Meeting new people? Scary. Reaching out to old friends? Awkward. Staying isolated and alone? Feels terrible. I see a lot of people asking for help on these, so here’s all the best advice I’ve found.

Genuine Curiosity In Others

Insecurity/anxiety in conversation usually comes from thinking about yourself and worrying what other people will think. The best fix is to be genuinely interested in the other person, their thoughts, and their feelings. By authentically wanting to know more about them and asking good questions you’ve taken the spotlight completely off of yourself. Bonus: It’s very flattering/charming to your audience to think other people are interested in what they think and feel. 

This is easiest at Meetups centered around common interests. You know much more about people there than a random stranger, and it helps to have a group of candidates that all have at least one thing in common with you. And since you’re not thinking about yourself as much, you won’t be as nervous or insecure. 

It’s pretty easy for me to talk to anyone now just because I’m curious what they think and not shy about asking questions. Regardless of if you want friendship, dating, collaboration, or just a nice talk with a stranger….you’ll get better results when you connect with them as a human being and understand their feelings and thoughts. Read Dale Carnegie’s How to Win Friends and Influence People for tons more here – that book has had ripple effects in my career, social life, and relationships that I never could have predicted, hope it helps you too!

Learn to reach out first

You know that person you used to be close to and haven’t chatted in forever? Or that person you connected with recently but neither one of you set anything up? I think you should message them. What’s the worst that could happen? You continue ignoring each other? I was scared of sending the first message for a long time, but the truth is the risk/reward ratio is very good for you. It takes almost no time and even if only 20% of attempts lead to success, that’s infinitely more than 0. 

It helps if you expect nothing, people are busy after all and you don’t want to feel let down. But there’s a good chance they think about you too and they’re feeling too shy to reach out. They’d probably love to hear from you. I have several friends that are too shy to message me, I reach out first most of the time anyway. We usually have great calls/hangouts that could not have happened if I didn’t initiate. It’s okay that some people drift apart. But losing a great friend because neither wanted to reach out first is a tragedy. Learn to reach out first – you’ll nurse several great friendships back to life I promise.

Strategic Vulnerability

You don’t want to open up too fast (it can make others uncomfortable), but at the right time it is incredibly powerful. For example I noticed a coworker allude to how she struggles to make everyone happy and always feels spent. I noted that I had struggled with codependency in the past and she looked relieved and more comfortable. Everyone has their own issues, but no one wants to look like a screw up. When you can identify common struggles in another, it validates them greatly to know they aren’t alone. It’s a delicate tool, but creates a deep connection between people to feel understood and not judged.

Throw out bad fish

Meeting new people is good. Reaching out to old friends is good. Having a nice conversation with a stranger is good. But keeping toxic people in your life just so you’re not alone is not good. Sometimes toxic people can tear us down and make it harder for us to meet other people that would be better for us. They can make us feel bad about ourselves and discourage us from creating newer, healthier relationships. They can keep us in unhealthy habits and hobbies that put us in crowds we don’t want to be a part of. Look carefully at the people in your life. Do any “friends” take away more from your life than they add? If you remove them you’ll have more room for people who build you up. And if you see someone as toxic you’re not doing them any favors either by pretending to be their friend. Like I said, it’s okay that people grow apart sometimes.

That’s all for now. Please know there’s a ton of awesome people out there and I’m sure some of them could make your life a brighter place, you just need to find them and take the first step. I promise finding one awesome person completely outweighs the effort of sorting through the rest. And once you polish these skills, your confidence will skyrocket because you’ve seen yourself succeed time and time again. You can do it!