Writer Damon Young dishes advice in new column

Trymaine Lee: For most of us, it's nearly impossible to make it through the world on our own. We need input or wisdom from other people to help us figure stuff out, the big stuff like how to land a new job or work through a conflict with a spouse. And we sometimes need advice on the small stuff too.

But it's not just friends, or family, or mentors we're seeing helping from. Since at least the early 20th century Americans have sought out advice columns as a way to tackle some of life's everyday questions.

Arguably, the most famous is the ground-breaking "Dear Abby" column, which was started by Pauline Phillips in 1956.

Pauline Phillips: I get about 300 letters a day that sound just like this one, "Dear Abby, I'm a girl of 14 and I like a boy of 15. When I see him in the halls at school, I say hi and then he says hi. Then if I don't say hi, he never says hi. Who should say hi first?"

Lee: Dear Abby still runs today, written by Pauline's daughter Jeanne, with newer additions like Cheryl Strayed's "Dear Sugar," and "Slate" magazine's "Dear Prudence". The tradition of getting advice from trusted, but often white, writers at some of the country's mainstream publications has continued to grow.

But now there's a new voice in this space.

Damon Young: And I mean, I'm just here. Anything you got a question on, boom.

Lee: Damon Young is a writer, a critic and satirist who became hugely popular by writing about race, culture and politics for his blog, "Very Smart Brothers." In his work, Damon blends humor and incisive cultural critique into a refreshing and insightful look at blackness in this country, like on his podcast, "Stuck with Damon Young."

Young: I consider grief to be just like I don't think that you could be a Black American and travel in the South without grief being heavy on your mind everywhere that you go.

Lee: Back in 2020, Damon came on this very show to talk about an op-ed he'd written in "The New York Times," called "Yeah, Let's Not Talk About Race, Unless You Pay Me."

Young: So I take these walks around my neighborhood at nighttime and there are times when people who see me recognize me and most times it's like, "Hey, hey, Damon. How you doing? Loved your book," whatever. But every like fifth time it's, "Hey, yeah, so watching George Floyd die like that," you know?

Lee: (LAUGH)

Young: And I'm like, "Yo, I'm just walking." (LAUGH)

Lee: I hate to laugh, but that sounds terrible. Right?

Young: (LAUGH) I'm just trying to get my steps in. I've got my app up, my steps app. I'm just trying to get my 10,000 steps in. And you want to talk to me about this terrible, awful thing right now?

Lee: Yes.

Young: Like, OK, well, if you want to engage me on these very difficult topics, then this has to be worth my time. And so, you want to make it worth my time? Then pay me. Give me some money to do this.

Lee: "Ask Damon," a new advice column, debuts tomorrow in "The Washington Post." And Damon is ready to help us sort through the mess of everyday life.

Young: I am not, you know, some omniscient, omnipotent, perfect being. Like, I mess up, I get things wrong in my life all the time. It's more of, OK, I know some things, but we're going to figure these things out together.

Lee: I'm Trymaine Lee and this is "Into America."

This week, I sit down with my guy, Damon Young, to hear about why he's cut out to give advice to others, what he hopes to make of this new gig, and he answers some of your burning questions.

Young: Hit me. Hit me. Let me see what you got.

Lee: The last time Damon was on the show he was a senior editor at "The Root," where he oversaw "Very Smart Brothers." He's since struck out on his own with a column at "The Washington Post" and a podcast called, "Stuck with Damon Young" from Crooked Media and Spotify.

Young: And we had 12-episode first season. I guess the premise of the podcast was like the collision of self-consciousness and social consciousness. All right, for instance, my daughter is going through the first grade, right.

Lee: Wow.

Young: And, you know, it's an important decision for Black parents to make and it's a decision that has all of this, you know, historical, cultural and racial context. Because it's like, well, do you want to send your kid to a high-performing school that's probably going to be predominantly white or do you prioritize sending her to a neighborhood school, right, a city school, a public school where they might not be as high-performing but she's going to be around more kids that look like her, more teachers, perhaps, that look like her? So, I had Nikole Hannah-Jones on to talk about that.

Nikole Hannah-Jones: We moved to New York when my daughter was one. If you are familiar with New York and, I would imagine, other deeply divided cities, then you know the first conversation that people have when they find out you have a child is, "Where are you going to send your child to school?"

The middle-class parents we talked to said, you can, you know, you can't put your kids in a neighborhood school. You'd have to get them into, you know, one of the testing schools or a private school.

So our decision, which I informed my husband of, that this was going to be our decision, was that we were going to put our child in a segregated high-poverty school, that I cannot write about these things, I cannot argue that our system is immoral and then play my part in it.

Young: Mm-hm. First of all, Nikole Hannah-Jones and I live in Bed-Stuy. And we've had this conversation many times because her daughter goes to a school that's literally right around the corner from me. And my daughter goes to one that's a little further down, another public school.

But we've had these conversations about, you know, what do you do when there aren't great options. But then you, there's that tug and pull between that performance, but also, that kind of the cultural enrichment, right, and the social enrichment --

Young: Yes.

Lee: -- they might not get in a hostile environment like a predominantly white middle school or elementary school. What are you going to do?

Young: Yes, and I mean the thing is, you know, it comes down to, it's like: well, is it about me and my politics? You know, how much should I allow my politics to get in the way of my daughter's and my son's education?

And I don't have an answer. I know where we decide to send her, but that could change in a year. You know what I mean? And so, yes, I think this is just a topic that every Black parent --

Lee: Yes.

Young: -- every Black parent, you know, at least every conscientious Black parent, you know what I mean, has and it's just one of the things where there just doesn't seem to be any right answer. There's just the answer that feels the best --

Lee: Exactly.

Young: -- for the circumstance.

Lee: Damon says leaving "Very Smart Brothers," which he started back in 2008, was a tough decision. But it was just time to go.

Young: With the sort of writing that you have to do when you're writing five times a week, I felt like I had mastered that, right. Because it has to be reactive. It has to be, not necessarily sensationalistic but it needs to have the sort of quality where people are immediately taken by it, right. And it has to be like these short, like, microbursts of language, of humor, of heft, of rigor. And I felt like for that format I had gone as far as I could go with that.

Lee: Damon says there's definitely a difference between working at a Black publication and a place like "The Washington Post." But for the most part, he can bring his whole self to the work. The biggest change, though, has been the target audience, "The Root's" is Black, while "The Washington Post's" is not.

Young: Does that impact how I write? It doesn't. But it does impact, like, how people respond to my work.

Lee: Like just last month, Damon wrote a column about how his daughter somehow came home with a white doll.

Young: Like a blonde, long-haired doll. And so, my wife and I look at each other like, yo, where did that come from? We don't buy her white dolls. Where did that? Where did this little Chucky doll come from, all right? And so, I wrote about that for "The Post."

And I wrote about why we don't buy our daughter white dolls and the whole, like, context there. I wrote about, like, some fantasies I had about how I was going to get rid of the doll. Like, I was going to sneak into her room in the middle of the night and disappear it, like I was John Wick or something like that. And so, I felt like it was a funny piece.

But there were some white people who read that piece and were like, "Yo, so what if a white person wrote this about a Black doll? This is reverse racism, which is worse than regular racism because it's racism in reverse."

Lee: (LAUGH) It's backwards. It's this way.

Young: (LAUGH) "It's backwards. It's backwards, so that's devil racism." So I had some of that; whereas, if this were at "The Root," I doubt that there would have been any sort of response like that with that sort of piece.

Lee: You, obviously for a very long time, have been very smart, right, very funny on all these things, these like kind of snippets life, your own life and experiences as you move through the world as a Black man. But arriving at an advice column is something a little different.

Young: (LAUGH)

Lee: Are you a good advice-giver? Are you a good advice-taker? Like how do you get here? Now you're Damon Young advice columnist.

Young: I mean, we'll see.

Lee: (LAUGH) I guess we're going to find out.

Young: Yes, we're going to see if I'm any good at this. You know, one of the things that drew me, I always read advice columns too because I'm just interested in how, you know, there's a problem and it's almost like solving a puzzle. Where there's a problem and it's like, OK, so how is this columnist going to come at this problem.

And also, I think there could be a lot of really dope writing that happens in the advice columns. So I think there is that. And also, too, I think that I'm more of an ethicist. I hope I'm pronouncing that word right. (LAUGH)

Lee: I don't know, bro. I guess somebody's going to tell us. I'm like, it sounds right to me. Ethicist sounds right.

Young: But where I think through things and, you know like, OK, what is the most ethical thing to do, right, even if it's not necessarily the most right thing and even if it's not necessarily the thing that I would do. And I feel like I'm trying to bring that to the column.

And also, with the acknowledgement that I am not, you know, some omniscient, omnipotent, perfect being. Like, I mess up. I get things wrong in my life all the time. And so, I don't want to write this as, like, someone who has everything figured out. It's more of, OK, I know some things but we're going to figure these things out together.

Lee: So Damon Young, advice columnist will be growing and working through all this with you. What about Damon Young in real life? Do people come to you for advice? Do you give advice?

And also, what's the worst advice you've ever gotten? Because sometimes people give some bad advice, man. Depending on who in your circle, you might get some bad advice.

Young: Let me come back to that, because I have a lot of Hotep-adjacent buddies who've given me some of the worst advice about, like, dating, about diet. Man.

Lee: You got soak a man with vinegar. (LAUGH)

Young: Yes, I mean you could go on and on and on. Like, people do approach me for advice about stuff, advice about situations, advice about dating sometimes, about relationships, about race. I wanted to be very careful not to brand this as like an ask-a-Black-man sort of thing.

Lee: Which it could very easily become.

Young: Yes, where you just have white people unpacking all of their questions, all of their guilt onto me, and I'm here to just alleviate it. Like, I'm going to answer questions about race, but this is not going to be that.

But in real life, or in my in-person life, I do get a lot of white people asking me questions about race and racism. And sometimes it's like fun. Sometimes it's just like I'll be in line then a white person will come up to me and it's like, "Damon, I just want to let you know that I hate white people too,"

Lee: (LAUGH)

Young: You know what I mean?

Lee: Like I'm with you.

Young: Like, "I'm with you. I hate us. I hate my skin, I hate white rice, I hate piano keys, Australia and Nicole Kidman, everything white. I hate it." And it's like, dude, (LAUGH) I never said I hate white, I didn't say that. (LAUGH)

Lee: That's crazy.

Young: But, yes, I get that. I definitely still get that.

Lee: When we come back, I ask Damon some of your questions and get his take on some recent headlines.

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Lee: We're back with Damon Young. We wanted to know what problems you, our listeners, needed some help with. So we put out a call on social media, and it turns out a lot of y'all wanted relationship advice.

Young: Hit me. Hit me. Let me see what you got.

Lee: All right this first one is one that's come up a couple times, OK. And it's some variation of this.

And I'm going to read this one from Sharonda (ph) from L.A., and this is via IG, "Dating during two pandemics is hard. It means you have to ask questions about who else people are dating much earlier because of how COVID and monkeypox are spread. How do you ask questions about who else someone is seeing without sounding like you're moving too fast, all in their business or rushing toward monogamy?"

Young: Just say that. You know what I mean?

Just say, hey, you know what? We're dealing with two pandemics right now. I'm not trying to wife you. I'm not trying to "house you" or "spouse you," like Beyonce said.

I just want to know, is your behavior going to impact my health? So if you are dating multiple people and you're like going on dates in restaurants and things to that nature you should let me know. Because, you know, it does feel like with the pandemic there are two Americas, where there are people who are over it, who felt like this (EXPLETIVE DELETED) never happened.

And then there are people who are still masking, who are still conscientious, who are still doing all the things that we were supposed to be doing this whole entire time. And so, if you are one of those people who have been very vigilant then, yes, it doesn't make any sense to compromise your health just for a date.

I think you could ask it that way without even going into the multiple partners. Just like, well, what are you doing? Are you still masking, right? Are you vaccinated? Are you boosted? And I feel like just those questions alone will, you know, will weed people out and also, you know, get you to the answer that you want to get.

Lee: It's always amazing to me just how fraught some of these questions can be and how scared and concerned we are about asking straight up questions. Like, are you having sex with anybody else? Do you use protection? You tested?

Like just asking questions that will be protecting your health, but we get really nervous about what even asking that question might say about us, when I don't know if it should be. I mean obviously, we know it's tough, but it shouldn't be that tough.

Young: Yes, I mean I put it this way. if you're interested in somebody and they are offput by those sort of questions, then that's a sign that you don't need to be with that person.

Lee: Here's another question. Again, most of these are dating-related, so put your seatbelt on.

This is Kylie (ph) from New York City. And I get the sense from reading through these there's, not just a theme, a little projection here.

Young: (LAUGH)

Lee: This is Kylie (ph) from New York City, "Why do you think more Black women are beginning to date outside of their race? What is it we're finding in non-Black men that we aren't finding in our own?"

Young: I just think that, as we progress and we have access to different types of media and different types of people, then I think it's a natural progression that we are going to date interracially more frequently.

And now, there's also some culture, some political, and economic things happen there too, where Black women, you know, it's been studied and written about how Black women are achieving, getting degrees, getting certain job opportunities at higher rates than Black men are.

And so, you might just have Black women who are in these professional spaces and in these social spaces, and there aren't as many brothers there. Do you wait until, you know, your company hires, you know, a brother and everyone is hollering at them? Or you know, do you date the men who are available and who might be interested in you?

I think that it's one of those things where, I keep coming back to the social media point, but I think that there is such a thing as not just social proof but seeing. Like, you know what I mean?

Seeing other relationships, seeing other people who have had success dating, you know, outside of their culture, outside of their race and witnessing that. And being like you know what? Whatever mental, emotional shackles I had, whatever issues I might have had about this thing, I see other people doing it and maybe that gives me more confidence to do it myself.

So I don't think it's some like biting indictment of Black men because these conversations tend to turn into like this is what Black men are doing wrong, this is what Black women are doing wrong, et cetera, et cetera. I just think people, you know, are recognizing that life is short, and you need to find love where you can find it.

Lee: I don't know, in this context, what bad faith would be. Because it's your life, and you're dating and she's asking questions.

The second part of that question though, "What is it we're finding in non-Black men that we aren't finding in our own?" there's something happening in there. There's something in there.

Young: Yes, you know, I don't know this woman, but I think that the least healthy way to date interracially is when you're doing it because you feel like the other person is better. Your own is lacking in some way, and so you're going to go to another culture, to another race because they have it. They got their (EXPLETIVE DELETED) together and we don't. You know what I mean? And I hate when Black men do that --

Lee: Yes.

Young: And I think that, you know, when Black women do that too, I think it's something that needs to be acknowledged. It's something that needs to be unpacked, right, because I think you could date interracially without insulting Black men or Black women.

Lee: Here's another question, and I think this might be one of my favorite ones, from Anonymous, "Dating a man who joined a Black fraternity recently and well after college. He's in his 40s, he is buying and wearing all the paraphernalia all the time."

Young: (LAUGH)

Lee: (LAUGH) "It's a lot and very corny. I've tried suggesting he appears a little too eager to show off his new affiliation, but he insists I don't get it since I'm not a member of a sorority. It's so corny it's a turn off. How do I tell him that?"

This is probably my favorite one. He just stepping, blah (ph).

Young: (LAUGH)

Lee: Like, man, watch your knees, brah.

Young: Yes, he's going to tear his Achilles or something. You should tell him that. You should tell him. Like, dude, you're going to, you know --

Lee: (LAUGH) You going to hurt yourself.

Young: You're going to tear an ACL doing all the stepping.

I probably would not be a very good full-time relationship advice columnist because my advice is always to break up.

Lee: That's it.

Young: Yes.

Lee: Be out.

Young: Like, that's always my advice. It's like, well, you're just dating. He's very obviously into this thing. You are, not just irritated, I think she used a word like disgust. Did she say disgust?

Lee: She's turned off.

Young: Turned off.

Lee: She said it's corny and she's turned off.

Young: It's a turnoff. OK. I mean, this thing means a lot to him. And so, maybe it's a thing that he'll get over eventually. I think we all fall victim sometimes to we do a new thing, we join a new club, or whatever, even buy something new and it's -- we are just doing that thing repeatedly, over, and over, and over again. We don't moderate sometimes.

You know, my wife jokes with me like when I buy some new shoes, I start wearing those shoes. I wear them out the store.

Lee: (LAUGH) Put the old ones in the box, you just walk out (ph) --

(CROSSTALK)

Young: Right. Yes, I'm wearing them out the store, right. And so I think this could be that for him, where he is wearing his new shoe out the store.

She doesn't say in the message how long he's been doing this, if it's been, like, weeks or if it's been months.

But I think you should tell him how you feel. You know, I don't think that there's a problem with that. But you also have to understand that you telling him that this thing that's very important to him is corny, he might react a certain way.

And I think there are also levels of corny. Most 40-year-old people are corny in some capacity. And I think that there's a corniness that is acceptable to some people and there's a corniness that ain't.

And I think you have to ask yourself, you know, is this the brand of corny that is acceptable to you. And if it's not then, again, I'm one of those people I don't think of it as a bad thing to break up over presumably petty reasons. Because, you know, those sorts of things usually are kind of indicators of something else.

So maybe she just thinks that he's corny.

Lee: And if this is the point of a turnoff, then it's like he's corny to you, it's a turnoff to you.

Young: Yes, if he's corny to you then that's a big thing.

Lee: Maybe you shouldn't be entertaining this.

Young: That's a big thing, if he's corny to you. And so, yes, I would have that conversation with him. And I would also be prepared to just break up.

Lee: I love how he just joined but he's like, you wouldn't even understand this life. (LAUGH) Like, you wouldn't even understand this lifestyle.

Young: (LAUGH) And the thing is, you know, I'm actually with her --

Lee: Yes. (LAUGH)

Young: Right. I wouldn't (LAUGH) like it if I was dating someone who all of a sudden pledged and then they became an AKA yesterday, and now everything is pink and green. Then I would probably have an issue with that too.

Lee: You're just a hater. You don't understand this. (LAUGH)

Young: I mean, I'll be a hater. I'll be that.

Lee: We had a bunch of stuff come in, you know, on social media. And then we had some staff questions. This is from us here.

Young: OK.

Lee: OK? And I know you're a baller. I'm an O.G. New Jersey Nets fan; Kenny Anderson, Drazen Petrovic, Derrick Coleman.

Young: OK.

Lee: Kenny Anderson is the greatest guard ever to emerge out of New York City in the country. So I'm a real Nets fan.

But now we've got Kyrie and Durant. And there's been, you know, lingering rumors about Durant wanting out. He's kind of said as much, and he's a little cryptic.

What advice would you give to Kevin Durant? Should he stay in Brooklyn, should he move on to greener pastures? And what advice would you give in the context of what legacy means, if it means anything at all, in terms of his career and the way he's moving?

Young: I mean, I think legacy is a living and breathing concept. And what we consider the metrics that we evaluate with someone's legacy change.

Like, for instance, the NBA did not become rings culture until M.J., until Jordan. Before that it was like, yo, you could win the finals MVP on a losing team. That's what Jerry West did. Like, people didn't necessarily always look at, when evaluating, OK, who was the best player, they didn't automatically just go to, OK, who won the most championships, right.

And that's the thing that the Jordan-era brought in. So that's how I guess an understanding of what constitutes a legacy has shifted. And so, 20 years from now the things that K.D. is doing now might be looked at in a different light.

You know, it might be looked at as he was one of the vanguards of the player empowerment movement, where even in the present day it might turn a lot of people off. But again, if we're talking about legacy, legacy is not necessarily determined by people who are existing right now. The legacy that K.D. leaves now will be determined by people who are looking back and assessing 15, 20 years from now.

Lee: What advice would you give to former President Donald Trump, who allegedly had been hoarding top secret documents, allegedly. He feels as if the politics had been weaponized against him, it's an affront on democracy, and it's the libs in the left undermining everything that the make America greater movement has built over these last years. What advice would you give to him?

Young: Retire.

Lee: (LAUGH) Be done (ph) --

Young: You are old. No offense to anyone old listening (LAUGH) to this, no one old that's listening (ph) --

(CROSSTALK)

Lee: Big shout to our old listeners.

Young: Yes, shout out to my dad, who's also old. My aunties, my uncles.

But yes, go live your life on your golf courses. Go spend time with your grandkids. Go spend all that bankrupted money or whatever that you have, and just bow out. Like, you've already done enough damage to the country.

Yo, and you've already done what you wanted to do in terms of just, you built your name up into this brand, you made yourself more valuable. So boom, you got everything you wanted to get out of the presidency, out of Washington. So just leave, just go. Go retire, go spend time with your grandkids, great grandkids, whatever. Whatever, I don't know.

Lee: He won the presidency. He started this movement. He can go --

Young: Yes.

Lee: -- away. He won. Right? But he's snatching (ph) --

Young: Go with your boy Elon. Go to Mars.

Lee: (LAUGH)

Young: Go ahead. Go on that first shuttle to Mars that probably isn't going to make it to Mars, going to make it to like Australia or whatever. But be on that. Go on that and go live your life and spend your money and leave us alone.

Lee: Thanks for joining us as we got some sage advice from Damon Young. And thanks to all our listeners who submitted questions. We hope Damon was able to help you out. You can find his "Ask Damon" column every Friday in "The Washington Post."

Young: And again, any questions you have about caviar (ph), about the best way to eat Brussels sprouts, about the best shoes to wear to a jazz cruise. I mean, I don't know. I'm just --

Lee: (LAUGH)

Young: (LAUGH) Any questions, you know, you can ask us about beard tips.

Lee: Listen --

Young: You know, I see your beard doing the thing. I see it's moisturized. I see it's smooth, it's probably soft --

Lee: Glistening. Oh, it's supple. It's soft and supple.

Young: I'm trying to get like you --

Lee: (LAUGH)

Young: And so, maybe you need to start a column about how to get your beard looking luscious like that.

Lee: Listen. You all hear that, team? We're doing something fresh and new for the people.

Young: (LAUGH)

Lee: Damon Young, brother, as always, man, thank you again. You're welcome back any time, brother. Thank you.

Young: All right, thanks for having me on (ph).

Lee: Follow "Into America" on Twitter, Instagram and Facebook using the handle @IntoAmericaPod or you can tweet me @TrymaineLee. That's @TrymaineLee, my full name. If you want to write to us our e-mail is intoamerica@nbcuni.com. That was intoamerica@nbc and the letters uni.com

"Into America" is produced by Sojourner Ahebee, Isabel Angell, Allison Bailey, Mike Brown, Aaron Dalton, Max Jacobs and Joshua Sirotiak. Original music is my Hannis Brown. Our executive producer is Aisha Turner.

I'm Trymaine Lee. Catch you next Thursday.

END