So I have had a crush on my dad's best friend's son for the past ten years, we grew up together and some of my best memories are with him and his family. As much as I would love to date the son (my crush) I understand that now may not be the time. But he's been acting super strange around me, especially when he's with his friends. I have suspicions that he likes me. At the funeral I sat in the row across from him and he kept looking at me and when I would look back he would smile and look away. I texted him a couple days after his dad passed, a lengthy message with my condolences, and he replied with a fairly lengthy message thanking me. We hardly ever text though, and I feel like it is on a need to know basis. I feel awkward texting him first (he rarely texts me first) because our text conversations don't last very long. I do not want to come off as clingy or annoying, and the last thing I want to do is tell him that I like him and be rejected and have everything blow up. He doesn't need that right now, and if he doesn't like me back, I will be forced to live with the shame everytime our families see each other. Alternatively, instead of texting him, I was wondering if I should try and see if he wants to do something. We have never hung out just me and him, so I don't want him to feel weird about it, he may even turn me down or not reply if I sent him a message about it. Any thoughts or ideas? I love this kid to death and I would do anything to be with him.
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Update: I texted him yesterday saying "Hey, how are you doing?" Because it is an open question rather than just asking if he is okay. He never replied and I feel like shit.
Right now he's mourning the loss of his dad. Just tell him that when he's ready to talk about losing his dad you are willing to be there for him to listen. Then just wait and give him space.
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I think asking to hang out is a great idea :)
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