Hi! I’m sorry that this took me a while to answer! I hope you like it tho ;-;
(I didn’t include Daishou because I’m not familiar with him)
Sawamura Daichi: Before suggesting anything he’d ask his crush if they had anything particular in mind, and if their answer was no he would propose going to the movie theatre. He would probably want to go into the newest action movie and would be over the moon if his crush was up for it. (more plus points if they’re into action stuff and/or comics)
Oikawa Tooru: Wants to go window shopping/take a walk through the city and will 100% end up buying his crush some corny key-chain and tell them how happy he’d be if they would hold it dear to them and think of him whenever they’d be taking out their keys/phone (he’s so cheesy it’s gross). Afterwards he’d suggest to settle in a nearby café, and to enjoy the remaining time of their date talking and with a slice of cake.
Kuroo Tetsurou: Would probably fetch his crush after school and ask them to accompany him to his favorite eatery in the neighbourhood, and invites them over to his place afterwards for a movie date. Another place he might suggest would be going to a cat/owl café.
Bokuto Koutarou: Theme park dates are his thing! He would want to go to a amusement park, partly only to show his crush how tough he is by going onto all the big rides. If his crush would be fine with more people being present he’d suggest going to a karaoke bar with a few more people.
Ushijima Wakatoshi: A museum date would be what comes to his mind first, mostly because he thinks that a quiet and calm atmosphere for a date might be suitable. Either that or he’d just ask them to go grab lunch and drink a coffee with him. He wants to get to know them better so he’d like a place where they could just sit down and talk.
Terushima Yuuji: Totally the type to ask his crush to come to a festival with him. (includes booze and smoking pot of course). If he knew they weren’t as much of a party animal like him, he’d like to take a stroll through the mall to grab a milkshake and chit chat. He’d definitely say yes to a movie date as well.
Moniwa Kaname: Moniwa would invite his date over to his place to cook together. He’d either ask them if they wanted to go ingredients shopping together or would already have everything ready at home. After they cooked (his crushes favorite meal ofc pft) they’d eat together and enjoy the evening with a movie.
These are great! I totally forget about Kaname, why? He’s amazing! And no worries about Daishou, I don’t read the manga so I don’t know his character at all except that he exists.