How to Hit on a Woman When You're Shy

Use eye contact to gauge a woman's interest before you approach.
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It can be scary to approach a woman when you are shy. You might worry that she will reject you or that you will make a fool of yourself. You don't have to be a slick pick-up artist to get her attention -- be yourself and let your best qualities shine through. Most women prefer a guy who is curious and interested rather than someone who is egotistical or a show-off.

1 Eye Contact

The first step in making contact with a woman is with your eyes. If you are at a crowded party, try to catch her eye from across the room. If she holds your gaze for a few seconds, that is an indication that she might be interested, asserts the Social Issues Research Centre article, "Guide to Flirting." Though you might feel shy, don't let too much time pass after you first lock eyes. Take the initiative to go over and talk while the mood is right and the two of you have started to establish a connection.

2 Get Close

When you approach the woman after you have made eye contact, be wary of invading her personal space. Stay about an arm's length away when you first start flirting, so that she will feel comfortable -- but don't stand so far that she feels you aren't interested. If there is an opportunity to sit side-by-side, take it. Sitting alongside each other is less threatening and allows you to move closer without making her feel uncomfortable, according to the SIRC.

3 Comment or Compliment

Forget cheesy pick-up lines and jokes -- it's best to stick with a simple comment about the situation or a genuine compliment when approaching a woman, recommends the SIRC. For example, you might say, "It's really crowded in here tonight, isn't it?" or "I like the color of your sweater; it matches your eyes." You don't have to say something clever or witty, as the goal is simply to show your interest and create an opportunity to have a conversation.

4 Be a Good Listener

As a shy guy, you probably have the advantage of being a naturally good listener. Use your skills to show interest and curiosity. Ask her open-ended questions such as "How do you know the host?" or "Have you always lived in this area?" Being curious will also make it easier to feel less shy, suggests social psychologist Jeremy Nicholson on "Psychology Today" online. If you find it doesn't work out with one woman -- don't despair. The more you practice your approach, the easier it will become, says sociology professor Brian G. Gilmartin in an interview on the Interpersonal Science blog.

Arlin Cuncic has been writing about mental health since 2007, specializing in social anxiety disorder and depression topics. She served as the managing editor of the "Journal of Attention Disorders" and has worked in a variety of research settings. Cuncic holds an M.A. in clinical psychology.