How to tell him how I feel?

[CrazyCat]

So... I have a crush on my one and only friend.
We first met about 5 years ago at this club for kids and teenagers with developmental disabilities (both of us have high-functioning autism) and for the first 4 1/2 years I didn't really pay attention to him for two reasons: 1. I was battling a crippling depression
2. I didn't really feel any need to make social connections
And during that time, he talked to me and I just listened quietly not saying anything until he went away.
Nowadays it's completely different. Now that my depression is mostly under control and I have started to feel the desire to socialize, I have been talking to him when our club meets and we have been able to talk about the stuff we're interested in. Mostly video games and internet stuff. We've also started role-playing (clean of course) via Steam's chat service and now our relationship has gotten very close. When I talk to him via Steam the topic sometimes veers towards rather personal things.
Anyways after the last few times I've met him and the time I've spent chatting with him on Steam, I've started to fall in love with him and I have no idea what to do now. While I have fallen in love, nothing has come of it (except in one occasion involving an absurd amount of luck) and I want that pattern to change. Only thing is, I have absolutely no idea how to tell him my feelings. I simply don't know about these kinds of things, so some sound advice would be appreciated.
Many Thanks.

[SapiensUrsus]

Hey CrazyCat,

I'll tell you what seems to have done ok for me.
The short version is: the next time you talk or see him, ease into the topic. Test the waters before you Explain your feelings.

Basically, if you feel this way, you need to be honest about your feelings.  Don't Be ashamed of them. But I wouldn't recommend jumping into it; We're not going for shock value. (;
Make sure he's comfortable talking about the topic of relationships, and then ease your way into explaining how you feel. Be certain that he'll hear you through, and be sincere.

Cheers, CrazyCat. Hope this helped in any way, and I hope all goes well. If I ended making myself sound like an idiot I can flesh this out a little more :p

[CrazyCat]

I know better than to flat out tell him, but I want to know is how to ease into the topic, like you said. Especially if the topic of relationships never comes up.
So yeah a more detailed explanation is needed, but not cause you're an idiot. The issue here is that this is stuff I've never handled and have absolutely no experience with.

[SapiensUrsus]

Sure thing. I think I can do that.
During a lull in the conversation (as conversation is wont to do from time to time) Ask him if he ever feels like being in a relationship. Then ask him if he's found anyone he's thought about going out with. After he responds, I would consider that to a proper time to delve into your feelings. I don't really know how else to put it. If I think of anything else I'll post it here, if you don't mind.

[CrazyCat]

Sure thing. I think I can do that.
During a lull in the conversation (as conversation is wont to do from time to time) Ask him if he ever feels like being in a relationship. Then ask him if he's found anyone he's thought about going out with. After he responds, I would consider that to a proper time to delve into your feelings. I don't really know how else to put it. If I think of anything else I'll post it here, if you don't mind.

Ok that makes sense, and if you come up with anything else feel free to post it. I'm here to learn

[HagenK]

Just wanted to share some of my thoughts, dont take it personally. When a person reveals his love for someone in a serious manner, he/she basically says you owe me your love, thus not allowing for a partner to choose freely, because it would be really wrong to not respond in the same way, especially if you recently did a favor for him. And then he tells you that he loves you, he is obligated to or at least pretend, so not to feel foolish by acting in inconsistent way, therefore creating unnecessary tension in a relationship. Again I'm not an expert in such things so not sure how much of this hold true. If you truly love him it should be obvious even without telling.

[CrazyCat]

Just wanted to share some of my thoughts, dont take it personally. When a person reveals his love for someone in a serious manner, he/she basically says you owe me your love, thus not allowing for a partner to choose freely, because it would be really wrong to not respond in the same way, especially if you recently did a favor for him. And then he tells you that he loves you, he is obligated to or at least pretend, so not to feel foolish by acting in inconsistent way, therefore creating unnecessary tension in a relationship. Again I'm not an expert in such things so not sure how much of this hold true. If you truly love him it should be obvious even without telling.

I have absolutely no idea what you're talking about...

Post Merge: September 17, 2015, 02:35:22 AM

Sure thing. I think I can do that.
During a lull in the conversation (as conversation is wont to do from time to time) Ask him if he ever feels like being in a relationship. Then ask him if he's found anyone he's thought about going out with. After he responds, I would consider that to a proper time to delve into your feelings. I don't really know how else to put it. If I think of anything else I'll post it here, if you don't mind.

Question.
So assume him and I are on the topic of relationships in general. How do I then change the topic into my feelings in specific without it seeming too forced or awkward?