Me and this guy had a special connection when we were 16, then carried again when we were 19. Once he moved away, we met new people and stopped talking for years. We are now 27, and reconnected a year after we broke off our relationships. We are flirting, talking on the phone constantly, good morning messages, etc. I am a slow mover, and want to get to know eachother as adults to see if things would move further. He says things like "we were so in love" constantly which kind of pushes me away, because I want to focus on the now. I got out of an engagement, as did he a long time ago which has made me more cautious on pursuing future relationships. On top of that, I am a single mother. He says things like "How should I be, if I were a step parent?" And he would ask me questions about marriage, etc. I told him he has to slow down, and I just want to have fun together and live in the moment. I am not leading him on.. I have been very honest with him. I do like him too but he is pushing me away right now. It makes me want to walk away..
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I think he is a stand-up guy with serious intentions who is not going to make a mistake. Seems like a good find to me and it seems like he doesn't want you to get away again. We do not ask these questions without a potential Wifey vision.
He is just asking the extremely important and called for questions in the world of adult dating. If you're just wanting to screw around and be casual then tell him so.
And if you have and he's clearly after a different goal than you, break up.
You should have a discussion saying basically what you said in your post. What he is doing would drive me up a wall and put me off too.