I'm replacing 'worst' with a 'meh' category involving dates that might seem good but might become mediocre, since a lot of the 'worst' dates are going to involve predictable stuff like disability restrictions or obvious personality mismatches.
Emi -
Great: Scavenger hunt. She'd need the right feet for the job, but she gets to go cross-country as quickly as possible and look for stuff! It would be a nice twist on what she normally does.
Meh: Watching a sporting event. You'd think she would have a blast, but it seems like she's not into sports for the competition itself. She would get antsy and want to just leave and screw around in the parking lot.
Hanako -
Great: "Cozy" camping - like with a rented cabin with some modern conveniences. She's not a rough and tumble girl, but she can appreciate being in the middle of nowhere.
Meh: I'd have to say the karaoke. It could go well if it were a private thing or there weren't many people. If there's more than a handful of people, all it will take is one mistaken lyric and it's a spiral down from there. I mean, lord, you're shining spotlights on someone who doesn't want to be visible!
Lilly -
Great: Others have said concerts, I'm gonna say male strip club. Get her a dancer, explain to him some special considerations about physical contact, and let him drive her wild. Hisao can just wait in the parking lot or something until she comes out, adolescent sex drive in full gear.
Meh: a musical would be seriously hit or miss. A lot of the songs would be catchy, but keeping up with the plot would depend entirely on the quality of the writing. Heaven help you if it's one with a lot of visual gags.
Rin -
Great: a circus like Cirque du Soleil. Rin collects unique people, after all. Just put her in a tent full of people doing amazing things with their bodies. They have a good selection of colors, too.
Meh: Poetry reading. It's artsy, yeah, but we have no idea how well-read she is, or if all this language would remind her of how inarticulate she can be.
Shizune -
Great: A legislative meeting, followed by a light meal and boozy drinks to discuss the proceedings. She would think that everyone in there was wrong, of course, but she would love every second of it. Arouse her Ambition Boner. (I'm making a bit of an assumption here - Many states in the US allow people to sit in during this sort of thing, and Japan might. If not, replace it with a business seminar or something?).
Meh: Ridiculously expensive restaurant. Oh, you've got something to prove by throwing money at her? Good job being exactly like her dad.
Misha -
Great: Small restaurant with a long series of courses with a variety of flavors. Don't worry about your thighs, honey, we'll get some exercise later
Meh: Heart-shaped bed. Low candle light. Blue wig. Glasses. Sex toys. Night of her life, or a reminder of emotional trauma?