Im 18 years old (male) and my best friend is 21 (male), he has a sister thats 16 and i have liked her for a while but and my feelings just arent changing i think i need to switch my brain into "you only have one life" mode because i need to tell her how i feel, im fairly confident that things could go smoothy but at the same time i dont know how her brother would feel about it because me and him are best friends, compodres, amigos, i know he has enough respect for me to know what my intentions are with this but what else could come into play. Is it perhaps him i should tell first that i have liked his sister, or should i somehow get some private time with her and tell her. whether its him or her that i should tell, perhaps i could have some help with choice of words, im not one for these things because i have been numb to this dating thing because of one damn rejection in the past, i need to get past it with a little help from you fine people of course, ill simply conclude this with..

a little help?