In my work with teens I’m learning that for a variety of different reasons, today’s teens are becoming more isolated from face to face encounters and are beginning to dread face to face interaction. I’m learning that for most teens, the anxiety and fear (which can be compounded with anxiety disorders, trauma, etc) is less about rejection, but the painful awkwardness that happens when they don’t know how to keep a conversation going. This is not only true for teens talking to new people, but even their close friends and people they know well.

Here are some tips for helping teens keep a conversation going:


When you smile you send a signal to other people that you are friendly, approachable and likable. You may not be aware of thinking that when you see someone smiling, but you probably are. Don’t be concerned about being a fake or forcing it. Just like any habit, it will take practice. And you’re being intentional about it is different than faking it.


Pay attention to the other person. What are they wearing? Where are you? At a concert? At school? Why are both of you there at the same time? These observations are all material for asking good questions–which we’ll get to next. How old are they? Where do they go to school? Do they seem nervous to be there? Do they seem shy? outgoing? What’s happening in your community or the world that day, week or month? What events, experiences, releases, people might you and someone your age have in common that are current and relevant.

Ask Questions

Most often when people run out of things to talk about it’s because they ran out of good questions. Good conversationalists collect good questions and are good at asking a variety of questions about the other person/people in the conversation. They understand that people, in general, like to talk about themselves and will do so when asked the right questions. In addition to being open, smiling and observing they walk into any encounter with some standard questions they’re prepared to ask in a variety of situations.

Really Listen and Don’t Interrogate

I’ve seen some teens attempt to practice this skill and get so focused on the asking and remembering the questions they forget the single most important communication skill there is: to really listen. If you’re really listening to the other person, they’ll know it and be grateful for it. When you’re not really listening and just rattling off questions you can come off as interrogating the other person rather than conversing with them.


Just like with smiling, asking questions will take practice. I ask questions for a living, and trust me it’s taken me a lot of practice. Timing, how fast you speak, tone of voice are all important in asking questions. You’ll learn these through practice.

Watch Others Who are Good Conversationalists

Pay attention to people of all ages who you deem to be good conversationalists. Watch how they hold themselves and interact with others. Listen for how they go back and forth in the dialogue. Listen for the questions they ask, especially people your own age. Remember those questions. Type them into your phone if you have to so that you can refer to them before having a conversation with someone.

Don’t Interrupt

This is really hard to do. Especially if you’re deathly afraid of the awkward silence, when you think of something to say that’s relevant to what the other person is saying, you want to jump in “Oh yeah, I remember when…” This stops the other person from talking as much and tells them that you really don’t want to hear what they have to say. I’ve watched teens (and adults) interact and often the awkward silence happens right after an interruption because the other person decides to not talk anymore if they’re not being listened to.

Don’t Experience Match

It can be really tempting when a friend talks about an experience they had this summer to immediately (even if you’re not interrupting) counter with a similar experience you’ve had. You really want to watch out for sharing an experience that “trumps” or one ups the other person’s experience. If they said they went to New York this summer and attended one off Broadway play, following that by saying “Oh yeah, we went to New York and saw three Broadway plays and then went to Boston for a Red Sox game” is not cool. Even though you’re not intending to do this, you’re basically saying to your friend “My experience is better than yours.” which makes your friend feel bad.

Avoid Talking On and On About Yourself

This is a conversation killer. We all relish the opportunity to talk about ourselves, especially to someone who seems to care and is a half way decent listener. During a conversation, pay attention to how much you’re talking about yourself vs. how much you’re getting the other person to talk about themselves.

Don’t Give Up

Even when you feel like  you failed, you didn’t. You overcame awkwardness and made yourself get out of your comfort zone. Pat yourself on the back. Now you’ve expanded the number of situations you now know that may feel awkward but won’t make you’re head explode and kill you. You survived to converse another day. Awesome! Keep going and you’ll be a better conversationalist in no time!