Starting conversations with strangers is hard for many people but it’s especially hard when you are shy. Outside the defined roles at work, there is a whole world of unstructured relationships out there. By being able to start conversations with strangers, you can start to open up your whole world to new experiences, new connections, new love, and new opportunities. Even if you have failed in the past, it’s time to get out there and try again.

By having a simple plan to follow, you can break out of your comfort zone and strike up that conversation and leave the rest up to chance.

It’s easy to be overwhelmed by this concept.

Who do you talk to?

There are so many people. You only need to do this one person at a time.

I’ll mess up or I will be stuck talking to someone I don’t like!

The interaction doesn’t have to be with the perfect person and it doesn’t need to go perfectly either.

Instead of seeing this activity as painful process where you are in the spotlight, as an opportunity. Realize there is another person on the other side of this. It is up to them as well. See the good in people and don’t expect them to disappoint you.

It’s important to start trusting yourself as well in your relationships. See yourself as interesting, it just takes willingness and practice. I guess it all comes down to seeing relationships as something positive, as a way to build a network of love, support, caring, good times, and laughter while being your true, interesting self.

Starting conversations can be intimidating. I don’t believe I initiated any of my childhood friendships. It doesn’t have to be this way. You could have had double the relationships and maybe with people like you. I haven’t had too many shy friends and I guess that’s because I left it up to them to come find me. Make the choice to become a leader in your life.

Treat people the way you want to be treated and really get to the heart of who the real person your spending time with is. Don’t wait to be perfect or better to make friends. You are worthy of strong relationships and strong friendships wherever you are. Your real friends will care about you, flaws and all and you should care about them, flaws and all.

Starting Conversations is all about two people genuinely connecting.

Connection starts with truth. Be yourself, tell the truth, and more than anything it’s about listening, really listening to what they are say.

Here are some great tips to build a genuine connection with a conversation with anyone, one person at a time. You will not regret taking that step and you never know who you will meet and where it will lead.

1. Establish a connection. The first step is really just about not being stand-offish. Be approachable by keeping an open posture and making eye contact and of course, smile. Think upward and outward because it makes a world of difference. If you can control the environment, great music, drinking coffee or sharing an appetizer can go a long way but we don’t always have control over these things.

2. Introduce Yourself. Ok, this seems obvious but you need to introduce yourself. Say your name and ask them for theirs.

3. Build Rapport. I heard that if you subtly mirror or match the tone, expressions, and behaviors to the person you are speaking with, you will naturally gravitate to one another and you’ll both perceive it as a more positive interaction. Subtle is the key word and just don’t let it take you away from what they are saying.

4. Be Interested in Them. By this, I’m talking about paying attention, becoming absorbed in what they are saying. Really listen, imagine, and get curious. The more you do this, the more you will effortlessly. Get out of your head and start to really get to know this person. Also, it will help you connect and find that you potentially have things in common. Make learning more about them your number one priority. Want more on this? I like this podcast from Arel Moodie on The Art of Likability podcast to start conversations. Check out How to Start a Conversation with Anyone to get the conversation started naturally and How to talk to anyone to keep the conversation going. Get opinions and advise from others. Things you really want to know. Use softening statements.

5. Ask Open Ended Questions. Instead of asking “So, what do you do?” Ask if they are working on or planning anything exciting. This is more personal and less generic sounding and you are likely to get a more interesting answer that will take the conversation in a more exciting direction. Remember, it takes two. This isn’t all about you so do a lot of listening.

6. Give and Take. This is just about not oversharing. Pay attention to the other person’s response to you. If they start to wiggle in their chair or look away, maybe scale back a little. Consider what would apply to them. Too many details about your trip to grandmas will cause them to tune out. Be sure you are asking them open-ended questions when they respond and really listen. Don’t feel the need to share every relevant story you think of when it pops in your head. Self-edit yourself. Listen, share, and find a sweet spot balance. This is a two-way conversation.

7. Natural Humor. I say natural because you don’t just want to tell structured jokes. It should just flow naturally as you enjoy talking to them. Just keep the humor respectful and genuine.

8. Limit or Exclude Alcohol Entirely. There are so many reasons to not drink when you are shy and anxious but we’ll save that for another day. You want to remember the conversation and the person, you want to be yourself, and you want to be your best self, not a drunken, sloshy person (I speak from experience).

9. End the conversation on a positive note and move on. You won’t click with everyone. That’s ok. If you found something in common, maybe you could mention doing that thing sometime. Naturally grow this relationship. Exchange numbers and move on. If it doesn’t feel like a good fit, then genuinely thank them for the conversation and move on to the next activity in your life.

10. Don’t Break The ChainYou will get better and better at this the more you practice. Jerry Seinfeld makes a big 365 day calendar every year and uses a big red market to make a big red x for each day he writes a joke. The idea is to not break that chain. There is a free app out there for this as well. Make a goal to have a conversation with someone every day and see how your conversations improve every day and where it leads.  Instead of having lofty goals, just start one day and one conversation at a time.

Find a direction you want for yourself. A future you want. Friendships and relationships you want, all while being your three-dimensional self. Not being held back from being your true self. Practice and become connected, comfortable, relaxed, smiling, laughing, and enjoying life around others, even around strangers.

Eventually you will feel less judged and judge others less and less. You will look back on your shy and hesitant self in a whole new light.

Do you feel a strong desire to change? Resolve that enough is finally enough. You are entitled to rich experiences and friendships. What will your relationships look like if you continue on the path you are on in one year? Five years?

What if you take a new path towards building that first relationship?

You can even become that strong person who helps other people who are shy.

What are your strategies for starting conversations?

Share your experiences in the comments below!

SASSY Samurai


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