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Taking the Initiative With Shy Guys

by Leah Campbell

For women navigating the dating world, knowing how to best approach a man can often seem overwhelming. Societal wisdom tells a woman that if a man is into her, he will take the lead. Sometimes, though, men are simply shy and in need of a little extra push during those early stages of courting.

Become His Friend

If you are interested in a shy man, the first step is to integrate yourself into his life on a friendship level. Shy men sometimes struggle with self-confidence as a result of society’s view of shyness, according to psychologist and author Laurie Helgoe. Becoming his friend first will allow him the opportunity to get to know you without the additional stress and pressure of dating. Create opportunities to spend time with him, even if it is just coffee before a shared class or lunch in between meetings.

Lead the Conversation

Don’t take his relative silence as a lack of interest -- shy men tend to think more about what they are going to say. Author Jane Ganahl recommends starting with light topics of conversation and being comfortable with doing most of the talking at first. As his comfort level grows, he will contribute more to your conversations. In the meantime, you can use this opportunity to let him know more about you and to ask general questions about him and his life.

Respect His Comfort Level

While you may be comfortable with sharing the juicy details of your life, Ganahl explains that many shy men will cringe at learning information they deem private too early. Follow his cues when it comes to sharing, avoiding topics which might make him squirm. If you invite him to a public event, understand that he may not be as adept at socializing as you, and be willing to leave early if it seems he is not enjoying himself. Don’t push or have expectations that he open up sooner than he is ready -- accept his shyness as part of the package deal, rather than trying to change this aspect of the man you are interested in.

Express Your Interest

As you are getting to know each other, drop subtle hints that you are interested in more than just a friendship. Shy men may also need a more direct approach in order to recognize a woman’s interest. As long as he seems interested, don’t hesitate to suggest dates or to eventually make the first move. Pay attention to his body language and other hints that he may have romantic feelings for you, and if you feel confident that he does after spending a fair amount of time with him – take the lead and go in for that first kiss.

About the Author

Living in Alaska, Leah Campbell has traveled the world and written extensively on topics relating to infertility, dating, adoption and parenting. She recently released her first book, and holds a psychology degree (with an emphasis in child development and abnormal child psychology) from San Diego State University.

Photo Credits

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