No harm, no weapons. Yes, it is painful, because you don't know where it will go from there. Don't be afraid of being rejected or that you won't have anything intelligent to say. It won't kill you. You will learn how.
Good conversations have to be cultivated and produced.
The point of conversation is not to impress others or to enhance your popularity, but to learn about others. That is our most common mistake. When you talk to the guy in the plane, don't let him know by the end of the trip how many trophies you won and what investments you made. You are not interested in information like who won the ball game and what is the price of gold on the market. That is not conversation.