How do I put shyness aside and make a good impression on a date?

GingerMiss asks:

I’ve been single for over 2.5 years. My last relationship is the only real one I’ve had. Everything about it fell into place so easily. I signed up for online dating, met him three days in, and even though I was basically mute our first date, he still wanted to see me. We were together for three years. Since then, I’ve had strings of terrible dates. I can’t seem to get myself to get over my shyness when I’m on a date with someone I’m interested in. I haven’t had many second dates, and even fewer third. It seems like people lose interest quickly when I’m not as outgoing in person as I seem through text. I’ve been asked out by a guy I went on a date with earlier this year. He’s already seen me super quiet, which he said he assumed was just first date jitters. Something feels different about him compared to other guys I’ve talked to, and I don’t want my shyness to get in the way. I need some advice on how to put my shyness aside and give the best impression of myself on my date next week.


Demetrius says:

Would it surprise you to learn that I grew up as a very shy kid? I understand what it’s like to be stuck in a conversation. Wanting to say something, anything, but not being able to gather all your thoughts in a cohesive way. I also know what it’s like to feel so much pressure in social settings that you freeze up, and your mouth stays shut. If we’re being honest with each other, I still consider myself to be shy, I just compensate for my inherent shyness by faking it. I’ve never figured out how to not be shy, but I have figured out a way to compensate for it. Here’s how I do it, hopefully you can get something out of my tips.

There are three “basic” things that I do to overcome, or push past shyness. Now the work itself isn’t basic per se, but the concepts are. Here are the three things I do:

  • Research
  • Experience building
  • Practice

This might not be true for everyone, but in my case, I find that the more I know about something, the more comfortable I am speaking about it. I don’t need to be an expert in a field, but doing a bit of research on, let’s say film making, allows me to speak a bit more confidently about it. So how does Research play into overcoming, or at the very least getting past your shyness? If you’re like me, you’ll become more and more confident speaking in public when you talk about subjects you consider yourself to be knowledgeable about. When I was a kid, the only things that could get me talking in most social situations were any conversations about dinosaurs, cartoons and comic book characters, and random animal facts. As I got older, and I got more interested in researching more than just cool dinosaurs and fictional characters, I become more comfortable with talking about broader subjects.

The inverse of this is also true too. If you’re trying to get a shy person to open up, get them talking about something they’re knowledgeable about.  Trust me, it works wonders with peers, friends, family, even kids. People like talking about things they like.

Next, work on Experience Building. If you want to get comfortable speaking to people, it helps to have interesting things to say. If you also want people to go on second dates with you, they need to learn about you, not random trivia. That’s where having interesting things to say about yourself come into play. Having cool anecdotes and the like are good for bridging conversations, and starting new conversations, but you should also have things to say about yourself so that people can learn about you and decide whether they’d like to learn more. You know what makes it a hell of a lot easier to have interesting things to say about yourself? Having interesting experiences. You don’t need to travel extensively, engage in extreme sports, or be at the top of your industry, you just need to have experiences you think are worth sharing. Some experiences will happen by chance, some will be things you do for the experience, and some experiences you’ll work to create. Talk about that time you were featured on NPR. Or the time you got mugged on a first date. Or your (currently on hiatus but not for long!) podcast. Start a blog and talk about it, literally everyone does. Talk about the first time you held your baby niece (who is on the verge on turning 16), and the last time you held your latest baby niece, who is adorable.

Research and Experience Building on their own won’t do much, and that’s where Practice comes into play. Let’s say that through research, you learn a bunch of cool facts, anecdotes, and random trivia that you think would make for great conversation. Or, you’ve done so many cool things that you think are worth sharing. That knowledge and those experiences on their own are a good starting point. If you’re shy, you’re probably not a natural storyteller, so you should practice to get better. Practice telling people about all those random things you learned. Practice telling people about your accomplishments, hobbies, experiences, and lessons learned. Run through anecdotes in your head so you can refine them. If the idea of practice sounds silly to you, consider that comedians regularly practice taking the some joke, over and over, in different situations and comedy clubs. Comedians are really good, or at the very least really practiced public speakers, so take their best practices and put them to use for you.


If you do more and learn more and use those experiences to craft interesting stories, it will become a lot easier to push past your shyness.

One last piece of advice for overcoming your shyness: Assume that people actually want to hear what you have to say, so talk. If you do the work to develop interesting things to talk about, whether it involves your own experiences or not, assume that people want to hear what you have to say. If someone is on a date with you it’s safe to assume that at a minimum, they want to hear what you have to say. Worst case scenario with this assumption is that they end up not being all that interested in you. Best case scenario, you go on more second and third dates. This piece of advice has helped me overcome shyness not only in my dating life, but also professionally as well, in both my day job and with the blog and podcast.

Good Luck Out There.


Also published on Medium.

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