This sounds like me. I've gotten a lot better at saying no, I still feel a little trepidation when asking from others, but if I'm surrounded by non-deciders, I don't feel bad about making a decision. Also, I am much bolder about asking for things in a business environment than a personal one. I have a hard time getting dates because somewhere deep down I have been trained that it is an insult to ask someone out who does not already want to date you. Which is absurd.

I hate the passive-aggressive asker. Over the weekend I got this text from my ex: "What time are you picking up the kids?"

I heaved a big sigh. I was hoping he'd drop them off when he was done, but I knew I wouldn't be getting that, and chose not to argue about it with him.

So then I texted back, "What time do you want them picked up?"

He sent back "7".

I sent back "K".

Why could he not just have asked that in the first place? Like, "Could you please pick the kids up at 7:00?" Just to annoy me? Good job!

Because he's not an akser, he's a guesser and that's what guessers do.
The gist of the article is that they don't do it to piss off askers it's just the way they do things.

I may be a bit confused but I'm seeing some blurring between discussing how people make requests and how people respond to requests.

Lani is more than capable of asking for what she wants but when it comes to responding to an open ended question from me (such as "where do you want to eat") she tries to guess what I must secretly want her to say. She's not trying to manipulate me (or feel me out so I want what she wants) she's just trying to give an answer that'll make me happiest when she doesn't have a strong opinion.

Though we've had this conversation several times:

Me: "Do you want A or B"
Her: "Uh, B. Is that ok?"
Me: "If I weren't fine with B I wouldn't have given you the option."

That.

And then there's the mirrored problem.

Her: "Do you want to do this chore?"
Me: "If I don't have a choice, why are you phrasing it like a question?"

I'll let you know when that exchange ends up working well for me.

ETA: Which reminds me of a good tip I picked up in my short ineffectual stint selling insurance. If you want to make it a question so that the person you're requesting something from feels like they have a choice, make sure you're actually giving them a choice, even if the essential request isn't a choice. e.g. Instead of, "When do you want to pick him up?" "Which would work better for you, picking him up at 7 or 8?"

I've mostly brought Lani around on this type of thing. She finally realized that if she says "would you do the dishes now" I will almost always happily do so (and if I don't there's probably a good reason) whereas "do you want to do the dishes" gets a "no I don't" and "would you do the dishes when you can" gets me doing them when I get around to it."

Now, the logical question is why I don't just learn to interpret "would you like to..." to mean "do...". Well, obviously it is because "would you like to..." actually means "would you like to..." and I can't reward ambiguity.

Do you offer seminars?

You're not helping!

When I was full-on pregnant and later, fully engaged in first time mommyhood with daddy at home 24/7, I got much better at saying "could you please do this." I have slipped back into my old ways now and believe me, every time I say "Would you like to do this?" I inwardly cringe. Seems I have to really, really need something done that I really, really can't get to myself in order to ask for help directly.

Maybe if I talked slower I could force it out? I think that's how I got it happening before. "Would you...please...do this?" It's hard. I know you logical types think it's easy, but you are wrong. It means admitting that I can't get it done myself, and worrying that the other person thinks I'm lazy or leaning on them too much. After nearly 8 years of marriage you'd think I'd be over it.

A related sin - "We need to do this," along with an expectation that the other party overhearing will just get up and do it. Ugh. How I wish I didn't say that. :(

This sentence I wrote was missing a word:

If when Lani said that it never actually presented an option then I would just be a jackass for demanding that she change to my preference rather than vice versa.

Compensatory annoyance is given though since I, when talking to her (though not with anybody else) I am physically unable to say "Idaho" without pausing to say "No, you da ho." Love is finding reason to overlook the fact that the other person is really kind of douchey sometimes.