Ask Polly

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12/25/15 - It’s Christmas! In this phone-a-friend episode, Ann talks with writer Heather Havrilesky about her existential advice column Ask Polly, making friends on the internet and how we can improve our advice-giving.

Transcript below.

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CREDITS

Producer: Gina Delvac

Hosts: Aminatou Sow & Ann Friedman

Theme song: Call Your Girlfriend by Robyn

LINKS

Heather’s Ask Polly column is so good

Archives of the OG column at The Awl

The world’s first misandrist advice column?



TRANSCRIPT: ASK POLLY

Aminatou: Welcome to Call Your Girlfriend.

Ann: Ho, ho, ho!

Aminatou: [Laughs]

Ann: I can't resist. I'm sorry. I'm sorry.

Aminatou: That was amazing.

Ann: Okay, wait, I'm Ann Friedman.

Aminatou: And I'm Aminatou Sow.

Ann: Oh wait, a podcast for long-distance besties everywhere. Woops.

Aminatou: We're keeping the intro like that this week, because guess what? It's Christmas and there is forgiveness in the air. It's fine.

Ann: This year has been a slog. I'm like . . . Christmas is like oh, yeah, sure, whatever. It's a dominant Christian holiday. But it's also basically just like goodbye 2015.

Aminatou: Yeah. I don't celebrate Christmas. For me it's mostly like ugh, this is the first . . . you know, it's like Thanksgiving is the first real break you get in the fall and if you don't have weird Christmas family stuff like me then Christmas is the time where you're like yes, I finally get time to myself. This is great.

Ann: Yeah. I feel like that week between Christmas and New Year's is just delicious. Like we're on the cusp of one of my favorite weeks of just sitting around reading novels and getting stoned all day.

Aminatou: No, exactly. Preach. That's where we are. Also, Ann, can I tell you my skin is so soft from our weekend at the spa. I'm dying.

Ann: Ugh, the mud bath? I mean I nearly had a claustrophobic meltdown in the mud bath but I was so relaxed after I forgot about the stress of the Han Solo carbonite mud bath experience.

Aminatou: It's okay, I had a meltdown in the sauna that was too hot and then the next day somebody did confirm to me that it was in fact too hot so I was not being a baby.

Ann: You bolted out of the sauna. I thought they were going to flag you as an insurance risk and tackle you.

Aminatou: Listen, this one drop of water dropped on a spot on my head that was just prime for it and it felt like it scalded my scalp and I was like I've got to get out of here.

Ann: I mean I don't think we're painting the picture that we had the most relaxing couple days at the spa but . . .

Aminatou: We had the best time. We had the actual best time at the spa. It was great.

Ann: Ugh.

(2:00)

Aminatou: I'm just shocked at how soft my skin still is days after.

Ann: Yeah. Again, though, great things to do on the cusp of a new year. Treat yourself.

Aminatou: Yeah, that's right. Shout-out to the Napa Valley. Thanks.

Ann: Oh man, other shout-out is to all of our awesome listeners who together you guys have collectively donated $5,000 to Zana Africa which is the period supply donating organization that we selected for a group-giving endeavor which is so good.

Aminatou: I honestly cannot believe how many people have written us and are tweeting at us and all this. You know, people are really good. It's like just for $10 you can sponsor one Kenyan girl with period supplies for a whole year. That's amazing.

Ann: So basically 500 -- I'm trying to do my math correctly but thanks to the people who listen to this . . .

Aminatou: Five hundo.

Ann: Five hundo Kenyan girls are getting their period supplies taken care of thanks to Call Your Girlfriend girlfriends which is awesome.

Aminatou: You guys are amazing. Obviously we're nothing if not overachiever so if it's kind of on your mind that you want to do this or you're still looking to spend some of that last-minute holiday cash or give a gift in honor of some of your friends definitely go to zanaafrica.org. Do what you've got to do.

Ann: Oh yeah, the year is not over yet. When you're having your digesting/half-asleep/Tumblr time, whatever you're doing with your laptop in bed when you're on this calm break between holidays, yeah, zanaafrica.org. And multiples of ten are awesome. We suggested that everyone give 40 dollars last time which tons of you did which is great but any amount is really welcome and awesome.

(3:50)

Aminatou: That's right. Yay periods, man. I love that, you know, having a period is not going to keep girls away from school. That's awesome.

Ann: Also this podcast, all these menstruators walking the walk. I love it.

Aminatou: [Laughs]

Ann: Everyone is just like, I don't know, it makes me really happy also about all of us and all of you guys and whatever. Warm fuzzies. Warm holiday fuzzies.

Aminatou: I'm trying to play it cool but I did get a little emosh. This is really cool.

Ann: So if you feel like you want to be part of it, not too late. We're going to get to 10K I swear. We're going to come back to you in 2016 and be like "Yo, you guys donated 20K," or something huge. I just know it.

Aminatou: Yeah. It'll be like this is going to be amazing. Okay.

Ann: Yeah.

Aminatou: What else is on the horizon for us? So we announced to everyone that we are launching a newsletter in 2016 called The Bleed. If you go to callyourgirlfriend.com/thebleed you can sign up. That's going to be awesome.

Ann: It's going to arrive once a month to remind you of your power in fertility. [Laughs]

Aminatou: It's going to be great. Also we're launching a website for some swag. Every once in a while we'll update you with what you can buy in there. What's the name for the website, Ann?

Ann: Oh, shopcyg.com.

Aminatou: So many things happening in 2016.

Ann: I mean it's not really . . . I mean that's like all of this stuff is kind of in progress. I think we're announcing things before they're completely baked but what are we if not pseudo-professionals? [Laughs]

Aminatou: Exactly. And also it'll keep us honest.

Ann: Oh, and on the honesty tip you will very soon start hearing our very first ads on this very podcast which I think are good. We're not going to say yes to any sponsors who conflict with our views about things and so far the businesses that we've talked to have all been things that we're actually using and excited to talk about. But just a heads-up that is happening because we need to make some money.

Aminatou: Exactly. And also we just want to stay honest with all of you. Any ad that appears on this show are for things that we either use or that feels good.

(5:55)

Ann: Exactly. Our standards are high. They really are. It's not like . . .

Aminatou: Yeah, we're turning down big tobacco and shit left and right for you guys so . . . [Laughs]

Ann: Oh my god, yeah. You better believe it. Behind the scenes we've just been saying no left and right which is why we haven't had ads yet. Like our feminist principles. Just kidding. [Laughs]

Aminatou: [Laughs] 

Ann: What else is happening in 2016?

Aminatou: You know, more DJ Khaled in our life, more success, more just everything. Well, I guess also today's Christmas so Merry Christmas to everyone and if you celebrate happy holidays. If you don't we know it can be kind of a stressful time being at home and with your family sometimes.

Ann: Right.

Aminatou: So we just kind of, you know, we're trying to end the note on some really super-posi vibes and, yeah, give people some advice for stuff that they need.

Ann: Yeah, we're here for you. And in fact, so this is -- I know we are having a long conversation but technically this is a phone-a-friend episode. I talked to the advice columnist and all-around fantastic writer Heather Havrilesky who is the author of the Ask Polly column at New York Magazine and she's awesome. She talked a lot about how you even go about giving advice and the kinds of problems people have. And I think in general whether you are feeling burnt out on family or however you normally celebrate the holiday or whether you're just in chill mode it's going to be the perfect thing to listen to today.

[Theme Song]

[Interview Starts]

(7:52)

Ann: Heather, thank you for coming to my house.

Heather: Thanks for having me. I'm very happy to be here.

Ann: In case people who listen to the podcast are not familiar with your incredible work can you give us a little greatest hits/synopsis?

Heather: Oh, greatest hits? I can't do that. I don't know.

Ann: What do you want people to know about you?

Heather: I do so many things.

Ann: What do you want people to know about you?

Heather: People always say that. They're always like "Just put in the things you want people to know." It's like I want them to know about my dogs because I have two dogs that are great.

Ann: [Laughs]

Heather: The main thing, the kind of headliner I think right now is that I write an advice column called Ask Polly for New York Magazine. It's on The Cut. They're sort of, how do you describe it, lady kind of . . . they don't like it when you say lady though. They don't like it.

Ann: I don't know. The fashion and gender . . .

Heather: Almost sort of women's magazine portion but it's for men too.

Ann: Sure.

Heather: So I write this advice column called Ask Polly. It started as an existential advice column so it has kind of an existential slant I'd say but it also ranges far and wide and is profane, vulgar, aggressive, humorous, fun. Funny.

Ann: I think it's sweet. I think it's also very kind.

Heather: Sometimes sweet, sometimes -- and every single column should end with an epiphany. That's the goal.

Ann: Ah.

Heather: Which is troubled. It's a troubled goal to have. And then I also write cultural criticism which mostly means I criticize our culture and I write book reviews for Book Forum. I have a column in Book Forum. And I also write a cartoon for The Onion's new celebrity site which is called Star Wipe. And my cartoon is called Antimatter with Dana Wulfekotte. So yeah, I do lots of different things.

Ann: You're everywhere.

Heather: Yeah. I'm spread too thin is one way to put it.

Ann: Does it feel like you're spread too thin?

(9:50)

Heather: Right now it does. I feel like I keep saying yes. I just read this book, Shonda Rhimes' The Year of Yes. Year of Yes.

Ann: Oh, yeah.

Heather: I'm reviewing it for The New York Times.

Ann: And?

Heather: When does this podcast come out? I don't want to spoil my own review. It's really good. I like the book a lot.

Ann: Okay.

Heather: But yeah, I think I've been saying yes too much. I think I need a year of no.

Ann: I mean I think that that could be a bestseller. Does that already exist, The Year of No?

Heather: You know, I don't think it does. I'm realizing now that I'm saying yes to everything that I said no to things for about a decade. My husband recently said -- I said "You know, it's strange, I meet people out for drinks a lot and when I meet people online I say let's get together a lot." I'm very social now even though I have two little kids at home. And I was like "It's strange because I feel like I wasn't like that four years ago." And he's like "You weren't really like that ten years ago either. You were kind of a shut-in." So yeah, I think I had a decade of no.

Ann: You were just seized by the urge to say yes to people on the Internet and meet them in person. Like me, I'm an Internet person.

Heather: Well, you know, I feel like Twitter has kind of reformed my brain around virtual water cooler behavior though I'm kind of . . . I don't know. It's like a troubled relationship that one has with Twitter. You have some times that you're kind of like oh, it's so comforting to go on Twitter, and other times where it's like hey, I fucking hate these people.

Ann: I have like Twitter days. I'm like I'm really on Twitter today. But then other days I just barely pay any attention. That's how I do it.

Heather: Yes, me too. And then sometimes if I'm really on deadline and I'm behind I go on but it's bad. It's not good. It's like calling someone that's a friend and saying "Hey, so how are you?" when you're in a really bad mood. [Laughs]

Ann: The self-loathing scroll is what I refer that to.

Heather: Yeah.

Ann: Yeah, it's about that. It's about oh, god, I'm not doing the work I wish I was doing. I'm just going to scroll.

(11:44)

Heather: Yes, scroll and who is this? Him again? Why doesn't he shut up? I'm sick of that guy.

Ann: [Laughs] Well I mean there are many things we could talk about but the thing I most want to ask you about is about the business of advice, the phenomenon, the I don't know what else to call it, the trade that you're in which is essentially being a fantastic writer but also delivering epiphanies to people who have some kind of life crisis or minor quandary.

Heather: Yeah, it's a really strange trade to be in definitely and I feel like it's very addictive too. It's strange because I have been writing for so long. I started writing professionally when I was 25 years old? I'd say it's the most fulfilling work I've ever done and it's also the most challenging. I mean I guess that goes hand-in-hand. The writing itself flows better and is easier than anything else I write. I mean I sit down and I feel like I just . . . it all comes out and it's not a struggle to come up with a response and ideas. But then going back and figuring out what the best, most concise way is of saying something which I often fail to say anything concisely . . .

Ann: [Laughs]

Heather: I think that's the really big challenge. And also obviously there's this -- I mean the column is ostensibly about existential crises but there's a kind of built-in existential crisis that I have in approaching the column because there's this sort of feeling like almost any time where I'm really failing at something in life, which you know, we all fail constantly obviously, every little failure there's kind of a voice in my head that says "You give people advice. What world have you -- what crazy, upside-down world have we stumbled into?"

Ann: Well, so talk about how you stumbled into it. What was the road to Ask Polly appearing on The Cut?

(13:40)

Heather: Okay, the first job I had I wrote for a place called suck.com that was like a dot com -- one of the first dot com magazines or sites, daily websites. And it was mostly pop cultural commentary and I was a staff writer. And I started to write a cartoon called Filler that was just weird takes on dot com culture. But then as the site was starting to go under, as the dot com bubble was sort of bursting in 2001, we needed cheap content and one of the things that I came up with was an advice column that was called Dear Tiny Little Penis. [Laughs]

Ann: How did I not know this?

Heather: It was sort of like aggressive -- very aggressive advice, faintly marketed to the threatened male.

Ann: Wow. Is this the world's first misandrist advice column? Maybe?

Heather: So welcoming.

Ann: Lost to the Internet archives. Was it ever aggregated anywhere? Can I read it?

Heather: All of Suck has a mirror site.

Ann: Okay.

Heather: So anything -- yeah, I don't know. I've never done a search on . . . I used to own tinylittlepenis.com actually.

Ann: Ugh, wow.

Heather: But I gave it up at some point because I was like this is kind of inherently evil. I don't know.

Ann: Please tell me you sold it for a lot of money.

Heather: I didn't. Nobody wanted it. Nobody ever approached me for it. If it were Big Fat Penis or, you know, Giant, Hulking, Throbbing Penis I probably could've sold it for a lot of money. But as it turns out not many vanity sites were attracted to that URL. So I did that for a while. I was very aggressive and funny and strange. And then the site went under and I started a blog. I was talking to some friends and they were like "Everyone is blogging now. You should start a blog in 2001." So I started a blog called The Rabbit Blog and, you know, I was just looking for ways of still writing while being unemployed essentially. And I started to give advice on my blog also, so people would write to The Rabbit. And at first that advice was very aggressive and kind of funny but as I got older -- I mean I was 31 when that started. And then as I grew older and my life sort of got semi-sorted out, I settled down, I started having kids, my advice was sort of more attuned . . . I got great letters at that blog actually. A lot of people had followed me there from Suck so they were very funny, smart, cynical, strange people with great problems. And mostly just almost self-mocking letters. I'd get a lot of kind of "I'm your typical . . ." You know?

Ann: Tiny little penis.

(16:25)

Heather: Those are the people encapsulating -- yeah, people who encapsulated themselves and made fun of themselves in their letters which I kind of miss. There's a little of that on Ask Polly. But anyway I did that for ten years and then meanwhile I was a TV critic, I was doing other things. And then at some point I decided that The All was my favorite website anywhere and that I should be writing for them and I wrote a few humor things for them. But I wanted to write a column for them, but I wanted it to be something easy that I knew had a right -- that would not require any reading of books or watching of television.

Ann: [Laughs] Sure.

Heather: So I was like how can I sell a talking out of my ass column to The All? So I wrote to Cory, The All's founder, and I told him just let me write an existential advice column and just pay me a tiny amount and I'll do it every week. It'll be great. It'll be fun. And he said done. He just wrote back one word, "Done." And I said "Okay, I'll send you the first one tomorrow." So I sent him this crazy . . . I mean, you know, the first column was sort of aggressive and funny and weird. I used one of my old Rabbit letters that I still had because I needed something that was sort of real obviously.

Ann: Sure, a prompt.

Heather: I couldn't just make one up. And I used to answer two letters at a time then eventually Cory said "You know, I kind of like these ones where you just do one." You know, I had one that went on and on. He was like this one's good. I mean The All is such a strange place. They're like "I like it when you go on for 5,000 words. That's my favorite thing."

Ann: [Laughs]

(17:55)

Heather: Anything that doesn't seem like it should belong in a magazine or on a normal website, that's what they like. So it was a great place to start the column because they embraced all my insanity and weirdness and my swearing and it kind of grew into something that was my favorite thing to do and it still is my favorite thing to do. Then New York Magazine came and they made mean offer to actually pay me real money.

Ann: You couldn't refuse.

Heather: I mean The All paid me perfectly good money but New York Magazine had more money and so now I'm doing it for them. I started the column in 2012 and New York Magazine approached me two years later, a year ago, in the fall of 2014. I'm giving you the encyclopedic version. [Laughs]

Ann: No, I'm wondering. I'm wondering as you say this because Rabbit ran for a long time.

Heather: Yeah.

Ann: And actually two years of writing an advice column even somewhere like The All, a lot of changes can happen. It's like if you were to sort of hold up one of your Cut Polly columns today against a Tiny Little Penis era Suck column like where are the threads that we could draw all the way back that have stayed in it?

Heather: The Tiny Little Penis stuff was just look for the joke definitely. I was not earnest at all. I think I was 28? Let's see. I guess I was 29, 30 years old. You know, my voice was half-formed almost kind of as a writer even though I'd been . . . you know, I'd been writing cartoons. So the early stuff was just sort of gracefully and secretly insult the person who's writing to you for the sake of humor and then insult yourself then make another joke and get out, something like that. Very short. Then The Rabbit started as sort of almost pathologizing everyone who approaches immediately and then making jokes about personality disorders. [Laughs] You know, it was kind of a different era both in my life and in the world.

Ann: You've really evolved, yeah.

(20:00)

Heather: Yes. But also, you know, obviously the online world has changed a lot. People don't really love for you to make fun of stuff as much. [Laughs] You know, you can make fun of yourself but you can't really do the things you used to do as a grumpy Gen Xer in the old days.

[Ads]

(23:35)

Ann: So do you feel that the current state of Polly has had to reflect that change? Or if you had your druthers would it still be kind of mean?

Heather: You know, I don't know. I kind of feel like I'm less mean although there are people who probably would not agree with that. Part of doing a good job as an advice columnist, at least for me, is definitely trying to look for a person's blind spots to some extent but then also cultivating a lot of empathy for the person because if you don't have empathy -- I mean it's like I answer the letters where I sort of feel like, I mean whatever. I get too many letters to answer all of them. But when I feel like I could generate some movement for the person by putting myself in their shoes and empathizing with them and also by kind of envisioning a path out of the whatever kind of stuck place they're in, that's what appeals to me.

So, you know, I mean my editor actually says "Oh, I love it when you get a little mean." You know, if I say like "You don't even see what you're doing," she likes that a lot. And I mean certainly there are times when I'm in that mood. Because I broke my foot recently I've been not working out as much so I'm a little bit angrier than I have been. [Laughs] I should probably take advantage of it.

Ann: Between the lines of your column. So I'm curious if you get more letters than you can respond to -- obviously I'm not surprised to hear that -- do you open them all and skim them? What's your process for deciding which gets a reply?

Heather: The letters are kind of like my other Twitter feed so they come in steadily and I read them and see if anything kind of sparks a feeling that this is something that people should hear. The problem is that, [Sighs], I tend to have a little bit of a prejudice towards let's see what this week's letters are. You know, I don't look back far enough. If I get busy sometimes I just . . . I mean I have unread letters in my inbox. And I'm sure there are people who are much more compassionate and thorough, or at least they would give you that impression, which is a kind of different topic. But, you know, I think if there's one thing that kind of makes Ask Polly stand out against the self-help realm or just the advice realm I'm very against seeming like I know special things. I don't know if that comes across always because I am very opinionated and I do say, you know, "You can't do that! You must do this." I am aggressive and probably reckless at times.

(26:14)

I was thinking about this recently because I was writing about Angelina Jolie and, you know, she's a very admirable person but she also is extremely careful about not showing the seams of her . . . like she says humble things but they sound kind of like a press release. She's kind of this strange combination of approachable and very humble and vulnerable but there aren't any details -- messy details where you could say . . . and it's understandable given her place in the culture obviously. But I was talking to my mom about it and my mom was like "Well you really hate it when people don't show their asses. Like you really don't like that." And it's true. It's like I can't . . . I don't think that's a way for me to lead anyway, you know what I mean? If I am a leader at all, which is highly questionable, it's sort of through being the biggest clown in the room. [Laughs] Like oh.

Ann: Sure. But it's funny because what's interesting about delivering -- what Angelina Jolie has in common with sort of dispensing advice is sort of saying like okay, well I'm going to select what I show you about my experience. I mean obviously . . . well maybe not obviously. Do you have a gut reaction to things sometimes that you have to then walk back? Is there ever a letter where you're like ugh, this person is so annoying, but then the resulting column never betrays that initial ugh?

Heather: Oh yeah. I think that one of the things that keeps the column varied and fresh is that I'm an extremely moody person. I remember getting a letter pretty recently, within the last three months, that I read it and I thought god this person's so messed up, you know? There's just so much dysfunction just so apparent, almost to the point of being aggravating. Which that's a good letter. You want to be a little bit like "Come on!" you know?

Ann: I'm sure people hate-read advice all the time.

Heather: Yes.

(28:08)

Ann: Like be like my life is so together. I'm not this person. Yeah.

Heather: Yeah. But, you know, I favor a feeling of oh, god, oh, god, look what you're doing moreover like "My cousin's aunt wants to visit and where is she going to . . ." You know?

Ann: The Ann Landers variety of . . .

Heather: Yeah. Well, you know, I think Dear Prudence is much more like that than I am.

Ann: Yeah.

Heather: Cheryl Strayed was much more the big problem, like how do I find the will to keep going kind of thing, which I think is probably a little bit closer to my neighborhood. But she also has more . . . she's almost more of a religious leader than I am, you know what I mean? [Laughs]

Ann: Yeah, for sure.

Heather: She's more of a figurehead, you know? I'm more like I lead by bad example and she's more like that's what you want. That's where you want to land. I'm more like -- I'm at the halfway point, you know? Like you want to kind of get up to where I am and hopefully surpass me. That's my goal for you.

Ann: Right, just lift people up right past you. Yeah. [Laughs]

Heather: Yeah, go on. I'm not like Oprah. Fly. Come sit on this couch. This is heaven right here. Oh, now you have to go back to your sad little life.

Ann: Right.

Heather: No, it's more like go. You can do more than this!

Ann: Have you ever asked a stranger for advice?

Heather: Yeah. I remember when I was younger. Okay, I never wrote to an advice columnist at all but when I was younger I did write a few terrible, really long-winded fan letters to people. I wrote one to Cynthia Heimel. Do you remember her?

Ann: No.

Heather: Cynthia Heimel was the greatest female feminist single woman humorist in the universe. She wrote a column -- I think she wrote a column for the LA Times. She had a few books that a friend of mine turned me onto when I was about 25. You should go see if you can find a book of hers. I mean she was, god, she's just super. One of the first . . . I mean the thing is, okay, these days a lot of writers are very voicy and funny. The Internet is just kind of made for that, especially right now. But in the old days it was sort of like Fran Lebowitz and Dorothy Parker and Renata Adler and Joan Didion. You know, everyone my age read Joan Didion and every aspiring writer read every word that she ever wrote. There weren't like a million . . .

(30:33)

Ann: I think aspiring writers still do.

Heather: They still do that? Okay.

Ann: Anyway, but go on.

Heather: There weren't like a million sources of inspiration.

Ann: Sure, sure.

Heather: I feel like the Internet is just flooded with . . . I mean, granted, there are obviously people who are kind of bland and there are people who are kind of really spicy and interesting. But there are a lot of really funny voices -- female voices I think now out there.

Ann: Sure.

Heather: So anyway, Cynthia Heimel, I wrote her some letter and I was like, you know, I just want to be you. Tell me all about you and what you do. Just the typical, you know, how do you do what you do? Just tell me. I need to know. I'm your best friend. I'm outside your apartment right now.

Ann: Did you hand-write this letter and put it in an envelope and walk it to her door?

Heather: [Laughs] I think I sent it to some address on one of her books or something, just totally pointless. [Laughs]

Ann: So you didn't get a response?

Heather: No, no. You know, maybe . . . let's see, was there email at the time? Did I find an email address for her? Is that possible? No. I just remember writing this terrible -- and it was the kind of fan letter that you write the whole thing and then you read it and you almost hate yourself that you even wrote that. Just sullied -- you just were so obsequious that you can't even live with yourself anymore.

Ann: And did you specifically say . . . I mean I know you said "I want to do what you do," but did you say and how can I? How do I do that?

(32:00)

Heather: You know, it was sort of more like you read some writers and you just feel like this is my best friend when you're done with the book. I mean I hadn't read a ton of really self-deprecating, interesting, funny women writers at that point in my life, you know? It's like 26 years old, everything was wrong. I mean I remember my bad years really well. I think it comes into play a lot in my advice column, you know?

Ann: Yeah, true.

Heather: You have to have a really clear memory of the bad times in order to I think do a good job of -- whatever. Do the job that I want to do, right?

Ann: Right.

Heather: I mean I think that people do a really good job of inspiring people when they've arrived higher than where I am. [Laughs]

Ann: So what else do you feel like you need to draw on as you're responding to people?

Heather: I mean honestly, and this is a very kind of Oprah couch answer, but . . . [Laughs]

Ann: We are on a couch right now.

Heather: We are sitting on a couch so maybe that's why it's making me think that way. I've been thinking lately about how I just have a lot of built-in challenges as a human being. I mean I think everyone can see themselves that way probably but I think that I'm realizing more and more as, you know, I'm 45 years old, and I kind of see more and more how I'm like a very high-maintenance house plant. I require a lot of different kinds of care in order to thrive.

Ann: [Laughs]

Heather: And you take away one of the things. I'm like one of those orchids that you move across the room and it just dies, you know?

Ann: Like a Trader Joe's orchid. The most delicate orchid.

Heather: Yeah, although I have to say I do . . . my first orchid, I always thought orchids were really high-maintenance and somebody gave me an orchid as a gift and it's the most amazing thing. It stays flowering all the time. I move it anywhere I want to. It's like a very flexible friend.

Ann: This is a free metaphor for you to use in a future column.

Heather: [Laughs] I know, write that down. I actually think it helps me, the fact that I . . . almost every day is its own kind of challenge and I never really know. I mean I'm an extreme . . . you know, I don't think that I'm bipolar. I've been kind of flirting with am I bipolar? I am moody to the . . . I'm definitely pathologically moody, you know?

(34:12)

Ann: Sure. A light flirtation with being bipolar.

Heather: [Laughs] But then there are these eras where I'm just doing all . . . most of it I think is physical. It's like there are times when I do all the physical things right. And I know that not everyone is ruled completely by the physical. I do think as you get older you're more ruled by it. But anyway I've just been marveling at how much I need to do really well but then when I am doing really well . . . I mean I definitely had just started to define myself as a solidly happy person, you know, I would say two years ago. Like I started to say no, I am . . . a friend of mine said to me "What does that mean, happy? I mean what is happy?" What does that even . . . no one's really happy. And I remember saying I am genuinely happy, especially compared to the old days, but I mean I'm always happier and happier. But now I would say I own the word happy. I'm definitely happy.

A knowledge of how just sort of fragile happiness can be even when you're genuinely happy overall, it helps, because I feel like I constantly have my hands on all the levers. You know what I mean? And I recognize that I'm just very self-conscious about how much it takes. I think there are people who give advice that it's sort of more like, you know, you just have to do this. Like the simplicity of it I find frustrating because I know there are just many different dimensions to it.

Ann: Yeah. And it's funny, as you were saying that I found myself thinking about authority and how I think at first blush a lot of people would say that in order to be a good advice columnist you would have to really be in the place where you are now and sort of say oh, I've got it. I'm happy on some deep, underlying level, not just this afternoon because I had a good day. But really in terms of having material to draw on and being a good advice columnist I feel like you're better qualified if you aren't.

(36:10)

Heather: Aren't completely happy?

Ann: Yeah. That's kind of what you're saying. Or at least having had significant experiences where you are dissatisfied and unhappy.

Heather: Yeah.

Ann: As opposed to having a lifelong got it together veneer of, I don't know, whatever kind of perfection you might define.

Heather: Yeah. I mean I think that -- I can't decide. Sometimes I think that I have more . . . do I have more trouble just navigating life than anyone else? Or do I just talk about it too much or do I think about it too much? Or am I just attracted to these subjects? You know what I mean? This is the other thing. Am I just a connoisseur of . . .

Ann: Problems?

Heather: You know, love and problems and suffering and analysis? Do I think too much? I mean I do think that a lot of people who are attracted to my advice column are a little bit neurotic and usually kind of smart dare I say? The over-thinkers definitely . . .

Ann: Over-thinkers, for sure. Over-thinkers Anonymous. Oh my god, that's the Ask Polly club right there.

Heather: Over-thinkers, definitely. But it's also there's a base level of optimism because you wouldn't read advice columns that remind you of your own onboard optimism which I think Ask Polly tries to do if you didn't have some in some tank somewhere. I mean if I were . . . I think that if I were just a really dark, dark, dark person I would not be attracted to my particular advice column. It definitely appeals to people who are reasonably optimistic and hopeful but who have possibly depressive biology or a lot of neuroticism or all of the above. A shitty boyfriend. [Laughs] That's a very large category actually of people.

(37:55)

Ann: Is there some lesson or piece of advice or general point that you seem to find yourself making or maybe wanting to make over and over? Maybe not every column but something that you're like oh, wow, I'm ending up here again?

Heather: Yeah, I definitely . . . I've been thinking about trying to write a bunch of tarot cards for Ask Polly.

Ann: Oh my god, please.

Heather: Which it's very dangerous and difficult to think about doing this because going back to old columns you look back and you say oh, look, I found another metaphor for a non-committal boyfriend. How interesting. Oh, there's another way of saying that you should own your flaws. I mean definitely -- okay, the most fundamental . . . which I hate to boil it down because . . .

Ann: I mean I asked you to boil it down kind of.

Heather: You know, I want to reinvent -- not only do I want to reinvent the wheel of oh, look, I'm writing about the human condition and it involves the band Yes, you know? I want to like have a feeling of discovery every time I write the column because I think it creates all of this energy and weirdness when you do that. You know, I'm probably a little bit of an idiot savant that way though because I'm not necessarily like . . . you know, I could just probably read a few really great books by Thoreau and Walden and I'd suddenly be like oh, they said everything that I've been saying.

Ann: Why am I even writing a column? Yeah. [Laughs]

Heather: Yeah, exactly. This has actually been -- you know, my greatest fear . . . I think for any writer the greatest fear is like oh, it's all been said. I have nothing to add to the pile, you know?

Ann: I kind of disagree with that actually.

Heather: Really?

Ann: I think that -- and maybe this makes me not a real writer or something, but I actually think that sometimes the same point could've been made or the same thing could've been said a million times before but saying it in a certain tone or with a certain amount of supporting evidence or in a certain context, I don't know, the world in which that writing appears is different when you create it now. And I think that yeah, sometimes you're like okay, that is legit just a thing that someone has written a million times. But I think sometimes at first blush things can appear like they have been written before or it can be like oh, yeah, that's the same general argument. But really it hits a new generation or a new type of reader or a new moment. I don't know.

(40:20)

Heather: Well, it's also . . . I mean I do think that everything is just a matter of kind of repeating itself in different ways.

Ann: That's kind of what I'm saying, yeah.

Heather: Yeah. But it's kind of a good feeling too. It's sort of like oh, I used to think that the world was just an endless . . . you know, there was endless wisdom out there and you had to just navigate to it and digest it and find some more. And it's sort of nice at some point to realize like oh, this is a little bit recursive. The seasons are a metaphor for so many things, you know?

Ann: [Laughs]

Heather: That's okay and the human condition is sort of all about love and hope and opening your heart, you know? These basic things that you resist when you're younger like oh, Jesus, opening your heart again. Go fuck yourself. But and yet, you know, you do realize at some point like okay . . . I mean you realize this when you're younger than I am but the cliches are true and there are actually all kinds of interesting ways to express the same idea. There are also a lot of really boring ways to express the same idea.

Ann: Yes.

Heather: Right now I'm reviewing Nicholas Sparks for Book Forum.

Ann: Oh, wow.

Heather: It's like each line, every single line, is a clich. It's just a -- a tumble . . .

Ann: A cascade of clich?

Heather: Nothing is new. It's all like I feel like I've read this and this and this. Anyway, I'm just an asshole. But the bottom line is I'm an asshole, I think, but where were we? [Laughs] You tell me.

Ann: I mean a couple of questions back . . .

Heather: Yeah, exactly.

Ann: I was talking about pieces of advice that crop up again and again.

Heather: Yeah, yeah. That crop up again. Yeah.

(42:00)

Ann: Sort of like oh, this is something that I want to tell lots of people even if their questions are different.

Heather: The basic I think thrust of most of my columns is that one of the most crucial parts of being an adult and also finding love for yourself and finding love with other people -- finding connection with other people -- it's really hard to connect with other people when you think that there's some deep-seeded flaw in you that needs to be expunged. And I think that most people feel that way about themselves actually. The more I've been doing what I do the more I feel exposed to that basic problem.

I used to think when I was younger that it was, you know, you go to therapy and you find out who fucked you up and how they did it. [Laughs] And then you're angry for a while and hopefully you forgive the people who screwed you up because they made such big mistakes and then you try to set out. And of course you're setting out to never make the same shitty mistakes those bad people who fucked you up did.

There's a point you kind of realize we actually all find ways of drawing a line from our feeling of being unacceptable and not good enough and an impostor and a misfit and not quite right and not in the stream of things, we find ways of looking at that stuff. You know, I'm not happy enough. Everyone else is happy. I'm not cute enough. I'm not cheery enough. I don't fit in. We find a way of drawing a line from that to the past and saying this is why. This went wrong. That went wrong. I mean I wrote a memoir that was kind of all about that.

Ann: I know, I read it and I liked it a lot.

Heather: [Laughs]

Ann: Not sucking up, I swear.

(43:55)

Heather: Thank you. But it's a great process, you know? And I think I stand by most of the lines that I drew in that narrative but I do think that there's a point where you have to say hold on, I'm not . . . it's not my . . . this very specific thing, this narrative I've been drawing is not actually -- it could apply to anyone. The point at which you can say to yourself wow, I wasn't the ideal friend or the ideal girlfriend to this person or that person so they moved on, but that actually wasn't some verdict on oh, I really am not good enough, you know? I lost this job or I quit this job because I wasn't good at it but that wasn't actually me finding out it's true, I'm a loser just like I suspected. There's a point where you just say oh, I am kind of a wreck and I always will be. I'm always going to be redefining who I am. I'm always going to be learning new skills. I'm constantly going to be trying to improve myself. I'm constantly going to be failing people left and right. Of course, you know? Because I'm a human being and we all actually are in the same fucking boat and we're all fumbling through and trying to do the best we can.

That definitely is the first piece of it. And then the second piece is once you accept that feeling your connection to other people. You know, feeling how good actually it feels to be just another sort of misshapen freak in the world. It actually feels great, you know? It's like to me that is happiness. It's happiness to say I can't do everything perfectly, you know? And maybe that's just a very modern our culture kind of problem to think that you should be able to do everything but maybe it's just a side effect of how beautifully everything is marketed to us now and how beautifully everything is designed. Humans are designed so beautifully. They're so polished, you know? And they say the right things and they're so poised.

(46:00)

I think that we live in a pretty anxious time as a result of the way that we are presented to each other in the world. And I think that there's something totally freeing about just saying I don't have to be that successful. I don't have to even sound very good. I can sound kind of like a freak and life goes on. And people will like you for you, you know? Once you decide that you're acceptable and that you are good enough. Again this sounds like every other thing in the universe when I really spell it out, but yeah. How many things can there be really?

Ann: We didn't really set out to take listener questions but we setup an email inbox. I don't know what we thought people would send there, maybe links. But they frequently do send us questions and life dilemmas and we are universally terrible. Like we decide this is a great question, we're going to answer this one, then one of us reads it and then we both go like uh, uh, uh. Like we just kind of make a bunch of noises that I'm sure Gina edits out most of them. But yeah, so what advice do you have for us as sort of super amateur-level readers and givers of advice?

Heather: [Laughs] What I like is listening to someone's problem and then thinking about the one area of the problem that seems a little different than everything else. Like there are these tells, you know? When you find the little thread that seems off you pull it and the whole sweater comes apart. It fits in with every other problem that they have. The thing that interests you the most about the question is the linchpin to the whole question. Does that make sense? And it's sort of an instinctive thing.

(47:50)

Often what people say they're asking, it's not even their reigning issue. The issue is sometimes what they say they're good at, you know what I mean? Like I got this great letter that was like everything's fine. My life is going forward in a perfectly fine way. I broke up with my boyfriend and he told me in a really nice way, and I talked to my therapist about it and she said you handled it perfectly and it was great so I know I'm on track. I don't have any big questions about whether I'm worthy or not. And it was like then the whole letter . . . what she kept saying is "I'm not asking you if I'm worthy or not. I'm not asking you if I'm good enough or not because I know that I am. I know I am. I'm healthy. I'm healthy. I'm healthy." And it was like oh, so you're wondering if you're worthy or not?

Ann: [Laughs] Right. Right.

Heather: Because you keep saying that's not what you're asking. That's not what I'm asking. I think looking for that thing that someone really doesn't . . . sometimes it's like the thing that someone doesn't want to address is the thing that they absolutely -- is the first thing they should address, right?

Ann: Sure.

Heather: So I mean it's hard to do that in real-time though, let me say. I don't mean to be . . .

Ann: And again it's not really comparable to what you do or to even what someone would do on a call-in advice show. But yeah. It's funny. It's not that I . . . I don't think we thought it would be easy, but I think it was like oh, people are sending us these things so we should maybe respond to some of them. It wasn't even like oh, this is no big deal; everyone does this.

Heather: Well you could process it by . . . I think writers think on the page better than they do probably live. I mean clearly I think on the page much more clearly than I do live.

Ann: As do I, yeah.

Heather: You're a little smoother than I am. You're a little better at . . . you see how I compare? See my hierarchy of values?

Ann: I know. I was just thinking -- I was like what would Ask Polly say about that? [Laughs]

Heather: I'm very weak. I know. I know, I'm very weak. One of the giant fears about doing what I do and kind of . . . it's going to be fun for people to see just how fucked-up I am. People think that I just -- like oh. I'm really a mess too a lot of the time. It's like oh, sure Polly. You have it all figured out. It's like no, it's quite apparent to most people who know me actually.

Ann: Right.

(50:05)

Heather: Life is about struggle.

Ann: Struggle is real. That's what we say on the podcast, the struggle is real. [Laughs]

Heather: The struggle is real? That's great. That's your motto.

Ann: I mean it's one of many but yeah. I feel like it comes up frequently.

Heather: The struggle is real.

Ann: The struggle is real. It's like when there's nothing left to say.

Heather: [Laughs] That's great. That's really good. I'm going to take that. I'm stealing it.

Ann: Ugh, please do. Heather, thanks for chatting for the podcast.

Heather: Thank you so much for having me, Ann. I really appreciate it. It was so fun.

[Interview Ends]

Aminatou: That was really cool. That's really awesome. I'm really glad I got to experience that.

Ann: I know. We were side-by-side and Gina sat across from us and recorded it. It was the most Barbara Walters I've ever been in my life. Soon -- maybe 2017 we'll be doing these on video and you can get the full soft-lens effect.

Aminatou: I don't know, man. Face for radio over here so . . .

Ann: Don't even lie. Don't even lie.

Aminatou: Mostly what I'm saying is the only way that I will take this show on video is if I can wear sweatpants all of the time.

Ann: I mean I think that would be a core tenet of our show, caftans and sweatpants on camera.

Aminatou: Right? I feel like that's the Rachel Maddow thing, right? Like she's only ever wearing the blazer on top but on the bottom it's like all pajama bottoms or something.

Ann: Business on the top, party on the bottom.

Aminatou: That's right. That's right. Well you know what? Happy holidays everyone and we'll see you on the Internet.

Ann: See you on the Internet in 2016.

Aminatou: You can find us many places on the Internet, on our website callyourgirlfriend.com, download our show on the Acast app, or on iTunes where we would love it if you left us a review. You can tweet at us at @callyrgf or email us at callyrgf@gmail.com. You can even leave us a short and sweet voicemail at 714-681-2943. That's 714-681-CYGF. This podcast is produced by Gina Delvac.