What a Liberal and a Conservative Learned From Their Friendship

“I think it’s important that you remember who your friend is, that they are not just a set of political policies.”

An illustration of the two friends sitting on blue and red colored building blocks.
Wenjia Tang

Each installment of The Friendship Files features a conversation between The Atlantic’s Julie Beck and two or more friends, exploring the history and significance of their relationship.

This week she talks with two friends who didn’t like each other when they first met as kids, and who grew up to hold very different political values. One is a Democrat, the other is a conservative who no longer considers herself part of the Republican Party since the election of Donald Trump, and both consider themselves feminists, though that wasn’t always the case. They talk about overcoming first impressions, going into business together, how they’ve shaped each other’s worldviews, and their advice for navigating friendships across the political aisle.

The Friends:

Annie Newman, 25, a campaign staffer who lives in Missoula, Montana
Lindsey Weiss, 25, an M.B.A. student at Dartmouth College who lives in Hanover, New Hampshire

This interview has been edited for length and clarity.

Julie Beck: What drew you to each other when you met? How did you become friends?

Lindsey Weiss: We met when I was 11 and we did not like each other!

Annie Newman: Lindsey and I are both Jewish and grew up in north Texas. I remember Lindsey joined my temple [when she moved to town], and I walked into Yom Kippur breakfast and saw her. Lindsey was a “cool girl,” and I was super not. I saw her at the breakfast and was immediately judgmental, as an 11-year-old girl, and I was like, I don’t like her. And we didn’t really become friends for three years.

Lindsey: I can tell you my exact outfit, because it was actually a cause for concern.

Annie: It was! My mom was like, “Who is that? What is she wearing?”

Lindsey: I had these four-inch-high, cherry-red Jessica Simpson heels. I wore them with a black skirt and a black-and-white striped top, and red lipstick. It was not necessarily an appropriate outfit for an 11-year-old to be wearing, but I did look great.

Annie: In freshman year of high school, we did this thing called “Odyssey of the Mind,” which is a very cool problem-solving competition. Lindsey’s brother did it, and her mom wanted her to join too. So her mom pushed her to join the team that I was on. I was so mad about it.

Lindsey: Annie cried when she found out.

Annie: [Odyssey of the Mind was] a little bit of an escape from high-school social hierarchy. At the time, I thought, Oh no! It’s not going to be that escape anymore, because [Lindsey’s joining]. But that’s how we became best friends.

Lindsey: I remember the time where I realized, Oh, okay, Annie is going to be my best friend forever. I had some trouble with an eating disorder when I was 15, 16, and I had to go away for a while. Annie dropped off this trash can that she had decorated called the “Bucket-o-Fun.” It was filled with trinkets and board games and things to entertain me while I was in the hospital. I still have it in my room.

Beck: How did your friendship evolve after high school?

Annie Newman (L) and Lindsey Weiss (R). (Courtesy of Annie Newman)

Lindsey: Annie went to school in Scotland. She went to St. Andrews. I went to the University of Oklahoma. We couldn’t have had more different college experiences or been farther away from each other. But my favorite moments in college were when I was staying up late doing homework and Annie was waking up early. We talked every single day via Facebook Messenger.

Annie: I remember being kind of surprised that it was so natural to [keep in touch]. In college, I had the insight that this was the first relationship I ever had where I knew it was going to be forever. To this day, we still talk at least every other day.

Beck: You’ve now grown up to be a Democrat, Annie, and a Republican, Lindsey, and you both consider yourselves to be feminists. How did your friendship evolve along with your values, and what role did the other person play in shaping or challenging your worldview?

Annie: I was always interested in politics. My parents are Democrats, so I was always a Democrat. I wouldn’t say it was a part of my identity, but it was a given. I was a Democrat; that’s who I was. And when I was a junior in high school, I remember reading Lean In by Sheryl Sandberg—which is problematic, but whatever—and having my first taste of Oh, this is feminism!

I don’t want to put words in her mouth, but I think for Lindsey, being a Republican was a family thing. Lindsey’s father was a Republican. Her parents met working at the RNC. It’s a really sentimental thing.

Lindsey: I was always also super interested in politics. Real talk: I went to University of Oklahoma. I was very pragmatically a Republican at times, just because [if you want to] enter politics in the South, it’s much easier on the Republican side. My parents were always very socially liberal, and fiscally conservative. They were Reagan Republicans. Full disclosure: I am no longer a registered Republican, but that doesn’t mean my views have shifted. I just think the party has shifted away from something I am comfortable supporting.

Annie: For me, that was probably my first time interacting with someone who I respected but disagreed with. This was obviously before Donald Trump, so it was kind of a different time. But I think I have a very similar relationship with the Democratic Party that Lindsey does with the Republican Party, because of my family. [I understood] Lindsey’s relationship with the Republican Party was valid both because she believed in some of those values and also because of what it meant to her family. [Family] is an important part of politics, and that is okay.

Lindsey: My first interaction with feminism was when Annie and I were interning in D.C. together one summer in college. I remember watching something on TV and saying, “I feel like feminism is weird,” and Annie was like, “No, Lindsey, feminism is really important,” and she sat me down and she explained it to me.

Annie: I don’t remember this at all.

Lindsey: I had the wrong idea about what feminism was. I thought that feminism was about coddling women, giving women opportunities that they maybe didn’t deserve just because they were women. I don’t think I realized the extent to which the playing field was not level. I think for a very long time, especially in the environment that I was in, I really thought that my job was to be a pretty girl, a nice, quiet girl, and not take up that much space. To get complimented.

Annie taught me to understand that certain things about the way that I was being treated weren’t acceptable. I really thought it was just a given that I got my ass slapped in an office. Annie was the first one to say, “Lindsey, you need feminism because you shouldn’t be treated by people like that.” Obviously, it was not just through one conversation, but through affirmation from Annie and from people I’ve worked with. I was really able to find myself and realize I deserve to take up space. I have so much more to offer than being a pretty girl in an office. I need feminism in order for people to see me that way and for me to see myself that way. That’s my feminist journey.

Annie: It’s funny you say that, because, before Lindsey, I had never met somebody so secure in their womanhood. I know we were teenagers, so at times you weren’t, but it always seemed like Lindsey was 100 percent confident in her body, and comfortable with her sexuality at a really young age, in a way that I was not at all. Lindsey really taught me that is not something to be ashamed of. Your body is your body; it is really powerful and amazing, and we should be able to show it off or cover it up however we want, whenever we want. She has definitely made me more comfortable wearing things that I feel really good in, that I feel really sexy in. She was like, No, I am fucking powerful in the way that I look.

Beck: How much do your politics come up in the course of your friendship? Some people like to argue and debate, and others just want to ignore their differences and focus on things they both enjoy. What has worked for you guys?

Lindsey: Oh my God, we argued like an old married couple for years.

Annie: We did. It’s trailed off since Donald Trump has come on the scene, just because Lindsey is very much not a Donald Trump Republican. There is less to argue about because we both agree that this is nuts. Before Donald Trump, we would argue over health care, social security—stuff that we really didn’t know much about. The big one was Obamacare.

Lindsey: We lived together in D.C., so we would have hours of couch time watching 30 Rock and arguing about the Iraq War.

Once Donald Trump got elected, I was like, If this is what the Republican Party is, I am not a Republican anymore. I started studying for the GMAT pretty shortly afterwards. I thought, It is time for me to go to business school. There doesn’t seem to be a place for me [in politics] right now. I am very socially liberal, I am pro-choice, I am for marijuana legalization, but I am also fiscally conservative. There was a point in my life where I found those views to be at least somewhat adherent to the Republican Party. Am I a Republican at heart? I don’t think my views have changed very much at all, but if this is what Republicanism is now, then I don’t want to be a part of it.

But Annie makes me feel that there is always a place for my opinion, even if it’s not necessarily represented in the media right now. She’d listen to me. She affirmed me. And even if she disagreed, she didn’t disagree with my right to have the opinion that I had.

Annie: We lived in D.C. [in 2016], so we would go to marches, which happened all the time right after [the election]. When Lindsey came with me, she felt excluded at times. For her to have to say “This is what I believe, but I don’t think it is represented anywhere and I don’t know what to do about it” is a struggle that I do not envy.

Lindsey: We are in emergency times. We need to band together and put aside those differences. We can debate semantics in terms of “why is it wrong”—because it violates this law or because it is morally wrong. It doesn’t matter: It’s wrong; we both believe so. That was a difficult but also a very [formative] time in the way that I saw politics and the way that I saw my ability to reach across the aisle and work with people I disagreed with. I was able to prioritize the things that I did agree with and work with others on that.

(Courtesy of Annie Newman)

Beck: So as a result of all of this, Lindsey, you decided to stop working in politics and instead do business for a while. Is that what led to you two starting a company together?

Lindsey: The company started after the Women’s March. We were both pretty enraged, the kind of righteous anger that comes after examining the patriarchy for a day straight. I knew that Annie had a future in politics and that was her calling. I don’t think politics is my calling. This is where I am supposed to be, and it is because Annie believed in me to be a businessperson.

The pitch for the business is that women’s breasts fluctuate three to five cup sizes while they are nursing, but no bras on the market account for that. So it means that women have to buy new bras to accommodate for all of the fluctuations. Our bra is a nursing bra that is adjustable up to five cup sizes. It is the first bra that a woman can wear through every stage of her breastfeeding journey. That’s the short pitch.

Something that Annie actually insisted on is that our whole supply chain be female-founded. From the factory to the distributor. We have prototypes, we signed a contract with a manufacturer, and we were hoping to do a soft launch in Boston this summer.

Annie: She won’t brag about herself, but Lindsey won a ton of pitch competitions for this, and she definitely has taken on the lion’s share of [work].

Beck: Have you learned anything new about each other from going into business together?

Lindsey: Something I have learned is—I am going to gush for a second—just how talented Annie is. You don’t often get to see your best friend performing their job; you’re not at work with them every day. Annie is really good at all of this marketing stuff. To watch her come up with a logo on the back of her hand, writing shit down on napkins, it’s just so cool.

Annie: Thanks, Linds. I think Lindsey has been undervalued at various times in her life, whether in personal relationships or in a job. She is so talented and so smart. To see her take something that we created together and run with it is just … I love seeing her do it, because I think she proves people wrong on the daily. It makes me very proud of my friend.

Beck: Do you guys have any advice for other people who may be feeling friendships strained because of differences in values, especially in the Trump era?

Annie: I think you should just talk about it. Lindsey and I, this was not an instance of a Hillary and Donald Trump supporter being friends—it just wasn’t. But we talked about how Donald Trump affronted my values and how that made Lindsey feel as a Republican. There were definitely times where I remember feeling frustrated, but we did talk it through. If we weren’t able to understand each other, maybe we wouldn’t have the friendship that we do.

Lindsey: Annie’s not “a Democrat” to me; she’s my best friend, Annie. I think it’s important that you remember who your friend is, that they are not just a set of political policies. Especially when you’ve known your friend for so long, you can see where these values have been folded into their lives. You have to have a certain level of empathy and understanding that those values are just as important to them as the values that you have woven into your life. Annie and I never try to convince each other that we’re right.

Annie: I am someone who works in politics still, and I think my friendship with Lindsey has made me better at my job. I am currently working in Montana, which is a purple state at best. Having years of experience loving someone different from me, and learning so much from her, helps me in my job day to day. I think it could be really easy to hate the voters, and I don’t.

Lindsey: Hate the sin, love the sinner.

If you or someone you know should be featured on The Friendship Files, get in touch at friendshipfiles@theatlantic.com and tell us a bit about what makes the friendship unique.