I think it would be a whole lot of fun to take Willie Nelson wherever he wants to go (offer currently valid in Colorado and Washington).
Edward Norton is super intelligent and sweet, as well as worldly and civic-minded. And sexy as fuck.
He would no doubt be an intellectually stimulating dinner partner but I might get over-stimulated on all fronts and not be able to converse let alone eat.
I think such a situation might cause me to burst into flames. I will pass.
I’ve been waiting 44 years for the chance to sit down with Alan Alda. It would definitely be worth it.
I’d like to have dinner with Steve Martin, but honestly, I expect I’d be too shy.
I would gladly take such an opportunity to have a meal with Leslie Fish. I would take her to a place that serves good whiskey and food(probably my go-to, The Portland City Grill), and we would talk about politics, anarchy, and compare notes on(and brag about) our polydactyl cats.
For payment, I would take you to the same restaurant.
Sure, why not? I pick up the tab for my friends all the time (and they occasionally do the same for me.) I’d have a very hard time picking the right person. There are a lot of talented actors and musicians out there, but I’m not really a “fan” of any one in particular. I don’t need a deep understanding of anyone’s art, just a good time. If I were going to do it, maybe someone fun like Lewis CK or Woody Harrelson. Can I pick Obama?
Not Obama, but you could pick Trump, since he’s an actor.
I think I’d stick to a local celeb or a has-been. I can’t imagine a major celeb being excited to have dinner with a random person, and I don’t really want to spend time with people who have to be paid to pretend to be having a good time.
Think of it as them being hired to do a personal performance just for you.
That might be fun!
You could BS with a musician or a performer or a writer(or dare them to Karaoke with you to the music plying in the background). Talk about petty nonsense, food, politics, wine, and maybe even just words that start with “N”.
“Nu.”
“That’s not a word.”
“It is so… its French!”
“Challenge.”
“Really? We’re going there!?”
"Garcon…! Dictionary…! pause …now, was that the word ‘nu’, or was that just your answer to playing that game…?
Lets see… there’s the fun list of people, the people who I think I’d really like.
There’s the people who I think I could get to laugh… maybe.
There’s the people who’d be worth te price of the meal just to make their eyes roll like Aubrey Plaza…
There are the ones you could have a whiskey and a cigar with… could you imagine sharing scary ghost story ideas with Stephen King…?
There are politicians who I’d love to say “Thank You” to (that means YOU, Mr. President) and the ones who I’d love to just wish good luck (Yeah, somehow I’d come up with the cash & I’d spring for Bill too).
There are the ones who I’m pretty sure would want to try to take a punch at me. (Oh, that’d be a riot!)
Then again… last but Not least… imagine if you could have 60-90 minutes and 3 courses of food just to tell Donald J Trump EXACTLY what you thought of him…?
(…and you thought the Ghost Pepper Fried Chilis braised with Insanity Sauce was hot…)
Thank Goodness there is no such contest; how in the world would I ever afford the bail? (…but if there is one, PM me. Life’s short; lets make it Fun.)
During the run of the *Dead Zone *T.V. show, there was a contest in which the grand prize was a personal tour of the set and lunch with Anthony Michael Hall. I was a big fan of the show and Anthony, so I entered. And I won…second prize, which was *Dead Zone *DVDs. At the time, I didn’t even own a DVD player. So close…
Penn&Teller (yes, I know, the contest is for one, but I mean, it’s Penn&Teller). No lack of good restaurants in Vrgas, probably Ruth’s Chris Steakhouse. Only condition is that I could duct-tape Penn’s mouth if he started to get too overbearing…
I pick The Boss. Or Stephen King, just to give him the line I’ve got ready in case we ever meet: “I’m SUCH a BIG fan…of your son.” Or Bill Murray, and I’d steal french fries from his plate.
I would take it and invite Weird Al Yankovic. There’s a few other people I would consider as well, but I think Weird (May I call you Weird?) has entertained the most consistently over the past few decades than any other performer.
I’ll recuse myself, since I just did this, more or less, with one name above and about five others.
I’d take Morrissey to McDonalds.
I’d take Emmylou Harris to Outback. I’d enjoy talking music with her.
Wouldn’t mind a deep-dish Chicago pizza with Cecil Adams. Seems like an interesting fella.
You are truly History’s Greatest Monster. 
I’d love to talk to Bono over a dinner at a mid-level sit down place. Nothing too fancy or expensive, but where I could have a decent steak and a beer or drink or two.
Of course, one of the things I’d be saying would be “You know, before Songs of Innocence, I was seriously wondering if you even remembered being that kid in Dublin.” 
Since we’re limited to stars, the only ones that I possibly have a good enough understanding of their interests, to be able to hold a conversation with them, is the Mythbusters. But Jamie would probably be annoyed by the whole ordeal, and I don’t know enough engineering to really hold my own in that conversation. And I feel like Adam would mostly be bored if it’s not a group of 4+ people for him to talk at.
I’d love to be able to take Antje Traue out on a date, but fundamentally I doubt that I’m of sufficient caliber to interest her so I expect that I’d mostly just feel creepy. 
(If you disagree Antje, I’m available!)
I do have a movie script floating around. So really what I would do is figure out which star is best placed to get it brought up to the correct producer. I’d have to do some investigation to figure that out.