I have a friend, who is a boy. We have been friends for 5 years. We tried to date 2 times, but it didn't work. And I've liked him since we started being best friends. And I think he knows it. He is more of a guy who is calm and never flirts and stuff. He is nice and he never does "bad" things. But I really want him so badly, but most of the people say that I might lose him forever. He likes me, I think, he said once. But he is really shy. I really want him and I want him to start it. Even if I start it I don't even know how... what should I do?

Changing your relationship from friends to boyfriend/girlfriend is difficult, but can sometimes work out well. Just having sex with a friend usually ruins the friendship.

What happened to two times you tried to date?

How old are you?

Why do you think he feels the same way? Possibly he's not interested in dating you or having sex with you. You said you tried dating before and it didn't work out, why not? Maybe he only wants a friendship with you.

You think having sex with him will make him want to somehow be in relationship with you but it won't.

Trying friends with benefits is not a good idea because you already have feelings for him so your feelings for him would only get deeper while his may not.

You need to stop focusing on this guy and find someone that wants to be with you.
Didn't you say the two of you tried dating but that didn't work--so why do you even want to attempt adding sex to the mixture? That won't work either.

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Originally Posted by jjwoodhull

Changing your relationship from friends to boyfriend/girlfriend is difficult, but can sometimes work out well. Just having sex with a friend usually ruins the friendship.

What happened to two times you tried to date?

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We were good until I had to break contact with friends and stuff because I was too busy paying attention for studying, I didn't know that he felt rejected and I was the 1st who said we can't date anymore... the second time me parents told me that they have problems with his parents, and they (my and his parents) stopped us...

So again I ask: How old are you?

If your parents tell you who to date, then you are not ready to have a sexual relationship with him or anyone else.

Pursuing your lust will cause more problems than you already have. Even worse, sex is not your best way to keep a friend, it's the worst.

You build the foundation of relationship first and sex just comes after.

If your friend really likes you, ask it again and ask what he thinks about taking your friendship on the next level-again. Maybe he meant " I like you but not that much." If he says no-again, then better start making distance w/o a drama. At least you gave it a shot one last time. Nothing to look back as you move forward.

People who are always together but has other motive in mind only creates confusion, pain and waste of time. Be realistic and don't cling into false hopes.