Talk to him about the one thing since childhood that he is very proud of
Everybody has ups and downs in their life. Facing difficulties is a compulsion for every living being. Although the number of difficulties or the challenges will vary from person to person, it could be something as qualifying a simple test or securing a seat in their desired university. It could be getting a job at their dream company or getting a promotion. Whatever it may be, asking him about it, it will make him feel proud and instantly happy. His proudest moment is something that will be very close to his heart and it would mean the world to him that you cared enough to ask him about it.
Coffee Shops
Almost every time pick-up lines involve getting coffee or drinks. Drinks aside, talking over coffee is the easiest way to know a person. The coffee can be stimulating and helps us to be very involved in the chatting and focus on what he is saying. This can be a very casual encounter where superficial stuff is discussed but it is a start. Coffee shops are one of the best places to talk.
Most coffee shops provide the perfect ambience for connecting with people. It definitely feels nice to sit and chat with someone with a cup of coffee in your hand and the urge to know him more.