I liked Alate's answers. But I'm providing my own.
1) Hillary Clinton, your husband has had numerous affairs, has had sex with an intern and he settled a sexual harassment case with Paula Jones. Incidentally, there are far worse accusations than that against him that haven’t been proven. So, isn’t it fair to say that your husband is part of the war on women?
What does this have to do with Hillary? Dumb, don't ask.
It's interesting, isn't it? Conservatives are violently sex-negative, but they can't help but lead with the sex. We can see what their priorities really are.
2) Hillary Clinton, in the first debate, you said you were proud to have drug companies and health insurance companies as your enemies. However, your campaign and the Clinton Foundation have received millions of dollars from both industries. Will you be giving that money back?
Good question. I'd like to see an answer. Add the banks in there too. Ask.
3) Hillary Clinton, in Bob Woodward’s book, The Choice, he noted that you communed with former First Lady Eleanor Roosevelt and Indian leader Mahatma Gandhi from beyond the grave. Your husband also confirmed in a 2012 speech that you used to commune with Eleanor Roosevelt; so this isn’t something that you can credibly deny. Can you explain why you did that and what you believe you learned from talking with the dead?
Eh, some people talk to Jesus. Who cares? As long as it's not a routine part of her decision-making, how she finds inspiration is up to her.
4) Hillary Clinton, do you think someone who hasn’t even driven a car since 1996 is in touch enough with the average person to run the country?
Well, she can't drive. The Secret Service won't let her. Dumb, don't ask.
I think it's true that she's out of touch with the average American. But I don't think this is terribly probative of anything.
5) Hillary Clinton, in the first debate, you were proud to have Republicans as enemies. Since that is your attitude, wouldn’t electing you as President guarantee non-stop partisan warfare?
Good question. Ask.
6) Hillary Clinton, the constant refrain from Republicans has been that you’re not qualified to be President. Can you name your 3 biggest accomplishments that you believe qualify you to be President of the United States?
I think she's been asked this before. But ask.
7) Hillary Clinton, the Clinton Foundation took in millions in donations from foreign governments and defense contractors, some of which you helped rather significantly when you were the Secretary of State. Your husband also collected some rather extravagant amounts in speaking fees. According to the International Business Times,
"Under Clinton's leadership, the State Department approved $165 billion worth of commercial arms sales to 20 nations whose governments have given money to the Clinton Foundation...The Clinton-led State Department also authorized $151 billion of separate Pentagon-brokered deals for 16 of the countries that donated to the Clinton Foundation....American defense contractors also donated to the Clinton Foundation while Hillary Clinton was secretary of state and in some cases made personal payments to Bill Clinton for speaking engagements. Such firms and their subsidiaries were listed as contractors in $163 billion worth of Pentagon-negotiated deals that were authorized by the Clinton State Department..."
This is unethical on its face and it raises serious questions about whether you took bribes from defense contractors and foreign governments as Secretary State. If you had it to do over, would you have done things differently?
I think she should be asked about this, but she probably has a ready answer, and it will probably be good enough to satisfy anyone who's already inclined to give her the benefit of the doubt. And of course, those who aren't so inclined will howl about how she's playing by special rules, which will resonate with some people, and then feed into the bifurcated narrative that always surrounds the Clintons.
Ultimately, there are legitimate ways to handle potential conflicts of interest, and unless you can show that those aren't being done, you're speculating. Get some more evidence, or don't bother asking.
8) Hillary Clinton, back in 2002, after reading the same intelligence reports that George Bush did, you took a position to his right on whether Saddam Hussein had WMDs. You said, “It is clear, however, that if left unchecked, Saddam Hussein will continue to increase his capacity to wage biological and chemical warfare, and will keep trying to develop nuclear weapons." Given that you made the same mistakes that George Bush did when it came to knowing whether Saddam had weapons of mass destruction, do you think it’s unfair for people to accuse him of “lying” about the evidence?
Well, she voted for the war, so it wouldn't be too shocking. But that statement, in isolation, doesn't really specify what sort of action should be used to "check" Hussein, and given that the US had been enforcing sanctions and no-fly-zones in Iraq, she could well have been referring to similar measures. And further, she doesn't suggest that he had weapons of mass destruction, as the Bush administration would go on to claim, incorrectly, as it turns out, to justify the war.
9) Hillary Clinton, you were caught lying to Americans when you claimed a video was behind the Benghazi attack.
Meh. There was legitimate confusion about the attack from different agencies. If you haven't figured out yet that you're hurting yourself more than you're hurting Hillary by prolonging this ridiculous debacle, by all means, ask away. Otherwise, find a better issue.
You were also caught lying when you claimed you came under sniper fire in Bosnia.
There you go. Ask about that. I'd like to see an answer.
You’ve also been caught lying about whether you had classified information on your private email server among other things.
It's possible she didn't know there was. We probably won't know for sure for a long time.
Why should the American people trust you after you’ve been caught lying so many times?
It's a fair question, but it's also been asked before.
10) Hillary Clinton, you’re going to be 69 years old next year and you suffered a very serious head injury in 2013 after you fainted. That caused a blood clot in your brain along with a concussion your own husband said it took “six months of very serious work” to get over. Are you healthy enough to handle a job as incredibly demanding as being President of the United States? Additionally, can you assure the American public that there was no brain damage from your injury that might make it difficult for you handle the position?
The way you prove you don't have serious brain damage or impairment is by demonstration. So far she's doing better than most of the GOP field, and frankly, many of her opponents for the Democratic nomination. Dumb, don't ask.
11) Bernie Sanders, in a 1972 essay, you said, "A woman enjoys intercourse with her man - as she fantasizes being raped by 3 men simultaneously." Do you believe most women fantasize about being raped by 3 men simultaneously and what were you trying to get across with that comment?
He's been asked about this, and honestly, he recognizes that it's an embarrassing comment. But I don't think he plausibly could have been saying that, and I don't think it's relevant to anything. And it's a comment from 43 years ago. Who cares?
12) Bernie Sanders, you have attacked Uber on multiple occasions. You’ve called it “unregulated,” you say it has “serious problems” and yet your campaign has exclusively used Uber instead of taxis because it’s cheaper. Does that make you a huge hypocrite?
The fact that Sanders wants Uber regulated like the businesses it's potentially displacing seems: 1) only fair, and 2) perfectly consistent. He didn't, as far as I know, say he wanted to end Uber. He just wants a fair market versus regulated services, which are, after all, regulated for a reason.
13) Should a woman be able to abort a baby that can survive outside the womb? Should she be able to abort a baby the day before she’s born? At what point, if any, should an abortion become illegal?
Ask away.
14) Do you think men who claim to identify as women should be allowed to use the same bathroom as women? If your answer is “yes,” do you think this is unfair or even potentially dangerous to women?
If you can find a way of asking your question that's not horribly transphobic and misgendering of trans people, ask it. Otherwise, die in a fire.
15) All the candidates on the stage are strong supporters of the Affordable Care Act which was the centerpiece of Barack Obama’s agenda as President.
I'm not sure that's true. I think Sanders is lukewarm at best, but he'd say it's better than what we had before, if marginally.
However, the ACA was sold to the American people with a lot of untruths. Barack Obama said that if people like their plan and their doctor, they could keep them. He claimed that the ACA wouldn’t raise the deficit. He said the average family would save $2500 in premiums per year. None of these promises turned out to be true and yet, none of you have criticized the President for misleading the American people. Since that’s the case, why should anyone believe your promises?
I'm not going to address any of the claims about what Obama said about Obamacare, but what does that have to do with any of the current candidates? Dumb question, don't ask.
16) There are hundreds of thousands of American citizens who have been victimized by illegal aliens who wouldn’t be here in the first place if our border were secured and our immigration laws were enforced, something nobody on this stage plans to do if elected as President. What do you say to the victims and families of the victims who’ve been raped, assaulted, or robbed by illegal aliens? What do you say to an American mother whose child has been molested, murdered or killed by a drunk-driving illegal alien?
The law as it stands is unenforceable, inhumane, and impractical. I don't want to see it enforced with 100% efficacy. Moreover, why focus on the criminality of immigrants, which is lower than that of non-immigrants if you ignore the immigration violation itself? Keep your xenophobia to yourself.
17) How much of a problem is white privilege for America and if you do think it’s a problem, what can we do to combat it? Also, what would you say to white people who disagree with the idea that they have white privilege?
I take it that last question refers to you? I don't know what you expect to learn from this that you can't learn from Google. But by all means, if you think there's something to be gained, ask it.
18) Do you think an illegal immigrant who takes welfare on behalf of his child should be allowed to become an American citizen? What about an adult illegal immigrant who has never paid income taxes? If the answer is “yes,” how does allowing people to become citizens who will be drains on the taxpayers help America?
A little obsessed with immigrants, are we?
19) Please raise your hands: Would anybody on the stage be willing to make the White House a gun-free zone to reduce the chance of gun violence there? If not, then does that policy really make sense for our schools?
The White House is a gun-free zone, in the same way that schools are. Only authorized people are permitted to be armed on the grounds.
20) Since 2008, the Democrat Party has lost 69 House seats, 13 Senate seats, 910 state legislative seats and 12 governorships. Has your party gotten so far out of the mainstream that it will make it difficult for a Democrat to be elected President in 2016?
Partially a result of very effective gerrymandering, partially the result of how our elections work, and the tendencies of Democratic voters to congregate in cities. In any case, there's a good chance that the Democrats will retake some of the ground in the next cycle. The last midterm election was brutal for Democrats, but the prior election before that was very good for them. The notion that one election represents a commentary on the party is a little dubious, especially since the elections with high voter turnout tend to be quite good for Democrats.