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Should I talk to him over the summer about us? Or is this a disaster I should just run away from?

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Question - (21 January 2011) 1 Answers - (Newest, 21 January 2011)
A female age 30-35, anonymous writes:

Alright, so - this guy and I hooked up the day before I left going back to college. I was completely surprised when this happened because Ive known him for a while; we went to high school together, but he was two years older than me. He's in a band and I suppose that makes girls gush over him, but I mean, I fell for it too. He doesnt get with a lot of girls though, by any means. My friends and I always sort of liked him. But then we hooked up.

I assumed it was a one time thing but the minute I left he contacted me and texted me until we both fell asleep the other night. He knew I was sick and sent me a song online. I mean, its adorable and he is adorable. And Im guessing when I go back home in two months that well, we will start hooking up again and then in the summer?

Heres the problem - he doesnt go to school and doesnt have a job. He doesnt like this fact and he isnt a leech or anything. He has pretty radical views and one of the reasons I guess he likes me is because I agree with him. He doesnt like grades, he doesnt like corporate america. Neither do I, but I mean, Im still at school. He wants to go to school and all, he is just unsure of his future and is pretty unhappy now. Im afraid if I get involved with him I might get myself in all this mess.

I reallllllllly like him. And I know he really likes me. I mean, I obviously wouldnt say I love him yet, but everything is so right and Ive thought this for a while and always lamented how his personality/opinions clicked with mine and how I should just let it go because it will never happen. I feel like i *could* be in love with him, down the road. Which is pretty uncommon for me - Im really picky and emotionally, I dont open up often. Im not really sure what to do, I know its silly to think of future plans so early but I cant help it. Im already emotionally invested in this. Should I talk to him over the summer about it? Should I just hope he figures things out? Is this a disaster that I should just run away from?

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A reader, anonymous, writes (21 January 2011):

I don't mean to sound dismissive, but I would let this guy go until he sorts out his life for himself.

Men who are politically minded, yet can't seem to even get involved in something as basic as a job are a dime a dozen.

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