Most Helpful Girl
Its strange feeling when you still dont know the guy and he is wearing sunglasses. A bit awkward. Because you want to look into his eyes while talking, but you see only your reflection. So I wouldn't be comfortable on a date with sunglasses (unless both wears them).
Most Helpful Guy
I personally think it's okay, but take them off after you'll sit down somewhere with her, so she can look into your eyes 🙂 even if she'll have them on, take you ones off for her sake 🙂