Man, I feel supremely lucky after reading this thread.
Aside from my uncle in Toronto, my entire close family is super nice.
soo...My worst ones are all kinda silly.
1)
My dad is on my computer for some reason and I'm on my bed with a textbook. For whatever reason, my kirby plushy takes this exact moment to fall onto my book. I chuckle and give it a brief cuddle before putting it back above my bed. I turn to see my dad giving me this weird look.
Me: "What?"
Dad: "Y-you just cuddled a little pink thing!"
Me: "And? It's Kirby! Kirby is awesome!"
Dad: "You're a 22 year old guy! It's a cute pink thing!"
Me: "What, so guys can't like cute things from time to time?"
Dad: "...You REALLY need a girlfriend, man. You're CLEARLY becoming desperate".
Me: "I'm keeping my eyes open, no need to get all crazy about it..."
*about 4-6 months later, I have a girlfriend and I invited her over. She saw the kirby plushy and 'aww'd' over it. I told her the story and she laughed and found it awesome"*
-after GF leaves-
Me: "Hey dad, remember the Kirby incident? The little pink puffball?"
Dad: "Yeah?"
Me: "She loved it. And she had the same reaction I did to it. Oh, and she found the story hilarious and likes me even more now.

"
Dad: "*shakes head* I do not understand your generation."
In fact, I get the "I do not understand your generation" thing a LOT. XD
2)
*Toronto uncle after a 'debate' about politics in which his only points were "your sources are biased and wrong!"*
- "You're a CHILD. A naive foolish CHILD. Grow up learn how the world works!"
Bear in mind he's RIDICULOUSLY conservative to the point where he thinks all "leftists" are this cult that only wants to enslave everyone. And he practically worships our Prime minister (Stephen Harper), refusing to hear anything against him because "Everyone else is worse", without offering any other justification.
3)
Actually, now that I think about it, there was one talk my family had with me that made me pretty mad, although it wasn't exactly an insult...
Basically, they said that I should "keep my eyes open for other girls". I gave them this funny look and said "Uhh...Wat? I'm in a relationship, guys. That's not exactly a good idea. I mean, I don't AVOID girls or anything and I'm fine with making new friends and-"
And then they tell me that they're worried that my current relationship is a "dead end" because I don't see that much of her because she's always "busy", so maybe I should keep my eyes open in case I find someone who can actually make me happy. Bear in mind, my GF and I are both at university, with pretty heavy course loads most of the time. And we've been together for nearly 3 years now. I tell my parents she has valid reason to be busy, and besides, we're still doing good together. My parents continue to take issue that she's always "busy". I tell them again that she has the right to be busy. She has schoolwork. She has other friends she wants to hang out with. She wants to hang out with her own family, and I'm not the kind of guy who's going to pressure her by demanding she cut down on her own life to be part of mine. Besides, I like my personal time too.
My parents then go on about how when they were dating, they saw each other basically every single day. Even though my mom was working a full-time day job AND going to late night university classes. I told them that just sounds unreasonable and they looked at me like I was crazy.
So yeah. I didn't like the implications of the conversation and told them so, prompting a STREAM of apologies for not wording their talk properly. I mean, yeah, I WOULD like to see more of my GF, but I'm mature enough to realize she has her own life and I that if I demand she put in on hold for me, that's just being selfish.