The tone of Charlie's voice when he asked if Oliver was really taking him out for dinner, made Oliver grin and a warm feeling settle down in his stomach. Oliver, too, had not had much experience with dating people, at most having gone for a second date with one or two people. It felt nice to know that he could do something right, even if it was something as little as booking a table at a restaurant for Valentine's Day. Even if the restaurant was owned by a friend. A friend who Oliver used to have quite a lot of sex with. That wasn't... awkward, was it?
"I think you might need to dress smart," Oliver told him, quite obviously faking a sadness in his tone. He actually quite looked forward to seeing Charlie in a suit. "It is the opening night, Theseus might get annoyed if we show up in jeans and t-shirts," Oliver explained. "You can probably borrow something of mine?" He offered. "I don't think we're too dissimilar in size?" And Oliver did own a lot of suits, mostly for Quidditch promotion stuff.