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Letters From Teenagers


This episode was originally released on July 30, 2015.
For most of us, our teenage years were marked by feelings of insecurity, loneliness and uncertainty. This week, the Sugars revisit an episode in which they discussed questions exclusively from teenagers.
They're joined by Tavi Gevinson, founder and editor of Rookie, a digital magazine for teenage girls.

Dear Sugars,

I'm a junior at a great high school that I really love, but I'm terribly and hopelessly lonely. I don't have a single close friend out of the 300 people in my grade. I'm friendly with lots of people, but I can never seem to get to the next stage of friendship with anyone. I eat lunch by myself every day. I don't even try to find people to awkwardly sit with anymore.

The last time I had close friends was in elementary school. I had some good friends in middle school from time to time. At the start of high school, I had one friend, but she abandoned me for more popular people. Since then, I've been on the outskirts of a certain friend group with people I kind of like, but I get more and more distant from them each term.

I'm sick of not having a single person to talk to and confide in. I've been struggling with depression, and my mother is the only person I have on my side. I look at Facebook and see all these girls in my grade having fun together while I just sit at home cuddled up in bed with my laptop and phone.

It's been so long since I've had a friend. I'm afraid that this will only get worse as I get older. What do I do so I don't spend the rest of my life alone? I feel like I've tried everything, spending all this energy trying to be social with people and never getting anything in return. These are supposed to be the best years of my life in terms of close female friendships.

I'm just so lost, Sugars.



Cheryl Strayed: Lonely, my heart goes out to you, and I know your feelings are real and deep, but I want to assure you that you aren’t alone. There are so many people out there who have been in your shoes. It’s a universal feeling that we’ve all had — that other people are at the party that we’re not invited to.

Steve Almond: One of the crises of depression is that it’s a time where you’re so desperate to not be alone and lonely, and yet, you feel completely unworthy of human company. It’s difficult to summon the courage to put yourself out there. Lonely, you should talk to someone about your feelings — a school counselor or someone else — because those feelings of depression are the essential problem, and one symptom is, it’s very hard to find friendship.

Cheryl: I was interested in how Lonely describes her background of friendships over the years. One of the things at play seems to be that she is depressed, but it also sounds like social interaction is not the easiest thing for her to do. That doesn’t mean that she can’t succeed at it. It means that maybe she needs to learn how to get more comfortable with her discomfort. One way to do that is to join a group that forces you to connect with other people. If things aren’t going well in one environment, they can go beautifully in another. So I challenge Lonely to find a group that is connected to her school and another that is not connected to school, so she doesn’t bring to it all of this baggage and sorrow that she feels at school.

Steve: Lonely, there are things you are passionate about, that you are good at, and that you really care about a lot. The time you spend looking at Facebook is only reinforcing your unhappiness. If you want to use social media, use it to connect with people who are interested in the same thing that you are. It will be much easier for you to connect with people if you are all interested in the same thing.

Cheryl: I remember very distinctly the idea that your high school years are the best years of your life. And even when I was in high school, I thought, “You’ve got to be kidding me.” We need to quash this idea. It’s not the truth, and so many friendships during your high school years are born of a kind of fear and anxiety about not being accepted or loved. My whole personality in high school was essentially a construction. From 18 onward, I began to have more authentic relationships. Lonely, this feeling of alienation is not connected to whether you’re going to have friends in the future or not. You will have friends in the future.

Steve:  Lonely, you have agency in this matter. You have the capacity to pay attention to your own life and the things you are passionate about. That leads to the people who share those passions and helps you form an organic connection.

Cheryl: Even if Lonely doesn’t go out and find a great friend tomorrow, part of what allows us to persevere is knowing that there are people who are out there like us.

Dear Sugars,

I am a perfectionist. Or at least, I have been a perfectionist. I am sometimes not sure what I am anymore, and I don't know what to think about that. I am a sophomore in college, but when I was in high school, I was a master of self-discipline. I was a varsity cross-country runner and trained the hardest of every girl on my team. I was valedictorian, and made sure that I studied for each class to the best of my capabilities, even if that meant getting four hours of sleep each night. I was also anorexic, and am only now coming to terms with that fact. I ate fewer than 1500 calories each day (I know, because I counted), even though I was running 40 miles per week. I grew up in a small town, and everyone constantly heaped praise on me. They told me and my parents how brilliant I was, how skinny I was, how fit I was.

But since graduating high school, I've struggled with loss of my identity. I started to burn out last year, and realized what I was doing was unsustainable. I gained a little weight, and started running for fun instead of competing. I now get a mix of A’s and B’s, and focus more on self-care. However, these changes don't feel as positive as they sound. The constant narrative in my head is that I've failed, peaked early, and that I'm not as good as my high school self. That past self feels like a shadow who follows me around, constantly reminding me of what I'm not. When I go home, I even imagine that my family and friends are judging me for letting myself go. It doesn't help that I go to an elite liberal arts women's college on a scholarship, and find myself surrounded by girls who act and perform just as I did in high school.

I can't go back to the level of discipline that I had in high school, but I also can't let go of that part of me. I am in limbo.

What can I do? How do I reconcile the changes I've gone through with my persistent desire to excel?


Followed by a Shadow

Cheryl: I really relate to this letter. The person I was in my teenage years was designed to get people to like me and approve of me. Followed by a Shadow is trying to get love and approval by doing everything “perfectly” — to meet everyone’s expectations of her physical appearance, academic achievement, athletic achievement and willingness to work hard. Some of those achievements are fantastic, but she how does she to accept the more human, more complicated, and therefore, less perfect version of herself? That is who her authentic self is.

Steve: The foundational myth of humanity is, “I must be great to be loved.” It is quite different to be loved for what you can do and achieve than to be loved for who you are. Followed by a Shadow, you have course-corrected, which is a beautiful thing to witness. But it has brought with it doubt, which is the old voice — “I must be great to be loved, I must eat this many calories and run this many miles.” And you are surrounded by others who are using the same standard.

Cheryl: She’s in a period of transition, where she is growing from her old teenage self into his new era of her life that is more about self-definition and less about social approval. When I was a teenager, I starved myself skinny. I got an enormous amount of attention for being so thin. And when I went to college, I almost immediately gained weight. I would go home to my town and feel very self-conscious about the fact that I was no longer the skinny girl. I was afraid of what people were thinking of me. I finally realized, we all want to make people think we are perfect. That desire never goes away. But the question to ask yourself is, at what cost? Sometimes we come to a crossroads where we realize, “I know what people expect of me, but I am not willing to pay that price anymore.” Followed by a Shadow, you are in that moment where you are saying, “I am not going to let those expectations rule me in all of my decisions.” Congratulations to you. What a beautiful thing. And the great truth that grew out of making decisions that came from being less “perfect,” the right people loved me more. Because they loved me for real reasons. As much as we all strive to be seen as perfect by others, there’s a false logic there. We don’t like perfect people. We don’t believe perfect people. Because we know they are not perfect. That they are hiding something, or sacrificing their humanity in order to appear in a way that isn’t quite human.

Steve: I grew up in a very ambitious family. I think of my older brother — he and another kid were the top of their class. They both went off to Harvard, and we thought, “They are golden. They are going to excel.” My brother’s friend took his own life his first year of college, and my brother dropped out because he was profoundly unhappy. Part of the lesson for me was that that kind of ambition is a tool for self-punishment. Followed, you are finding a greater happiness by discovering who you really are. You cured yourself by refusing to measure yourself up to an unrealistic and unhealthy standard. Continue on the same path. If someone says, “You’ve let yourself go,” say, “Yeah. Join me. It’s fantastic.” And remember, your capacity for discipline — you still have that power. Just put it in the service of something you want to do, rather than something other people are choosing for you.

Dear Sugars,

When I was 5 years old my mother was diagnosed with cancer. She was sick for a long time, and then when I was 13, she died. I’m now about to turn 16.  As you can imagine, as you know, Cheryl, it changes a person deep inside, to lose their mother. To lose that pillar of life in their world. I have never had a regular adolescence. I have been transformed by my mother’s illness and death. I’m different than people my age. And every time I say this, I sound stuck up, but here it is: I feel that I have wisdom that goes beyond the scope of my age group's understanding of the world. Not because I am some marvelous being, but because I have already lived through pain on a level so deep, only a person who has felt similar pain could understand.

And yet here is the problem. I often feel as if all of the wisdom I have accumulated is worthless in the face of other high schoolers. I don't enjoy going to parties, getting drunk, and giving blowjobs to the high and mighty boys who walk the halls of my school. Because of this, I am seen as the prudish, shy, quiet, young girl who no one wants to invite to the fun. I’m tired of not being asked to join the fun. There is this whole other girl in me that is funny, and loves to dance, to hike and swim and do silly teenager stuff. I’ve just never been given the chance to let her out.

Sugar, how do I give myself the chance? I want to stop being scared of having fun. I want to honor my mother, because she always had fun. And she was happy. I want to stop being so shy and serious all the time, and be happy too, but I don’t know how. I tell myself, “You just have to do it. That’s the only way things will change.” But then I freeze up. How do I let myself out of my own head? I want to be part of the fun, and I want people to see me, the whole person, serious and fun and dancing and happy and confused and free, and broken, but healing. More than that, I want to enjoy myself.

I feel so misunderstood, because I would love to have a boyfriend. I don't have a problem with getting a little buzzed and having fun, but I also want to be careful. Perhaps the biggest problem is that I allow myself to think that everyone else’s opinions and perceptions of me are right: that I am the lame one, that I am the naive one, that all that I deeply know to be true is in fact a lie, because it’s not what everyone else my age believes. Sugars, how do I change this? How do I solidify my belief in my own wisdom? And mostly, how do I merge my own, deep knowing, to the frizzy excitement of adolescence? How can I allow myself to be young whilst not betraying this very old wisdom within me, simply for the sake of fitting in?

Signed,                                                                                                                                                                            Old in a Young Place

Cheryl: Old in a Young Place, I’m so, so sorry you lost your mom. I relate to this feeling that you are alone in a sea of people who have absolutely no idea of the deep sorrow you feel and the profound loss you have experienced. I really encourage you to find a grief group, online or in person. There are so many people out there who feel your sorrow. Nobody is going to take your suffering away, but people can help lighten that load by being there and looking you in the eye and saying, “I know what you mean when you speak your truth.”

Steve: I agree that you have to find other people who have dealt with the same kind of loss and can help you feel less alone in it. But Old in a Young Place, there are plenty of people who haven’t necessarily experienced that loss, but who are ready to meet you where you are. You can’t go through life thinking, “Well, you haven’t had this, so it’s impossible for us to ever truly know one another.” There are people in your own community who will hear what you have to say and will affirm the parts of joy and connection that are in you. And when you are ready, you need to dispel yourself of the myth that you carry around such a heavy burden that no one wants to come near you. That’s an internal feeling that’s real, but it’s not actually the external reality of your high school life. I would warrant that there are some kids in your high school who value people who are deeply thoughtful. They might be a little less accessible, but they are there.

Cheryl: We talk about teenagers as if they are a different species, but this whole conversation reminded me of how connected we are. You guys really aren’t alone. Welcome to the human race, our teenage friends. We are with you in the struggle, we are with you in the sorrow, and we are with you in the beauty.

New episodes of Dear Sugar Radio are released weekly. Do you have a question for the Sugars? Email

Amory Sivertson Twitter Senior Producer, Podcasts
Amory Sivertson is a senior producer for podcasts and the co-host of Endless Thread.



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