Do I give up trying to be with this guy?

When I was like 15, I was in this relationship with this guy. I guess you can call it puppy love because we use to stay up all night talking on the phone and he was my first. We dated for a year and some months. after we broke up we still remain friends but, the only time we talk to each is to give each other relationship advice. he was like my best friend, I could tell him anything. I'm single and he was dated this girl they was in a relationship for 4 years and they broke in the summer of 2009. I was there for him every time he needed someone to talk to or just for someone to listen. he could call me at anytime to tell me about his problems. well somehow we start back messing around and I guess we got feeling for each other but he would always tell me that he wasn't ready for a relationship . I guess my feeling got stronger for him and his didn't and like now all we do is argue about any little thing and yesterday he told me that he was really feeling me but he can't see himself with me because I hurt him just like his ex girlfriend. I was trying explain to him that he shouldn't hold that against me because I was younger and really didn't know what love is but now since I'm older I could some him that I'm ready. so the questions I'm asking is should I let him go or try to win him over.

Updates:
now I even more confused on what I should do because today he told me that he have feeling for me he's just why he act like that because scare of being hurt again. what should I do now I really need some help on this one

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  • RE: Update

    My answer stands. Let him go.

    This is what we like to call 'mind games'. Once he has figured out that he can play you like a deck of cards, he always will.

    Do you really want to be with someone this confused about what they want?

    I can tell you from the perspective of someone who has had bad relationships eventually to find true love - 9 times out of 10...when it is real, it won't feel confusing. It won't feel like work. It won't need sorting out. It won't come with strings attached. I will just be...

    If you force a square peg into a round hole, you get splinters.

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  • Let him go.

    Simple as that.

    Just because you have feeling for someone does not obligate them to feel the same way about you (or feel about you with the same intensity).

    I think you need to take a break from chatting with this guy and get your life sorted out a bit. Learn to function without him in your life. Then, a few months/years down the road, if you really think you want to chat with him (you probably won't if you have truly gone on with your life) then give him a ring.

    But it seems to me you are just wasting days from your life you could be spending being happier.

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