How Do You Overcome Shyness and a Lack of Confidence on a Date with a Guy?


I recently read your blog entry regarding dating non conversationalists. I consider myself a very outgoing person, and can usually carry on a conversation with anyone. My problem is that I freeze up when I talk to guys. I can’t seem to come up with anything to say, I become shy, quiet and introverted. I think it is that I am afraid to look or say something “un-cool”. I had a little self confidence until a few years ago, and didn’t “date” anyone until I was 23. I feel like I am now going through what most people go through in High School or College, but at a later time.

Is this a common problem? If so, any advice on how to overcome dating shyness?


Dear Jessica,

Ready for Lasting Love?
Ready for Lasting Love?

There is never MORE to talk about than when you know absolutely NOTHING about someone.

However, your question is an important one, because it’s something that my coaching clients ask me somewhat regularly.

”What should I talk about?”

And, as I see it, unless you’ve already covered the topics of his work, his family, where he lives, how long he’s lived there, what he aspires to, how he enjoys dating, and his various tastes in movies, literature, music, and travel, you should probably have plenty to say. Especially if he’s kind enough to ask you a few questions as well.

Granted, I have a little diarrhea of the mouth and could probably use a few kicks under the table to shut me up at times. But the point remains the same. You can talk about pretty much ANYTHING on a date. Yes to politics. Yes to religion. Yes to sex. Yes to ex-boyfriends. As long as you’re not putting down another’s opinion, or pining for a former lover, you should be pretty safe.

As you can tell from your own experience, the worst thing you can do is worry about what you’re going to say. Fear being uncool, and you may actually become uncool. The coolest people I know are those comfortable in their own skin. Nerds who embrace being nerds? Very cool. Average guy posing as a “cool” guy? Uncool.

And let’s face it: occasionally you’ll stick your foot in your mouth and say something stupid. That’s life. You just need the confidence to play it off afterwards. Hell, that’s what always kept me going. I can literally write a book on all the foolish things I’ve said or done on dates, and I’m sure my ex’s can write another two volumes about my idiocy. All you can do is recognize your mistakes and attempt not to repeat them. Just know that the more you tie yourself up with worry, the less likely you are to be your authentic self. I can’t help but to think of a baseball player overthinking a big at-bat, or an actor freezing on an audition. The only way to succeed in something this visceral is to turn off your brain and get out of your own way.

This reminds me of a personal anecdote. It was 2004. My first book had come out and a prospect had gone out to get it in advance. Research, I suppose. When we were talking on the phone prior to our first date, she confessed that she was really nervous about meeting.

“Don’t you get nervous before a date?” she asked.

I paused for a second, considering.


“No…actually I don’t.”

I thought about it some more.

“I just figure that if I’m being myself on the date, and you don’t like me, there’s not much I can do about it. Why spend any time worrying beforehand?”

And it’s true. Worrying has never helped anybody become a better date. Being on time does. Asking questions does. Staying positive does. But what can I possibly gain by going into the experience like I’m a nervous college graduate interviewing for a job?

My advice to you, Jessica, is to create a subtle shift in your thinking. Instead of thinking that you’re the nervous college graduate, pretend that you’re the boss — confident, secure, not determined to impress. Trust me, you’ll be more impressive.

The best advice I can give about how to “be” on a date is this: Think about the people in the world with whom you’re most comfortable. Your mom, your high school friend, your sister, whatever. How are you when you’re around them? Comfortable. Honest. Vulnerable. Silly. Real. Try bringing that same persona and energy to a date. If that’s you at your best, why would you choose to be any other way ?

I know there’s a big difference between talking the talk and walking the walk, but I’m telling you — if you go into each date with the assumption of success, you’re more likely to have real success.