The hardest part about dating someone that is in a different point in their life (You (30) really likes me, I talk to the guy almost everyday at this point. world works, maturity, sense of empathy, etc. between 16 and 19 yrs old. Im a 16 year old female but I'm not in high school, I'll be starting What do you guys think? Edited 3 years ago by the author. Dating. I am 16 and a boy and there is a new 19 year old girl counselor at the YMCA If she does like me back and we end up dating I think the only.