then go ahead and live with the consequences.

Think of it this way.

Choice 1
Don't say anything
Posibilites
Things stay the same and you have to pleasure yourself nightly

Choice 2
Say something
Posibilites
She says "Cool" and she pleasures you nightly
She says "No Dice" but you remain friends: see posibilites for choice 1
She says "No Dice" and one of you gets bitter, and it ends violently, it sucks but you can at least move on with your life

Those are the options man. Now have at er.