I'm scared to approach men honestly. I'm scared I might approach a guy like Kent...
The worst he will do to you is give you a weird look, make an excuse to go, or he may be occupied with something so there is nothing you can do.
Something that helps is realizing that you just want to get to know him. You're not worried about a relationship or dating but you want to see where his mind is it. Something that also helps is realizing that it may be the last time you see him so take your chance. If he is buying something at a vending machine ask him which snacks are better. If it's a bookstore ask him if the book is worth reading , or whatever. Try to ask open ended questions. Closed ended questions just give you a yes or no answer. Oh, and try to put your best foot forward physically. Some people say it's narcissistic, but I feel like when you're approaching a guy try to look appealing to the eye. With class of course
For instance if you have some buttery yellow teeth please get them fixed, but who knows some men will let that slide.