How to get a guy to ask you out? Details included.

Here's the scoop. We have been friends for about 8 years now. Over those years he tried to date me once and recently admitted that he didn't think he tried hard enough (I guess I told him that but forgot). I had never reciprocated romantic feelings for him but now I do. He has always told me that I deserve the best, especially when a guy breaks me heart. He and I both agree we are kindred spirits and no matter how much time goes by without talking we resume as usual. We hung out a couple of Saturdays in a row and each time he paid for whatever we were doing. The last time we "spent time together" as he calls it, he had me go with two of his closest family members but I felt like it was just us the whole time and they were just there. He would offer me food or water and nothing to them, he would walk with me and not invite them to come. At the end of the night he inquired about our "next adventure" and asked that I text him when I got home to ensure I was safe. I decided to put it out there a little that i am interested in him but saying that I have been enjoying spending time with him and that he makes me smile. He reciprocated by stating that he is enjoying spending time with me to. Since then he texts me every single day and now says Goodnight including my name (which was an oddity to me). He text me when he was on vacation, and was sending me pictures of what he was looking at. My only dilemma? He has not asked me out, he hasn't even mentioned just hanging out so I am wondering if there is more I should be doing. Over the years of knowing him as a close friend, he has had one girlfriend and has struck out with numerous women, which sadly includes me. I know traditionally people would say, "he's just not that into you," but I am thinking maybe i need to encourage him a little more?


Most Helpful Guy

  • You can't encourage him if he doesn't want to. This time is your turn to make the moves. If you really want to get a guy going, try physical contact (no ass grabbing or anythign grabbing for that matter), try to flirt and be a nughty bad girl ;)


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What Guys Said 2

  • I don't think encouraging will help, he seems like a genuinely nice guy and if you rejected him once, he'll respect that, and if you try to encourage him it might just confuse him.

    Just talk to him, tell him you changed your mind about your feelings for him and that you'd be willing to try something.

  • You don't deserve his love.


What Girls Said 1

  • Well.. He already tried and you rejected him, right?
    You want him, so why don't YOU try asking him out instead of trying to get him to try again.
    Tell him that you want something.