Getting to know a new person can feel extremely daunting. You want to make a new lasting connection but maybe you're afraid. The standard "get to know you questions" might seem cliche. Here's a strategy I use sometimes to make the other person feel comfortable: I reveal random things about myself that you wouldn't necessarily ask. This is the litmus test to determine whether they will feel like they can share with me too.
For example, I might say something like: "I'm anxious about the harsh winters in Portland, but then again, I have anxiety so I am anxious about a lot of things." See? I revealed something about me that you might not know and now it makes the other person feel more comfortable about opening up and sharing parts about themselves. People tend to feel safer when they see that the other person is nonjudgmental. Falling on your proverbial sword will make your new friend feel like they can share more with you.
Humor is your friend
Make a joke about something that actually bothers you. Sarcasm is a great way to break the ice and invite other people to be real about what bothers them. Who doesn't like to complain about random life annoyances? Caution: try not to gossip. When you talk badly about another person, it reflects poorly on you. You want people to see you as someone they can trust. Gossiping will make you appear untrustworthy. Stick to complaints about public places, institutions, or common societal issues like paying the phone bill or going to the DMV or Costco.
Sometimes during the course of getting to know someone, your new friend might reveal something personal that happened to them that was traumatic. That's normal and a part of life, but it's important to keep in mind that when your friend does this, put on your empathy hat. Ask them how they feel about what happened. They may or may not want to talk about it, but you offered to listen and that's what counts.
Find something in common
Maybe you both like sushi or the same Netflix series. Finding a common ground will make you both feel more comfortable. Talk about something you like and then see what the other person offers up. Maybe they like that thing too or they share with you another thing they are into. And when they do that, you can ask more questions about what they reveal.
Getting to know people is an adventure
Getting to know someone doesn't have to be scary. Think about it as an adventure. Be curious and ask questions. Imagine yourself as a detective who wants to learn more. Your curiosity will help you fortify some solid bonds in the future. You'll learn more about the person and find ways to connect. We've gone over some strategies that will help you get to know people and make long-lasting friendships. Getting to know people takes time. Be patient with yourself and the person you're learning more about.