I’d bring a bottle of Jack to Ke$ha’s house. After that, the possibilities are endless.
Ok, scratch Portman. Write-in Kristen Bell.
She’s just going to brush her teeth with it. What a waste of bourbon.
Incredibly hot. I mean, they have access to starlets. I doubt ordinary women would really attract them, except maybe for a quickie or a blowjob.
I think it’s pretty pointless for women, too.
All my Hollywood crushes are dead. In most cases, for decades.
I guess I’d go blow something up with Kari Byron. I’m not sure just what we’d blow up, though, that would impress her… I need to think more on this.
So more JFK, James Dean, Jimi Hendrix dead rather than Ernest Borgnine, Andy Griffith, Marlon Brando dead.
Or Beethoven dead? Atilla the Hun dead? Utzi dead.
I’d have no chance…seriously, Scarlett Johansson dated Ryan Reynolds…I’m a straight man, and even I have to admit he’s pretty much a male Adonis, at least physically. My only hope is to win her over with my fantastic wits…
So yeah, I’m fucked…and not in the way I’d want to be by Scarlett. 
She seems like a real classy gal, though, so it’d have to be some sort of fancy, black-tie affair, which I certainly never get invited to. And it’s not that classy to force her to being me as a date somewhere, so…yeah. At that point, I might as well ask her to pay for everything and drop me back off at my mom’s house when we’re done.* :rolleyes:
*I don’t actually live with my mom, just going along with the theme of “pathetic guy doing everything in his power to NOT win over a woman.”
I think I’d have a much easier time with another crush, Kat Dennings. I think she’d be totally down with just hittin’ some bars, getting a little tipsy, and seeing where the night takes us…which I hope would be drunken skinny dipping in some random person’s pool and/or hottub that we sneak into. 
I’d take Maggie Cheung hiking in the Alps.
I’d invite Meg White over to my place. I’d cook a simple dinner, then we could watch a movie or listen to some music. With all the rich guys who throw these fabulous dream dates at celebrities like her, I imagine she’d be up for something a little more down-to-earth.
I think her music’s good, but I’m by far not her biggest fan, which might actually work in my favor. 
I would rent a yacht and crew so Carla Gugino and I could spend the day together on the Chesapeake bay getting to know one another. When we get hungry we will pull into a waterside restaurant for blue crabs. I will pick the crabs for Carla, so she doesn’t have to risk cutting her hands.
Hey, you don’t know that Megan Fox doesn’t want to help me alphabetize my comic books. Don’t judge me. :mad:
Ronald Colman and Fredric March dead.
I’ve only had 3 celebrity crushes in my life. Someone you see on film, in particular, isn’t necessarily going to be of an age where you’d be interested in hitting on them IRL. One of my crushes is dead, another is in her late 80s, and the third is in her late 60s.
I think I’ll stay home with my wife and kid, and forgo the prospect of a celeb date altogether.
Well, the premise of the OP is that you do have a chance. Somehow, perhaps magically, you’ve got one date and need to make it count.
I recall an interview from a few years back in which Ms. Johanssen said she’d always loved going to Disneyland, so that’s where I’m taking her. As a deliberate antithesis to the “classy black-tie affairs” that celebrities probably get tired of, I’ll just relate to her like a normal person rather than some godess on a pedestal. We’ll geek out and go on all the rides, and laugh and have a day of silly fun, and in my fantasy she finds this behavior so refreshing that she can’t help but fall madly in love with me. 
Zzzziiippp
Ya’ like that baby?
[fantasy]
Well, one idea would be to take her to a historic village near the Delaware Water Gap where they have older houses and a blacksmith’s shop and even a barrel cooper. After a an hour or so exploring the town & a nice walk, dinner at The Walpack Inn, where they have good wine, better food, and picture windows by some of the tables. There are corn feeds outside of those windows, and at dusk, deer will feel right on the other side of the glass.
But there, my luck would change. Because as she’s getting her dinner, doubtless some little boy at a table behind us would say, “Look, Daddy! do you see what I see?” And before she could say “Awwww…!” he’d pipe in with “That’s Fresh Venison! I want some! Git me some, Daddy? Please???”
And if that didn’t ruin the mood, with my luck, Ole Bambi would suddenly go rabbid and start slamming his head into the glass. Now lets be serious: What LA Smokin’ Hottie is going to be able to enjoy her steak with a deer face-planting into the glass along to the beat of Vivaldi??? :smack:
She’d throw down her fork and you know what she’d say?
“This is why I don’t work with children or animals…!” …and I’d never see her again. 
Then again, it wouldn’t be my first idea. My first idea would have been a nice icecream shop just around the corner that still has a soda-fountain counter and walnut-wood booths in the back. There are jukeboxes in them as well as those old fashioned wooden puzzle games. They serve icecream sundaes on glass dishes. Unfortunately,its already been done. Technically, using it could be considered stealing from The Mob. Rumor has it that Bill Clinton tried this once in2007… and he was Never President Again. :eek:
Well, that and some people say Applegates has better icecream. And others say Denville Dairy has better icecream. Still others are Coldstone Creamery fans.
Hmmm… wait a minute… what about a totally different idea? Something that nobody else has come up with?
Concept: Acme Date Idea # 3
Icecream. Tasting. Road. Trip.
Part icecream date, part road rally with some elements of a wine tasting thrown in! You could print up a tasting checklist, complete with a section of tasting notes and little golf pencils, map your stops, and take her the scenic route to each and every one with the roof open or the top down.
I know, I know, ‘woman does not live by icecream alone.’
(…but wouldn’t it be fun if they could???) 
“…M’am, for your own safety, Step Away from the Creative Dater. Please be careful, but walk quickly. Your icecream is melting…”
[/fantasy]
With good behavior it’s more like 3 - 5. Plus since the gun isn’t loaded it isn’t armed robbery.
I’ll invite Adrien Brody to join me in a hot-air-balloon breakfast, then spend the day at Cedar Point. We’ll come back to my house for dinner, and I’ll show him my paintings and photography. Then he’ll pose for me . . . in progressive degrees of nudity.
A working date with Bernadette Peters. “Pennies from Heaven” comedic duet somewhere, her choice; I sing but I have difficulty enunciating with a fast tempo. She’d take the fast parts and I’d be like, “Let me know when you’re ready to slow down!”