How to Date a Shy Guy

Dating a shy guy? You're interested in him -- for sure, but you want to figure out the long-term prospects. While you may be carrying the conversation most of the time, you need an array of ideas to get him to open up.

Handling Conversation

Dating a shy guy at first may feel like dragging carpet. You may find yourself leading the conversation, a lot. Help the conversation by asking open ended questions rather than questions that lend to yes-no answers. Open ended questions can enhance dialogue and may make conversation more free flowing.

Activity Dates

In the early going, try some activity dates like miniature golf. Activity dates keep the date flowing through times of awkward silence.

His Interests

Dating a shy guy may mean finding his comfort zone. This could mean asking him about his hobbies, interests, and work. This allows him to talk about things in his life at his pace, and in turn, it may help him come out of his shell.

Getting Personal

When you feel the timing is right, try putting yourself out there by telling something personal about yourself. This signals that you're not afraid to put yourself out there. He may reciprocate because a foundation of trust is being formed.

Family and Friends

As you continue dating a shy guy, introduce him to one friend at a time. Bringing him to a party where there is a large group of people may be intimidating from his perspective. Ease him into your circle of friends. Along these lines, introduce him to family on a piecemeal basis. Taking him to a family reunion to meet the whole gang in one shot may be a little much at first.

Compliments

There can be some rewarding mileage in complimenting your shy guy. Tell him he looks good before meeting your parents for the first time, especially when it's time to meet that wise guy uncle. This gives him a little confidence and allows him to ease up before meeting those close to you.