Most Helpful Guy
Risk it. Do it.
If you can't determine anything from his actions yet, and you're kinda sure he's not into someone else, it won't be weird.
Best case scenario, you'll date him.
Worst case scenario, you'll get friendzoned and forced to move on.
It will also serve you well as life experience.1
Most Helpful Girl
Go for it. He won't think you're weird. In fact odds are that he will appreciate it.1