How To Tuesday: 3 Tips to Slay Your Shyness

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“Do you mind if I give you my number?”

That was a question our waiter asked at Ruby Tuesday last night. Yeah. Ruby Tuesday. For the salad bar. I was wearing dirty blue jeans, too. What?

Anyway, the waiter asked that question because he overheard my guy friends talking about their television production work in our conversation. I could tell by the way he asked, he mustered up some serious courage to do it. He asked if they were in television and when they said yes, he said he was an actor, and was looking for new opportunities and if it was okay – he wanted to give us his number.

All of us were impressed with him by the way he asked. He was genuine about his dream and what he’d like to do, he wasn’t pushy about it, there was no games involved with it. He just simply and kindly asked and 3 people at the table took his number just in case a job came up that he could be called for.

I don’t know, honestly, if I would have the guts to do what he did. Sometimes I might. But there are plenty of times in my life that I look back on moments where I could have talked to idols of mine, or possibly been able to be able to make an awesome friend or dream connection, and I didn’t act on it because I was afraid to.

The interaction with the waiter sparked a conversation with my friends about ways to overcome shyness. It’s a process, of course. It’s not going to be all solved by our fucking three easy tips or whatever…but this is what we came up with – Jeff, Burke, Paul, Jordan and I – at 2am this morning. We all perceive ourselves at different levels of shy/bold, and here are some tips that we thought might help you out a bit:

Photo by Fatboyslimgirl
Hiding behind a camera.  Photo by Fatboyslimgirl

Tip #1: Make “How Are You?” Be a Real Interaction.
Think about it. You probably get asked how you are in causal conversation at least once a day. If you want to take it to the next interesting step above and beyond just mindlessly muttering, “Fine. You?” – this tip is for you. The question “How are you?” is a key to conversation, a verbal foot in the door. Slay your shyness by answering this with enthusiasm or interest because almost no one does.

Here’s what you do: The next time anyone asks you: “How Are You?” – make sure to answer in 3 complete sentences. Make those 3 sentences true and interesting things about what you are doing, working on, etc. Your fourth sentence should be “How are things going with you?”

Example: A girl who is a regular at the coffeehouse I go to, makes room for me to sit on the bench and automatically says, “Hey, how are you?” I think she’s cool and seems interesting and could possibly be a friend – so I say: “Today I’m trying to be productive. I’m working on writing a chapter in my book and then I’ve got this dance thing I’m going to later. So it’s going to be busy, but awesome, hopefully. How are you doing?”

Replying like the way I did to her question will encourage her to give me more information about her life and her day and both of our replies can be great hooks for deeper conversation like: “Oh! You’re a writer? What are you working on?”

Conversation started. Shyness lost.

Tip #2: Practice being Badass and Bold on People in the Service Industry. I’m talking about waiters, the guy behind the counter in the deli, the girl who cuts your hair, the guy who makes a mean cup of coffee for you in the morning….because, let’s face it, part of their job is be nice to you, so this is good practice ground.

The first year I landed in New York, I was a waitress. People rarely engaged me in any kind of meaningful or interesting conversation. In fact, they rarely looked me in the eye when they ordered. They would bark out their order looking down at the menu and then shove the menu at me to take while continuing the conversation with their friend. It was like serving a bunch of zombies.

I had to be there for an 8 hour shift. And trust me when I say this, I would have been really happy to have a genuine interaction or a friendly human exchange somewhere in there. I would have welcomed it wholeheartedly.

So practice a short conversation on your waiter or your morning barista. Even if it’s a simple “Hello, how’s your day going?” or another question like “Hey, what do you think is the best coffee here?” Make eye contact. Smile. Ask one question.

Making eye contact and acknowledging another human being is half the battle. We’re all freaked out. We all get stressed and shy. There is no such thing as 100% superhero self-confidence. It doesn’t exist. Everyone on this earth is here working out some bullshit. Trust me on this. Don’t ever think that everyone else is okay and you’re the only one struggling with this. They are probably more freaked out and struggling and worried what you’ll think about them! So shake it off. And dive in.

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Tip #3: Channel Your Inner International Spy.
Fuck being seen as shy! Turn that into being “mysterious” or “the silent type”. Observe and ask them questions. Put the pressure on them to carry a conversation. People love talking about themselves and their interests. So if you are one of the more “mysterious” type, you might have trouble figuring out what to say. Instead of planning it out awkwardly or stressing about generating a conversation… simply take a minute to observe them and ask a genuine question. Like: “Where’d you get that scarf?” or “I see you’re on a bike…you know any good places to ride around here? I just got a bike myself.”

Do you have any other tips to share? Hit us. Start a conversation in the comments.

Don’t be shy….*wink*


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