text: if a guys really interested in you will he definitely ask you out? this guy i know has flirted with me sometimes, was mean a couple of times.  but now he's been really nice to me lately.  but just in a really friendly way not flirty.  sometimes he makes eye contact and sometimes he doesn't even acknowlege i'm there.  he's 23 and i'm 33 do you think this could have something to do with it?  i feel he's giving me mixed signals but maybe he just likes me as a friend. guys who are secure and confident in themselves will ask out girls they are truely attracted too. so the answer is not, definitely, yes. if he hasn't asked you out, he may just want to be your friend but, more likely, he might really be interested in you but not sure enough of himself to ask you out. if he wants too but doesn't, then you don't want him anyway. he sounds afraid, confused and frustrated to me because he is sending you mixed signals. this would suggest that he want's to ask you out but doesn't know how to, or is afraid of rejection. he probably is intimidated by your age. sounds like an infatuation and he's trying different approaches to feel out the best way to grab your attention. i could be wrong but he doesn't sound very mature or experienced.