Shy Single: A Bold Guide to Dating for the Less-than-Bold Dater

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First Date Dos

Dress well. For a first date (and, really, subsequent dates), choose clothes that make you feel beautiful, handsome, sexy, and free. This might seem like an obvious bit of advice, but your appearance can provide you with 'props' that aid the conversational flow and bolster your confidence from the outside in. As I mentioned earlier, consider wearing a "signature" pair of earrings, hairstyle, or shade of lipstick -- or pocket square, bow tie, or watch -- that can trigger conversation about how you got it, where you found it, or who gave it to you.

Breathe. And breathe again. This is a concept worth repeating. If you're in the grip of stage two, and babbling is your tendency, resist the urge to fill the void or interrupt when your date is talking. Take several deep breaths instead. If your forte is to freeze up, try turning your date's words or phrases into a question, such as "You grew up in Idaho? What was that like?" People love to talk about themselves. Intently listening to your date conveys interest and generates goodwill. Listening is an underrated virtue; it makes others feel valued.

Come prepared. As in other social situations, think up a list of reasonable, activity-specific questions to casually pose to your date to get her talking so you have something to respond to. Then listen with openness and add your own two cents, when appropriate, disclosing something human about yourself that doesn't reveal too much personal information. For instance, if you're ice-skating, you could say, "This is great. I haven't ice-skated since I was a kid. Have you?" If you're visiting an Egyptian museum exhibit, you might say, "I've only starting learning about the pyramids from the History Channel. Have you been interested in them for a while?" Revealing personal details indicates a willingness to be open. Sensing your generosity, your date may offer her own self-disclosure and voilà! -- you're conversing.

Cut yourself (and your date) some slack. A multitude of my shy clients are impossible to please, though they may perceive themselves as just the opposite. Their dates are never good enough. "What can I say? I'm picky," admitted Jennifer, a shy writer in her late forties. She's not alone. Many of the shy singles I've worked with have the tendency to find fatal flaws in their suitors before they've had their first sip of Chardonnay or ordered their cappuccino. They silently criticize their dates for such things as talking too slowly or quickly, not knowing how to order at Starbucks, or using their napkin as a Kleenex. Because Shys are highly critical of themselves, few people can meet their standards, especially if they show interest in them. To Shys, Groucho Marx's famous line, "I'd never want to be in a club that would have me as a member," isn't such a joke.

Think about it. If you can't accept yourself, how can you give others the benefit of the doubt? If that sounds like you, I urge you to dig deeply, turn the tables, and consider how your own lack of self-acceptance may actually be interfering with your ability to accept and love others. Self-kindness and awareness, free of self-criticism, increase your chances of making emotional space in your life for others. Jennifer, for example, learned to distinguish characteristics about her first dates that truly annoyed her from those that were a reflection of her own self-criticism by making a mental list of things she found annoying about her date afterwards. "Then, I divide the list into two categories: 'things that may have more to do with me than him,' such as 'he ordered steak' (I'm an aspiring vegetarian), and 'legitimate complaints,' such as 'he chews with his mouth open.' Then I focus on my own shortcomings to gauge whether I can live with what I perceive to be his legitimate ones. My line of reasoning may go along the lines of, 'Do I chew with my mouth open? Well, not that I know of. But maybe I do. And even if I don't, perhaps this habit can be fixed down the line with gentle reminders.' Generally, I weigh the good with the bad to come up with a more realistic assessment of whether I want to continue dating the person," she said. Jennifer's system seems to be working. "I've gone on a lot more second dates than I ever had before this strategy," she noted.

Highlight mutual interests. Discovering that someone you're attracted to likes the same things you do can be exciting. You have an instant common bond, a little bit of emotionally validating Velcro, that may help a relationship "stick." So when you learn about your shared interests, speak up instead of just keeping them to yourself. An example: "I can't believe you like to cook, too. Most of my friends just go out to eat. What do you enjoy making?" It's refreshing to meet a kindred spirit.

Tell it like it is. An obvious strategy is to say, "Okay, I confess. I'm shy," to help your date better understand your reactions and relieve your stress level. The typical response is often "So am I" or "You don't seem shy." "When I told Martha I was shy, she said, 'Really?'" said Charlie, a shy single in his late twenties. "Then she recounted all the things I had done that didn't seem shy -- from asking her out to sending her a 'looking forward to our date' e-mail. I had to convince her I was. It also made me realize that maybe I'm not as shy as I thought I was, or at least, I can fake it if I need to." In any event, the more you're able to put your feelings into words, the less likely you'll enact them in a way that isn't your conscious intention. Giving voice to our fears can be liberating.

Reprinted from: The Shy Single: A Bold Guide to Dating for the Less-Than-Bold Dater by Bonnie Jacobson, Ph.D., with Sandra J. Gordon © 2004 by Bonnie Jacobson, Ph.D. and Sandra J. Gordon. Permission granted by Rodale, Inc., Emmaus, PA 18098. Available wherever books are sold.