Tig Notaro and Caitlin Reilly

Summary

Wrong Turns with Jameela Jamil

Episode: Tig Notaro and Caitlin Reilly

Release Date: July 9, 2026
Guests: Tig Notaro, Caitlin Reilly
Host: Jameela Jamil

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Episode Overview

This episode of Wrong Turns is a masterclass in comedic vulnerability, mortification, and the camaraderie that comes from sharing your most cringe-worthy “wrong turns.” Host Jameela Jamil welcomes acclaimed comedian Tig Notaro and internet sensation Caitlin Reilly to unpack their most embarrassing disasters, both minor and major. The theme? "Where dignity goes to die"—no morals, no neat silver linings, just the giddy recognition that everyone’s life is a rolling disaster sometimes.

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Key Discussion Points and Insights

1. Opening Banter & Setting the Scene

(01:13 – 05:07)

• Jameela introduces Tig and Caitlin, recapping their many comedic credentials.
• The trio riffs on party stress, introvert vs. extrovert energy, and the peculiar intensity of milestone social events within queer Hollywood.
• Tig confesses she’s not much of a party person, preferring tidy closures to messy gatherings.
  • “I like a one-on-one dinner or a group of friends…But a party always sounds fun and then…” (03:55, Tig Notaro)

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2. How They Process Disasters

(05:07 – 13:19)

• Jameela probes: Do they lean into disastrous moments or recoil?
  • Caitlin admits she uses humor to process pain but ends up with “unprocessed trauma and grief" (05:24), joking:
    • “I’ll laugh about it and then I’ll get a kidney stone.” (05:42, Caitlin Riley)
• Tig describes her current “fuck off tear” season, a period of returning to unresolved grievances for clarity and closure.
  • “I have noticed…that I make things okay in the moment, I walk away, and it takes me a beat to process, and then I have to go back to clear the space.” (06:10, Tig Notaro)
• The group riffs on conflict resolution—Caitlin’s freezer jars of “names” (from TikTok) for people who’ve wronged her, to “ice them out” symbolically.
• Jameela: “I’m a straight in the moment person. The second the tone changes, I’m like, ‘Hey, why did the tone just change?’”(10:32)

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3. Professional & Personal Ghostings

(13:19 – 16:34)

• Caitlin details getting professionally ghosted after confronting someone about repeated cancellations; the pain of never getting closure is palpable.
  • “I confronted this person…in a very respectful, adult, professional, kind way. And that person never responded to my text. It has now been two months and I’m losing my fucking mind.” (12:18, Caitlin Riley)
• Jameela and Caitlin bond over the agony of sending vulnerable texts and being ignored.

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4. Sibling Struggles and Apologies

(16:34 – 18:19)

• Caitlin discusses crying during family arguments, being the “baby” sister, and apologizing excessively—especially when the fight is with those closest to her.
• The trio jokes about familial hierarchies and fraught adult sibling relationships.

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5. Micro-Humiliations: The Everyday Disasters

(18:19 – 28:44)

Tig’s Story: The Shirt of Shame

(18:34 – 21:55)

• Young Tig, newly arrived in LA, is pursued by a closeted but curious comedian. When the woman loses interest, Tig pathetically (in hindsight) dons a “cute” shirt to try to win her back—only to be received on the porch, not let inside, and left cringing for years.
  • “I was so mad at that shirt for so long. I was like, God, what did I do?” (21:23, Tig Notaro)

Caitlin’s Story: Mother-Daughter Catastrophe

(23:14 – 28:44)

• Caitlin is strong-armed into emceeing her high school’s mother-daughter luncheon—at the all-girls Catholic school she loathed.
• She’s asked to “just do 30 minutes of stand-up,” despite not being a stand-up, leading to a mortifying set before unenthused moms, one of whom interrupts:
  • “Who are you? What do you do?” (27:06, mother in audience)
• “It was a humiliation ritual at my high school that I didn’t ask for.” (28:26, Caitlin Riley)

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6. Major “Wrong Turns”

(31:08 – 55:28)

Tig’s Wrong Turn: The Sundance Saga

(31:20 – 40:14)

• Early-career Tig volunteers at Sundance Film Festival alongside a competitive comic friend. Through a series of lucky breaks, she gets better jobs and a hotel room while her friend gets bunk beds.
• After a brief, lackluster romance with another volunteer, Tig finds herself ensnared in a web of drunken advances and hotel room drama, thanks to her “friend” setting her up.
  • “She is on her knees next to my bed saying, ‘Will you make out with me?’ in the darkness…I was so embarrassed. This was nearly 30 years ago.” (37:49, Tig Notaro)
• Jameela hails the story as a perfect buddy comedy movie setup.

Caitlin’s Wrong Turn: The Hot Tub Horror

(42:22 – 53:47)

• High school Caitlin falls madly in love with a senior boy, endures an AIM breakup (the transcript printed and later stolen from her locker), and years later, is courted again—but disaster looms.
• She hosts him at her parent’s hot tub. Bliss turns to horror when, unbeknownst to her, she gets her period on a white towel in front of him and friends.
  • “There is this massive red spot in the middle. It looks like the flag of Japan.” (52:49, Caitlin Riley)
• The boy makes a quick, silent exit; they never speak again.
• The trio riffs on the mortification, the universality of period embarrassments, and how the pain recedes (mostly) with time.

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Notable Quotes & Memorable Moments

• Jameela: “This podcast is about disaster. It is unifying, as we have just expressed how unifying themes of discomfort can be.” (18:14)
• Tig: “I am running a list of like—not enemies—but just like, hey, I need to revisit this.” (06:34)
• Caitlin (about her teenage crush): “I was in love with him, I was in love with him, I was in love with him.” (43:48)
• Jameela (post-handler): “It was very cleansing for me to be able to tell anyone that story about me and this actress…I’ll tell you who it is after the show.” (17:48)
• Caitlin (toward the hot tub disaster): “All the blood in my body had just exited me onto this towel in a perfect circle.” (52:49)
• Jameela (on period shame): “You could literally shake one [tampon] at boys and they’d like, run away screaming.” (54:05)

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Timestamps for Key Segments

• Opening banter, intros, party chat: 01:13 – 05:07
• Disaster-processing styles, “fuck off tear,” freezer jar ritual: 05:07 – 13:19
• Ghostings and conflict, professional/emotional boundaries: 13:19 – 16:34
• Sibling dynamics and apology overload: 16:34 – 18:19
• Micro humiliations (Tig’s shirt, Caitlin’s standup ordeal): 18:19 – 28:44
• Major wrong turns (Sundance saga, hot tub horror): 31:08 – 55:28
• Takeaways and outro: 55:28 – End

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Tone & Atmosphere

• Warm, loose, and confessional: The vibe is that of three friends cackling at each other’s mortifications while gently affirming survival.
• Vulnerability meets dry wit: Emotions are real, but the humor is even realer. Often self-deprecating, the stories are told with an edge of theatrical agony.
• No room for platitudes: As promised, there are no “lessons”—just collective catharsis.

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Where to Find the Guests

• Caitlin Riley: Instagram: @hicaitlinriley, appearing on Hacks (Season 5)
  • “Are you directing all of this to the woman in the crowd at your school?” – Jameela, 56:15
• Tig Notaro: On tour (tignotaro.com), podcast Handsome (also on Hulu)
  • Tig: “Too many people want me.” (56:40)

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Final Thoughts

This episode is a comedic exorcism: mortification provided in service of communal laughter and relief. If you’ve ever cringed at your own desperate pursuit, been ghosted by a friend, or bled through a teen romance, you’ll find kinship here. As always, the take-home message is clear: The more embarrassing, the funnier—and the less alone we all feel.

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End of Summary

Transcript

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[Jameela Jamil]

How's everything?

[Tig Notaro]

How is everything? Yeah, I mean we can't get into everything, but I'm. I'm here, I'm breathing, I'm gay and plant based still.

[Jameela Jamil]

Hello and welcome to Wrong Turns with Jameela Jamils. The podcast where dignity goes to die. Where I bring on my favourite funny people and they tell me tales of woe that make me feel less alone in my own deeply mortifying life. I have with me today two of my favorite women, my favorite humans in the world. I have Emmy, Grammy and Oscar nominated writer, actor, producer, comedian from one Mississippi the morning show and her latest comedy special. Hello again. She produced the incredible documentary Come see me in the Good Light and co host the podcast Handsome. It's take Notaro.

[Caitlin Riley]

Jesus Christ. Hello.

[Tig Notaro]

Hello.

[Jameela Jamil]

I love that you slow clapped yourself.

[Tig Notaro]

Oh, I was slow clapping both of you.

[Jameela Jamil]

Iconic. And we also welcome a writer and comedian from shows like Hacks Loot, Dead Boy Detectives and Love la. She's the funniest person on the Internet. She recently appeared on Dropout comedy series Very Important People. It's Caitlin Riley.

[Caitlin Riley]

Hello. Thank you so much.

[Jameela Jamil]

How are you both? What's going on?

[Tig Notaro]

Don't you love doing since Austin?

[Caitlin Riley]

Nothing.

[Tig Notaro]

Yeah, she was our guest at the Live Handsome podcast.

[Caitlin Riley]

That was so much fun.

[Tig Notaro]

It was a good time.

[Caitlin Riley]

You were stressed out.

[Tig Notaro]

Was I?

[Jameela Jamil]

Yeah. You were also stressed the last time I saw you because here we go. It was your birthday party a few years ago. You weren't invited.

[Tig Notaro]

Sorry, I was not invited? No, I didn't know about you yet.

[Caitlin Riley]

No, no, no, no, it's okay. No, it's okay. Like, you don't have to.

[Tig Notaro]

I wish I could go back in time.

[Caitlin Riley]

When? What year was it?

[Tig Notaro]

2022. Oh, okay.

[Caitlin Riley]

So a lot of people knew me then, but you did.

[Tig Notaro]

We crossed paths.

[Caitlin Riley]

It's fine. It's fine.

[Jameela Jamil]

I was the biggest birthday party of anyone I've ever been to. It was like the whole of specifically lesbian Hollywood was there, but also just the funniest people. So many of my faves. I was deeply starstruck the whole time I was in there and changingly fun for me. But every time I saw you, you looked a little like there was just something going on behind the eyes of. Eyes darting around, looking for what? Mess.

[Tig Notaro]

Joy.

[Jameela Jamil]

Yeah, I was.

[Tig Notaro]

Yeah. I. I realized because I. I was having a tough year in 2022, and my wife Stephanie was like, you came through that and you need to just have a massive blowout party. And so I went big and wide.

[Jameela Jamil]

You're not normally a party person?

[Tig Notaro]

No, I'm a little more. I like a one on one dinner or a group of friends and. But a party always sounds fun to bring everybody that you know and love together and then.

[Caitlin Riley]

Except me.

[Tig Notaro]

Except.

[Jameela Jamil]

Well, it was people that she knows and loves. I'll get over it.

[Caitlin Riley]

It's okay. I'll get over it. No, I'm being ridiculous.

[Jameela Jamil]

It wasn't on our radar, Tick. It's not our fault. I'm being ridiculous.

[Caitlin Riley]

That's fine.

[Tig Notaro]

But I. I think there was maybe residual stress. And then also it was hitting me at that party that I don't think I'm a party person. And so. And I had gone so big and so big. And I also love to tidy and consolidate. And Stephanie really teases me when she walks in the kitchen. I'm consolidating things, but I'm just. I'm tidy and I was looking to tidy up and I don't really know

[Jameela Jamil]

how to party, but it's nice to see you here. You seem more relaxed now.

[Tig Notaro]

Good to see you as well. And you.

[Caitlin Riley]

Good to see you.

[Jameela Jamil]

I mean, I know disaster has. Has found you both in its ways. What do you mean? No, nothing, nothing. No, you're already.

[Caitlin Riley]

I don't want to talk about that.

[Jameela Jamil]

And you're perfect. Yeah, exactly.

[Caitlin Riley]

I'm not here to talk about that.

[Jameela Jamil]

Do you lean in immediately to disaster, or does it take you several months to recover when it occurs?

[Caitlin Riley]

Well, I think life Experience makes you funnier.

[Tig Notaro]

I agree.

[Caitlin Riley]

So I'm funnier and funnier by the day, but I don't know, I do a little bit of both. Like, I. Something bad will happen and I'm like, it's fine. It's totally fine. I'll use this. It's all good. I'll use this. And then a year will go by and then I'll have a nervous breakdown. Unprocessed trauma and grief. Got it?

[Jameela Jamil]

Yeah. Yeah. I'll laugh about it and then I'll get a kidney stone.

[Creative Planning Representative]

Right.

[Jameela Jamil]

Come out through that. What about you, Tig?

[Tig Notaro]

Well, I am smack dab in the middle of what I'm calling a fuck off tear. And what is that? Well, I'm realizing when something. Let's say somebody does something.

[Jameela Jamil]

Yeah.

[Tig Notaro]

To me.

[Caitlin Riley]

So you've been wronged.

[Tig Notaro]

Let's say I've been wronged.

[Grow Therapy Advertiser]

Okay.

[Tig Notaro]

I have noticed that it, like, in a series of events, that I make things okay in the moment. I walk away and it takes me a beat to process, and then I have to go back and return to it to clear the space. Sure. And so I am running a list of like.

[Jameela Jamil]

Of enemies.

[Tig Notaro]

Not enemies, those who have. But just like, hey, I need to revisit this.

[Caitlin Riley]

Can I interject? Have you put a jar of names in your freezer?

[Tig Notaro]

I get asked this all the time.

[Sponsor Voice]

Do you really?

[Tig Notaro]

I don't know what you're talking about.

[Caitlin Riley]

Okay. I have about two jars of names in my freezer.

[Jameela Jamil]

Wait, are you serious?

[Caitlin Riley]

Are people who've wronged me?

[Sponsor Voice]

Is this.

[Jameela Jamil]

Wait, is this like, witchcraft?

[Caitlin Riley]

It's. You know what? It's whatever you want to be.

[Tig Notaro]

But I think you should try this. Did you invent this?

[Caitlin Riley]

I saw it on TikTok.

[Tig Notaro]

Oh.

[Caitlin Riley]

I saw it on Tick Tock. And you write down someone's name and on a small piece of paper because

[Jameela Jamil]

you're icing them out.

[Caitlin Riley]

You're icing them out of your life, out of your energy, and you're. You're returning the karma to sender. No, but you're.

[Pura Fragrance Advertiser]

You're.

[Caitlin Riley]

You're righting the wrong karmically.

[Tig Notaro]

Yeah, I'm. I'm not. I'm not necessarily going in to be like, I'm done with you. It's more like I have processed this in the moment. I. I couldn't process it. Now I have. I would like to revisit this.

[Jameela Jamil]

Okay.

[Caitlin Riley]

And so often people are like, it's too late. What are you talking about?

[Tig Notaro]

And that's fine.

[Caitlin Riley]

Okay.

[Tig Notaro]

But if somebody is like, you're honoring yourself. Yeah, I have to. Here's the thing is what I realized is there are some situations where I feel like somebody has dumped garbage on me.

[Caitlin Riley]

Yeah.

[Tig Notaro]

And I've been walking around holding the garbage, and then I was like, this isn't my garbage. And so I have to return it to them and then just, you know, explore what happened.

[Jameela Jamil]

Yeah. You're handing it back. It's like, you've given me this shit. I'm giving it back to you. I don't want to carry it.

[Tig Notaro]

Right. But I also. I'm open to hearing how we miscommunicated and.

[Jameela Jamil]

Why are you doing this?

[Tig Notaro]

Because.

[Sponsor Voice]

Why now?

[Tig Notaro]

I mean, I had a real. I've been having massive breakthroughs in my life recently.

[Caitlin Riley]

It's the year of the Fire Horse.

[Tig Notaro]

Of course.

[Creative Planning Representative]

I don't know. Of course.

[Tig Notaro]

Of course. The Fire Horse. I don't know even, like.

[Caitlin Riley]

Of course.

[Grow Therapy Advertiser]

Naturally. Yes.

[Jameela Jamil]

Talking about TikTok, you are saving your piss in the oven, Right? Of course. What's wrong with that? Just making sure. Okay.

[Tig Notaro]

I just. I realized I was having my brain occupy. There was too much occupying my brain with things such as, like, I.

[Jameela Jamil]

This feels like a Coen Brothers film. Just so you know.

[Tig Notaro]

I press. I pressed goodbye on Instagram because I was looking at it, and I was like, I didn't even know what the Met gala was, and I didn't know until now. And then all of these politics and conflicting. I thought you were this person. And then I was like, what am I doing? Like, I didn't even know about this before. Why am I allowing this in? I was like, I got it. I got to get rid of this.

[Caitlin Riley]

Because that's, like, my dream. By the way, is. Is deleting Instagram. It's like a wet dream. I can never do it. I will never. I'm not brave.

[Tig Notaro]

It's a clear space. I. I want clear space.

[Jameela Jamil]

Can I ask you something? Okay. So, because you're so busy and also quite difficult sometimes to get hold of, I was really surprised when you were willing to come here today. And I was. And just now, across my mind, I was like, has she come here to deliver a clear space to me?

[Tig Notaro]

Here's the thing. Do we have.

[Caitlin Riley]

We're here to clear space.

[Tig Notaro]

I have changed my work schedule.

[Jameela Jamil]

Okay.

[Tig Notaro]

In a general sense, to clear space for myself, because I was realizing I was saying yes to things that I wasn't consciously thinking about.

[Jameela Jamil]

Yes.

[Tig Notaro]

And so now I'm only touring a long weekend a month. I'm doing my podcast, and then I'm just popping in and out of things.

[Jameela Jamil]

Oh, means you actually want to be here. That's really nice, but I meant, like, you haven't come here to, like, clear any air.

[Tig Notaro]

It depends on how things go.

[Jameela Jamil]

As long as I haven't fucked up up until now, I'm fine.

[Tig Notaro]

Even to clear the air, it doesn't mean, like I said, that I'm icing anybody out. No, it's that, like, hey, we need to revisit this.

[Jameela Jamil]

Yes.

[Tig Notaro]

And I'm willing to have the conversation. Are you?

[Jameela Jamil]

Yeah, yeah, yeah. I'm a straight in the moment person. Like, the second the tone changes, I'm like, hey, why did the tone just change?

[Tig Notaro]

Yeah.

[Jameela Jamil]

I can't let anything just be cool or normal. It's my. I am my boyfriend's nightmare.

[Tig Notaro]

Well, and my therapist is saying that is why they say fight or flight. You. You are in the moment or you take off. And she was saying either is right and okay. Because it's your survival instinct.

[Jameela Jamil]

Yes.

[Tig Notaro]

But once I fly, I have to return back home and say, hey, that didn't feel good.

[Jameela Jamil]

Yeah, yeah.

[Tig Notaro]

Or I'm confused or. Can we have a discussion about this?

[Jameela Jamil]

This is wonderful. I really like this. What about you? What's your conflict style?

[Tig Notaro]

So I'm sorry I called it a fuck off tear.

[Jameela Jamil]

No, no, it has to stay. Okay. I love it and I'm gonna steal it now.

[Caitlin Riley]

So a fuck off tear is great. I'm a very, very anxious person. I don't know if you could tell.

[Tig Notaro]

No, no. But I'm willing to hold your hand platonically. I don't want you getting weird ideas.

[Caitlin Riley]

No, no, no. I love energetically and I do feel the handhold and I do appreciate that I'm an orphan, so.

[Tig Notaro]

Oh, me too.

[Grow Therapy Advertiser]

Oh, good.

[Tig Notaro]

My parents are dead.

[Caitlin Riley]

Oh, me too.

[Tig Notaro]

Yeah.

[Jameela Jamil]

You sadly still alive.

[Caitlin Riley]

Jesus. Well, that must be nice. But no, I kind of live in the middle. I am fight and I'm also flight. So I'll start to devolve into madness when I'm trying to oscillate between the two and choose which one I'm going to do. I usually fight with people I'm super comfortable with, like my husband and, like, think that's it.

[Jameela Jamil]

Right.

[Tig Notaro]

That's the only person you're comfortable with.

[Caitlin Riley]

Yeah, I would say so. And maybe my.

[Jameela Jamil]

Do you ghost? I never ghost anyone.

[Caitlin Riley]

I recently got ghosted professionally in a way that felt fucking insane to my whole system. And I confronted this person in a very respectful, adult, professional, kind, generous way.

[Jameela Jamil]

Yeah.

[Caitlin Riley]

And that person never responded to my text, it has now been two months, and I'm losing my fucking mind.

[Tig Notaro]

Do you want me to get involved

[Jameela Jamil]

almost on your fuck off tattoo?

[Caitlin Riley]

Yeah, it is. So that's something I'm.

[Tig Notaro]

That's.

[Caitlin Riley]

That's causing a big fight or flight in me. I can't really do anything else otherwise, if I do a second thing, then it's crazy.

[Jameela Jamil]

Yes.

[Caitlin Riley]

Like, if you double respond, you can't double confront. I can't. Exactly. You can't double confront. So now I'm kind of just living in the ether of being, like, in my face, ghosted by this person who I had a professional, working, collaborative relationship with.

[Tig Notaro]

I have to get a name.

[Caitlin Riley]

After we did not respond to my very vulnerable, direct, very kind, but honest

[Jameela Jamil]

face, I went through the same thing

[Caitlin Riley]

about being canceled on. And I was canceled on for, like, the 28th, 29th, 37th time in the span of us working together. And it was really disrespectful and not okay. And I got this text of cancellation that was so fucking sideways that I didn't respond in the moment. And then I took a week and I sent a text back being like, hey, it's me. I just wanted to take a second to intellectualize my thoughts. I feel like you do this a lot, and. And it. And it's a consistent thing, and it just doesn't work for me, and it makes me feel really awful. And so I just wanted to be honest and talk about it. Maybe there's something you need from me. You know, let's chat. I want to be here for you, but I just, like, I can't operate this way. Let's.

[Jameela Jamil]

And they looked at it, and they

[Caitlin Riley]

were like, in so many words. That's what I said. And they saw that text and just went.

[Jameela Jamil]

I had that actually with a.

[Caitlin Riley]

And never responded to me.

[Tig Notaro]

So how do you know they went?

[Caitlin Riley]

Because everyone's on their phone for the most part. Maybe not you, because you are smart about your brain.

[Tig Notaro]

No, I. All I'm saying is I deleted Instagram, and that's. And I have an Apple watch.

[Jameela Jamil]

I am. I had the same thing as you with, like, a. An actor that I know very well who I had worked with. And I wrote them, like, a long message about how destructive our relationship had been with each other and everything. Like, I didn't understand friendship. It was. Yeah, it was. It was a sort of like. It was like somewhere between. It was a working relationship, but I was like, these are all the things that I feel and wanted to say all those, you know, Times or years. And then they just didn't respond. And months had gone by and so I bumped into them at the actors strike, where you bump into everyone, tell them hilarious. And I was like, hey, hey, do you get that message? And they were like, oh, no. And I was like, oh, okay, I'll just quickly send it to you again right now. Resent it to this person. And other people were around, so I knew and they want to be polite. No, but I, I was like, read it now. I was like, it's not very long. Just. I was like, you can just read it now. And she was like, why? While you're here? And I was like, yeah. And I just stood there, I waited for her to read it and then I got Uber turned up and I was like, I'll wait for your response. I just got in the cab and I felt.

[Caitlin Riley]

But you never. But you never got a. Like, I got a response. What do you do? What did they.

[Jameela Jamil]

Sorry. And explained their side of the things and said some nice things. And then we just buried the hatchet. But it was great. But I've never, like, I was like, I felt like my thighs were pushing apart from how big my balls were becoming in the moment. I was just like, oh, I have a thigh gap. I was like pushing them apart. But yeah, it was very intense.

[Caitlin Riley]

Oh, my God.

[Jameela Jamil]

But I really, like 12 year old

[Caitlin Riley]

me just went, yeah, seriously, I can't. I mean, I cried. Start crying, actually, I think I just start crying.

[Jameela Jamil]

Yeah.

[Tig Notaro]

When there's conflict.

[Caitlin Riley]

Yes. I start crying like immediately.

[Jameela Jamil]

Oh, yeah, yeah. I'm in the moment.

[Caitlin Riley]

Yeah. Like, if I'm, if I'm fighting, it's really, really bad with my sisters. Because I'm the baby.

[Jameela Jamil]

Yeah.

[Caitlin Riley]

And they're older than me and like, they're just like, you're young and you're an idiot. And I'm like, But like, you can't

[Jameela Jamil]

say that to me.

[Caitlin Riley]

Because if you say that to me, that's like, actually wrong. I do have a voice and I do have thoughts and opinions and like, I'll just start.

[Tig Notaro]

Do you apologize if that's voice?

[Caitlin Riley]

Oh, my God, yes. Like, I'll apologize when it like my sister. I got in a big sister fight with two of my sisters recently where one sister was.

[Tig Notaro]

So how many sisters?

[Caitlin Riley]

Oh, God. Well, you met one of my sisters, actually.

[Tig Notaro]

Yes.

[Caitlin Riley]

And then you went into my sister. This is going to be so, so weird. But you went into. She's fine.

[Grow Therapy Advertiser]

Good.

[Caitlin Riley]

Why did you ask like that?

[Tig Notaro]

I don't know that I remember.

[Caitlin Riley]

That's okay. Oh, I was worried that you weren't gonna remember me.

[Tig Notaro]

Of course.

[Caitlin Riley]

Okay, well, I wasn't invited to your

[Jameela Jamil]

party, by the way. Gone off onto a whole other therapy tangent.

[Caitlin Riley]

Wait, where was I? I have add. I'm sorry, your sister. I'm neurodivergent.

[Jameela Jamil]

But we haven't started the actual full. Okay, we haven't? No. I mean, we have.

[Caitlin Riley]

We didn't start. The part of the podcast has not started.

[Jameela Jamil]

No, it has. I have to get the themes.

[Caitlin Riley]

It's going to.

[Jameela Jamil]

It's going in a direction that I have never seen it go before, but I'm loving every second of it. And it was very cleansing for me to be able to tell anyone that story about me and this actress. And I'll tell you who it is after the show. Sorry, everyone. Sorry, everyone.

[Grow Therapy Advertiser]

Listening to.

[Jameela Jamil]

Anyway, now we're changing course to the story of more disaster.

[Caitlin Riley]

I actually was in the middle of something

[Jameela Jamil]

like. Caitlyn, shut the fuck up.

[Caitlin Riley]

Okay, I'm sorry. Sorry.

[Jameela Jamil]

Okay, so this podcast is about disaster. It is unifying, as we have just expressed how unifying themes of discomfort can be. I like to start people off with little micro humiliations. And so I feel as though. Tig, I'd like to know a micro example of a humiliation that you've endured or caused.

[Tig Notaro]

This was something that I had to breathe through because it made me cringe for years. Luckily, I am friends with this person now. Right. But years ago, when I first moved to la, this comedian pursued me really hard. Okay. And I really liked her and I was interested, but, like, she was pursuing me hard, and she would admit that, like, it was. It was funny and did like other people around. No, no. Because she had never felt that way about a woman before.

[Jameela Jamil]

Okay.

[Tig Notaro]

And so I think it was, like, confusing her.

[Caitlin Riley]

An awakening.

[Tig Notaro]

She's married to a man. She has kids. But she was just like. She told me she had a day job. She asked a friend, she was like, who was gay. And her friend was like, don't call her. And she was like. And I walked into my office and I called you right away. She was like.

[Jameela Jamil]

I just.

[Tig Notaro]

She was like. I was out of control. And so. So she was.

[Jameela Jamil]

I think this is still an awakening.

[Tig Notaro]

No, no, no. I think she's very. Whatever it was. Anyway, so then, yeah, she completely lost interest. And what did that do? I was like, well, made you interested.

[Jameela Jamil]

Yeah.

[Caitlin Riley]

That's so funny.

[Tig Notaro]

Where did that. Where don't you like me? And I wore this T shirt all the time that she used to tell me she was like, you look so cute in that shirt. And, you know, because I was, like, not quite at the level she was. I was just like, oh, okay, cool. She likes me in this shirt. Well, when she lost interest, I put that shirt on, and I happened to be in her neighborhood, and.

[Jameela Jamil]

Oh, did you?

[Tig Notaro]

Yeah, I did. And I was like, hey, I'm in your neighborhood. I went over. That's how I felt for years. Cringing. I'd be like, at the grocery store, and I go, oh, God. And I can't believe it. And so I put my little shirt on. I head over to her. Apart.

[Caitlin Riley]

What was the shirt?

[Tig Notaro]

It was just like, a baseball jersey that had little baseball patches and. I don't know. I can wear it sometime for you. Let me know if it does anything.

[Jameela Jamil]

It's an egg of their own, the porno. You know what I mean?

[Tig Notaro]

It's so obvious. I was not in her neighborhood. I have my stupid shirt on, and she comes outside. She doesn't invite me in. She comes outside and she sits on the front porch with me and. And chats with me for a good 10 to 15 minutes.

[Caitlin Riley]

You're a bad kid.

[Tig Notaro]

Yeah. And then she. She's like, okay, well, I have to go. Go back to whatever I was doing. And then I had to drive home with my stupid cute shirt on. And I was so mad at that shirt for so long. I was like, God, what did I do?

[Caitlin Riley]

I'm so stupid.

[Tig Notaro]

Like, you know, like, yelling at myself all the way home. And then, you know, we were kind of distantly friends in the scene, but, like, now we're totally pals. And I actually have. When I say totally pals, I. I barely see anyone but my family. But I adore her, and I. I believe it's mutual. And every time I see her, I'm.

[Jameela Jamil]

I. I have.

[Tig Notaro]

I don't think I've shared this.

[Jameela Jamil]

I was gonna ask.

[Tig Notaro]

Yeah. But I should give her this gift.

[Jameela Jamil]

Yeah. I'll clip it for you. Okay. You can just send it so you don't have to face saying it again and again.

[Caitlin Riley]

So I feel like we've all been there.

[Tig Notaro]

Yeah.

[Caitlin Riley]

But it wasn't there for sure. I've absolutely been in someone's neighborhood before.

[Jameela Jamil]

I.

[Caitlin Riley]

A few times.

[Tig Notaro]

Yeah.

[Jameela Jamil]

I thought it was totally natural and casual and breezy to go into my local video store 19 times a day, and it wasn't at all obvious that I had a crush on someone who worked there.

[Caitlin Riley]

Yeah.

[Jameela Jamil]

To be like, yeah, I. Yeah, I already saw it. I saw the film. He's like, you're watching all these films every day. I must have spent my entire summer savings just renting films I didn't have time to watch. So embarrassing. What was yours?

[Caitlin Riley]

Micro humiliation. This happened recently? This was, I think, the year before last.

[Jameela Jamil]

Yeah.

[Tig Notaro]

Where?

[Caitlin Riley]

Excuse me. I have like an air bubble in my throat. It's disgusting. Hold on.

[Tig Notaro]

They're called burps.

[Caitlin Riley]

No, it's like, you know when something, you know.

[Jameela Jamil]

Sorry, I just had like a little air bubble coming out of my ass,

[Tig Notaro]

If you want to call it that.

[Caitlin Riley]

Yeah, no, it's like, you know when

[Tig Notaro]

you're like, we know.

[AWS Advertiser]

Yeah.

[Jameela Jamil]

I'm never saying queef never again.

[Caitlin Riley]

No, you know, there's like a. There's a saliva film over your voice box and then you kind of like that. Yeah, Then, yeah, that's what it was. Okay, I said it wrong.

[Jameela Jamil]

My God, you guys, we're bullying you.

[Caitlin Riley]

So my sister, who you met. Old, old past.

[Tig Notaro]

How is she?

[Caitlin Riley]

She's well, she's.

[Sponsor Voice]

Well.

[Caitlin Riley]

She and I went to the same high school, but we're like 20 years apart, so we, you know, miss each other anyway.

[Tig Notaro]

You and your sister 20 years apart?

[Caitlin Riley]

Yeah, she's 19 years older than me. So I'm the product of a second marriage.

[Grow Therapy Advertiser]

Right.

[Tig Notaro]

You're the baby.

[Jameela Jamil]

Yes, same.

[Caitlin Riley]

Yes.

[Jameela Jamil]

My sister's a 20 something years older than me. Wow.

[Caitlin Riley]

So my sister's best friend is a mom at our high school and, like, helps run events for our high school. My sister had a great time in high school. I had a terrible time in high school. I went to an all girls Catholic high school. I was depressed. I wanted to go to an arts high school. My parents didn't let me. I was really bad in class. I didn't do math, didn't do chemistry, didn't really do anything pertaining to school. Had a really traumatic.

[Jameela Jamil]

I knew you were going to be famous.

[Caitlin Riley]

I knew I was going to be famous.

[Tig Notaro]

You knew this podcast episode was coming your way?

[Caitlin Riley]

Yes, yes. And so I just had a really tough time. Hated the school, was fighting for my life. Really tough.

[Sponsor Voice]

Four years.

[Caitlin Riley]

Anyway, my sister calls me. She's like, hey, they're doing the mother daughter luncheon at the school and they love you and they wanted you to come talk to the students and, like, host the fashion show. Because for the mother daughter luncheon, they would do a fashion show. It's a private school. So I was like, you know, thanks, but no thanks. I don't want to do that. We get in a big sister fight. She's yelling at me. I'm crying. I'm apologizing for nothing. I end up going, right? So I go with my sister. And, you know, I'm talking to old alumni and I'm talking to old teachers who hated me, and they're like, oh, so happy that you're here. And I was like, the only one they can get for the fashion show. It's raining, and so we're in the gymnasium, they're doing this whole luncheon, and it's time for me to go on stage. They put me on stage, give me a microphone, and I'm like, okay, great. Well, here's the fashion show, guys. They pull me aside, they go, wait, wait, wait.

[Grow Therapy Advertiser]

We're.

[Caitlin Riley]

We're sort of.

[Grow Therapy Advertiser]

We.

[Caitlin Riley]

We need you to sort of extend. Can you just do like, some stand up for 30 minutes?

[Jameela Jamil]

30 minutes?

[Tig Notaro]

Did you do stand up at the time?

[Caitlin Riley]

I don't do stand up at all. I'm not a stand up comedian at all. And I don't have. I don't have five minutes. I do. I do care. It's. Yeah, no, it's a nightmare. And so I'm in my high school gymnasium on, like, I'm literally in the ep. I'm in the epicenter of my trauma, and I'm in the nucleus of my origin of my villain origin story. And they say to me, they're like, can you. Can you just do like 30 minutes of stand up or, like, vamping or just something just, like, be funny and they don't get it.

[Tig Notaro]

Vamping, whatever.

[Caitlin Riley]

Yeah.

[Tig Notaro]

What is vamping?

[Caitlin Riley]

Like, just sort of like, hey, you know, like, hey. And what are you? What were you like?

[Tig Notaro]

Shake your shoulders.

[Caitlin Riley]

We're here having a good time.

[Jameela Jamil]

MC vampire.

[Caitlin Riley]

And so you vamp all the time?

[Tig Notaro]

No, Tig, I didn't know.

[Caitlin Riley]

Yeah, you vamp all the time.

[Tig Notaro]

Of a podcast.

[Jameela Jamil]

If there was a word to describe you that I think everyone has, it's vamping, shimmying, vamp. Take Notaro.

[Tig Notaro]

Anyway, so you're vamping.

[Caitlin Riley]

So they asked me to do that. I go, oh, no, no, no. I. I can't do. Like, I do. I was like, I do, like, characters and sort of like, Like, I do, like, performance pieces. They're like, we don't know what that is. Can you just, like, be funny for 30 minutes? So I'm on stage and I'm like, okay, well, God weather, right? It's like I just start telling. I'm not a stand up.

[Jameela Jamil]

You're in a fugue state.

[Caitlin Riley]

Yeah, I'm like, do you guys want to hear about the time I peed? On stage when I was four and I start telling these like horrible, unfunny, embarrassing stories. Then in the middle of me talking, one of the parents dead silent gymnasium goes, who are you? Who are you? And I go, oh, I'm sorry. And this woman goes, who are you? What do you do? And I go, oh, thank you so much for asking. I'm an actor and a comedian, but I've never seen you before. Oh, okay, yeah, I'm on the show.

[Grow Therapy Advertiser]

Hack.

[Caitlin Riley]

I don't know what that is. I'm having this full blown back forth conversation with this mother in the audience and it's awful. And I can feel like tears welling up and my sister's crying.

[Jameela Jamil]

Oh yeah?

[Tig Notaro]

You crying?

[Caitlin Riley]

Yeah, no, I cry.

[Tig Notaro]

Yeah, right. I was listening. When things go awry, you cry.

[Caitlin Riley]

Yeah, so I wanna cry. And we're just asking. Cause we just wanna know how we can support you in your career. Like, it's all moms feeling sorry for me. They see this young woman on stage, it's genuinely, truly. I sit down, I turn to my sister, I'm like, I'm never doing this again and I'll never forgive you. There's a mom that comes up to me, she's like, thank you so much for doing this. It's so great to see, like, you know, you do your thing. But like, it's just nice that you're coming so we can finally figure out how to get like real celebrities here. You know what I mean? This is like a really nice. This is just like a really nice test run. And so what do you do exactly?

[Tig Notaro]

Like, it was like, I do stand up.

[Caitlin Riley]

It was a humiliation ritual at my high school that like I didn't ask for for like. It was so awful. It was so awful. So yeah, that was, I. I guess that's a micro humiliation.

[Jameela Jamil]

That is a macro micro humiliation. Nominal. Both of you.

[Tig Notaro]

Phenomenal.

[Caitlin Riley]

Yeah.

[Jameela Jamil]

Outrageous. We'll be right back after the break.

[Sponsor Voice]

This episode is sponsored by zocdoc. Have you been putting off a doctor's appointment or need a dentist and you don't know where to start? We've definitely been there and that's why we use ZocDoc. Actually. Over the holidays, Michael had a dental emergency and seemingly every office was closed. But we hopped onto zocdoc, found an in network dentist, had great reviews, saw real time appointments available, which was key. It was on New Year's Day and booked an appointment in just minutes. It took so much of the stress out of the already stressful situation. Zocdoc makes it easy to search and compare over 250,000 local in network providers across more than 200 specialties so you can find the right doctor or dentist and book instantly. Taking care of your health just got easier. Download the ZocDoc app today and book that appointment on your to do list. That's Z O C D O C

[Grow Therapy Advertiser]

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[Creative Planning Representative]

If you're looking for something predictable and low friction over the long term, public markets may be a suitable option. But the moment you want different investment characteristics, it may be time to consider the private markets. See how your wealth can work [e-mail] Access.

[Jameela Jamil]

And we're back. Okay, I actually don't know what could possibly be left, but there is something bigger to come. Still, Tig, what would you say was your big wrong turn?

[Tig Notaro]

Well, you know, after listening to your story, I'm feeling a little self conscious and embarrassed because well, this is a new embarrassing story.

[Jameela Jamil]

A new wrong turn.

[Tig Notaro]

Yeah, I'm having a wrong turn within a wrong turn.

[Jameela Jamil]

I were you the woman in the

[Tig Notaro]

audience in her story? No. I'm realizing I've chosen two stories where I set myself up as wanted by women. Oh love. Okay. But I I didn't mean to do that.

[Jameela Jamil]

Sure.

[Tig Notaro]

And I. Okay, I did. I'm very sought after.

[Jameela Jamil]

You literally are.

[Tig Notaro]

But I am married. But I need everyone to back Hollywood baby. Nobody cares.

[Jameela Jamil]

All of my straight friends like they don't know where they stand when they see you. So it's you. You are wanted.

[Tig Notaro]

Here are more stories about that Robert Pattinson no, I this was so my when I first started again started in stand up nearly 30 years ago I made a friend and we had kind of, we had both started around the same time and we had this kind of friendly, competitive relationship. It was truly very competitive. And she was like, oh, I've always wanted to go to the Sundance Film Festival. I had never heard of that. Well, guess what? I was house sitting for this woman who managed the Sundance Film Festival. And I was like, hey, I'm working for this woman who manages the festival. And she said she could get us in as volunteers. And she was like, oh, this is great. So we go to Sundance. She chose a job because it was, she was the, she was seating people, the usher at movies, but she had to work a whole day. I chose the half day job of being the shuttle monitor because you only have to work four hours, but you have to stand out in the cold. I'm like, that's fine. And turns out once the shuttle arrives and the movie starts, they let you sit in and watch the movie anyway. So I'm like. At first she was like, haha, I won't. You're going to be out in the cold. And I'm like in the theater going, ha ha, you didn't win because now I'm just in the theater with you. And I go, I get to go snowboard for the rest of the day. Okay.

[Caitlin Riley]

Hell yeah.

[Tig Notaro]

Also, when we checked in for our accommodations, she was ahead of me in line. I skipped this part. I'm just teeing up. What's to come here?

[Grow Therapy Advertiser]

Great.

[Tig Notaro]

She gets her accommodations, which is bunk rooms. You know, you're sharing, you're in bunk beds with strangers. Other volunteers?

[Caitlin Riley]

No.

[Tig Notaro]

Okay, exactly my feeling. I come along next in line to check in for my bunk room and they go, we don't have you here, but we have set aside hotel rooms so you'll get your own hotel room. And my friend is like, are you kidding?

[Caitlin Riley]

You're like Stuart Little.

[Tig Notaro]

And it feeds. My wife calls me Forrest Gump by the way.

[Caitlin Riley]

Forrest Gump, that's perfect.

[Tig Notaro]

Yes. So we're having our fun, like haha, I'm winning thing. Okay, then when I have my half day wrap up, there is another volunteer that's relieving me for the day. And it's this woman who I'm chatting with whenever we're handing off our job. She asks me towards the end of the festival, would you like to go for a drink some night? And I was like, like, that's crazy. I tell my friend and she's like, I can't believe. And then you meet a girl here. And I'm like, I, I didn't know that this was.

[Jameela Jamil]

And you have a hotel room to talk to if you need to.

[Tig Notaro]

By the end of the festival, a lot of people have left the festival, so they start consolidating. You know, I love to consolidate, but they start consolidating hotel accommodations. So you start getting moved from your. Where you're staying into another place because they're downsizing, okay? So at this point, I am moved out of my nice hotel. And it's in the last few days of the festival. I. Oh, I went out for a drink with the girl, make out with her. But I'm thinking, not really into her. Very nice.

[Caitlin Riley]

Classic tick.

[Tig Notaro]

Classic tick. We got a couple days left of the festival. I tell my friend. I'm like, she's very nice. I'm not into her. Whatever. I'm moved to a new hotel room, okay? I have a roommate in this hotel. I drop my luggage off. I don't know who my roommate is. There is the big final Sundance bash, okay?

[Caitlin Riley]

The final dance of Sundance.

[Tig Notaro]

The final dance of Sundance. I'm there with my friend, who I've essentially been winning the whole Sundance because of Jesus, because of my Forrest Gumpness. And so the girl is there, and I say to my friend, hey, I think I'm gonna just bail so I don't have an awkward situation. I'm gonna go back to my hotel. My friend was like, where are you staying? And. And I was like, oh, at the Alpine Inn or whatever. Much worse accommodations than my original situation. And so I go back, the lights are off, my suitcase is there. I have not met my roommate. There's somebody in a bed, and it's just a single bed. There's a side table, an end table between our single beds. I get ready, I get into my bed. I go night, night. Well, there is a knock at the door, and my roommate opens the door, and it is the girl. And my friend said to her, tig had to leave, but wanted me to tell you that she was staying at this hotel and to swing by

[Caitlin Riley]

to

[Tig Notaro]

get me in the very end. Okay? So here's where the embarrassment part, and this is also where it. I really kind of pat myself on the back of, like, women want me, but this woman, I mean, relax.

[Jameela Jamil]

The first one wanted you for, like, 10 minutes.

[Caitlin Riley]

Okay?

[Jameela Jamil]

Yeah.

[Tig Notaro]

This woman comes in. She is trashed. It's like two in the morning. It's dark in my hotel room. She is on her knees next to my bed saying, will you make out with me?

[Caitlin Riley]

Oh, my God.

[Tig Notaro]

In the darkness. In the darkness. I Haven't met my roommate. And I'm like, I go, I have to get up early. I have an early flight. I was like, I. I have to go to bed. And she was like, please, let's just make out one more time. Like that kind of like drunk situation where I'm like, you have to get. She would not leave. My roommate turns the light on. She's like a 70 year old woman who is volunteering and she starts reading a book in her bed while this drunk woman is begging me to make out.

[Caitlin Riley]

So she woke up, turned a light on and then opened up a book

[Jameela Jamil]

because she probably the Bible.

[Tig Notaro]

She would not leave. Okay. She was. Was so drunk.

[Caitlin Riley]

This is not embarrassing for you.

[Tig Notaro]

Yeah, I understand. It's embarrassing for. I was so uncomfortable. I was so embarrassed. This was nearly 30 years ago. Do you understand? Like, I was not my 55 year old self. That could be like, my apologies. You need to. You know what I mean? Like, I was losing my mind. Like, you need to. It was so bad.

[Caitlin Riley]

But it was.

[Tig Notaro]

I don't know. I must not be.

[Caitlin Riley]

And that woman was Helen Hunt.

[Jameela Jamil]

My favorite part of it is just how much you were winning. And then your friend really fucking dunked me. Duck it to you in the end. The level of anti bro code that is is so outrageous. I can't even imagine being spited by a friend like that. That is a hilarious wrong turn. I really, I think you would be remiss to not make that into a movie. It's the buddy movie that the world has been waiting for and we don't really have something like that between two women. I would love that. It's an amazing scene. I love all of it. Please use the clip as the ip.

[Caitlin Riley]

A buddy movie at Sundance is called Sundance Done.

[Grow Therapy Advertiser]

Yeah.

[Tig Notaro]

The only thing I feel bad about, which of course she could hear, that is. But hopefully she has a sense of humor. All these years later, hearing me tell if. If she stumbles upon this.

[Jameela Jamil]

Dude, she sounds like she was so hammered. She has no recollection of this.

[Tig Notaro]

Yeah, yeah, don't worry. Yeah.

[Caitlin Riley]

Now you just go to a hotel room. You can get on your hands and knees. Please make out with me.

[Tig Notaro]

Like with the lights on. That is while someone's reading. She should be on this podcast.

[Jameela Jamil]

She is coming over right now.

[Tig Notaro]

There she is.

[Caitlin Riley]

Helen Hunt.

[Jameela Jamil]

We're gonna go to a quick break.

[Sponsor Voice]

This episode is sponsored by zocdoc. Have you been putting off a doctor's appointment or need a dentist and you don't know where to start? We've Definitely been there. And that's why we use ZocDoc. Actually over the holidays, Michael had a dental emergency and and seemingly every office was closed. But we hopped onto zocdoc, found an in network dentist, had great reviews, saw real time appointments available, which was key. It was on New Year's Day and booked an appointment in just minutes. It took so much of the stress out of the already stressful situation. Zocdoc makes it easy to search and compare over 250,000 local in network providers across the more than 200 specialties. So you can find the right doctor or dentist and book instantly. Taking care of your health just got easier. Download the ZocDoc app today and book that appointment on your to do list. That's Z O C D O C zocdoc.

[Creative Planning Representative]

Because you didn't just say, how can I provide these investments? You'd be, how do I holistically provide everything? How do I bring in the legal, the accounting, all this and do it at a price point no one else is doing it.

Learn more about how we approach wealth [e-mail] Integrated AI isn't just digital.

[AWS Advertiser]

It's physical. Hospital floors, factory production lines, autonomous systems making real time decisions in environments where the stakes are real and the margin for error is not. The engineers taking AI from prototype to physical deployment need infrastructure that's been proven under pressure. That's AWS purpose built to help you move from concept to production at scale without compromise. The next frontier of AI is in digital. AWS is ready to take you there. Visit aws.comai AI that's ready when you are.

[Jameela Jamil]

And we're back. All right, Caitlin, what in the Jesus could possibly be your big wrong turn?

[Caitlin Riley]

Okay, So I was 15 years old. I was a theater kid. I know that that's shocking. I did the plays in high school. I know that that's shocking.

[Tig Notaro]

You were vamping.

[Caitlin Riley]

We're vamping. And so there. Because I went to an all girls Catholic high school, there would be boys from other high schools that would come to our school to be the boys in the play. And so I went to Immaculate Heart, same high school as Megan Markle. Hold for applause. Thank you so much.

[Tig Notaro]

Did you all go at the same time?

[Caitlin Riley]

No, we did not. She's older than me. I'm young. She's also. I'm not. I'm not 55.

[Tig Notaro]

I can move into a retirement community.

[Caitlin Riley]

Shut up.

[Tig Notaro]

I can.

[Caitlin Riley]

No.

[Tig Notaro]

Do you remember the first time you

[Jameela Jamil]

met me on a podcast? You at one point offered to Let me come and live in your ouse.

[Tig Notaro]

Oh, yes, yes. Not my ouse, but guest house.

[Jameela Jamil]

Oh, guest house. That's it. Yeah.

[Caitlin Riley]

Still, I was there for.

[Jameela Jamil]

Did she invite you to.

[Caitlin Riley]

No, but I was there for that conversation. I do that, too.

[Tig Notaro]

Yeah.

[Caitlin Riley]

No, that was. That was nice of you to do that. She was such a mess, but.

[Creative Planning Representative]

Yeah.

[Tig Notaro]

No, I understand.

[Jameela Jamil]

Yeah.

[Caitlin Riley]

Yeah, I know.

[Tig Notaro]

That was a really.

[Caitlin Riley]

That was a fun night. Where did we go?

[Tig Notaro]

I don't know.

[Caitlin Riley]

It was that coffee bean on Hillhurst.

[Jameela Jamil]

It was over zoom, but cool.

[Caitlin Riley]

Anyway, so there was a boy from Loyola High School. It's a boys high school out here. Who would frequently do the plays at our school. And I was in love with him. I was in love with him. I was in love with him. I was in love with him.

[Jameela Jamil]

So how long have you been in love with him?

[Caitlin Riley]

Before he ever, like, gazed at me. I was in love with him for a full year.

[Jameela Jamil]

And that's dog years when you're a teenager.

[Grow Therapy Advertiser]

Yeah.

[Caitlin Riley]

So his name is.

[Tig Notaro]

How long.

[Caitlin Riley]

His name is Jack. So when I was a freshman, he was a junior. When I was a sophomore, he was a senior. So I. We did a play together when I was a freshman, but we never. He never spoke to me. He was like, the moment.

[Jameela Jamil]

Was it that real kind of like, heart shaking limerence?

[Tig Notaro]

Yes.

[Caitlin Riley]

No, I was. It was. It was disgusting. I've never seen anyone beautiful. He was so funny. He loved Led Zeppelin. I was like, would you laugh so

[Jameela Jamil]

loud at his jokes?

[Sponsor Voice]

Yeah.

[Caitlin Riley]

But he didn't talk to me. So I'd hear him say a joke and I'd be like. Like from across the room. It was awful. It was awful. I was like, california with an ache in my eye.

[Jameela Jamil]

Yeah.

[Caitlin Riley]

He also loved the Eagles. So, like, the song Hotel California was my aim away message for a long time.

[Creative Planning Representative]

The.

[Caitlin Riley]

The lyrics to Hotel California. Because I was like, I also love classic rock. That's so crazy. The Eagle. Anyway, so sophomore year, I sort of came into my physical own a little bit more, let's say. Okay. And he started to notice me a little bit more. We would have these long rehearsals at the gymnasium.

[Tig Notaro]

I like that you elongate that word. Yeah. I would call it a gym.

[Caitlin Riley]

It's a gymnasium. The gym is like Equinox.

[Jameela Jamil]

It's romantic. Back then.

[Caitlin Riley]

2005. Okay. The killer's Hot Mess album had just come out huge. Okay. Huge, Massive. And so we started to talk more in rehearsal. And we would flirt with each other, and then we exchanged AIM screen names. And his AIM screen name Was Smacky Jack. And I was like, that is so funny.

[Jameela Jamil]

Like, that is. He's.

[Caitlin Riley]

That's so him. Like, that's. He's so like that, you know? And my AIM screen name was Bitter.

[Tig Notaro]

It's aim.

[Caitlin Riley]

Oh, my God. Okay.

[Jameela Jamil]

Like, instant messaging.

[Caitlin Riley]

Instant. Instant. It was like DMing, but it was. You had, like, your AIM in your email. It was. It was. It was like it's within. It was its own thing. It was like, within the Internet, within aol.

[Tig Notaro]

Okay.

[Caitlin Riley]

Anyway, it's how teenagers first were able

[Jameela Jamil]

to communicate with each other off the landline.

[Caitlin Riley]

Yeah. This was, like, before Facebook.

[Tig Notaro]

Okay.

[Caitlin Riley]

Before social media, anything.

[Grow Therapy Advertiser]

Yeah, yeah.

[Tig Notaro]

Okay.

[Caitlin Riley]

And so my AIM screen name was bitterly sweet 912.

[Tig Notaro]

That's so you.

[Caitlin Riley]

And that's so me.

[Tig Notaro]

It is.

[Caitlin Riley]

I'm bitter. I'm also sweet. And then my birthday. And so, like, bitterly sweet 9 12. Yeah, yeah, totally.

[Jameela Jamil]

So cool.

[Caitlin Riley]

So we would talk and talk and talk, and we did the play together. And it was like there were some hummings around the crew that it's like, something's going on with Caitlyn and Jack. Haven't you heard? Something's going on. We would talk, we would text. I had, like, a specific ringtone for him, which was Ticket to Ride by the Beatles. And one day.

[Tig Notaro]

We're classic rock.

[Caitlin Riley]

Yeah.

[Tig Notaro]

Yeah, we're classic rock.

[Caitlin Riley]

So he took me to his formal. I was like, oh, my God, I feel like I'm marrying, literally. Prince of England went to the formal. We're on the dance floor. Like, I'd never been kissed by a boy. I didn't know what a penis looked like. I didn't know how sex worked. I was like, you want me to do what? Put it where? Like, what is going on? I was very afraid of boys. And so he kissed me. It was not with tongue, but he kissed me. That was my first kiss. We hung out all night.

[Tig Notaro]

You were how old?

[Caitlin Riley]

I was 15.

[Tig Notaro]

Okay.

[Caitlin Riley]

It was my first kiss. And so we hung out for the rest of the night. I was, like, afraid to be with him alone. And then. Oh, you know, a week after formal, we're texting and texting. I'm noticing he's not talking to me as much. Then he breaks up with me over aim. Over aim. And I printed out the entire conversation, and I brought it to school to show my friends. And then I put it. And then I put it in my locker, and then it got stolen out of my locker.

[Jameela Jamil]

Oh, my good God.

[Caitlin Riley]

And I wanted to die.

[Jameela Jamil]

How did that happen?

[Caitlin Riley]

I don't know. Someone Got wind and stole it out of my locker because I didn't put a lock on my locker because I can never remember the combination. So I was like, kind of a badass that way.

[Tig Notaro]

Yeah.

[Caitlin Riley]

Got stolen. Someone was making fun of me somewhere. The reason he broke up with me is he went back to his ex girlfriend, Kristina Okrimovskaya, who was. She was Russian. She was a grade above me, but she and I looked a lot alike. We would be mistaken for each other on campus all the time. Meanwhile, when Jack and I were dating, I had given him my Livestrong bracelet, sort of like as a promise ring.

[Tig Notaro]

Sure.

[Caitlin Riley]

And so the breakup had happened. I was distraught. I did not know what breakup felt like. I felt like I was dying from the inside out. I was walking to Spanish class, and one of the girls that was in the, you know, theater crew with us stops me, goes, hey, Jack wanted me to give you this and gives me back the Livestrong bracelet. This is part one.

[Jameela Jamil]

Oh, that is crushing. This is.

[Caitlin Riley]

We're not even to the worst part. We're not even to the macro Part.

[Jameela Jamil]

Bracelet. Dr. Zhivago.

[Sponsor Voice]

Yeah.

[Tig Notaro]

And Livestrong is cancer.

[Caitlin Riley]

Livestrong is. What's his name? Armstrong guy.

[Tig Notaro]

Yeah.

[Caitlin Riley]

Lance Armstrong. Had cancer, lost a testicle.

[Tig Notaro]

And then from.

[Caitlin Riley]

That was like, I'm going to make bracelets.

[Tig Notaro]

Yes.

[Jameela Jamil]

And you gave it to him. That's so romantic.

[Grow Therapy Advertiser]

Yeah.

[Caitlin Riley]

And it was. They were really, really hard to come by. And he sent it back to me. Yeah. It was like a return to sender. Anyway, cut to four years later, three years later, I'm out of high school. I'm now 18. Okay. He went to college, to Nebraska. I remember I got on aim when I found out that he's going to college. Nebraska, where I was like, have fun out there. Like he was going to war. That's the last time we talked. He was like, thanks. So anyway, cut to several years later, he's well back from College. I'm. I'm 18, 19. I'm out of high school. I'm not going to college. I'm in la. I'm gonna be a famous actor. Okay, totally. And so I'm just. My days are spent, like, hanging out with my mom and getting headshots and then going to a bunch of acting classes. And I didn't have any friends. They were all at college. And Jack starts messaging me on Facebook and we're talking again and we're flirting and he wants to hang out. And I'm like, oh, my God. Now, in between these times, I'D had a high school boyfriend, I'd lost my virginity. I had a whole life after Jack that he doesn't even know about. Right?

[Tig Notaro]

You could recognize a penis at point that this point.

[Caitlin Riley]

I had seen a penis. I dealt with one. I had been face to face with one. Yes, I, I, I was, I was privy to. And so Jack is like, why don't we hang out? And I'm like, I'm gonna marry this. And I'm like, yeah, let's. So I'm still afraid to be with him alone, cuz he's like big scary Jack. So I invite him over to my parents house where we're gonna hang out in the hot tub. I bring two of my other friends over that we all, we all did the plays together. So I'm like, oh, it'll be casual, there will be buffer there, whatever. So he comes over, we're all hanging out and I'm sort of trying to be hostess and I'm getting up and getting chips for him. Do you need another beer? My parents said it's okay if we drink beer. It's totally fine. I'm walking around in my bikini. I'm like, do you want anything? You want more towels? I'm gonna go inside, get more towels.

[Jameela Jamil]

So again with these shoulders.

[Caitlin Riley]

The only towels that my mom had were like white towels, white robes, disgusting, right? So I am sitting on my towel and I'm kind of getting in and out of the hot tub and I'm like, you know, have my towel wrapped around, sitting on the towel, whatever. And I'm getting up and getting more chips and snacks and my friend Samantha's like, caitlin, just sit down. Just, just stop walking around. Just stop walking around. Just sit down.

[Tig Notaro]

Okay, I know what's happening.

[Caitlin Riley]

And she's, she's telling me, she's like, no, just don't get, we don't need beer, we don't need chips. Just sit down, stop moving around. I'm like, what are you talking, what do you mean? Thought she was like being, I don't know what she was doing, but I was not catching on.

[Jameela Jamil]

She's not being a vibe.

[Caitlin Riley]

And I'm just sort of noticing the energy is shift. Jack is, I'm noticing it. Jack is not like kind of making eye contact with me anymore. I'm like, right, I mean, wasn't. Hello. And, and I'm like, do you want another beer? He's like, no, no, I'm, I'm okay. I don't need anything. Just sit down. At one point, Jack very solemnly goes I'm gonna go inside and use the bathroom. He goes inside and uses the bathroom. My friend Samantha turns to me, she goes, caitlin, you just got your period. I look at her, I go, what are you talking about? She goes, look at your towel. I stand up, I take my towel off. It looks like the flag of Japan. There is a. This massive red spot in the middle. It is, it is just no spot in my body. All the blood in my body had just exited me onto this town and a perfect circle.

[Tig Notaro]

And she's like, had the moment to say it was the flag of Japan.

[Caitlin Riley]

Yeah.

[Tig Notaro]

You know, anyway, but go on.

[Jameela Jamil]

Where were you when we needed you?

[Tig Notaro]

I know.

[Caitlin Riley]

I, I look at her. She goes, that's why. That's why I kept telling you to sit down. That's why Jack is upset. That's why he went inside. That's why the vibe shifted. I'm mortified. I'm like, I, I, I don't know what to do. So I go inside, I get a tampon, I take care of myself, I change into pajamas. I go back outside. Jack has his backpack. He's putting his stuff in his backpack. Just kind of silently. Everyone's kind of cleaning up on my behalf. Like a death has happened between my.

[Tig Notaro]

Well, there was blood, right.

[Caitlin Riley]

And so I just sort of announced the backyard. I go, I think I'm gonna go to bed. My stomach hurts. And Jack is like, yeah, I'm gonna go home. So we kind of like say bye and give an awkward hug, and he leaves. And I never see him or speak to him again.

[Tig Notaro]

Oh, sweetheart.

[Jameela Jamil]

Yeah, I mean, he'd like, he sounds like a little. But.

[Sponsor Voice]

But also.

[Caitlin Riley]

Yeah. So now that I'm like 36 years

[Tig Notaro]

old, depressed, I don't know.

[Caitlin Riley]

I don't know anything.

[Jameela Jamil]

Like, he was actually probably suppressing her.

[Sponsor Voice]

Like.

[Caitlin Riley]

Yeah, he was probably, like, absolutely disgusting. He was like 20.

[Jameela Jamil]

If you even have a picture of tampons at all. Or like, had a tampon in your bag that was, like, unused in a packet. You could literally shake one at boys and they'd like, run away screaming.

[Caitlin Riley]

Yeah. Like period blood to a 21 year old guy.

[Jameela Jamil]

On this podcast yesterday. Lose it. When we started talking about periods. He's 36 years old.

[Grow Therapy Advertiser]

Yeah.

[Jameela Jamil]

He's in a relationship. Woman.

[AWS Advertiser]

I know.

[Caitlin Riley]

But we are out there.

[Jameela Jamil]

Yeah.

[Tig Notaro]

Yeah.

[Caitlin Riley]

That is harrowing.

[Tig Notaro]

And it's been how long?

[Caitlin Riley]

It's been years.

[Jameela Jamil]

It's been exactly 18 years.

[Caitlin Riley]

Yeah. But we are Facebook friends. He did work at the Long Beach Aquarium at some point. He does wear transition lenses. I do see that sometimes on his photos.

[Tig Notaro]

Could you have ever imagined all those years ago that you would be on a podcast talking about the flag of Japan and, Jack, I mean, if you

[Caitlin Riley]

had to explain to me what a podcast was, I would have never.

[Tig Notaro]

No.

[Caitlin Riley]

So it's sort of like a radio show, but it's not a radio show. It's on your phone, but it's on an application on your phone. You'll get there at some point, but it's also filmed. So it's like a radio show that's filmed. It's not a TV show, but it is sort of like a radio. It is a broadcast that you can watch. Like a TV show, but it's.

[Tig Notaro]

I know what a podcast is.

[Caitlin Riley]

Yeah.

[Jameela Jamil]

Well, well done, Tig. Congratulations.

[Tig Notaro]

Yeah.

[Jameela Jamil]

You have one.

[Caitlin Riley]

I do, yeah.

[Jameela Jamil]

And it's great. That actually brings us perfectly to a close. You've both been a delight. This has been so funny that I've had to keep my arms crossed over my stomach because I've been laughing so much.

[Tig Notaro]

Oh, you might have a bubble in your stomach.

[Jameela Jamil]

Yeah.

[Caitlin Riley]

An air bubble.

[Tig Notaro]

Yeah, an air bubble.

[Sponsor Voice]

Yeah.

[Tig Notaro]

You don't want to let that out.

[Jameela Jamil]

No, exactly. I will never say any of the other words for that. That's what I'm saying from now on. And I'll finally be a lady. Before you go, will you tell people where they can find you and what you have that you want them to listen to and watch? Caitlyn.

[Caitlin Riley]

Oh, God. You can find me out there. You can find me out there on Instagram. It's. Hi, Caitlin Riley. You can find me there. And I'm just kind of here doing my thing, you know? You can watch season five of Hacks. You'll see me on there. I'm there. And are you directing all of this

[Jameela Jamil]

to the woman who was in the crowd at your school?

[Caitlin Riley]

Yeah, you can see me there.

[Jameela Jamil]

And Tig, can't find you on Instagram anymore.

[Tig Notaro]

Can't find me on Instagram.

[Caitlin Riley]

What a loss for all of us.

[Tig Notaro]

I know. It's so funny because I wasn't verified and it was just my cat's name.

[Jameela Jamil]

How is that possible?

[Tig Notaro]

Well, because they would offer. I didn't want to be verified.

[Jameela Jamil]

I didn't.

[Tig Notaro]

I didn't. I just didn't want to.

[Jameela Jamil]

You like the mystique?

[Tig Notaro]

I was just like, Yeah.

[Jameela Jamil]

I started. Too many people want me.

[Tig Notaro]

Too many. Too many pictures. I was. I started to post pictures of my cat, and I was like, I don't need to verify this. Anyway. Can't find me there. But I am on tour. You can go to take notaro.com I'm hitting all the minor markets.

[Jameela Jamil]

Great.

[Tig Notaro]

And before I build up to the major market part of my tour.

[Caitlin Riley]

Pakistan, Iran.

[Tig Notaro]

That is correct.

[Jameela Jamil]

Yeah.

[Tig Notaro]

And then I do have a podcast called Handsome and we also are available on Hulu. Yeah.

[Creative Planning Representative]

A day early.

[Tig Notaro]

We're available on Hulu a day early.

[Caitlin Riley]

Before the episode.

[Tig Notaro]

That's correct.

[Caitlin Riley]

Wow.

[Tig Notaro]

I know you guys.

[Jameela Jamil]

It's hilarious. It's with Fortune, Feamster and. And May Martin, one of my very, very good friends. You're both absolutely hilarious. I can't believe I got you both here, especially together. What a fucking dream come true.

[Caitlin Riley]

It's been such a dream.

[Jameela Jamil]

Yeah.

[Tig Notaro]

Thank you for having me.

[Jameela Jamil]

Goodbye.

[Tig Notaro]

Goodbye.

[Caitlin Riley]

Get out.

[Tig Notaro]

Okay. Will do.

[Jameela Jamil]

Wrong Turns was created and produced by me, Jameela Jamil and Stuart Bailey. And thank you to consulting producer Colin Anderson. You can email us a voice memo of your own wrong turns. All you have to do is email personal disaster storiesmail.com you can find full length videos of our episodes on YouTube. And don't forget to subscribe, like review wherever you get your podcasts and tell your friends about us. And if you are also enjoying me as a person, I have a substack. It's called a low desire to please. That's enough of me. I'm gonna fuck off now. Bye.

[Creative Planning Representative]

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