How do I ask a friend with benefit if he every thought of dating me without making things awkward between us?

We seen each off and on for about 5 years. He only had one girlfriend in that time (not while we were doing anything) and he said it didn't feel right. Why does he keep coming back? I figured in that many years he would find a girl he liked. I feel like we are suppose to be together but at the same time if he said he doesn't want to date me I wouldn't be devastated by it. I would just move on. What should I do?


Most Helpful Guy

  • He's happy getting pussy without effort. Time for you need to take the lead. Pick a movie you want to see and tell him (TELL, don't ask) that he's taking you. Not meeting you there, but picking you up and taking you. A week or so later do the same thing with another activity. He will either accept and gradually come to think of you as his girlfriend, or he will refuse outright. He might have zero respect for you and sees you only as a cum-dumpster that isn't worth "dating." After so long, you should at least find out for sure. Either he steps up or you need to move on.


Most Helpful Girl

  • Just bring it up in conversation, I mean you've been fucking for five years... it would be strange to NOT have the conversation.

    Woman up and have the talk with him.


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What Guys Said 2

  • If you don't ask, you will regret it for the rest of your life. Take a chance and ask him.

  • There is no way you can ask that question and not make it feel awkward


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