Should i ask her out ?

Should i ask out my friend kiana or emily out? Emily-she`s smart,pretty,funny,goofy,and ive known her since the 2nd grade or my friend kiana-also smart,pretty,funny,teaser,but she doesnt want to get hurt. so should ask one of them out? if u want 2 know anything else email me Armando3604@yahoo.com.Thanx.