Be kind to yourself and to your interesting stranger: have something prepared before you find yourself asking, "So, what do you do?" If you must rely on that old standby at least rephrase it. "Tell me about your job," asks the same question without the immediate whiff of cliché. Talking about the weather or a job is an easy way to open a conversation because there's no wrong answer -- these are safe. But there are better topics, and better approaches.
Let the conversation flow naturally. Share your name and ask for his. Give a detail about yourself, but turn the conversation spotlight on to him. Ask open-ended questions rather than anything that can be answered with a yes or no, and listen to what he's saying rather than waiting for your turn to talk. Look for topics aside from the weather, and work to kick off a conversation. If there's a game on, talk about sports. A band playing? Remark on it.
Dr. McGann says, "Commenting on someone's T-shirt is a simple one -- if you notice someone with a music festival T-shirt that reads 'North Forks Music Park,' a great opener may be, 'Is that in Rochester?' It poses a question, which obligates the other person to at least respond. After the initial exchange, someone who is interested is likely to pick up the conversational thread and go someplace else with it."
Remember: If you don't ask for what you want, you won't get it. You don't want to seem desperate or overbearing, but if you want to ask for his phone number, then ask. Getting his number isn't demanding commitment. Let him know you enjoyed talking and that you would love to chat again sometime. If you still aren't comfortable asking for his number, offer him yours.