Expert: Azure - 7/10/2007

Question
There is this guy I met back in October that I'm beginning to care about. He is my best friend's friend from highschool, and when we met there was a comfortable click; our personalities balance one another incredibly well.

Back in January, we were with friends and the subject of women breaking hearts came into the conversation. I can be very aggressive about this subject, so I turned to him and asked if he was hung up on some girl that is leading him on. His answer was yes, and I told him to get over her - move on and live on. He talked it out, and by the end of the night we were sleeping in the same bed and he was holding my hand. When he left to take a shower, he kissed the top of it which is about when I began to see him as someone other than a friend.

However, I've had bad relationships with people in the past, so I can be very shy when a nice guy gives me this kind of attention. I even introduced one of these bad relationships to him back in April, but after I dropped off that bad relationship, I ended up spending the night dozing off and talking to him about men and bad decisions. I left the bad relationship and returned to single status.

Just last week, he invited me and a few friends to go up to his family's house three hours away from the city. I got a chance to meet his dad and the rest of his family, and I just fell in love with them. They absolutely loved me too and are now messaging me back and forth, keeping in touch. But on the trip, he wasn't as open as he usually was and often kept to himself.

Thing being, he is going to go to the army in six months for training, and I have a very short time frame to charm and win him over. I feel like I had my chance back in January but blew it because I was being too cautious, and now he thinks I only see him as a friend. Another problem being, he also lives about forty-five minutes away so it's kind of inconvenient to hangout.

I guess I feel like I can make him happy and vice versa. We've both been pretty beaten up by people who take advantage of our niceness, but I don't want that to interfere with something wonderful. However, I don't know how to approach someone who doesn't seem aggressive when it comes to this. What should I do? I don't even know where to start.

- Judith

Answer
no need to "do" anything, especially seeing he's not gonna be around for long; if he's interested in being with you, he'll ask you out; just let whatever happens naturally unfold, but keep expectations low, as i doubt he wants to get very involved with his whole life changing in a few months...