It sounds a bit silly on asking this question considering im 20, but i really like my work colleagues sister. She's 17 (18 this year) and i've known her only a little while but we have been out a few times for drinks as part of a work night out and id love to get to know her more and hopefully be able to take it a step further. My work mate is 26 and he's the funny sort of character so if i say to him directly "I quite like ..., would you mind me asking if she'd possibly like to go out sometime", to me it just seems a bit because although he will take the piss (even though i enjoy the banter with him and the others), its important to me so it would seem rather awkward him doing that or saying something because knowing me id lose all confidence then lol.. I don't really know how to go by it since if i just asked her it would seem kinda weird because of the fact i work with him on a daily basis, (i know full well i don't need anyone's permission) but when its something like this, i just feel i need to let him know first for the fact i work with him. Could just use some helpful tips on this as i feel a lot different compared to feelings for other women i've got to know/met up with.