Harry:
Harry decided to take you to a classic fancy Muggle restaurant. Even though it was a little cliche, it was still fun. The waiter messed up your order, so Harry put a charm on a roasted chicken, making it dance. You two had an amazing night : )
Draco:
Malfoy took you to your favorite childhood hangout. It was a sweet gesture, but it was freezing! In the end, you decided to go back to your flat for hot cocoa and a movie. It was a really great night, even though it didnt go as planned.
Ron:
Ron, being Ron, took you to a quiditch game. He bought loads of food, and cheered really loudly. It was a little disgusting and boyish for you, but he agreed to let you choose where to go next time ;)