This is going to depend a lot on what you're saying and why you want them to have heard it. If you're actually communicating about a problem/project that you're collaborating on, I think there's more room to repeat yourself because the consequences of misinterpretation can be pretty major.
If instead you're navigating a social arena (either for its own sake, or to gain status that you'll need later) then I think it's almost always going to be better to go with the uncertainty.
If you're worried that people DON'T think your statements are valuable, then it's probably better to focus on that. And in that case, it may be worth the status hit to ask point blank a few times:
"Hey, did you hear what I just said"
"yeah?"
"Why didn't you respond?"
"...because I (didn't care/wasn't funny/etc"
"why didn't you care?"
"Uh, because X, I guess"
This is NOT a good general practice. But it may be a necessary cost to figuring out how to communicate better. Save it for people you at least reasonably trust (but who are close enough to the average social person to have advice that is generalizable).
"why didn't you care?" "Uh, because X, I guess"
Data point: If you did this with me, then you'd need to be pretty careful not to sound defensive. I tend to shrug, grin, and make a fairly non-specific response because usually when people ask that question, I'm just trying to get them off my back. If you wanted to me to try and give you a thoughtful answer, you'd want to convey curiosity, even prefacing the question with 'I'm curious..."
Edit - many apologies to anyone that feels that this discussion was a waste of time.
I just ran across an article (http://techno-anthropology.blogspot.com/2011/04/rough-guide-to-social-skills-for.html) on Hacker News that gives the barest minimum of a guide for social interaction. Unfortunately this isn't the high-quality advice you need to really handle social situations, though it will help with a few of the worst problems.
A few other rules that will help:
On the physical side:
This is a long list, and it isn't even close to complete.
I'm linking to http://lesswrong.com/lw/372/defecting_by_accident_a_flaw_common_to_analytical/ at the suggestion of David Gerard. It has a lot of deeper discussion into why this is worth knowing.