Hi Emily,

I'm 21 years old and have only had one boyfriend. That relationship occurred about 7 years ago and lasted for about 2 months. I have been crushing on this guy I know, off and on, for about 2 years. We are really good friends, but I have no idea if he would be interested in starting a deeper relationship. I am in a dilemma with this situation because he is 19 and does not have a car or a job. We live about an hour apart so if we did start dating, it would seem like it would depend on me to drive up to see him and back. I was thinking about driving up near his town sometime this week and going for some coffee, but I just don't know if I'm wasting my time. I need help weighing my options! Should I go out on the limb and see if he's interested?

---------------------------------Miss Emily's advice-------------------------

I'm hesitant to think you should pursue this because, without a car or a job -- and the distance, it is going to depend on you to get you and him around -- and he has no money to spend on a relationship. I know your heart is in the right place, but is it practical? I think, even if he were on board, the blush could soon be off the rose if he weren't capable of carrying his own weight. And people have pride. Most wouldn't want to be a freeloader -- and if they did, it's not a respectable trait. You're ready for a relationship with a guy who can give something back, and not be restricted by the issues you mentioned.