It depends on what type of restaurant it is. If it's places like "The Olive Garden" or "The Cheesecake Factory" you would probably want to be a little more on the classy causal side. If it's fast food places like "McDonalds" or "Burger King" (Yes, I know but trust me some guys are actually that cheap, I've seen it happen many times) then you'll want to dress down.
Also, I should mention that it really does depends on your body. If you have curves, it's probably better to wear form fitting clothing. We can't really pick an option if we don't know what you look like.
Side note: What do you mean by "stuff"? You said "dinner and stuff" but what does that actually mean. It could be bowling, the mall. I wouldn't suggest going bowling wearing something that might not come over well when bending over especially if you're not alone with him in the bowling alley. :P
Gosh, you're going down the wrong path here, girl! You look like you're out on a mission of conquest... just the thing to make the average guy run a mile — and that's (a) in the opposite direction and (b) in record time.
TAKE IT EASY!
We can assume from your careful framing of the options that the answer matters... and I suppose that's just the trouble. Whatever you actual feelings about the man, you must not reveal to him anything more than a casual interest. So dress like a lay nun, and work backwards, undoing a button or two, adding a flounce or two, to indicate that you're a normal, sexy girl. But these elaborate, carefully-accessorised catwalk outfits? No, no and again NOOOOOOOOOOOOOOOOOOO!
(By the way, they are all terrific... so keep them as a way to treat him AFTER you are going steady. Then, in the donning — and no doubt the removing — they'll be both appropriate and welcome.)
Honestly none of them are casual enough for the types of places I'd want to take a girl on a date. But then again I was never a fan of doing JUST dinner and a movie. I was always a fan of doing things that require being active and actually having fun. Personally I don't like any of those looks though.
WOW, YOU HAVE GOOD TASTE! I like option 4 best for a dressy restaurant, & option 5 for casual, but ALL are pretty, sexy, stylish & cute! In fact, option 1is a CLOSE runner up for either! ENJOY YOUR DATE...
The first one might be cute, if you cut down on accessories and got rid of the jacket - the red and that candyfloss pink would not be good together. So either jacket, or the accessories. If it were me I'd go with the jacket and those shoes in black and a simple black clutch or a neutral one like the base of the jacket.
Or I really like 3 if the dress were shorter. A jacket that length with a dress that length wouldn't look right. And get rid of the headband.
5 is too casual for dinner. 2 I think is a bit more ... night on the town than a dinner date; and 4 I just don't like.