Originally Posted by
Uchiha Barles
Other than some romantic comedy or another, I've never seen a person confessing his/her love to another person going well. The handful of times I've heard my friends talk about it, they said it seemed kind of pathetic, or that the guy was all "sooooooo adorable xD, but...naw..." Adorable...that's about the best you can hope to come across as, unless she's batshit madly in love with you too.
Normally, I don't care whether a girl has a boyfriend or not. If I'm interested, I do the usual probes to see if she's interested, and ask her out or not based on that. If you can come across as playful and flirty, yet unassuming, then you minimize the risk of prolonged awkwardness between the two of you should you be met with rejection. There's still a risk of course, because whether or not you appear as I described, depends both on your performance and on her perception, the latter of which you don't have much control over. Since this is your job, AND you're madly in love with her, I'd seriously consider NOT trying this. If you do, you really, REALLY, need to be skilled at this. If you're not...she's not the one to practice on.