How to Overcome Your Shyness and Get More Dates

Conversation Tips for All the Shy Guys Out There

Dear Shy Guy:

Approaching a woman at a bar or a party – or chatting with her on Tinder – can be intimidating. Even outgoing people have to power through those awkward moments, especially on first dates, which can be a death sentence for the night’s vibe. So here are some tips on mastering your shyness and getting more dates.

1. Genuine Interest

We all have enough to deal with, from the daily grind to mental health issues. So this isn’t an article on how you need to change for other people to like you. If you’re a quiet, sincere guy, don’t feel like you need to turn into a sportscaster to talk to a girl. Ditch the pick-up lines and say a solid hello to her. After that, keep the focus on her. (Remember, you went up to her.) Avoid yes-or-no questions. If you ask, “Are you having a good night?” you don’t want the conversation to fizzle out with, “No, not really.” Listen to her. Pick up on something she lights up about – her favorite beer, her love of paddle-boarding, whatever – and tell her a story about that thing. And if your story makes her laugh, you’re probably doing better than most guys.

Keep her laughing, then compliment her. Don’t just say, “You look nice tonight.” Find that thing that drew you to her in the first place. Is she really smart? Does she look stunning with her hair pinned up? Tell her so. Show a genuine interest in her, which will beam through your shyness.

2. Confidence

“Be self-confident,” author Zeynep Yenisey writes in Maxim. “Even if you’re just faking it.” You’ve heard it before: Confidence is sexy. That doesn’t mean you should be cocky. (An instant turn-off for a lot of women.) It means you know who you are and where you’re going. Granted, some men suffer from low self-esteem, which isn’t usually something you can just get over with a barside pep-talk. Perhaps the best way to feel better about yourself is to eat right and commit to a workout regimen. Slimming down, sticking to a schedule, and watching yourself set goals and meet them helps you glow with self-respect, even if you have to fake it sometimes.

3. Dress Appropriately

Just to be clear: Working out doesn’t imply that you have to look like The Rock to meet people. If you don’t have the perfect body, don’t worry. It’s more important to just be presentable. Get a good haircut. Buy the right shoes. Wear nice-fitting clothes. Taking pride in who you are is another sign of confidence, and that, too, will shine through your shyness. Don’t know where to start? Check out the Barbers Surgeon Guild blog, or stop in and ask about their products or ask for a cleanup so that they can make you look sharp.

“Just go for it, man,” guys often tell each other. Usually, all that does is ramp up the pressure on us shy guys. If you don’t want to talk to anybody tonight, that’s okay. Flirting isn’t a test or a performance. It’s a chance to connect with another person, a good conversation waiting to happen. And if it doesn’t happen, that’s okay, too. Everyone gets rejected now and then, and it’s pretty classy to stay gentlemanly even if she excuses herself. Overcoming shyness takes time. So have fun with it. Eventually, you’ll find the right person – someone else who’s just as weird and unique as you.

Yours Sincerely,

A Fellow Shy Guy