I have always been close with white women. Not casual “Let’s grab a coffee and catch up” (but only sorta meaning it) relationships. These are friendships of serious connection — in some cases, we’re like sisters. These women have, for the most part, fit seamlessly into my diverse circle of mostly Black girlfriends. Despite our different ethnic backgrounds, we share similar upbringings, educations, interests, and ambitions.

My very first white friend grew up in the house next door and taught the super-indoorsy me to climb trees while simultaneously fostering my obsession with the Nutcracker. And I met the woman I call SuperAce when we were in our crazy 20s working in politics. She inadvertently gave me mononucleosis during our daily ritual of a shared bagel and coffee. I have loved these women just as much as I’ve loved the women of color who also embrace my quirks and strengths and appreciate my saucy humor and unwavering loyalty. Our racial differences are obvious yet not obstacles.

Eleven years ago, I moved back to the Midwest from Houston. That’s when my relationships with white women changed. I’d lived in 10 cities in 10 years and had developed close relationships with women of many shades. I figured Chicago would be no different. I was so wrong.

When I had my baby girl the day after my 41st birthday, I needed a new community. My handful of existing friends in Chicago had already raised their babies and were wrestling tweens and teenagers. I pushed my daughter’s stroller around my mostly white North Side neighborhood — to the park and coffee shops and grocery stores. I joined local mom groups and invited complete strangers to my house for playdates, but those requests were largely ignored. And I felt like an outsider among the few mom friends I’d managed to make.

I’ve learned I’m not the only Black woman who has arrived in Chicago and struggled to find common ground with white women — who in some cases have never spent much time around Black people. I don’t talk about race with them for fear of putting myself in that awkward situation the Pulitzer Prize–winning New York Times critic-at-large Wesley Morris describes as the “trapdoor of racism,” in which a “slip of the tongue” that’s “not always anticipated” pops up like a hormonal pimple: ugly and painful. It’s happened more times than I care to remember. So I’ve kept these women at arm’s length, and they, gathering without me to support each other as they navigate new motherhood, have done the same. It has been lonely.

That’s in part what inspired this look at Black women and white women (and one nonbinary person) who are the closest of friends: I wanted to understand how these duos met and how they sustain relationships in a notoriously segregated city. I asked them about how being of different races has informed and affected their friendships. Their answers, for me, were unexpected: like the baby boomers who have strikingly similar backgrounds despite growing up in a deeply segregated society; the white mom who has been intentional about living in Black neighborhoods; and the childhood best friends who were never afraid of discussing race because of their shared faith.

JAQUIE & REGINA

Regina McGraw

70, Arcadia Terrace (right)

Jaquie and I met about 10 years ago through a mutual friend who set us up on a blind friend date because he knew we would connect. The three of us went to a restaurant. We instantly clicked: We have both dedicated our careers to advocacy and community organizing, and we make each other laugh. I know, for example — and this isn’t a true concern — that if the FBI showed up at her door and said, “Regina’s a terrorist,” she would say, “Go eff yourself.” That’s my criterion for friendship.

One of the reasons our friendship has worked is because I’ve really been intentional about learning about racism and have not thought, Oh, it’ll just come to me. I am aware her experiences are going to be different. When we were in Prague, we came out of the subway and the cops stopped us to see if we had our tickets stamped. It was one of those things where I wondered if they treated us badly because Jaquie was Black.

I remember the first time Jaquie told me about her son, Langston. Here’s Jaquie, this woman I love, whose 19-year-old son was shot in 1995 while helping his friend move, and I will never look at gun violence the same way. Of course, I knew that the killing of young Black men was a horrible, horrible thing, but I had thought about it in a general way. With Langston, I had a picture in my mind of this handsome young man being murdered, and it just magnified the horror.

When people you love have experienced systemic racism in various ways, there’s no way you can just sit back and watch it happen. It’s the injuries that people of color face on a daily basis that just wear away the soul. They are like bruises. Bruise after bruise eventually is going to affect how you view yourself and the world.

Jaquie Algee

69, Roseland (left)

Regina and I aren’t timid. We have the kind of relationship where we can always say what we feel, especially about race. We live in very different neighborhoods. Mine on the South Side is primarily Black, hers on the North Side is not. But when she asked me during the uprising last summer if I was hearing gunfire and helicopters, I didn’t take offense to it because I knew she was asking out of concern for me, not just lumping my neighborhood into one filled with violence. I might not have felt that way if someone else had asked me.

One day I was at an event and heard two Black men discussing systemic racism and listing a litany of reasons Black-on-Black crime occurs. The lack of jobs, education, good housing. After a while, I’d had enough. I told them my grandparents had come to Chicago uneducated and they worked themselves up to have a decent life. I told them that what’s missing is the moral fabric, and there’s no reason why we should have our kids out here getting killed, like my son, because someone doesn’t have a good school to go to or they don’t have a job. The men didn’t want to hear that. Later I was still upset, and I told Regina and I figured she would agree with me. I had to explain to her that while I understand why those young brothers feel that way, I’m still not condoning violence. And Regina, being white, didn’t understand those men in the same way I did, and she and I talked about it.

She listens and has opinions when we talk about race, which I’m open to. I know I can talk to her about anything — politics, my frustrations with white people, my frustrations with Black people — from an honest viewpoint. I think there’s a divide between whites and Blacks because both sides create that. You have to tear down those barriers. Regina and I are an exception to the rule.

MOLLY & CHI

Chinyere Nwosu

32, Humboldt Park (right)

I was at a party at Indiana University with my friends and we saw this cute little baby-blue cabriolet with a white stripe. I remember thinking, like, Whoever’s in that car, I need to know them. It was Molly.

When I was in my 20s, I came out to Molly as gay, and she was like, “Dude, that’s dope.” With my Black friends and queer friends, who are mostly people of color, I feel like I’ll bring up specific race stuff that I know they will understand because it’s an experience that we share together. So I think that maybe lightens the burden on me and Molly’s relationship because I don’t depend on her to be the outlet for that. We can just kick it and have a good time.

I taught Molly a few things about Black culture, like my experiences with getting relaxers or being friends with somebody who was a little bit lighter skinned. I would talk about the different dynamics that would happen when you go to the club, how guys want to dance with the pretty light-skinned girl. I didn’t quite fit in with white kids. I didn’t quite fit in with Black kids because I was like a weird African girl. I think Molly understood because she would ask me questions, really try to gain a deeper understanding.

She’s also really clear about when she doesn’t understand something. We were watching trash TV, Keeping Up With the Kardashians, and Kim was glammed up on screen, with her baby hairs laid as part of her look. I laughed and remarked that baby hairs are a tinge appropriative. Molly asked for more detail, and I explained to her the history of Black hair in this country and the pressure to adhere to a white European aesthetic, “neatness” and professionalism, and my interpretation of what “laying down edges,” or “baby hairs,” means beyond just the look. I also explained that when a Kardashian has her baby hairs done, it becomes a fast-fashion trend that often ignores the deeper conversation of history, access, and visibility. Molly doesn’t ask questions like strangers do, where the expectation is for me to be the educator. I know her heart, and we share knowledge equally.

Molly Sanford

30, Humboldt Park (left)

After I gave Chi a ride in my car and we hung out, they scribbled their name on a piece of paper and left it on my fridge, like it was a one-night stand. I told my boyfriend, “I met my best friend last night.” The next day, Chi came over, and we’ve been so close ever since.

When I was 21, I got pregnant, and moved to Chicago, with no family, to be near my daughter’s father. Chi moved here to be with me and basically helped me raise my daughter from the time she was 1 year old until she was 4. Chi’s family is having trouble accepting them as queer, and my family has completely embraced them. We spend holidays together. I can just be who I am.

There was this moment where we were hanging out with some friends and I was the only white woman there. The Black people kind of went on a tirade about white people and how annoying they are. And I was thinking, This is what it’s like for them? Wow. I felt left out or maybe embarrassed, you know? And I felt kind of ashamed, like, I’m so white right now in this room, which I think is probably a really frequent experience for a Black person in this country. Chi and I have had great conversations about race: Some things they’ve had to accept and some things I’ve had to accept. When we’re together, it’s just us and we don’t think about it.

MICHELLE & EMILY

Michelle Burgess

43, Austin (left)

We met about eight years ago at Suder Montessori Magnet Elementary School in the Near West Side. I remember walking up to Emily on the playground and starting a conversation. There was something about the way she talked and the passion in her voice that drew me. We said, “I’d love to get to know you more.” And so we built upon that and used after-school playground time as ours to talk.

I remember telling Emily I am a stay-at-home mom, that I’ve got three young children, and she said, “I don’t normally meet Black women who are stay-at-home moms.” I shook my head and said, “Yes, my husband, their father, is actively engaged in their lives.” It was an aha moment: I realized that I am what some people would think is an anomaly.

Emily and I began having very deep conversations, not dancing around race. But a relationship like this is not for the faint of heart. As a Black woman in America, as a deep-pigment-skinned woman in America, as a woman, period, in America, I’ve had to fight to get my voice heard. We would be talking, for example, in the hallway at school, and certain parents, even teachers, would approach Emily and acknowledge her and want to know her opinion, and they would ignore me, despite me being the head of the Parent Teacher Association. Emily recognizes when this happens and immediately begins to include me in the conversation.

I’ve always felt ignored by society — especially by white people. So when Emily would not respond to my calls or texts, I called her out on it. I needed her to be more attentive in our communication. There was a learning curve for her to understand that because she is dealing with someone who is African American, it is going to require more sensitivity and thought.

Being a Black woman is like walking through a path of half-dried cement. Everything takes a tremendous push because my voice has been muffled. I didn’t want to have to do that with Emily. Conversations with white people can be awkward and sometimes intense. But Emily would ask me very straightforward questions. It was a matter of just questioning each other and giving space for answers and not judging. My greatest gift from Suder was Emily.

Emily Fong

45, Bronzeville (right)

Michelle is just a really effusive person. She’s engaging and loving and kind, and she wants to help everyone feel like they belong. I’m a little more gun-shy when it comes to making friends, so Michelle has this knack for pulling out of me a desire to build friendships with people. She and I talk about things as humans, but there’s also the fact that we are from two different socially defined race groups. That difference informs our friendship in countless ways.

Let me explain. I don’t intentionally “ghost” people, but I am an introvert. Sometimes I just feel overwhelmed and pull back, or I will even go through times when I have no contact with anyone. Michelle told me it hurt her, and that she was imagining me being in touch with the white people we knew more than I was with her. It doesn’t even matter if she can logically think it through and be like, Well, Emily is telling me that that’s not true; she treats everybody that way. It still sometimes triggers painful experiences: All her experiences with white girls, and white women as she got older, were informing how she was seeing that. She was being really honest with me about it and told me, “I know that maybe this isn’t just me, but it still hurts me.”

And it has changed the way that I interact with her. It made me aware of the fact that I needed to know that every little decision I made or anything that I do in this friendship can be defined by the trauma that she’s been through. Because our friendship is so important to me, it was significant for me to put what she was saying to me first. I wouldn’t necessarily do that for anybody, but I would do that for sure for Michelle.

BRIDGET & JOCELYN

Jocelyn Reynolds

38, Northbrook (right)

Bridget was my very first friend. We don’t remember not being friends. I lived on one block in Glencoe, and she lived on the next. Our parents were friends, as we were both raised in a Baha’i household — my parents moved to the North Shore to work in the U.S. Baha’i National Center. I was raised in a household that was passionate about the Black-white issue. In the Baha’i faith, we believe that we are all one people, all one humanity.

For our entire lives, when we are together, sometimes people have looked at us with disapproval, like, What are those two doing together? And for us, it’s like, What is your problem with it? Eighteen or 20 years ago, we were downtown at a restaurant eating and someone passed by us. I don’t remember the comment, but it was like they were disgusted seeing us together. It’s not as if I don’t think color matters. But in the end, we are both human beings and spiritual beings, and Bridget is like my sister. I don’t know anything different. Despite her being a blond-haired, blue-eyed woman who doesn’t look like me, we’ve always loved each other. In this country we need to see these relationships like they are normal.

The only challenge we sometimes have is understanding one another’s experiences. There may be something I find challenging around being Black, and she may not completely understand it. But she’s not like, “I’m uncomfortable with this conversation because I don’t understand it.” It’s like, “OK, tell me more about it. Let’s start.” When we discussed my anxiety and fear about my son living and going to school in Northbrook and possibly being the only Black child in his class, she didn’t initially understand. I explained to her that teachers might not give him the attention he needs, try to put him in lower-level classes even if he excels, or treat him differently for negative behavior because he’s Black. She had empathy because my son is special to her too, and she would never want him to have those experiences.

Bridget Mora

37, Jefferson Park (left)

Jocelyn — I call her Ja — and I laugh because when we go out, we see and talk about how people react to us. We get funny comments sometimes, but good ones for the most part. People will just say, “Now that’s a beautiful thing.” [Laughs.] A lot of people have an appreciation of seeing Black and white together. I feel like it’s not a big deal.

I can remember from my youngest age her discomfort in some places. We didn’t talk about it, but I just could see it. Like even getting in the car going to school, because we’d carpool, I could sense it. And it just seemed like a sad feeling.

Jocelyn is kind, loyal, forgiving, patient, thoughtful, beautiful, positive, fun, loving, giving, an incredible mother, and a true friend to me. She knows me and has been there for me, and she will always be there for me. I know I will always be there for her too. We have had a bond of love since before we can remember. She is family to me, like a sister, even though we don’t talk every day.

It really upsets me [begins to sob] that she has to worry about her 6-year-old son for something he shouldn’t have to worry about. I worry about how my kids do in school and if they’re going to make friends, but when you have to worry about how someone’s going to treat your child, you just know there’s a lot of pain in the world.