When I decided to sell my tender soul and become an internet writer, the first task on my agenda was to confront my deep-seated fear of being alone (in addition to downloading Grammarly and buying a pair of Dr. Martens, that is). I’d heard rumors that media was a cutthroat field, that your closest friends would rob you of both your trusting nature and your bylines. As an extrovert, this kind of isolationist landscape terrified me. My fear was only further confirmed at my first industry job, when my manager took me into her office and warned me that I was in a gossipy environment. She encouraged me to rise above it, to keep my mouth shut and head down. I was devastated, worried that my days of carving out friendships like Thanksgiving turkey were behind me.

And then the wonky, weird universe brought me Willa and Mel. Talented writers and aspiring change-makers, they quickly grew into both mentors and confidants. We began to edit each other’s personal essays and breakup texts, and I came respect their moral compasses, as north-facing as a fleece jacket. And on days when the world wide web felt less like our professional promised land and more like a pile of empty promises, we reminded each other of our mission statements, why we cared—truly care—about putting in the work.

Because of them, I now have proof that honest, platonic intimacy doesn’t have to end just because our childhoods do; that being alone isn’t synonymous with feeling lonely, nor adulthood with alienation. I have also come to realize that adult friendship isn’t necessarily about logging a certain amount of years. It’s about providing people with the space to grow into themselves, creating a buffer in case they veer too far off course.

What makes two (or more) adults click? Is it a devoted sense of loyalty that weaves you together like a basket? The ability to diverge for many years, then gravitate back to one another as if no time has passed? Or is it something less convoluted, like a shared adversary in the form of a hard job? To seek answers to these questions, I spoke to three wise, older women—Judi, Susan, and Doreen—about the many forms that human connection can take, maintaining old relationships from adolescence, and forging new friendships as an adult. And surprisingly, all three agree that the secret ingredient to maintaining high quality friendships, as we grow up and apart, lies in a single cliché: Remaining true to yourself, above all else.


Doreen, 62, lives in the Bronx, and has never had a friendship that didn’t last.

I was born and raised in the Bronx, where I still live today. I am divorced, but I have a grown son who gave me three grandsons, not one girl.

I was working as a personal shopper at Saks when one of my clients told me that her daughter’s school was looking for a secretary. I guess she thought I’d be good, so I tried out. They hired me part-time, and I guessed they liked me, because then they hired me full-time. Funny enough, I never really liked children. I had never worked with kids. But now I love them, especially the little girls. You know, I always wanted a girl. But I think God didn’t give me one because she would have been a hot mess.

Middle school, in particular, is really tough for little girls and their friendships. They have their ups and downs in middle school. They divide into these little groups, these cliques. They become territorial, almost survival-like. They gossip, they start rumors about each other. It’s less about making a real friend, and more about having a group of friends. Everyone’s separated. But it passes, and they grow up. And the girls become friends for life. It’s really something. They’re really true to one another, they’re loyal. They accept one another for who they are.

On Maintaining Long-Term Friendships

My oldest friend lives in Texas. We went to high school together. She comes to New York once a year, and we go out to dinner; we’ve been doing this for a long time. We were in a leadership club together, we’d wear these little white uniforms. I have another friend who is down south, she owns a couple of McDonalds chains down there, so she never comes back to the Bronx. We connect on Facebook. Actually, she’s probably my oldest friend. I’ve had her since public school.

I care most about loyalty. We don’t speak to one another often, but when we do, it doesn’t matter. We speak like no time has passed. I don’t ask her why she hasn’t called me. In fact, she doesn’t call me and I don’t call her, but it’s okay. As long as we reach out every now and again. You don’t have to talk every day. Just look forward to seeing each other once a year or so.

When you’re my friend, you’re my friend for life. My friendship is unconditional. I take it very seriously.

Actually, I have made a lot of friends at the school where I work. And I also have some parents who are sort of like my best friends. I usually form a bond with the student first.

My attitude toward friendship hasn’t changed much over the years: Just accept your friends for who they are. Don’t judge. I’ve never had a single friendship that hasn’t lasted. If you want to stay friends with someone, give them their space. When you’re my friend, you’re my friend for life. My friendship is unconditional. I take it very seriously.

I have two sisters, one older and one younger. But they aren’t my friends. We grew up close, but as we got older, we lived different lives, so that bond is gone. But every friend I’ve made since has become my friend forever. My friends have become my family. I see everyone as a potential friend. Friendship just happens to me! I don’t look for it, I don’t put myself out there. It’s organic. If it’s going to happen, it happens. That’s a perspective that comes with age. After a while, you just get tired of trying so hard. You just let it be.

On Resolving Friendship Conflicts

A friend of mine, we had an altercation. She stopped speaking to me, but I didn’t know why! This went on for about two weeks. Then I got mad. I was like, wait a minute, I didn’t do anything! Why is she mad at me? Then I got mad at her. It escalated until finally, I just said, “You know what, we have to talk.” So we did talk. She told me what she didn’t like that I did, and I apologized. It was petty! I didn’t mean to, but I embarrassed her. But I’m so glad I asked her what was wrong. Now we’re back on being friends again! We put it in the past, and now I feel much better. Matter of fact, she’s going to take care of my birthday party on Friday.

When someone’s important to you, you put your pride aside. Don’t lose a friend to being too proud.

When I was younger, I never would have communicated in that way, I would have said, “Forget about it!” Now that I’m older, I’m not afraid to ask questions and find out hard answers. I value the people in my life too much for that. When someone’s important to you, you put your pride aside. Don’t lose a friend to being too proud.

Enjoy life to the fullest. That’s what I’m doing. Now, I’m just doing me. Enjoying me. It took me a while, but I’ve figured life out. It’s got to be about you. Do things your way, in your time. Make yourself happy.

Judi, 74, lives in the West Village, and has no lifelong friends.

My parents are both Japanese-American. I was born in 1945, when they were sending Japanese Americans to internment camps, but my parents avoided that by moving to Chicago. When I was five, my mother and I got on a train and moved to Los Angeles. My father was an orphan, raised by nuns, which meant that I was raised Catholic. I am no longer Catholic, but I find that my background has influenced me greatly, in terms of being an “other.”

I have a lot of good friends, but I don’t think I have a lot of friendships that have gone on for a long time. I haven’t kept in touch with a lot of my childhood friends. I heard recently from someone I went to high school with (I went to an all-girls Catholic high school in a blue-collar area). It turns out, she’s a Trump supporter!

I make many more friends now, they just don’t go way back. I connect with people in the moment, I look for that spark of curiosity. I value people who really listen. That’s the key to a long-lasting friendship: finding people who know you and hear you.

On Making Friends in Unexpected Places

I met one of my closest friends on the New York City subway. We were in a crowded car. She was sitting down, I was standing up, and there was a third woman sort of leaning toward the door. Somehow, that woman and I got to talking about her trip to Washington, D.C. I asked her if she was going to see the Holocaust museum because I had just been and felt very touched by it. She said no, she was going to see the cherry blossoms. Anyway, the holocaust museum brought up the lynching exhibit here in New York. Then the woman who is now my friend spoke up and said, “Well, I haven’t seen it, but my husband has!”

Moral of the story: Speak to people on the subway!

We ended up getting off at the same spot and she showed me how to get to BAM. As it turns out, her husband was, at that time, head of the NAACP. We ended up just connecting in a really special way. We exchanged information and started getting together for dinner. Now my friend—her name is Cynthia—she’s a teacher in East Flatbush, Brooklyn, and her school won an award because it has a 90% graduate rate. I was blown away, so I asked if her principal might let me shadow him. I had been a professor for 40-somewhat years teaching leadership and motivation, and thought he might make a fascinating case study. For a year and a half, I went to that high school and attended meetings with him. He became a friend, too. Moral of the story: Speak to people on the subway!

I met another friend through my work in the prevention of sexual abuse. In 2008, I was asked by West Point military academy to help them to prevent abuse on campus, and when I spoke with a colonel who was in charge of the initiative on campus, I came with with a checklist of actionable changes I’d like to see enforced. He was captivated. We ended up speaking for four hours. He’s still a friend.

On the Two-Fold Nature of Friendship

When I do field research, I have to observe really carefully. That’s exactly what being a good friend is like: Watching closely for problems they may be having with what’s going on, with you; trying to gauge their goals. Because you’re not blood relatives, you know? You don’t have any ties that link you together. You can go your separate ways. But if you want to maintain a friendship, you have to be there for the person, hear them, listen to them, and hopefully likewise have that come back to you.

If you aren’t helping yourself, you can’t help others.

My one piece of friendship advice would be to keep an eye out for yourself. Keep in mind what’s important to you and chase that goal, instead of thinking solely about the commitment you made to someone else. If you aren’t helping yourself, you can’t help others. I think women often fall into the position of serving and pleasing others, including other women. But follow your path. Don’t be concerned about something you said or did that led you on another path because of another person.

We can really help to make the world a better place. We can use our resources, our connections, our powers of persuasion, to make a difference. And we can do that by coming together and collaborating. For example, because of my connection with that then-colonel, who is now a general, I asked if he would consider introducing a sexual abuse prevention program in his army infantry division. And he said yes. That’s the power of friendships.

Susan, 65, lives on the Upper West Side, and is rewriting her friendships.

I grew up in Beverly, Massachusetts, right on the beach. Growing up, my mother always said, “Thank god you came out like your father.” I saw my mother as weak, dependent, and needy, but my dad as very strong. So I tried to appeal to my dad. And he was someone who was revered, a really down-to-earth, people-oriented guy, just beloved. However, I didn’t really have a strong relationship with him. It was very stilted. Then he died young. I was 15. I never felt contained or safe, like anyone really had my back. Not a great childhood, I must say. I was an enormously angry little girl. I felt really isolated—I didn’t know how to make friends.

Everything changed when we moved to Long Island. I made the decision that I was going to change my life. And I did, I turned it around. My mother, she didn’t have much of her own social life, and that was really limiting. So I had to teach myself how to make friends. I learned how to smile and became very popular, but only on the surface—I was president of this and that, blah blah blah. I made a lot of friends, especially through my Jewish youth group. I was kind of a crossover kid. I could float. I began to have a good life. Not by accident, but because I created it.

I recently reconnected with a high school friend, a guy. We were really close and stayed friends in and out of college. I think we were boyfriend and girlfriend at one point, but it was hard to tell. Anyway, he just became an empty nester and moved with his wife to the city. We’ve been trying to figure out what our next moves are in life, in terms of our careers and our contributions to society.

On What Makes a Good Friend

I have two women I consider best friends. One of them, we met through work. We were both up-and-comers at this big company in our twenties. This best friend was a real crazy woman, and she still is. I love her because we do nutty things together. We used to wear these flashy St. John knits to work. Because of her, I grew bolder. I was very influenced by her, and it wasn’t always a good influence. But we’re still very good friends. She’s still the first person I call. The person I celebrate all my birthdays with. But she’s never been reliable, in any part of her life. So you can’t count on her, ever, for the day-to-day friendship. But for the real, heavy-duty stuff? She’s always there. And that has real meaning.

The other woman… actually, it’s funny. She’s not a very reliable person, either. There’s a bit of a pattern here! Maybe it’s a result of my isolation. You know, I don’t want to get too close to someone. But she’s brilliant. She’s cultured, understands technology, is a musician, an accountant, a lawyer, and Australian. There’s something really special about her. She was always present with any big events that happened in my life, from playing early morning squash and very cool parties with celebrities as singles, to meeting my husband, to finding out I was pregnant, and even on that horrific 9/11 morning.

Here’s my motto now: You can’t become yourself by yourself. Isn’t that awesome?

I tend to bring people together, they connect and have meaningful conversations. I think I have some kind of ability to facilitate friendships. The first quality I look for when I meet new people is: Are they a mensch? Can I trust them? I care a lot about people who are curious, open, and receptive. People who want to make a difference, who really care. It’s all about intention. Here’s my motto now: You can’t become yourself by yourself. Isn’t that awesome?

On Finding the Power in Sisterhood

Up until the 70s, femininity was associated with weakness. I’d think, Why would I want to be labeled weak? I hated dresses and playing hopscotch, and getting the worst part of the playground. Back then, I did everything I could to behave like a boy. I had pictures all over my bedroom of these sweaty athletes on the cover of LIFE magazine. And I became very athletic, too. I tried to do anything I could to express how much I hated where I was in this world.

But now I’m rewriting my story. I am part of a Global Women’s Leadership Network, a ‘tribe’ of accomplished, self-selecting women whose mission is to help shift the role of women in the world in truly equal partnership with men. I went from absolutely “get me out of this girl thing, I’m out of here!” to “Oh my god, the power in the feminine is incredible.” It’s like I’m going through this rebirth. It is crazy amazing. I’m even hanging with a generation or two younger than me, feeling the energy, spirit, and new vision, igniting my own growth. It’s the same feeling I had when I first entered college: The newness, diversity of backgrounds and beliefs, meaningful conversations. Opening up a world that was a dream come true.

There’s a bazillion forms of friendship. It’s pretty cool when people really know you.

There’s nothing finer in life than having connections that are mutually supportive and growth-oriented. Friendship is an area that I’ve been evolving in, with a lot of trepidation. There’s a bazillion forms of friendship. It’s pretty cool when people really know you. My old boyfriend—wow, I keep saying boyfriend, I don’t know if he was my boyfriend!—he’s in that category, and he keeps reminding me of who I am. I’m in this new world that’s completely different from how I developed myself in the old world, which can be really scary. But change provides the opportunity to grow into what’s next.

It’s even changed my relationship with my mother! She was getting older, so I brought her down to New York to be closer to me. I finally saw her full self and realized that the environment we used to be in was so limiting, and she grew up in such a limited way. Now I see this incredible richness to her. The other night, we were watching PBS together, and my mother turns to me and says, “Susan, I think I’m growing.” I was in tears, I couldn’t believe it.

Everything is energy. If you want to connect on an emotional level, get out of your head and into your body.

Photos by Sabrina Santiago.

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