I need advice on me and my ex please read! I know it's long but help!

Shae • I love girl talk!
Okay so my ex and I broke Up 4 years ago, (he broke up with me cause we were 16 and his friends pressured him to cause they liked me and him being an idiot ).
Two weeks ago his best friend commited suicide and I went to the funeral on Saturday. After the funeral. I went with him and some other people for drinks and by the end of drinking, after 8 hours of drinking our friend drove me our friend and my ex back to his place for the night. All three of us talked for an hour and a half about his friend so we sobered up a bit. We went to bed and my ex and I were laying in bed almost nose touching and he kissed me. We had amazing sex. In the morning we cuddled and he said "you don't have to be nervous with me" later he drove me home and winked at me.
 A few hours later we met up and went to rehearsal (we're in a play together) after we went back to my place and we practiced some stuff and cuddled on the couch, when he was leaving I said "am I crazy to ask for a kiss?" He said "no" and we kissed. 
The next day we went to comedy night and after he drove me home, I invited him to come in and he said "I dont want to hurt you again and I'm  going to Mexico in 3 weeks. For a week." 
So when he gets back from Mexico should I hint and try to give it a shot! I still really really like him. And I'm the first girl he's been with h in a year. His best friend said he is attracted to me, he cares about me, and comfortable with me!