[ Midorima doesn't find it awkward either. He's the quiet type of person, usually only speaking if he has something he believes is important to say or if someone else prompts it first, either through action or their own words. He likes that Weiss doesn't get weird about the quiet and try to fill it unnecessarily. It's comfortable and it makes him less awkward by extension.

He does comment on a cafe he'd be interested in trying sometime on te way there, but otherwise the walk is likely just as quiet except for small talk. When they arrive, he has to consider which is luckiest. ]

The ability to utilize a lucky item to its fullest is the most adequate way to obtain luck, so the highest chance of getting the most out of your luck would be the easiest option. However- [ He points to the prison break room with his now marginally emptier cereal box. It isn't as if he minds the Candyland one- he'd be fine with it. However, his reasoning. ] Putting forth the most effort would make the luck much more effective as you've done more to earn it.