50 Things I'd Actually Want to Hear from Donald Trump

At this point, the relationship between Donald Trump and the press is the sort that makes Ike and Tina Turner seem like Mike and Carol Brady. The more he attacks his chroniclers, the more he enjoys it and the less the media seems to be able to do about it. In fact, every insult just brings him more airtime. He's the Kanye West of politics. Every ridiculous thing he utters becomes a headline that only encourages him to say more ridiculous things because he's been given a forum.

Don't get me wrong. I know a precious few interviewers have gamely attempted to bottle up the slippery garden snake that is The Donald's world view. For the most part, though, he still seems to be getting a free pass from the mainstream media because... let's face it... he is pretty damned entertaining! (Although so is Mr. Burns from The Simpsons and I'd never want him to be president either...)

As a lifelong journalist, it's killing me to see how few revealing questions he's ever answered honestly. And, as an unemployed journalist, I've got plenty of time to come with questions I'd love to ask him. Questions that don't allow him to reach into his stock answer bin. Questions to reveal the man behind the mouth. Questions you'd eventually want to ask any prospective life partner (and isn't that what a president is in the bigger picture?).

I realize he'll never see these inquiries but at the same time, wouldn't it be great to hear responses to any or all of these 50 things I'd actually want to hear from Donald Trump?

1) Seriously?
2) Have you ever felt guilty about anything ever?
3) Can you name three things in your life you regret?
4) When was the last time you reached into your wallet and handed a dollar to a panhandler?
5) Speaking of your wallet, how much cash is in there at any given time?
6) When was the last time you cried (and not tears of happiness for escaping any lawsuits related to the many big deals of yours that went south on you) ?
7) Rank the Seven Deadly Sins, from most favorite to least favorite.
8) So you said recently that because Mexico's president said he wouldn't pay for your border wall, it just got 10 feet higher. Does that mean it wasn't high enough in the first place?
9) A follow-up on that... exactly how tall does a wall have to get in order to become an effective wall?
10) Are you at all familiar with the meaning of the word "irony"?
11) Let's say that you woke up tomorrow as a woman. How would spend that day?
12) Fill in the blank. When nobody is looking at me, I _______.
13) Let's say someone falls out of your yacht and into the ocean, and he or she can't swim. Would you a) jump in to save them; b) look for a life vest to throw them; c) sign them up for swimming lessons when you got back to shore?
14) We're all told when we're young that any of us could grow up to become president. Do you actually believe that?
15) Are you at all familiar with the word "shame"?
16) What's your definition of a bully?
17) Let's say you're lost in the jungle along with an orphaned child from another country. A bear is chasing you and the kid falls, breaking his/her ankle. Do you carry him/her to safety or leave him/her there to distract the bear?
18) What if it wasn't an orphaned child but was a Victoria's Secret model instead?
19) What's the first thought you have when you wake up in the morning and the last thought you have at night?
20) What's the most embarrassing thing you've ever done?
21) When you go out to dinner, do you always offer to pick up the check?
22) If someone else does say they're paying, do you then intentionally order the lobster?
23) When there's a movie about your life - and you know there will be - what will it be called and what will the promo phrase on the poster be (you can't say "You're fired," by the way...)?
24) What's the best lie you ever got away with?
25) When I was really young, my favorite toy was _________.
26) I attended your final rally in New Hampshire, and before you came out, your supporters were told not to lay hands on a protestor. They booed. Loudly. Isn't that kind of scary?
27) It's a waste of time but I can't stop ________.
28) I hope nobody ever sees that picture of me ________.
29) Whose poster was on your bedroom wall when you were a kid?
30) If you had to pick just one, what song best defines your life?
31) What would your rap name be?
32) When was the last time you were completely and utterly wrong about something?
33) How often do you check yourself out in the mirror every day?
34) You've made it clear you think Mexico is sending us its worst. What country would you say is sending us its best (and sending swimsuit models doesn't count)?
35) Are you at all familiar with the word "humility"?
36) When was the last time you prayed?
37) What was the result of that prayer?
38) If you ever see me ______, just shoot me.
39) What's the deal with how you talk about your daughter?
40) A follow-up to that. If you heard Ted Cruz or Marco Rubio talk about your daughter that way, how would you feel?
41) What's the worst advice you've ever given someone?
42) The typical American family earned just over $53,000 last year. Could you live on that if you had to and, if so, how would you do it?
43) Who hurt you?
44) When you watched John Hughes movies in the '80s, who did you identify with more - Anthony Michael Hall's characters or the ones that picked on him?
45) If you were on the street and saw a fat person slip on ice and fall, would you laugh or help them up? (And it's not Chris Christie...)
46) Name three character flaws of yours that you wish you could change.
47) If you were president and God said there would be everlasting world peace if you resign from office, would you do it?
48) In what area of your life are you most immature?
49) Who have you not met that you would still love to meet (and again, swimsuit models don't count)?
50) I mean, c'mon... seriously?