Try to flirt a little bit (if you don't already have a flirtatious relationship) and see where it goes. Also invite him/her to hangout. Maybe try a group hangout at first and then pull them away during it for a few minutes alone so you guys can just hang (maybe go into a store that everybody else doesn't like or go grab some food while others are chilling or just tell him/her to come over for a second to look at something funny). If you get a good response and they either flirt back or accept to hanging out with you then its a good sign they like you back and you should bring up dating in a casual way. (use your friends..... "so Maggie (or whomever) said that we would make a cute couple... Thoughts on that?" and that will get him thinking. Be honest with him, even if he doesn't feel the same way getting it out there will make you feel better and it doesn't mean the friendship is over. However, if he/she only hangs out with you during group settings and turns down just the two or you or always wants to invite more people, chances are they are just wanting to stay friends. Hope this helped!! Ask if there is anything else you need :)