The Wayback #46 | Annie Lederman

Summary

Podcast Summary: The Wayback #46 | Annie Lederman

Release Date: November 16, 2024

Introduction

In episode #46 of The Wayback with Ryan Sickler, host Ryan Sickler welcomes comedian Annie Lederman for a heartfelt and humorous journey down memory lane. Together, they delve into childhood adventures, sibling dynamics, school life, and teenage rebellions, all infused with Annie's signature wit and candid storytelling.

Childhood Memories

Annie begins by reminiscing about her early days, sharing memorable moments from her family's vintage Pontiac minivan. She recounts the challenges of the sliding doors:

"And then the sliding door would get stuck, and if we were on the highway, it would just be, like, completely open." (03:08)

Ryan adds his own nostalgic touch, highlighting the universal experience of family road trips:

"Madison, Wisconsin. I'll be there Friday and Saturday, November 15th and 16th at Comedy on State..." (00:41) (Promotional segment)

Family Dynamics and Sibling Relationships

The conversation shifts to Annie's family, particularly her relationship with her twin brother and older sibling. Despite being fraternal twins born minutes apart, Annie and her twin don't look alike, leading to unique familial interactions:

"We were like, at a Quaker school together until we were in fifth grade. It was a really small school, so we were together every day then. So it was kind of like forced communication." (08:43)

Annie shares a poignant reflection on her parents’ perspective:

"My mom was very like, I wish I was a boy. Like, my mom would have been transfer attention." (34:16)

School Life and Quaker Influence

Annie's experience at a Quaker school profoundly shaped her upbringing. She describes the school's ethos of equality and the unique practices that fostered a close-knit community:

"Each of the teachers would shake your hand at the end of class and stuff like that was very cute." (10:09)

The duo discusses Annie's participation in Quaker youth retreats and camps, highlighting the blend of spiritual growth and youthful antics:

"We smoked cigarettes out here. We used to smoke cigs right out here." (14:17)

Annie's time at Camp Onus becomes a focal point, revealing the balance between disciplined activities and teenage mischief:

"I almost got kicked out for sneaking out... I just make noises in my sleep." (18:36)

Teenage Rebellions and Experiences

As the conversation progresses, Annie delves into her teenage years, marked by acts of rebellion and self-discovery. She narrates her adventures of sneaking out with her twin brother, Max, and the ensuing escapades:

"Max and I would dress in all black and we would sneak out of the house with flashlights at nine. We were like, maybe like middle school, maybe 10, 12 still." (25:57)

Annie candidly discusses her foray into alcohol at a young age and her first experiences with piercings:

"I went to the discotheca with the archery instructor. Was a lot older... I just make noises in my sleep." (05:15)

She reflects on her attempts to fit in and be "the pick me sister," striving to connect with her sports-enthusiast brother:

"I just tried for a while to be like a pick me sister that was like. I would watch Sports center and I would try to, like, learn stats and stuff to impress him." (07:11)

Annie shares a humorous yet revealing story about getting her nipples pierced at 14, highlighting the rebellious spirit of her youth:

"We snuck out... We met these guys at the Roosevelt Mall... We called the movie line hotline where you could hear all the movie show times." (21:19)

Reflections and Concluding Thoughts

Throughout the episode, Annie offers introspective insights into how her past shaped her present. From the challenges of navigating family dynamics to the thrills and missteps of teenage years, her stories are both entertaining and enlightening.

Ryan complements Annie's storytelling with his own anecdotes, creating a dynamic and engaging dialogue that captures the essence of nostalgic reflection.

Notable Moments and Quotes

• Sibling Bonds:
  "I have a twin brother. And I have a brother who's three years older." (04:38) – Annie

• First Encounter with Alcohol:
  "That's in Matuga, Mexico. That's when I started drinking." (05:05) – Annie

• Quaker School Life:
  "The headmaster would stand outside and shake our hands every morning." (10:12) – Annie

• Teenage Mischief:
  "Max and I would dress in all black and we would sneak out of the house with flashlights at nine." (25:57) – Annie

• Piercing Story:
  "We went and got our nipples pierced at 14, but right before she put the needle and she went, butterfingers." (21:35) – Annie

Conclusion

The Wayback #46 offers listeners a blend of humor, nostalgia, and genuine conversation. Annie Lederman's candid recounting of her life's ups and downs provides a relatable and engaging listening experience. Through shared stories of family, school, and teenage adventures, Ryan and Annie create a tapestry of memories that resonate deeply with audiences.

For those who missed the episode, this summary captures the essence of Annie's journey, highlighting the key moments that make The Wayback with Ryan Sickler a beloved nostalgia-filled podcast.

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Promotions

• Annie Lederman's Podcast and Tour:
  “I have my podcast annual. It comes out every Thursday on YouTube. It's just YouTube.com Annie Letterman...” (01:52)

• Ryan Sickler's Shows:
  “Get your tickets to those shows and all shows on my [e-mail].” (00:41)

• Follow on Social Media:
  “Ryan Sickler.com and Ryan Sickler on all your social media...” (01:02)

Join the Conversation

To stay updated with future episodes and live shows, visit Ryan Sickler's website and follow Annie Lederman on Annie Letterman's YouTube channel.

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This summary provides a comprehensive overview of episode #46, capturing the essence of Ryan and Annie's engaging dialogue while highlighting the key moments and insights shared throughout their nostalgic ride.

Transcript

[Libsyn Ads]

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[Ryan Sickler]

Madison, Wisconsin. I'll be there Friday and Saturday, November 15th and 16th at Comedy on State. And Portland, Oregon. I'll be at the Aladdin Theater Saturday, November 23rd. Get your tickets to those shows and all shows on my website@ryan sickler.com.

[Annie Letterman]

Hey baby, we going to be here all day.

[Ryan Sickler]

We going to be here all day, baby. I like that kind of party. Welcome back to the Way Back, everybody. I'm Ryan Sickler. Ryan Sickler.com and Ryan Sickler on all your social media, starting this episode like I start them all, everybody, by saying thank you. Thank you for supporting this show. Thank you for supporting the honeydew. Thank you for supporting anything I do. I genuinely appreciate it. I'm on the road. Come see me if I'm in your town when you're around. Tickets are on my [e-mail] Very excited to have this guest on with me today. Ladies and gentlemen, Eddie Letterman. Welcome to the Way Back.

[Annie Letterman]

What? Oh.

[Ryan Sickler]

First of all, thank you for being here.

[Annie Letterman]

Oh, what a treat.

[Ryan Sickler]

We've been catching up quite a bit. It's fun to sit down with you here. That's going to be you right there. Promote everything and anything you would like. Andy Letterman, all of it.

[Annie Letterman]

Well, I have my podcast annual. It comes out every Thursday on YouTube. It's just YouTube.com Annie Letterman. And then I'm on all the socials, Annie Letterman with a D. And then I'm on the road this weekend, November 14th and 16th. And I'm gonna have my next Annie Wooden friends November 19th at the Comedy Store. Then I'll be in Boston, Massachusetts, November 22nd, 23rd. And then I'm gonna be in Anchorage, Ohio, March 14th. I'll be in Toronto, Kansas City, Naples, Florida and Tampa and A bunch of places. Just go to Andy Lerman dot com.

[Ryan Sickler]

Those are 20, 25 days.

[Annie Letterman]

I don't know what the. I'm reading. It's just there, baby. I don't know. And by the way, I have a lot of 20, 24 dates that are not up, by the way. I'm like, where are they? I don't even know. And I don't know. I don't even know, like, where they are, what they are. I so much of my. I don't even have passwords to my things. I've given up way too much power. I have no. My. My manager will be like, hey, we need access to your Facebook. I'm like, good luck. I don't even own my Facebook. Some guy took my Facebook, like, four years ago, and he won't give it back. I'm like, I've never gotten paid off of any of my things. I have no clue how to get on. If I go to change the password, it just gets sent to him, and.

[Ryan Sickler]

He'S just like, I got this.

[Annie Letterman]

He's just like, oh, I don't know what's going on, why I can't give it back. I'm like, how much money are you making money off of me? You must be making money off me.

[Ryan Sickler]

Well, I usually start this episode, and I forgot to tell you this, but I start by asking. So this is the way back, and it's not just the nostalgic podcast. This is that back seat in the old school station wagon, that face traffic.

[Annie Letterman]

Oh, yeah.

[Ryan Sickler]

Do you remember that scene? Are you old enough to have sat in that scene?

[Annie Letterman]

My. Yeah, my.

[Ryan Sickler]

Who had it in your family?

[Annie Letterman]

My cousins had a place in Vermont.

[Ryan Sickler]

Okay.

[Annie Letterman]

And when we go to Vermont, they would. We would sit in those chairs and.

[Ryan Sickler]

Roll in that way back.

[Annie Letterman]

But we had one of those. Those minivans that was Pontiac, I think, that had the pointy tip. Yes. Yep, we had one of those.

[Ryan Sickler]

I forgot about that.

[Annie Letterman]

They're kind of cute. I do remember they're kind of cute. They're very dangerous now. If you see someone in it, run, scream, call the cops. That is. I mean, there's no way anything.

[Ryan Sickler]

Look at that.

[Annie Letterman]

There's a penis being rubbed in that car.

[Ryan Sickler]

Who had. This was your family.

[Annie Letterman]

This was my family car. And then the sliding door would get stuck, and if we were on the highway, it would just be, like, completely open.

[Ryan Sickler]

No.

[Annie Letterman]

And so my brother and I would spit. We would, like, spit out and would smack into the other person's face. We had a lot of fun in that like, when the thing got on, we were so happy. We'd, like, buck on, and we're like, it's stuck open again. Hell, yeah.

[Ryan Sickler]

And then it would just fly. That is good.

[Annie Letterman]

Sometimes you get yourself. You're like, damn.

[Ryan Sickler]

And so how many siblings do you have?

[Annie Letterman]

I have a twin brother. And I have a brother who's three years older.

[Ryan Sickler]

All right, so let's talk about. Because I'm a twin. I have a fraternal twin. We're four minutes apart.

[Annie Letterman]

Okay.

[Ryan Sickler]

I have a brother. We're fraternal, but we're Brother. Brother.

[Annie Letterman]

Do you look alike, though?

[Ryan Sickler]

No.

[Annie Letterman]

Isn't it where we see identical twins that don't look alike?

[Ryan Sickler]

Yeah. Do you look alike?

[Annie Letterman]

Kind of. Not really. He looks more like my older brother.

[Ryan Sickler]

Okay.

[Annie Letterman]

So my. They always thought my older. Oh, my God.

[Ryan Sickler]

Here we go.

[Annie Letterman]

That is one of my favorite pictures. I can't believe on that so quick. That's in Matuga, Mexico. That's when I started drinking.

[Ryan Sickler]

How old are you here?

[Annie Letterman]

13 or 12.

[Ryan Sickler]

That's where you first had alcohol?

[Annie Letterman]

I went to the. To the discotheca with the archery instructor. Was a lot older. That was one of my first. I think the first time I got someone fired.

[Ryan Sickler]

Why? Because he took you?

[Annie Letterman]

He was trying to make out with me and stuff. And I was like, he's a pedophile. I went down to the archery. I was like, he's a pedophile. My parents knew none of this, by the way. I just, like, had a whole thing happen and that.

[Ryan Sickler]

You didn't tell him or anything?

[Annie Letterman]

No, I was just handling it. I'm two feet apart from him. Look at this. Look at this little munchkin next to me.

[Ryan Sickler]

You do kind of look alike a little.

[Annie Letterman]

He looks like my older brother. And then I was taller, so I. They thought me and my older brother might be twins because we were more the same size as.

[Ryan Sickler]

How. How far apart are you? How many minutes?

[Annie Letterman]

Me and Max are six minutes apart.

[Ryan Sickler]

But there's something interesting.

[Annie Letterman]

But we were born at midnight.

[Ryan Sickler]

That's crazy.

[Annie Letterman]

He was. He was 1158, and I was 1204.

[Ryan Sickler]

So you have different birthdays?

[Annie Letterman]

Yeah, he's July 19th.

[Ryan Sickler]

But you're fraternal twins.

[Annie Letterman]

Yep. We got our own cakes.

[Ryan Sickler]

You did. You had. I was gonna ask. Separate birthday. See, I always was sharing a cake and a birthday.

[Annie Letterman]

I know it does kind of suck for life. And then you don't even. You're not even identical, so you don't get, like, the special treatment of a twin.

[Ryan Sickler]

My mom dressed us alike. Did your parents do that?

[Annie Letterman]

Not really. Maybe, like once somewhere. Babies.

[Ryan Sickler]

Yeah. This is me and my brothers right here. My two brothers. That's my twin up there. Look at the grass stains in the family picture.

[Annie Letterman]

Well, every picture with my twin brother. He fell off something. He always had, like, a cut on his face. Yeah, he always fell off of a.

[Ryan Sickler]

I mean, look at those teeth.

[Annie Letterman]

And look at that.

[Ryan Sickler]

So we don't look alike, but I will say this. We sound alike. There are times when I still.

[Annie Letterman]

I mean, you. You look like my little brother Israel. And he looks like Gaza.

[Ryan Sickler]

By the way, that's our Todd.

[Annie Letterman]

And then your baby brother looks like he. Someone asked him which side he wanted to choose.

[Ryan Sickler]

See, there's a bloody nose or something in there.

[Annie Letterman]

Oh, no, there's always. It's crazy with the little boys. It is very wild. Yeah, you guys look a lot different.

[Ryan Sickler]

But we sound. Even to this day. I'm 51. There are times I'll speak and I'm like, I can hear him. You know what I mean? I'm like, he would have said it just like that.

[Annie Letterman]

Do you talk a lot?

[Ryan Sickler]

We still communicate all the time. Yeah, but he's in Delaware. So he stayed. Yeah, he stayed. He just left Maryland, went to Delaware.

[Annie Letterman]

Well, that's not much of a. Nope.

[Ryan Sickler]

Do you.

[Annie Letterman]

Not much of a high.

[Ryan Sickler]

Are you close to your twin?

[Annie Letterman]

Not really. My brother is like. He's really into sports. He works for NBC Sports Boston, and he's really into sports. Like in. Almost like, not autistic, but like, it's just like his whole life is sports. And I just tried for a while to be like a pick me sister that was like. I would watch Sports center and I would try to, like, learn stats and stuff to impress him. And I got him for like six months in college. And then I was like, max, I'll see you later. You know, like, I. We'll see each other Thanksgiving. I can't. It was too much upkeep. And then his. His daughter. I'm very close with his daughters and with his wife now. So I just talk to Dane all the time on. But we went to different schools. Like, we. We were held back in kindergarten.

[Ryan Sickler]

Wait, why?

[Annie Letterman]

Because Max had learning disabilities. So then they held me back with him. And then my mom's like, but then we learned your learning disabilities in first grade. I'm like, likely story.

[Ryan Sickler]

So you guys get repeat kindergarten.

[Annie Letterman]

So we did kindergarten twice.

[Ryan Sickler]

So were you 19 when you graduated high school?

[Annie Letterman]

No. And then we went to different schools in. We were like, at a Quaker school together until we were in fifth grade. And it was a really small school, so we were together every day then. So it was kind of like forced communication.

[Ryan Sickler]

Elementary school.

[Annie Letterman]

Yeah. And then sixth grade, we went to a public school. We were on different sides of the school, so we didn't really see each other. And then seventh grade as well. And then eighth grade, I skipped eighth grade. I went to a. A alternative school that didn't have real. It wasn't school wasn't anything. So they just were like, all right, you can be in the upper school. And then I graduated early. So then I graduated in 2000 when I was 16, and then Max graduated in 2002.

[Ryan Sickler]

Okay, now Quaker school. What. What is Quaker school?

[Annie Letterman]

Okay. Quaker school was so cute.

[Ryan Sickler]

What is it?

[Annie Letterman]

It's okay. So Quakerism is a form of Christianity that's like very chill. There's two types of Quakers and it's program Quaker and unprogrammed Quaker. We were unprogrammed Quaker. That's like very chill, very hippie, very close to the Unitarian Church. Like very, like a lot of things go very open. A lot of gay people. There was like a Jewish guy in her. It was very weird. There was a guy in a full yarmulke with like one of the like Star of David shawl things that would come. I'm like, this is very weird. It was like kind of anything goes.

[Ryan Sickler]

So is this what your family's following? Religious? A lot of people go to Catholic school, but their families aren't Catholic. Is it sort of like that?

[Annie Letterman]

My mom started doing the newsletter for Green Street Friend School, the school that we went to. And then she really liked the quick. Green Street Friend School.

[Ryan Sickler]

Green Street Friend Friend's school. Where?

[Annie Letterman]

In Philly. How cute is that? Is that cute? Is it a little school? A little baby school?

[Ryan Sickler]

And this is for kindergarten through.

[Annie Letterman]

This was. Yeah, kindergarten. I think we might have gone to.

[Ryan Sickler]

Pre K. There it is still look pretty similar.

[Annie Letterman]

Yeah. That's so cute. And then so we went to that school and Norma, the. The headmaster would stand outside and shake our hands every morning. So Quakers was like shaking hands and everyone's friends and you call your teachers by their first names, but not in a molesty way, which was like how my high school was.

[Ryan Sickler]

Got it.

[Annie Letterman]

Like they just ever. It's like more of an equal playing field. And then so each of the teachers would shake your hand at the end of class and stuff like that was very cute. But anyway, so Quakerism, you sit and you sit. The church is that you sit in silence. So you go every Sunday, you sit in silence, you face each other, and then if you feel moved to speak, you stand up and speak. Which is definitely how I got into stand up.

[Ryan Sickler]

Were you getting up?

[Annie Letterman]

Max was like, oh, my God.

[Ryan Sickler]

What are some. Here we go. Look.

[Annie Letterman]

Am I in this class?

[Ryan Sickler]

This is grade one.

[Annie Letterman]

This might be maxi. I think I'm not in this one. That's Max.

[Ryan Sickler]

So where is he?

[Annie Letterman]

He's right there in the hyper color.

[Ryan Sickler]

Oh, in the bottom. Yeah, yeah, yeah.

[Annie Letterman]

I think we were in different color. Oh, yeah.

[Ryan Sickler]

Letterman.

[Annie Letterman]

Remember the snow boots? And they wouldn't be in color until you got in the snow.

[Ryan Sickler]

I had body glove. Was a few of them I had. And everybody was. So it actually was a bad idea for at least guys with shorts and stuff. Because when your body temperature would change the color of the garment you were wearing. Like you said the boots in the winter.

[Annie Letterman]

But do hypocolor shirt.

[Ryan Sickler]

I had a shirt. Yeah, and if we'd sweat on shorts, your dick and ball area would be all color changed and stuff.

[Annie Letterman]

Yeah, like hampering some people.

[Ryan Sickler]

I forgot about these.

[Annie Letterman]

They roll.

[Ryan Sickler]

Yeah. Hyper color.

[Annie Letterman]

They rolled. We probably all got childhood cancer from them. What the hell is going on?

[Ryan Sickler]

Why is everybody dying in their 50s if you fart in them?

[Annie Letterman]

And I lived in Umbros. I lived in umbros, too.

[Ryan Sickler]

Umbros.

[Annie Letterman]

I was such a tomboy.

[Ryan Sickler]

Umbros. We used to wear two pair at a time so you could pull them lower before they made the longer ones. You ever had to do, you being.

[Annie Letterman]

10 years older than me. So funny because you were in high school when I was a kid doing all this. Did you.

[Ryan Sickler]

What?

[Annie Letterman]

You must have worn belly shirts. Remember the mesh? Like football jerseys that were cut.

[Ryan Sickler]

I still wear them. Annie Letterman.

[Annie Letterman]

You wear them just around home.

[Ryan Sickler]

No. Yeah, yeah, yeah.

[Annie Letterman]

Boys wore belly shirts like a motherfucker.

[Ryan Sickler]

Okay, so this is. This is so white trash. God, you're giving me good memories. So we used to our family vacation mostly again. Everyone was dead and gone by the time I'm 16. So what we got before that was. We did like Disneyland or World. Excuse me? Twice. My dad worked for the airline, so we could fly free. So we just went and did that twice. But anything else, probably you're familiar with it. We would just go to Ocean City.

[Annie Letterman]

Yeah. Go to shore.

[Ryan Sickler]

That was. Pack up the family. It's nothing like it is here. People don't appreciate the beach as much out here. It's a day trip here. Back there, it's like. No, that's where we're going for a week.

[Annie Letterman]

And it's brown.

[Ryan Sickler]

And it's.

[Annie Letterman]

Yeah, it's brown.

[Ryan Sickler]

Yeah. It's a shit show. It's a carnival at the boardwalk.

[Annie Letterman]

Yeah. No, we were. But Jersey.

[Ryan Sickler]

Our big prize every year was that we were all allowed to get a T shirt. And it was an iron on.

[Annie Letterman]

Oh, yeah, yeah, yeah, yeah.

[Ryan Sickler]

Memory pressing.

[Annie Letterman]

You'd smell it, and would you do the family? Like, everyone would get the same one or. That's what we did. We would always like to. The boys would do the same ones, and then the girls would do the same ones.

[Ryan Sickler]

And I remember. I don't even know why my mom. Let me get this. This must have been middle school. It had to be, because I'm wearing a half shirt. It definitely wasn't high school. And it was Moosehead beer. It was a goddamn moose head beer, black half shirt, and just a child rolling around with that on.

[Annie Letterman]

Well, it's like the parents that put their kids in Hooters onesies. You're like, okay, I'm not. I'm not against this, but your kid will go to prison.

[Ryan Sickler]

So tell me about the youth retreats.

[Annie Letterman]

Out of that school. It was. I don't know how that ended up happening. It might have been through a Quaker meeting, but. Oh. What I was going to say is, on Wednesdays, they would make the whole school go to have a quicker meeting, which was torture. We all had ADD. It's 45 minutes of sitting in silence.

[Ryan Sickler]

Oh, silence.

[Annie Letterman]

And the whole school would be there, and you're all like. I used to have to, like, bring, like, a watch that would beep, and if I sat on it, you couldn't hear it. So I'd be, like, looking at it like, all right, when's it gonna go off? Okay. Like, I had have little tricks and stuff, because I'd lose my mind. But I would stand up every time Max said that. I was always. He said. He was like, you had good ones, too, because you were trying to get like. Like. Applause breaks.

[Ryan Sickler]

The ones you got up to say.

[Annie Letterman]

Yeah, I stood up once, and I was like. I was like. And you're. Everyone's quiet. And then. But you, like. So you'll fake out, like. Because the benches were creaky. So sometimes you go to. And you're like, I'm not ready. And then so people kind of look at you, and you're like, no, I wasn't doing anything. And they're like, okay, all right. Sometimes I think about, like, the kids in Somalia, like, not being able to Eat and I wish I could share my food with them. And Max would be like, you would have like teachers, they can't clap. They can't really clap. But teachers would be like. He's like, you were so full of. Yeah, I'd always be like. I'd hear like a keyword and I'd be like, what can make me sound? And my dad's by the way, like this. Like, my dad will call me with like great advice he gave someone. Like, my dad would be like, I got a good one, you know, so it's like my dad like, oh, I really impressed a crowd with this one.

[Ryan Sickler]

That's your origin story.

[Annie Letterman]

Oh my God. But so then the Quaker youth retreats, it was called Middle School Friends. This is the first one I went to.

[Ryan Sickler]

And are these like lock ins and stuff like that?

[Annie Letterman]

Like there was a center in. I think it was called Haddonfield.

[Ryan Sickler]

Quaker.

[Annie Letterman]

Quaker. Here we go. Oh yeah, we smoke cigarettes out here. We used to smoke cigs right out here. There was like a smoke bucket and it would be like, who was hot? We were wearing Janko jeans and I was like, hey, and this.

[Ryan Sickler]

Is this a sleepover?

[Annie Letterman]

Are you going to sleep over? Yeah, it would be a weekend. And then they had FPS friendly presences, which were just parents that would come. Like be like the chaperones. And you would bring your own suit, your own sleeping bag and stuff. But you know, you have your crushes and we're all had piercings and jankos and.

[Ryan Sickler]

And so what are you doing here? Like, what is the thought to what we did?

[Annie Letterman]

Songs like, we sang like folk songs, like Jody Joni Mitchell songs. And then we'd sing like. And then we'd. We'd have Meeting for worship and we would have. What the did we do on these things? I honestly don't know what we did. We like cooked for each other.

[Ryan Sickler]

Are you like learning life skills here.

[Annie Letterman]

And it's just hanging out? It was just. I was literally just me trying to like hook up.

[Ryan Sickler]

But it was something you had to do for the school though, right? Or is this optional?

[Annie Letterman]

This was just like youth, kids getting together. I don't know that we did anything. I honestly cannot remember us doing anything. I. I mean, I'm just blackout. Because I was just there for this, like to meet other people my age. And I was like, bad. So I would like corrupt people.

[Ryan Sickler]

We went. It's called Camp Hoshawa. It's in Maryland. This is it, Camp Hashua. So when we were in middle school, seventh grade, this was an Outdoor school, they called it. And they sent us. This is why I'm asking. They sent us here for a week.

[Annie Letterman]

School went, oh, that's fun. But everyone went out.

[Ryan Sickler]

It was warm weather, for sure.

[Annie Letterman]

Probably toward the end, it was still like your class, 100%.

[Ryan Sickler]

This was a week. Oh, we had Peak.

[Annie Letterman]

We went to a place called Peak.

[Ryan Sickler]

Yeah. So that was like learning how to environmental crafts. And they taught us how to build a fort. And it was kind of Boy Scouty. Girl Scouty is a little bit. I feel like they showed us how to make fire.

[Annie Letterman]

And PEAK was like an acronym for something. It might have been. Oh, but it was something. Yeah. We were going. I remember my friend Mark Burton, who was my birthday twin, who was a very short black kid. He. I remember we. We, like, went into the. There was a waterfall. We hiked down to it. And he, like, went. And he started getting sucked, and we.

[Ryan Sickler]

Had to save him. Like a whirlpool.

[Annie Letterman]

I was like, mark, he was getting sucked, and he was so little. I was like, mark, what the hell? Did you try to save him? And we used to go to Ringing Rocks was the place we went to.

[Ryan Sickler]

And that's in Pennsylvania.

[Annie Letterman]

Yeah, it's a hike. And then you would be on these, like, all these rocks, and you could throw rocks, and they'd all ring. You throw a rock at the rocks and they'd ring everywhere. Yeah. But, yeah, we had all these things. And then I ended up going to. I also went to a Quaker camp called Camp Onus.

[Ryan Sickler]

How you spell it?

[Annie Letterman]

O, N, O, N A S, O, N A, S, A, N, U, S. Can you imagine? Anus. But I did one of my. My young friends. Young Friends was like the high school version of middle school Friends.

[Ryan Sickler]

Okay.

[Annie Letterman]

So Young friends had a retreat at my camp at Camp Onus, too.

[Ryan Sickler]

I see.

[Annie Letterman]

That I almost got kicked out of because they said I was having lesbian experiences. But it's just. I just make noises in my sleep. And I fell asleep in my friend's bunk, and they try to be like.

[Ryan Sickler]

What noises are you making?

[Annie Letterman]

Because you're not allowed to, like, hook up at the youth retreats. But it's like, is this it?

[Ryan Sickler]

Onus a home?

[Annie Letterman]

Look at it.

[Ryan Sickler]

Without walls. Or having lesbian.

[Annie Letterman]

But it wasn't the camp. This was when I was with my Quaker at the camp. This. The camp was crazy. The camp was really wild.

[Ryan Sickler]

Yeah. See, I just saw that Camp H looks like it's YMCA now. It was not that when we went. This was just this. They called it outdoor school.

[Annie Letterman]

Driving into my Canyon. I remember the drive like being soaked. It was like the most exciting experience of my life. Like was probably like an hour or two drive from our house and just the panic and joy and excitement of going to sleep over camp. Cuz you could go for two weeks.

[Ryan Sickler]

Or four weeks and what would you do?

[Annie Letterman]

When we were little we did. Cuz we started when we were like nine. So we would go for two weeks when we were really little and my parents really did not care if we got diddled. They were like, they'll be fine.

[Ryan Sickler]

Shut up.

[Annie Letterman]

I mean we were gone. They had us out. I'm like eight. I'm like, where's my mom? But where's mom?

[Ryan Sickler]

There it is. Look at the little.

[Annie Letterman]

How cute. But we see the sign. I'd be like panicking. All right, we found it. Here's middle school Friends.

[Ryan Sickler]

Here it is. The goal of the program is supporting the spiritual growth of young Quakers who are in that peculiar, peculiar and wonderful stage of life commonly known as middle school. It's hoped that by participating in the MSF program they'll come away with a better sense of what it means to be a Quaker, establish and maintain meaningful relationship with other Quakers their age and develop a sense of possibility for what being Quaker Quaker could mean for them in their lives today.

[Annie Letterman]

So we have no answers. So we have no answers. We have no clue what this. But I will say that does sound like they're molesting us. And they weren't. They were very. It was actually very.

[Ryan Sickler]

Okay, good.

[Annie Letterman]

It was a lovely thing. But we ended up doing youth Youthquake, which was they took all of the high school youth group, Quaker youth groups from all over the United States. And we all met together in North Carolina at like a college in the dorms. And I snuck the fuck out of that. I almost got kicked out for sneaking out.

[Ryan Sickler]

For what?

[Annie Letterman]

Boys, smoking, hooking up with guys. I had just got my nipples pierced. I was like, how old are you? I was 14.

[Ryan Sickler]

And we got your nipples pierced at 14. That's four years from my daughter's age. I'm already getting back.

[Annie Letterman]

But they're different. They're different. How did the kids these days are children.

[Ryan Sickler]

Yeah.

[Annie Letterman]

Don't you think?

[Ryan Sickler]

Yeah. A lot of them are turning against.

[Annie Letterman]

The Internet like the littlest, cutest little thing. She's 12. She's so cute.

[Ryan Sickler]

What? I mean, where do you go to get your nipples pierced at 14?

[Annie Letterman]

Who's South Street Tattoo? This woman suit. Why don't you look up Sue South Street Tattoo and see if they have A picture of her south street tattoo has been out of business for years, probably for piercing children's nipples.

[Ryan Sickler]

Children's.

[Annie Letterman]

It's my sex organ too. It's like a.

[Ryan Sickler]

Well, yeah, that's what I'm saying.

[Annie Letterman]

But she was this big fat lady, but I'm assuming.

[Ryan Sickler]

Is there a curtain around you or your tits? Just.

[Annie Letterman]

We just had a fake. We just said that.

[Ryan Sickler]

Yeah, but I mean your 14 year old tits are.

[Annie Letterman]

No, I think it was just her. Maybe my friend was there.

[Ryan Sickler]

14. What made you want to do that? Was it a trend? Was it happening in school?

[Annie Letterman]

Like, a friend of mine, A friend of mine and I, we both had small boobs and we're like, oh, we'll just go get our nipples pierced and it'll be like, cool. We went and got our nipples pierced at 14, but right before she put the needle and she went, she's dropped it. She went, butterfingers. I was like, what the hell?

[Ryan Sickler]

Dirty ass needle fingers. You're kidding.

[Annie Letterman]

I was like, you better not have butterfingers when my dad finds out. And then you're gonna chase.

[Ryan Sickler]

That's a great question. How do hide that? I see that through a shirt.

[Annie Letterman]

My parents deserved it. I was like, you. I have my nipples pierced. I smoke, I do drugs. Like, I just would like throw it at them and fight.

[Ryan Sickler]

Did you have. Did you do belly piercing?

[Annie Letterman]

I. Well, my mom took me to get my belly button pierced.

[Ryan Sickler]

Tongue.

[Annie Letterman]

Did you have tongue? She said she would kick me out of the house if I get my tongue pierced.

[Ryan Sickler]

Did you ever want to do it, though? That's painful. You did.

[Annie Letterman]

But I'm glad I didn't. I would be. I have broken teeth and.

[Ryan Sickler]

Yeah, that should have hurt it. Look, it always. I. I couldn't stand the kid that would talk always rolling and I'm like, get the fucking thing out of my face right now.

[Annie Letterman]

I thought. I. I mean, I'm glad that was.

[Ryan Sickler]

It's.

[Annie Letterman]

The thing is, every time my mom told me not to do something, I listened to her and I look back fondly. But that was only. It was that time. And there was one time where I was hanging out with these like whiter white trash kids. Like the whitest white trash. Like really, really white trash. You know, where they're so white trash that they're kind of dirty.

[Ryan Sickler]

Yeah, for sure.

[Annie Letterman]

Yeah.

[Ryan Sickler]

You're like, are you got a dirt beard? I know those kids.

[Annie Letterman]

Yeah. And my twin brother was like, annie's hanging out with like the bad kids at Pember and the, the. Because we were like, bull Kids that looked like it. That pool. Yeah, but I was. My mom, like, came and she was like, get out. And I was wearing like little slutty shorts. Hanging out with those losers. I definitely would have like a. Would have been a teen mom and.

[Ryan Sickler]

What are you doing there? Smoke.

[Annie Letterman]

Oh, we were smoking or drinking and Max told on me. And then she, like, came. She embarrassed me in front of all of them. I don't remember any of their names. I never saw them again.

[Ryan Sickler]

So she showed up. It was good. Called you out in front of everybody.

[Annie Letterman]

Yeah. And it was like, great. But my mom was so afraid I would, like, stop liking her. Look up. Glen side pool was our pool. This is our glen. That was our pool. This is where you guys are safe there. Dude, that was my spot. That was my spot. Okay. The pay phone was over by the red thing. That's where we used to call the jerky boys. We'd call the jerky boys over there on the. And we call Hooked on Phonics. We just.

[Ryan Sickler]

With the phone, you would.

[Annie Letterman]

Yeah, anything that was like an. An 800 number.

[Ryan Sickler]

Was the plastic slide there back then or is that like an update that was like.

[Annie Letterman]

Came a little bit after me, but. Diving board and. And we had our swim practice there. Yeah, boy. And then the library was like right down the street. I like to the library. I would go and read the magazines because I didn't like to read books.

[Ryan Sickler]

Can you get into. I didn't either. I was the same way.

[Annie Letterman]

I just. I read a book recently and I was like, this is crazy.

[Ryan Sickler]

This is overrated.

[Annie Letterman]

I read a book that's good for.

[Ryan Sickler]

An ADD person because I used to do like where I'd read a half a page and I'd snap back and I'm like, oh, my God.

[Annie Letterman]

Yeah. But here's the thing. I read the Alchemist, which is a quick read and it's good and it felt right, really aligned with things I wanted to hear. So then I was like, I'm a reader. And then every read I've book I've tried to read afterwards, I'm like, I'm so bored. I'm so miserable.

[Ryan Sickler]

I used to read a lot. I stopped. You said you snuck out of there. Did you ever sneak out of the house?

[Annie Letterman]

Yeah.

[Ryan Sickler]

What you do? Where were you going?

[Annie Letterman]

Max and I, when we were little, would sneak out.

[Ryan Sickler]

All right, tell me. Well, how you would.

[Annie Letterman]

His friend Nick lived in Glenside and we lived in Wincote. And it was probably like a 15, 20 minute walk. So Max and I, we would dress this Is when we were like. Yeah, this was before. We were, like, really bad. But Nick's mom was this woman who was like. She was like a young mom. She was always 29. Every year she was 29, she kept turning 29 again. But she really liked us as her friends, which was very weird. But. So his mom was like my friend. I was like nine, and I. And she would bring. Get us, like, coffee drinks and stuff, and she smoked, and it was weird. But my mom was like, anyone that would take her kids. And so we hung out with them a lot. And we knew his parents wouldn't care if we, like, snuck out. The only reason they would care is if my mom got mad at them for finding out, you know, so they never cared if we didn't get caught. But. So Max and I would put on all black and we would sneak out of the house with flashlights at nine. We were like, maybe like, middle school, maybe 10, 12 still.

[Ryan Sickler]

Yeah, it's like fifth, sixth grade.

[Annie Letterman]

And it was, like, fun. And we'd, like. Someone would. We'd see a car and we would, like, jump into the bushes. And we weren't doing anything bad. We just were sneaking out. And then we would go, but we would also, like, hide. We would, like. We had binoculars. We look in the neighbors. There was like, an old man. We were always trying to catch the old man doing something, but he did nothing but old man stuff. And we were just nosy. We're just like, what's up with people? And. And then I started sneaking out. When I was older, I had a friend who was. All my friends in midd school got diagnosed with, like, bipolar. And they all went to, like. We all went to bad kid schools. But I actually wasn't that bad. My parents just very stupidly sent me to a bad kid school before I was even bad.

[Ryan Sickler]

That's where you learned to be bad.

[Annie Letterman]

I mean, well, what else was I gonna do?

[Ryan Sickler]

Are you sneaking out? They have cars and stuff then in high school.

[Annie Letterman]

Yeah, boys. That where you had cars? We would go to the Roosevelt Mall, and we would go to the Roosevelt Mall and we would meet dudes.

[Ryan Sickler]

Did you ever get caught sneaking back in?

[Annie Letterman]

Yeah, my friend Mickey's parents found us and. But we still got back in because we were, like, good. Like, we actually. It's almost like we were smart kids. We just used it towards evil. So we snuck out. We met these guys at the Roosevelt Mall. We got their pager numbers. Like, look at this trash mall. And it's like an outdoor mall. We're like such strip mall, just dressed like sluts. Like, we shopped at like Charlotte Russe and all the. And Deb, like all these sluts and we're like stealing like four dollar shorts. We're stealing from rainbow. And they didn't have a rainbow at the time, but I learned of rainbow later. But anyway, so we would meet guys. There's Deb.

[Ryan Sickler]

There it is. Great, Great job.

[Annie Letterman]

We had like our acrylic nails. We're just like 14 year olds with like acrylic nails. My crusty hair. Just like crust, crunchy hair. Just the Aussie scrunch spray and just flat bangs and big hoops. And we'd meet like these guys and they'd have like weapon. We were like, oh my God, you have weapons. So cool. We get their pager numbers, then we go home. We'd page them. Then we would call the movie line hotline where you could hear all the movie show times, movie phone. And then it would go to like call waiting rather than ring in the house. So then you could pick up and be talking to like boys all night. So we met these guys. This is gonna. This is a crossover. This is a crossover to Honeydew. Let's just say that I have to tell you, I make fun of you for Honeydew sometimes where I'm like, you go on. And you're like, well, yeah. And then I was gang raped. And then you're like, speaking of gang raping. Get gang raped on a purple mattress.

[Ryan Sickler]

Do you know who does that?

[Annie Letterman]

I know. You have to like. You have to like.

[Ryan Sickler]

Can I tell you?

[Annie Letterman]

You have to pop in with a sponsor in the middle of this. It's so funny.

[Ryan Sickler]

It's Annie, our producer. Annie does that. He works with Tom and those guys down at ymh. And I said to him one time, I go, why are you doing that? Why are you dropping. He goes. I go, people complain like someone's in the middle of like their death story and you drop at. He goes, they heard it though, didn't they?

[Annie Letterman]

Speaking of death, would you like an ego death? Grow your own mushrooms.

[Ryan Sickler]

He does that. That's 100. If he's got like a gambler or something, we got draft kings.

[Annie Letterman]

He'll drop it right Left us. He spent all of my tuition on.

[Ryan Sickler]

I love the best thing that you make fun of me. Yeah.

[Annie Letterman]

No, I would never do behind the back. It's funny.

[Ryan Sickler]

Oh, you can say. Always say it in my face.

[Annie Letterman]

But so, okay, so we stop. So we would meet these boys. We call, they call us back. So then they, like, snuck. They would.

[Ryan Sickler]

So wait real quick just to explain to even people that don't get it. You've. We've got call waiting now.

[Annie Letterman]

Now we have call waiting.

[Ryan Sickler]

Call movies. When they call you back from ringing out loud and disturbing the house, you're hearing the beep on the phone. You're clicking over. Now we got our call in stealth.

[Annie Letterman]

Parents think you're asleep.

[Ryan Sickler]

Great.

[Annie Letterman]

But you're smoking out the window. So I'm playing with your nipple rings. But.

[Ryan Sickler]

So, yeah, you got nipple rings. I forget.

[Annie Letterman]

So the guys. It was easier to sneak out of Mickey's house. So I would go to my friend's house, and then the guys would, like, pick us up, and we would either, like. I guess her dad would sleep on the couch. There was like, they kind of knew we were gonna sneak out, so they were always trying to. And they were very Christian, that family. But we would, like. I think we snuck out there. Yeah. We threw our shoes down, and then we would climb down the tree, out the window, and down the window and down the tree. And then when we came back, this is what it was when we got dropped back off after going into. So these gu. Drove us into the city to a house, and we all went through the window. We're like, why are we going through the window of the house? And like, we don't live here. We were just broke into someone's house.

[Ryan Sickler]

And what did you party in there? You robbed?

[Annie Letterman]

They had a pool. We were in the pool. We were. No, we didn't rob. Honestly, there was no robbing.

[Ryan Sickler]

Really sweet.

[Annie Letterman]

But they did all go to prison, and my guy was wanted for homicide. Mine was wanted for homicide. They picked us up from the wrong house once they went into the wrong house, and they got picked up for burglary for the house that they thought was the house we were in. So then they went to jail. It was like a whole thing.

[Ryan Sickler]

These guys come to see you guys.

[Annie Letterman]

And go to them, and we lied about our age. We said we were 16, which they were still like, 23 or something. But we're like, this is so cool. These guys are so cool. They think we're cool, but. So then we go like, we're going to the. Into the pool, hopping, and they're giving us, like. You know, the thing is, it all was, like, a cute transition because we were just like, well, they killed someone. They deserved it. We're just lucky we didn't die. But so it was just. It would just be like, me and Max and like, neighborhood kids. Like, just breaking into our local pool and, like, jumping in the mix, hope we don't get caught. And, like, running back home, no drugs, no drinking to, like. Like, the adult version of it, where it's like grown men are just taking us to pools. But very luckily, never got, like, assaulted by any of them or anything. But because they got. The second time, they're picking us. They got arrested, but so I guess that was the end.

[Ryan Sickler]

You got their number.

[Annie Letterman]

Oh. So we go back to the house. We go back to. To my friend's house, and her dad has obviously realized we're not in the house. So he's sleeping on the. We realize the door is locked and he's sleeping on the couch. So we're like. And they had locked the window. So we climb up and the window's locked. I'm like. But we see the key, the front door key. So we slide the window up, like, this much, and we. I don't know how we did it. We had got a twig or something, and we got the key, and we got to open the door, sneak by her dad and go into bed. And the parents were like, we. We know you weren't here, but we were trying to be like you. Just. We must have been in the bathroom or something when you came up. So then we weren't allowed to see each other again. We were done seeing each other after that.

[Ryan Sickler]

That was the end.

[Annie Letterman]

We got in trouble. We got in trouble. Yeah. But it was always funny because they always thought I was the bad influence, but I was like, I don't think I'm the bad influence, but maybe I was. I was just down for whatever.

[Ryan Sickler]

I was like, okay, tell me about. So I asked you before we started recording, you played sports, and you said you were on the boys. We had a girl. I want to say her name was Angie. I forget. It might have been Angela.

[Annie Letterman]

Was she hot?

[Ryan Sickler]

No. This was.

[Annie Letterman]

Yeah.

[Ryan Sickler]

This was Little League. No, she was not.

[Annie Letterman]

Yeah, but you have, like a. It wasn't like a.

[Ryan Sickler]

No, she was just.

[Annie Letterman]

She was in it for the sport.

[Ryan Sickler]

There was no. I mean, there had to be softball at the point, but she wanted to play baseball. And this is. This has gotta be.

[Annie Letterman]

It is a different sport than softball.

[Ryan Sickler]

This is early 80s. That's how long ago it was. And she definitely played with us, but she was the easy out. You know what I mean? She wasn't good. Her dad just wanted. She wanted to play baseball. And her dad did the right thing. He's like, well, then you're gonna fucking play baseball. And she did.

[Annie Letterman]

Yeah.

[Ryan Sickler]

I was batted ninth, played right field. You know what I'm saying?

[Annie Letterman]

Yeah. Look, I wasn't focused. I was in it. I just wanted to hang out with boys. I was just boy crazy.

[Ryan Sickler]

So did you ask for this or did your parents ask? Listen, I just want to say out of respect for tw. Whatever sport I was playing, my brother had to play and vice versa because my parents were like, we're not taking you to football and you to soccer.

[Annie Letterman]

Well, I wanted to, like, be on the same team as my brother and stuff. And I didn't like softball. My mom raised me to kind of like, not have girlfriends and not really like. Like girls that much. My mom was very like, I wish I was a boy. Like, my mom would have been transfer attention. Like, for sure, for sure. Look at her.

[Ryan Sickler]

Look at this.

[Annie Letterman]

Isn't that cute? Look at this family.

[Ryan Sickler]

That's a cute little.

[Annie Letterman]

Look at these schnozes. My older brother got a nose job since. And Max kind of grew into his nose. And then I was pretty cute.

[Ryan Sickler]

You are cute, Annie. How do you know how old you are there high school here? Yeah, I was gonna say you look like high school.

[Annie Letterman]

That's 14 at. Yeah.

[Ryan Sickler]

Your mom doesn't look old either. How old was she when she had.

[Annie Letterman]

She was 32 or something. My mom was probably. Probably my. Honestly, no. She was a little older than me in this.

[Ryan Sickler]

Isn't that great?

[Annie Letterman]

It's crazy. Well, I'm just like, if I have kids, I'm literally gonna be elderly. It's crazy.

[Ryan Sickler]

But you're not gonna look. I. Whenever I go do shows in balt. A bunch of married ladies that'll come out and say hi to me and see me from high school, and they all cross the board, look fantastic. My hairdresser is like. It's a lot of the hair these days, Ryan. I'm like, whatever it is, hair is.

[Annie Letterman]

One not even getting Botoxes up. But skin care people, like, are, like, going to bed and my mom's day.

[Ryan Sickler]

The ladies cut their hair short. I called it the. I give up.

[Annie Letterman]

This is the longest my mom's hair was. No, she had a boy haircut forever.

[Ryan Sickler]

I'm just saying you don't. 40 years.

[Annie Letterman]

Can you look at the modeling picture with man Max? Yes, we did a little modeling picture together, but Max was ugly.

[Ryan Sickler]

You look a little. Shut up.

[Annie Letterman]

He was a little.

[Ryan Sickler]

Who'd you used to get? Is it Scarlett? No. I guess she wasn't around back then, though, was she?

[Annie Letterman]

I didn't look like. Oh, you Know who I got when I was young? Hanson. I looked like the handsome brothers. I looked exactly like the handsome brothers. Crazy.

[Ryan Sickler]

The bop kids.

[Annie Letterman]

Oh, wait, this is me at my. At the. Oh, look at little kid at my Quaker camp.

[Ryan Sickler]

That's at the Quaker camp where he.

[Annie Letterman]

Was a little w. I was.

[Ryan Sickler]

This is like two years away from pierced nipples right here.

[Annie Letterman]

Oh, I already had him pierced.

[Ryan Sickler]

No.

[Annie Letterman]

Yeah, in this picture. Yeah.

[Ryan Sickler]

That is crazy. That girl looks so little.

[Annie Letterman]

Yeah, no, it's 14. This was the same girl that was sneaking into the. This was the age is the.

[Ryan Sickler]

This is the girl got the boys arrested.

[Annie Letterman]

No, the boys were one of the.

[Ryan Sickler]

Murderer got them arrested. You're right.

[Annie Letterman]

No, they were 23 year olds hanging out with quote unquote, 16 year olds. Yeah.

[Ryan Sickler]

Oh, Annie Letterman, I love you. Thank you for doing this. This is fun right there. Again, one more time. Promote your dates. Your.

[Annie Letterman]

Your power in 2026.

[Ryan Sickler]

In 2026. And where are all your dates?

[Annie Letterman]

Oh, they're@annie letterman.com shows just come. It's fun. There's a Boston. It's gonna. Everything's fun.

[Ryan Sickler]

Check out the podcast.

[Annie Letterman]

Podcast.

[Ryan Sickler]

Any live shows at the comments.

[Annie Letterman]

Live shows at the Comedy Store all the time.

[Ryan Sickler]

I did one. It was a lot of fun. Thank you.

[Annie Letterman]

The first one was very honored. When he rose it.

[Ryan Sickler]

It was the first one. I would love it. I'd love to do it.

[Annie Letterman]

And then we're booked, but. Oh, I'm sorry. We're booked. Oh, babe, we're booked. We're booked till the. We're booked till 2:26.

[Ryan Sickler]

All right, good.

[Annie Letterman]

But then. And then. Yeah, just Instagram is kind of my. So let's go, baby.

[Ryan Sickler]

Thank you, Annie. Let him.

[Annie Letterman]

This is so fun.

[Ryan Sickler]

Thank you guys as well. Come see me on tour. All tickets are on my website@ryan sickler.com. we' talk to y'all next week.