How to Approach a Divorced Shy Man

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A divorced man who is shy may have trouble dating again -- not because he isn't interested but because he is afraid to approach women. If you find yourself interested in a shy guy, it may be hard to tell if the feeling is mutual. He might not say much, avoid eye contact and generally seem aloof. In order to break through his defenses, you will need to take a proactive approach -- both in terms of his shyness and his status as a divorced man.

Initiate Contact

Shy men are less likely to approach others for dates -- so you will need to be the one to initiate the process by talking to him first. A shy divorced man may be doubly wary about putting himself out there, particularly if his marriage ended for reasons that were outside of his control -- such as a cheating wife. Pick up the phone, talk to him at work, make contact through friends -- whatever you need to do to put yourself on his radar screen. As Juliana Breines, a postdoctoral fellow at Brandeis University, notes in the Psychology Today article "When 'He's Just Not That Into You' Backfires," shy men require pursuit.

Don't Get Too Personal

Now that you've got the shy man talking, what do you talk about? Don't share too many personal details or opinions right away, says Laurie Helgoe, a psychologist, in the article "Getting to Know a Shy Guy." Shy individuals can become uncomfortable when intimacy is rushed. A divorced man may also feel the need for boundaries in the early stages of dating. Stick to small talk topics that help you get to know each other better, such as hobbies, entertainment and hometowns.

Make Him Feel Safe

You've made the first move and are starting to get to know each other better. But how can you get the shy man to open up? Show that you will love and care for him just as he is, Helgoe says. A shy man may have low self-esteem, particularly after a divorce, and will need extra reassurance when he starts to date again. You can do this with words or actions -- by telling him what you like about him or introducing him to your family or friends. It may take time, but a shy divorced man will eventually open up when he feels safe in a new relationship.

Emotional Baggage

Realize that you are dealing with a divorced man who could still be carrying baggage from his previous relationship. To make sure that you are up to the challenge, find out if he is ready to date and what practical or emotional issues he might still be coping with from his divorce, says clinical psychologist Jennifer Oikle in an article on her website, "Avoid Dating Disaster! 5 Signs that a Divorced Man is Ready to Date." Ask questions, listen to the answers, and realize that the shy man may take longer to heal emotionally after a divorce.