The awkwardness of asking another person out generally comes with the fear of being rejected, and many people have found that striking up a conversation is the best way to begin the process. They would rather have a good time while thinking of ways to ask the question than start with the request. It can give them a chance to see if the other person is really interested, and a good conversation between the two of them can give the odds of a positive response a bitter chance. Even if the other person refuses a date, at least they had a good time while chatting.
Topics for conversation with a stranger can be difficult to begin, so having a few facts in mind to start off is a good idea. Reading the local paper every morning might be a good way to find conversational gambits, and local events are generally advertised. Talking about an upcoming music festival or show could help the couple find common ground on a single subject, but it might be all they need to realize they might have something to enjoy together.
Special events generally have their roots in local history, so investigating them more closely can lead to some good topics for someone seeking a date. Knowing that the regional art festival is held in a certain city because a famous artist used to reside there can show a person has taken the time to learn about a subject. While there are those who find this type of conversation tedious, it might attract someone who loves to learn new things.
A sense of adventure can be a good way for two people to connect, and knowing the other person likes to learn can be an avenue to explore. Getting to know them a little through casual conversation can be a big hit when it comes to asking for a date, and it might even mean a positive response.