Should I cross the boundaries between love and friendship?

I have been knowing this guy since I was a little girl. We can talk about anything and we even act like we go out. Recently, I let him know that I had feelings for him more than a friend. He told me he had feelings for me, but he couldn’t act on them because he didn’t want to hurt his girlfriend’s feelings. Now they are broken up but he never mentions anything about us taking our friendship to the next level. I know that he likes because he gets jealous when I talk about guys and we almost kissed. He comes over my house about three times a week, and we talk on the phone almost every day. He just graduated from high school but he’s not going far away for college. He’s also going to be around the whole summer. I truly care for him and sometimes I think that I love him. Should I get enough nerve and ask him out before he leaves or should I just hold my feelings since he’s going to college?