I played DnD 4 with my little brother, once, back in August. I gave him a Dragonborn Fighter (Lv. 3) to play, and ran him through a little town and some kobolds. He liked it, we both had fun, and he said he'd be willing to try it again.
So why am I so nervous about telling him I have another session planned out and ready to go?
A little background: My little brother is a big sports fan. Football, baseball, basketball, it's his thing. And that's fine; playing in organized sports has been good for him. But he also likes reading novels, and he's big on the Twilight series and Harry Potter right now. He also enjoys choose-your-own-adventure stuff. So it's not like I'm throwing DnD at him out of the blue.
I planned it out, made some unique monsters, and I think it'll be at least mildly entertaining. The big thing I'm "doing" in this session is introducing him to the fantasy flavor of DnD - the first session I did with him was in the 'real world', and this will start there, but move to an Eladrin town, etcetera etcetera. So there's that - I don't know how he'll respond to the fantasy setting. But if he accepts it, it would certainly make things much easier on me to make more sessions for him, simply because then I can use the whole flavor of the system and not just he mechanics.
I talked this over with my girlfriend, and she suggested that I'm afraid of rejection here. I don't want him to say "blah" to it. And as long as I'm worried about the fantasy, or about not having the 'right' materials to play, as long as I'm anxious enough to not ask him... well, he won't have the chance to say "no".
So I'm going to gather up my courage, and ask him sometime tonight if he wants to play. Tonight, tomorrow, whenever, just try to set a time and go at it with him. That's my plan.
I'll report back with results when there are some.
EDIT: Of course he says "sure". So hopefully tomorrow, we'll play.
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