Dating Apps Are Completely Broken Now | Not Today, Pal

Summary

Podcast Summary: "Dating Apps Are Completely Broken Now" | Not Today, Pal with Jamie-Lynn Sigler and Robert Iler
YMH Studios | November 20, 2025

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Episode Overview

This episode of Not Today, Pal delves into dating in the digital landscape, focusing on the pair’s real-life gripes and misadventures with dating apps and relationships. As former Sopranos siblings, Jamie-Lynn Sigler and Robert Iler bring their sharply contrasting personalities to honest, funny, and sometimes vulnerable conversations about love, filtered expectations, dating disasters, and searching for common ground in the chaos of the modern romance arena.

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Major Discussion Points

1. Vacations, Homebody Tendencies, and Social Pressures

• Jamie and Robyn discuss their recent travels (Jamie’s acting trip to New York, Robyn’s family vacation in Mexico), their mutual “homebody” personalities, and how this relates to their relationship expectations.
• Highlight:
  • Jamie shares, “I never need to leave a house.”
    • [04:00]
  • Both hosts bond over discomfort with people who need constant adventure during trips, revealing that this attitude extends into their dating lives.

2. Dating App Dealbreakers and Filtering Fatigue

• Rob’s frustration with the endless “filters” required when using dating apps is a recurring theme:
  • He finds being a non-drinker and his dog allergy major stumbling blocks.
  • Jamie and Rob discuss how profiles are filled with travel demands, pressuring people who aren’t adventurous.
• Memorable Quote:
  • “The amount of filtering down I have to do when I’m looking at people to date is so bad. And being very boring is one of the big ones.”
    – Jamie [04:37]
• Rob estimates “eight out of ten” women mention travel as a requirement in their bios. [05:50]
• Rob is upfront about his lack of interest in travel, preferring to stay in and relax—an attitude rarely reflected in dating profiles.

3. Dating App Culture and The “Love Connection” Segment Idea

• Jamie pitches a “Love Connection”-style video matchmaking segment for Rob, but Rob rejects it, fearing he’d come off as mean for critiquing women. Cutter and Robyn chime in that it’d be uncomfortable and potentially hurtful.
  • “I’m not trying to hurt bitches’ feelings.”
    – Cutter [07:13]

4. First Dates: The Gift Card Dilemma

• Rob asks Jamie if a man paying with a gift card on a first date is a red flag.
  • Jamie admits it’d raise her “antennae” a little but isn’t a dealbreaker:
    • “It would plant a tiny seed. It’s not a dealbreaker. But I would be like, okay…”
      – Jamie [10:38]
• Rob and Jamie dissect the awkwardness of using obvious paper printouts or dealing with declined credit cards.
  • Jamie reveals she’s often overlooked financial things if she’s attracted to someone, making her an unreliable “average” for these scenarios:
    • “I’ve overlooked tons of things because I am incredibly attracted to somebody.”
      – Jamie [14:49]
• They share personal anecdotes about financial mishaps early in relationships, including Jamie taking Cutter to an expensive sushi restaurant when he had little money. [17:27]

5. The "I Love You" Timing Debate

• The group discusses how soon into a relationship it feels natural to say “I love you,” revealing a split:
  • Jamie confesses she’s always quick to say it—sometimes within a month.
  • Rob and Cutter are more guarded, often waiting for the other person to say it first.
    • "It's always them first, though. It's like, I'm not gonna say it until you kind of force me to say it."
      – Cutter [22:22]
• They try to script kind, honest responses when someone says “I love you” and the feelings aren't matched. AI and ChatGPT suggestions are read aloud and debated for their merits and coldness:
  • “That is… you might as well kick someone in the head.”
    – Jamie [23:56]
  • “Saying ‘yet’ is like, you’re giving her hope for no reason.”
    – Cutter [24:13]
• Rob notes that because he’s slow to trust, saying “I love you” takes time, sometimes only possible with someone he’s known for years.

6. Personal Stories: Vulnerability, Breakups, and "The Ick"

• Jamie admits she usually initiates breakups when she senses the “ick” and only stayed longer than she should have in one relationship where she wasn’t respected, meeting Cutter a month after that ended. [21:44]
• Both hosts share that awkwardness of mismatched timing for big relationship confessions can be hard to recover from.

7. Hilarious Reactions: Viral Clips, Physical Mishaps, and “Memory Lane”

• The latter part veers into fun, with Rob sharing viral video clips of people spinning uncontrollably on playground rides and amusement parks, sparking laughter and concern over potential “brain damage.”
  • “He’s in another dimension, right?”
    – Jamie [35:59]
• Jamie and Rob reminisce about a 2017 Cable Hall of Fame event, with behind-the-scenes commentary on Jamie’s early pregnancy signs and the nuances of “appointment sex.”

8. Quickfire: Getting Pregnant, Vices, and Relationship Milestones

• Jamie discusses knowing immediately the night she became pregnant.
• They banter about weed versus alcohol use in conception, and cycle back to relationship talk:
  • “We talked about dating, getting pregnant, doggy. We talked about doggy style. Overweight ladies spinning out of control on rides. What else did we cover today?”
    – Jamie [41:47]

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Notable Quotes & Memorable Moments

• On modern dating app fatigue:
  • “If you went through a dating app right now, I would say 8 out of 10 girls will mention traveling on their thing. […] I just want to sit, like… and if I were to go somewhere, it would be like, I’m going to sit in the house.”
    – Rob [05:50 - 06:16]
• On first date red flags:
  • “If you have a gift card, like, use it. That’s what I’m saying.”
    – Jamie [10:52]
• On emotional honesty:
  • “I don’t want us to be getting married one day and me know deep down that I said ‘I love you’ when I wasn’t ready.”
    – Rob [31:02]
• On being honest about vulnerability:
  • “I think always putting it on you, be like, ‘I’m fucked up. I’m weird. Like, it takes me a long time.’”
    – Jamie [32:48]
• End-of-episode humor:
  • “You guys keep out there. I think he said something like that, right?” – Jamie attempting a “Love Connection” sign-off [42:15]

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Key Timestamps

• 00:41 – Jamie and Robyn catch up on recent life and trips
• 04:37 – Dating “filters” and the trouble with being “boring”
• 05:47 – Dating apps’ obsession with travel
• 06:38 – Love Connection-style matchmaking pitch
• 09:20 – Rob’s disinterest in dating and wishing to “skip to the three month part”
• 10:38 – Gift card on first date discussion; social and psychological cues
• 13:55 – Deeper talk: whose financial “turn” is it in a relationship?
• 17:27 – Jamie’s story: taking Cutter to an expensive sushi dinner when they just started dating
• 21:16 – Saying “I love you” too soon or when not fully felt
• 23:25 – Best and worst ways to respond to “I love you” if the feeling isn’t mutual
• 35:05 – Watching viral videos; physical comedy/reflection segment
• 38:01 – Torch-passing: memory lane and Sopranos event anecdotes
• 39:43 – Conversation about pregnancy “light switch moment”
• 41:47 – Rapid-fire recap of all “important” (and hilarious) episode topics

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Tone, Language, and Dynamic

The podcast maintains its hallmark balance of sincere reflection and sharp-edged humor throughout—Jamie’s warmth and Rob’s Oscar-the-Grouch cynicism set against real-life relationship and dating scenarios. Listeners are treated to a rare mix of candid storytelling and playful ribbing, with both hosts openly revealing insecurities and moving quickly between gravitas and laughter.

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In Summary:
The episode offers a funny yet honest look at why dating apps feel broken for so many, especially those who don’t fit the adventurous mold; the real awkwardness of first dates; emotional pitfalls of opening up too soon; and why, sometimes, the best relationships are the ones that manage to find humor in life’s messiest moments.

Transcript

[Jamie]

Give it up for Chicago. Sebastian Maniscalco's new stand up special, It Ain't Right is coming to Hulu on November 21st.

[Announcer]

Thirty years ago, Jeff Bezos, complete nerd. Bezos now ripped to shreds on his super yacht.

[Jamie]

And the boxes keep coming. Sebastian Maniscalco, it ain't right premieres November 21st. Streaming on Hulu and Hulu on Disney. For bundle subscribers 20 terms apply. Hey, Amy.

[Robyn]

Hi.

[Jamie]

How was New York?

[Robyn]

Oh, New York was good. It was really good. So great to be back there. Yeah, I was there for, I don't know, five days. Yeah. Longest, like, time I've been there solo, so it was nice. It was really good.

[Jamie]

A lot of just hotel resting time.

[Robyn]

Or did you do some hotel resting time? I was on Long island for a couple of days because I'm doing a film, hopefully this indie film next year, and the writer director wanted to do sort of a proof of concept thing for the investors to see if, like, you know, show them what a scene of the movie would look like, you know, to raise more money. So I got to do some acting with my Long island accent, so spend some time with my family. And then I was in the city for a couple days.

[Jamie]

So when you know that you have an upcoming acting with Long island accent, do you even think about it or you're like, I show up on set, I just did it.

[Robyn]

No, you know, what was interesting was, like, a couple of days before, I didn't even. I. I constantly have this awareness of my accent because first when I finished Sopranos, I really tried to rid myself of it because I was getting that feedback in auditions. Like, her New York accent's, like, crazy. So I was trying to now consciously drop that, and it just felt so relaxing to, like, not talk like that and, like, talk more like this and, like, sit with my family and be like, yeah, yeah, it was wild. It was like. It was like an undoing.

[Jamie]

I think you should just bring it back.

[Robyn]

I know. Do you want me to do this entire episode on my Long Island Access?

[Jamie]

Yeah, you're done auditioning.

[Robyn]

All right, let's do it.

[Jamie]

Just be yourself.

[Robyn]

You're right. Fuck it.

[Jamie]

Yeah. Be Long island yami. Yeah, I love it. And then. How was Mexico?

[Robyn]

Mexico is awesome. Except apologies if you keep seeing me itch myself. I'd never been to Cancun, and the mosquitoes are wild there. Like, just, I'm covered in mosquito bites. But it was awesome.

[Jamie]

Everybody in the booth thought you were going through withdrawals, but they're happy to know it's just bug bites.

[Robyn]

Maybe I should. Yeah, maybe both.

[Jamie]

Yeah.

[Robyn]

What.

[Jamie]

What was. What was Mexico all about?

[Robyn]

Mexico is a. One of my dear friends, Stacy. It was her birthday, and so her and her family rented this beautiful house on the beach and invited us and a couple of other families to go with all the kids. So it was just a really lovely, relaxing time. We haven't done anything like that, really, ever with the kids. So it was. It was awesome.

[Jamie]

Back last night, Cutter said the girls were a little nervous before the trip. Right.

[Robyn]

Well, so we were supposed to go to Cabo, and then there was, like, a hurricane there, so we sort of, you know, redirected the trip. But, yes, the girls were nervous because of, you know. I mean, you hear that possibly Cancun's not very safe, but that wasn't.

[Jamie]

Out of nowhere. Didn't they, like, make an announcement, like.

[Robyn]

Like, the cartel?

[Jamie]

The cartel was like, yeah, we're gonna start going after Americans.

[Robyn]

Yeah, yeah, yeah.

[Jamie]

Like, let's go.

[Robyn]

But we obviously didn't leave the resort or the home that we were in. Yeah. Well, that.

[Jamie]

That's something else I wanted to ask you. So let's say you were in a house that had everything you needed.

[Robyn]

Mm.

[Jamie]

How. Because you know how people are always like, I need to get out of the house. Never get out of the house.

[Robyn]

I never need to leave a house.

[Jamie]

I feel the same. But how long do you think it would be really, before you were like, all right, I need to go do something. Because when some people. Some people say, I never have to go, and then they're like, well, after two days, I have to.

[Robyn]

No. And I have friends that can do that with me, and then I have other friends that are like that. Like, I have had times where we've all gone away together, and friends were like, I can't do that again, because we were in the house every day, and I was like, oh, I loved it.

[Jamie]

I know. I hate. I hate when people are like, oh, I need to get. By the way, if it's like, three days and somebody says that, it's like, okay, I understand. But some people are, like, an hour after you get somewhere, they're like, but we need to get. I need to get out. I'm like, we just got in.

[Robyn]

I know. And I also realized I'm like, I'm really boring. Like, I'm not the girl you want to invite to party with for a myriad of reasons. But, you know, I. I started to get down to myself, and then I was like, no, fudge it. I don't even like it. Like, what, what does it matter?

[Jamie]

Like, the, the amount of filtering down I have to do when I'm looking at people to date is so bad. And being very boring is one of the big ones. I mean, the drinking is number one. The drink is like, when I. As soon as I see somebody is like all their pictures of them drinking, I'm just like, we're not. When I see somebody with a dog that I'm allergic to, I'm like, no, this isn't going to work.

[Robyn]

Well, this is good though. I think these are positive things to really.

[Jamie]

It is. Unless you actually want to date because it's, it gets to a point, but.

[Robyn]

Like weeding them out though.

[Jamie]

But I'm telling you, and I know I about this a lot, but every woman is like, hope you're ready to travel. Hope you're ready to do this. And I'm like, I'm not. I'm not going. And I'm not gonna lie and be like, yeah, no. And then like start hooking up with her and then be like, actually, I don't lie. I'm just like, hey, no, yeah, yeah.

[Robyn]

You'Ve got to be.

[Jamie]

I know, but there's.

[Robyn]

There's no way that wouldn't be what I lead with, do I. Are there places in the world I want to see? Yes. I actually think I would be more into travel if it wasn't as hard as it is for me. Physically.

[Jamie]

Yeah.

[Robyn]

But traveling, listen, it's hard for us. Traveling has never been like number one for me. But some people, it's the most important.

[Jamie]

On, on dating apps, you have like a bio and like the. Before they're like, hey, the first thing is like, hope you're ready to try. I could work from anywhere.

[Robyn]

Hope you're ready to be running into this a lot.

[Jamie]

It's. It's. If you. Again, I say this all the time, but if you went through the dating app right now, I would say 8 out of 10 girls will mention traveling on their thing. And it's like every single picture is like my, my whole. I. I've seen 136 countries. Hope you're ready to see the rest with me. I'm like, there's that many. Like, I'm just, I'm so. Yeah, I'm just. I just want to sit, like. And if, if I were to go somewhere, it would be like, I'm going to sit in the house.

[Robyn]

Like, okay, I have an idea. I would love to have like a love connection show type thing. I can Be Chuck Woolery and. Can we just get some videos? No, no, it's like just some videos sent in. Can women now that you know. Okay, you can't have a dog that like sheds. You can't.

[Jamie]

You can't have a short hair dog.

[Robyn]

You can't have a short haired dog.

[Jamie]

No, no, we can't do it.

[Robyn]

Don't trap. Why? I just want some videos. I'm not saying you have to go out with them. Let's just try, you know, because then find your soulmate.

[Jamie]

Because then I have to be mean and be like, no, you know what I mean? It's not nice. It's not. I'm not gonna. I'm just gonna sit here quiet, you know what I mean? It's not gonna be okay. Yeah, it's gonna be. It's gonna be me critiquing women, which is not gonna turn out. I'm telling you. It's gonna be me.

[Robyn]

Couldn't wear a suit and a wig.

[Jamie]

Oh, yeah. Maybe we get somebody. Maybe we get somebody else. You could find dates for any. Maybe you find dates for any.

[Cutter]

Oh, oh, I'm good on that.

[Jamie]

Yeah.

[Cutter]

Yeah, I'm chilling on that. I'm not trying to hurt bitches feelings.

[Robyn]

You know what I'm saying?

[Jamie]

That's what. Yeah, it's not. It's not nice. You know what I mean?

[Robyn]

Where.

[Jamie]

When, Like, I don't know because also, like, I'm not at the age where it's like, going out on a date would be fun. Like I'm. I don't look forward to it. Like, I'm like, I have to. Like whenever I finally. It does break through. Like, it happened recently where like, I'm like, all right, I'm gonna go on a date. Because it seems like this is working. I'm. I'm not excited at all. I'm like, like, this is whack. Like, it's. It's just. I don't want to tell my story. I don't. I'm not really looking forward to getting to know. So I wish I could just cut to like the three month part where you're like three months in and you guys get each other and that. We're like sitting down and being.

[Robyn]

Listen to my podcast.

[Jamie]

No, that's the worst. That's the worst. I was dating a woman who heard this and it ended up really bad. Yeah.

[Robyn]

Did you talk about her?

[Jamie]

No, I think it was the opposite. I think you were like, so you see anybody? And I was like, nah.

[Robyn]

Well, you could just be like, I Want to keep this private, Jamie, you.

[Jamie]

Think just talking rationally works all the time? Because I'll tell you right now, talking doesn't. I, I, that's what I did. I was like, oh, well, I, I cuz before that I had talked about dating somebody. I'm like, that didn't work out well, so I'm just going to leave it now. And she's like, oh, so I'm, I'm no one. I'm nothing like, you know. And you're like, yeah, okay. Nice knowing you. Go travel.

[Robyn]

You're going to have to know though this to be with a woman, you got to deal with the es and the flows and, and some emotions. She's not always going to be. Yes, you. She's not always going to be perfect.

[Jamie]

No, I don't need perfect. I just can't deal with crazy.

[Robyn]

We're all crazy.

[Jamie]

That's why I'm single. Yeah, it's nice. Listen, me and any were talking about it the other day. It's, it's nice when you don't have to think about other people's feelings and you could just go and do your thing. I could wake up at 11am and none's the wiser. You know, nobody's on my shit about it. Yeah, I can just fucking, you know.

[Robyn]

Always have a comeback that I can't argue with.

[Jamie]

You know, listen, it's, you know, it hat. But, but you know, here's the thing. I think when it does, when it does happen, it is really good because I'm like, oh, I know this is like working. You know what I mean? Like, you saw the last time I was dating somebody, I was very happy.

[Robyn]

And it was very happy.

[Jamie]

But then when I'm not, it's like, it's, it's like, it's like it feels like a crowbar like, like trying to get. And I'm like, all right, I, I guess I could do this, but it's, it feels like a lot. But then when it's going, it's great. Yeah, it's just that initial.

[Robyn]

I feel like you're ready. You're ready for one now.

[Jamie]

I don't know, maybe when I'm like 50. Maybe when I'm 50, I'll do it. Okay, we'll be back. So no, speaking of the, of this. So I did the podcast with the first podcast without you.

[Robyn]

That's right.

[Jamie]

Last week.

[Robyn]

How was it?

[Jamie]

It was good.

[Robyn]

Yeah.

[Jamie]

Sal's really good. If it was somebody else, that's the thing, I wouldn't have done it. If it was somebody else, it was just because Sal was here and I knew he'd be great. We went for an hour and a half.

[Robyn]

Wow.

[Jamie]

We had really. It was fun.

[Robyn]

That's awesome.

[Jamie]

But here's the question I asked him. Now we get the woman's perspective. If you were going out on a date with a guy for the first time and he uses a gift card at the restaurant. Yeah. See, I know you could be honest. I know that that got you a little.

[Robyn]

And he picked it.

[Jamie]

Yeah, well, the guy has. You can't pick the restaurant on the first date. It's always. A guy is going to be like, we're going here.

[Robyn]

Like, why can't I pick it on the first date?

[Jamie]

We talked about that. Women don't like that. Women don't like when a guy's like, hey, so where do you want to go? What do you want? It's like, hey, we're going to go here.

[Robyn]

It's going to be this time. I mean.

[Jamie]

Yeah, see, guys, this is.

[Robyn]

It would. It would plant a tiny seed. It was not a deal breaker. Wow. It's not a deal breaker. But I would be like, okay, and how. But also, like, if you have a gift card. You got a gift card, like, use it.

[Jamie]

That's what I'm saying. So what's the seed? What's the seed that it plants?

[Robyn]

Just my antenna antennae are up. You know what I mean?

[Jamie]

Like, what does it say?

[Robyn]

Is he a cheapie? Is that. Is that what you're fishing for?

[Jamie]

No, I'm asking, honestly, is he.

[Robyn]

I don't know. Is just. I don't know, like.

[Jamie]

Oh, because you're thinking, did he pick this because he had the thing? Yeah, I didn't even go to that thing.

[Robyn]

Oh, where would you go?

[Jamie]

Just. Just that it's. Because here's. Here's what I said, right? If. If it's one of those things where, like. Because sometimes they just give you like a credit card type thing. If I could just hand that. And like, it's. It's. It's taken care of. Yeah, that's one thing. But then at the place, like, Uchi, if you've ever. If you've ever read the thing there, sometimes you're like, yeah, like, it's only a piece of paper. And like, because you have to print it out and then it's like, oh, yeah, B. There's like a whole bunch of numbers and that would be very.

[Robyn]

A little awkward.

[Jamie]

Awkward, yeah, for sure. But I didn't even think, like, smart.

[Robyn]

He would call ahead and be like, here is the gift card number for my reservation.

[Jamie]

Yeah, but see, that just feels.

[Robyn]

Why are you laughing?

[Cutter]

This is just funny that you called that smart. I would call that manipulative and deceitful.

[Robyn]

But yeah, manipulative people are intelligent usually.

[Jamie]

Yeah.

[Cutter]

You're not wrong. That's not mutually.

[Robyn]

They go hand in hand. Yeah.

[Jamie]

You know what? It was raining the other night. You know, a light little drizzle. You know what I did? I threw on my rag and Bone hoodie when I went out. It was perfect. Kept me warm, kept me dry. Felt good, felt amazing.

[Robyn]

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[Jamie]

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[Robyn]

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[Robyn]

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[Robyn]

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[Jamie]

All right. What if you were at. What if you were at a dinner first date, and the guy gives his credit card and they come back and they're like, oh, we're so sorry. This was declined.

[Robyn]

Oh, I feel so bad for him. I wouldn't judge. I would feel so bad. That's embarrassing.

[Jamie]

But then would you try and dig in and be like, so was that, like, an accident or.

[Robyn]

Back. So back. I didn't date much in my life. Like, I was a serial monogamist.

[Jamie]

But when you did, they were millionaires.

[Robyn]

No.

[Jamie]

What do you mean?

[Robyn]

When I met Gutter, he was dead broke. I think more of. I'm such a vibe person that it. I've. I've made not sacrifices. I've overlooked tons of things because I am incredibly attracted to somebody. So. Though I might be the wrong person to ask about this type of stuff. However, I've never been single for a very long period of time where you're having. Where you're, like, worn out and you're really aware of all these things and, like, immediately being like, nope, nope, nope. Like, I, again, I just would go off of physical attraction and chemistry, and I would overlook that immediately.

[Jamie]

So then do you instantly go, I got it?

[Robyn]

Yes.

[Jamie]

I don't know. Like, I would be so uncomfortable if my credit card got denied, the woman paid, and I don't know if I could do a second date. I guess it would just have to be really good, like, because I think I would be so. And you know what's weird? I don't even care about that. I think it's just, like, the stereotypical. Like, I really don't care if a woman thought that I was broke or my credit cards didn't work. I don't care. But that awkwardness of the, like, oh, I got it. And then, like, do it. Like, I don't think I could come back from just that. Whatever that is. Like, that would be like. And then I'm sitting there like, oh, funny thing. It worked yesterday. Like, I don't even know. I don't even know what, like, where you go.

[Robyn]

I don't know. You know, Cutter and I have had such a. Like, pass the baton of, like, who's doing better? Baton. Baton. My. Longer than I could.

[Jamie]

I could be. Oh, sorry. I don't want to shame you.

[Robyn]

Yeah, stop Judging the way I don't want to be.

[Jamie]

I don't want to Shame. I'm so sorry. This is why, see, I'm the reason. I'm so sorry.

[Robyn]

We. We, you know, very beginning, it was like, it was just clear of, like, who had money and who didn't. And then there have been times where I've been unemployed for a really long time, and he was doing well. And so it just. We. We were. That's just never been a judgment of or just a barometer of anything. Like, I think very. In the very early stages of our relationship. It was just like, whoever can support right now can support type of thing.

[Jamie]

Yeah, no, listen, I agree. 100. And when a lot of time when we talk about these things, it's like, if this happened on the first date, like, if. If this happened on the third date with a girl, I would be like, who fucking cares? Like, I let. You're just something about the first date where it's like, oh, it didn't work. And just.

[Robyn]

Did I tell you ever tell you the story of the first, like, nice restaurant Cutter and I went to, though, with, like, a group of friends?

[Jamie]

I know, I know, but have we heard this? No, I don't think so.

[Robyn]

Right, so there's this place in L. A. Called sushi park. It's like a dope omasaki place.

[Jamie]

Sorry, is that long Island? I'm sorry. I'm sorry. Omasaki. I'm sorry. I'm so sorry. That was long Island. My apologies. I shouldn't do that. That was me shaming you.

[Robyn]

It's a dope sushi place, and it's like, you know, very, like, you wouldn't expect anything. It's in a strip mall on the second floor next to, like, a dry cleaner. It's very small, but it's incredible. And, like, you know, 10 tables, not even. And I had told Cutter, I want to bring you to my favorite sushi place. And so his friend Adam came with us, and my friend Lindsay and I had every intention of paying for dinner because I knew this place is not cheap. It's like, minimum a hundred dollars a person.

[Jamie]

And you said, I want to bring you. Yeah, yeah, yeah. Okay.

[Robyn]

So I had gone to the bathroom, and Cutter wanted to do the nice thing by paying for. And, you know, there was no menu. It's like, yes, they just bring everything. That's right. I didn't want to say it and say it wrong. And when I got back, I saw them bringing the bill to him, and it was like, slow mo Where I was like, no. And I saw him open it and just like, like melt into the chair and just, and I wanted to be like, please, please. Like I, I brought you here. Like, I did not meet, I did not go to the bathroom in hopes you were going to pay this. Like this was not how. And poor thing. I mean, I think he like was overdrawn after that dinner.

[Jamie]

Well, yeah, he was a 22 year old minor league baseball player. Right.

[Robyn]

And his dad just went to jail. Like it was not good times for a guy.

[Jamie]

I know, but was that one of the moments where you were like, oh, he's a good or you don't even care?

[Robyn]

No, I did, I did think it was very kind for him to want to do that, you know, and spend any money that he had to do that. But I felt terrible.

[Jamie]

But you're also like, we've talked about this. We're like two weeks into a relationship, you're like, I love you. Right. Like that's. Yeah, I still think about that. I'm like, that blows me away.

[Robyn]

Yeah.

[Jamie]

Two weeks and I'm still like, do I even like this person?

[Robyn]

Oh yeah, no, I'm, I'm all in.

[Jamie]

Wow. What, what did we ever ask you guys back there? Like what, what do you think a normal or like for you when you say I love you to someone, how long that takes for me?

[Cutter]

As long as possible at least.

[Robyn]

Oh, that'd be nice. It took me five months.

[Jamie]

Yeah.

[Sponsor Voice]

Yeah.

[Jamie]

All right. We got some normal answers back there.

[Robyn]

I don't think it's ever been more than a month for me.

[Jamie]

Ever.

[Robyn]

Ever. Maybe one, maybe one boyfriend, maybe one Scott. Maybe that's it.

[Jamie]

How many? How many? So when you're.

[Robyn]

And it drove me crazy.

[Jamie]

When you're dating somebody, do you always, when you were dating people, did you always fall into the thing of like we're going to be together forever? Like, like a month in, like once you say I love you, are you like, well, I plan my, I'm planning my future with this person.

[Robyn]

I don't know if I was. Would go that far, but I would fantasize what it would be like to have a life with this person. Yes, but have you ever. Because I got married very young, I don't think I ever let myself go there too fast. Do you know what I mean? Like, I think because I had been married and divorced by 24, all the other relationships I had after, I would sure like fantasize and, and put it, assume like you're putting in this time. This potentially could Be the person. But never felt any type of, like, countdown to that needing to happen. Because all my boyfriends were like, you know, two to three year long relationships.

[Jamie]

But have you ever been with somebody and you're like, I love you and things are great, but in your head you're like, I know this isn't gonna last.

[Robyn]

No. No. Because then what am I doing? I'm in it, assuming that maybe this will go the distance. And then when I started to get the ick, I'd be out.

[Jamie]

Really? So it was always you.

[Robyn]

Most. Except for one. Yeah.

[Jamie]

Wow. So how did you handle it when it wasn't you, since you were only not well? Wow. And how long were you with that person?

[Robyn]

On and off a year.

[Jamie]

On and off a year. And they were just like, jamie, I can't do this anymore.

[Robyn]

But no, I didn't even get that. It was. It was more after. After a year, there was a final moment where I was like, wow, this person does not respect me at all.

[Jamie]

I'm out.

[Robyn]

And then I met Cutter like a month later.

[Jamie]

Wow.

[Robyn]

Yeah.

[Jamie]

And you bankrupted him.

[Robyn]

Correct.

[Jamie]

Take him to sushi park.

[Robyn]

Yeah, I picked him up.

[Jamie]

What about. What, you want some sushi? What's the fastest you guys have ever said I love you?

[Cutter]

I don't know. For me, I can't. I can't think of.

[Jamie]

I don't know.

[Cutter]

I don't know. I'm not sure. Probably a couple months, three months, something like that.

[Jamie]

Yeah.

[Cutter]

I don't know. It's always them first, though. It's like, I'm not gonna say it until you kind of force me to say it. And then like.

[Robyn]

Yeah, I've never said it first.

[Jamie]

Right, That's. So you guys would just. You and any would just go forever. No one would ever say it.

[Robyn]

Yeah, I've never said it first.

[Cutter]

Yeah. We play a game of chicken and I don't lose. I don't lose.

[Jamie]

The worst thing in the world is when someone says it and you can't say it back. There's nothing worse.

[Robyn]

You know my moment of that.

[Jamie]

Oh, yeah.

[Cutter]

I've had a few of those. It sucks.

[Jamie]

Yeah, that's.

[Robyn]

That's so bad. That's.

[Jamie]

I'm out. I'm out.

[Robyn]

Really?

[Jamie]

Like, yeah, I'm out for like a. Like, that's. That's a real bad. But I don't know. You know what? It might. I. I don't know, but it might be worse than being like, I love you and not getting it back. I don't know.

[Robyn]

I agree. But I Agree.

[Jamie]

It is.

[Robyn]

I. I would much rather be on the other end than be like, oh.

[Jamie]

Yeah, somebody being like, I love you, and you're like, oh, you do. Like, what is there like, a. Can we ask Chatgpt. What if somebody says, I love you, and you don't love them back? What should.

[Robyn]

What's a. What's a polite response?

[Jamie]

My girlfriend said, I love you, and I don't love her back. What should I say? Oh, man, this is. This is. Man, my eyes hurt just from thinking about this. This is a tough topic, and I.

[Robyn]

Don'T love them back.

[Jamie]

That's a tough moment, says AI. Yeah. And how you respond depends on your intentions and values.

[Robyn]

That's a nice one. I care about you a lot, but I'm not there yet. I really, really respect you for being open with your feelings.

[Jamie]

That. That is all. You might as well kick someone in the head.

[Cutter]

That's cruel.

[Jamie]

That is I respect you is horrible. Listen, I care about you, but I'm not there yet. Is okay. Saying I really respect you is. Is just trash. That is so. That is. You might as well just mush them with your hand, like, in your face.

[Cutter]

I feel like saying yet is up. That's like, we'll get there. It's just not right now. It's like, that's mean. You shouldn't say that. You should just say no. You should try to find a nice.

[Jamie]

Way to say it.

[Cutter]

But saying yet is like, you're giving her hope for no reason yet.

[Jamie]

No, but it might. It might be. It might be that, and that might be the truth. If that's the truth, you don't want to lie and say that. You want to say it if it's the truth.

[Robyn]

But I don't know.

[Sponsor Voice]

I feel like in.

[Robyn]

In the beginning is when the feelings are the most intense. So you would know, like, I'm. I'm in love with this person.

[Cutter]

You're just someone especially. Especially if that comes out and you're not there. That almost, like, poisons it. Like, it's over. I'm never gonna agree.

[Jamie]

Jamie, you're just very different than other people, including me. I'm saying me where, like, you don't have a guard up. I have a guard up. So when you're like, oh, the feelings in the first two weeks, that's when it's all there. Not for me. It's when I can, like, trust someone. When I could be like, oh, you're in my apartment. I could just leave. And I'm not thinking.

[Robyn]

That's my problem.

[Jamie]

Right. That's what I'm saying.

[Robyn]

To earn my trust.

[Jamie]

You have no go. Yeah, someone doesn't need to earn your trust. I'm like, yeah, I really need. That's why, like, some of my favorite, like, relationships have been somebody who I knew for years before. Because right away I'm like, I know I could trust this person. Like, I know how they operate and I'm attracted to that. That's the best. We're like, if I'm just meeting somebody off of a fucking app, like, I'm like, like I'm like watching them when they're like walking around my apartment. You know what I mean? I'm like, I don't trust. I have a full guard up. So like, that is a true statement for me. Being like, hey, listen, I care about you, but I'm just not there yet. Would be, would be true. I wouldn't be like, let's see, what are the other ones?

[Cutter]

But to say yet implies that it's coming, right?

[Jamie]

Well, but it could come. That it could come. I would only say that if somebody said I love you to me and I didn't care about them at all. That's not the response. I'm saying if the true response is, hey, I care about you, I'm just not there yet. That's, that's, I think that's a good response. Guys, the holidays are right around the corner. That means get togethers, gift giving, and the occasional holding your breath hug. Mando's got you covered when it comes to finding a gift that keeps on giving. Not only is it clinically proven 72 hour odor control, Mando is safe for the whole body. Take your pick between invisible spray, solid stick and invisible cream. All available in four cologne quality scents. Bourbon Leather, Mount Fuji Pro Sport and Clover Woods. Guys, I'm wearing Mount Fuji right now.

[Robyn]

Smell it. So nice.

[Jamie]

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[Robyn]

We're wearing his hoodie. I smell it.

[Jamie]

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[Robyn]

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[Jamie]

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[Robyn]

It still sting a little.

[Jamie]

Oh, and there is. The whole point is I don't think there's anything you could say where it doesn't sting. Is there anything you could say?

[Robyn]

No. But still no, of course.

[Jamie]

Okay. You want to go sushi? You want to go sushi? I love you like you want some sushi?

[Robyn]

You want some expensive sushi?

[Jamie]

Yeah. You want omasake? That means a lot. Okay, another. Another answer is that means a lot to hear. Oof. That. That doesn't sound. That means a lot to hear. I'm still figuring out how I feel. And I want to be honest with you as I do.

[Robyn]

What would you say if a girl. Okay, don't look at the screen. If a girl.

[Jamie]

I'm not gonna take. I'm not gonna cheat. What is this, fifth grade?

[Robyn]

Have you seen those memes, though, or not memes? Or those, like, reels of people that use chat GBT for everything? So, like, they walk in a store and they, like, see a cashier, and they look down to see what to say, and then the cashier's down asking, that's gonna be us soon. But so if a girl was like, the girl that you're definitely enjoying dating, it's seeming like it's going well. It's two months in, and she was like, you had just had great sex. You had a great. That's tough because I want to really.

[Jamie]

Set the stage here and way to know my order. I go, I go, sex, then dinner.

[Robyn]

Yes.

[Jamie]

She knows me so well.

[Robyn]

Because you don't want to be full when you're having sex. I know you. So then. And she's like, I think I'm falling in love with you. Like, this has been going so great. I'm so happy. Like, what do you do that I'd.

[Jamie]

Go, listen, I'm so full right now. Ah, man. It's. It's really. I think it really depends on the situation. It depends on the person and my. And our, like. But I think I would. I would go, you're into this girl.

[Robyn]

You're into her.

[Jamie]

I know, but I'm saying, like, what our dynamic is. Like, do we joke a lot? Do we are.

[Robyn]

Yeah, she's perfect.

[Jamie]

Yeah. I think what. What I would lean on is like, listen, I always want to be honest with you, and I don't wanna. I don't want us to be getting married one day and me know deep down that I said I love you to you when I wasn't ready.

[Robyn]

Okay, keep going.

[Jamie]

I'm saying that. So. So I'd be like, I. I just don't want to lie right now and say that I love you if. If I'm not there. And like, I. What did chat GBT safe. I'm not there yet. If I'm. If I'm not, like, I don't know. I would say something like that.

[Robyn]

I'd be like, here's my advice. I think you should say, I never say I love you this early. Like, this is. It's like, not just you like, but.

[Jamie]

That is, that is such a harsh cut off to someone who just said the most.

[Robyn]

I would rather hear that than just. I would hear. Rather hear that and know that this is historically how you are than what you just said.

[Jamie]

Yeah, that's the thing too, is like, I could say, yeah, that's a good, that's a good advice. Where I could be like, I, I don't.

[Robyn]

Man, you're so flustered for the first time. You're speechless.

[Jamie]

Yeah, I'm trying to think of the right thing to say. And in my head I'm like, I don't think they're. I think it's all.

[Robyn]

I think being don't. You don't have to be like, I don't want to regret this one day. Just be like, I, this is not, this is just that type of feeling. Saying that type of stuff just never comes this early for me. Like, I, that's good. I feel great about us in our relationship, but this is just like, yeah, I, I would just really just make it very clear. This is who you are and how you are versus, like regretting saying I love you too early. Why would you ever. If you're getting married, why would you regret that you said I love you too early?

[Jamie]

Because I was lying when I said it.

[Robyn]

Okay?

[Jamie]

That's what I'm saying. I don't want to lie in the moment and say I love somebody if I don't, because then years later I don't want to be, okay, remember, I lied. I was lying there.

[Robyn]

I just feel like always like putting on you be like, I'm fud up. I'm weird. Like, it takes me a long time.

[Jamie]

But here's the problem. That moment is so vulner that I want to go. Like in. I don't want to go if someone's like, I love you, I'll be like, I'm weird, like, I'm kooky because they won't love me anymore. That's an awful, I think that's an awful way to deal with it. I think I would want to be like, you know, like, kind of go in more and be like, listen, I care about you so much, and if we're gonna have a future, I don't want one day for it to seem like if I know that I'm lying right now or saying something that I don't mean, like, I don't. I don't want to regret it. So, like. But I listen again, I don't, I just don't think there's a good and no Matter how I say this, it makes me feel like. Yeah, it's just like a squirmy. What else did they say? I think we're in different places emotionally. That's kind of. I don't want to hurt you, but I also don't want to give the wrong impression about where I stand. Yeah, that. That seems like AI talking. I don't want to give the wrong impression about where I stand. If a guy says that, he's just done. Right, Jamie.

[Robyn]

Yeah.

[Jamie]

Yeah. I don't want to give. Honestly, it's ultimately the kindest thing to do in the long run, even if it's straight in the moment. Yeah. Okay. Let's turn this pot on its head. Let's go to. So, Jamie, I saw this clip that makes me laugh so hard, and it's. I'll just show it to you. It's a guy on a. On a playground here. Sorry. For those who are just listening.

[Robyn]

No, no, this is too much. Oh, no. He's gonna go flying. What the hell? How is he still on there? And why is only one leg dead? What? What happened to the one leg? Oh, my God. Is he alive? I don't like that.

[Jamie]

That is so crazy.

[Robyn]

I'm so upset. He's gonna have. He's never the same. What's happening?

[Jamie]

That's what I'm saying, that I would think. You're never the same, too.

[Robyn]

He's ruined himself.

[Jamie]

How are you not dead?

[Robyn]

He's dead. Oh, this is in another country.

[Jamie]

That's why he's not dead.

[Robyn]

No, that's why he doing that.

[Jamie]

I would think that. I. I don't know how.

[Robyn]

Look at his foot.

[Jamie]

I don't know how that thing lasts.

[Robyn]

Why is he making it keep going? Someone stop him. Oh. Oh.

[Jamie]

If somebody steps in, they're getting rocked.

[Robyn]

This is like what happens when you go to space. And people have to train for months to make sure that they can handle that.

[Jamie]

Come.

[Robyn]

What's h. Okay. Oh, my God. Oh, my God. Oh, my God. Oh, my God. Oh, my God. No mo.

[Jamie]

I'm a little dizzy. I'm a little dizzy just from watching.

[Robyn]

I can't look away multiple times.

[Jamie]

I can't imagine. I don't know how this guy's. But by the way, you know how football players get, like, brain damage? And he's got it. He's got to have a problem.

[Robyn]

That's what I mean. He's up for life.

[Jamie]

When he's 50, he's gonna be like, drinking out of a straw. Right? Look at his face.

[Robyn]

This almost Was worse than the Cheese wheel.

[Jamie]

People look at this guy's face, James.

[Robyn]

His.

[Jamie]

He's. He's in another dimension, right?

[Robyn]

Faces. His skin. He's fucked up his skin. He needs a facelift after this.

[Jamie]

You know where he is right now? He's in the bookshelf where Matthew McConaughey ends up in. What movie is that?

[Cutter]

Interstellar.

[Jamie]

Interstellar, yeah. He's in the bookshelf right now. He's like, don't do it. You know, this guy's fucking gone.

[Robyn]

Oh, yeah.

[Jamie]

I would love. You know what I would love? I would love to interview him right. When he's done with that and be like, hey, what would you do if a girl says, I love you and you don't love her back? And be excited.

[Robyn]

He's not going to speak English. Yeah, well, speak words rather.

[Jamie]

Yeah. Maybe you come up with. Maybe that's how you come up with the. The true answer to things in life. You got to. You. You do that, and then right away you answer. Maybe he'll know.

[Robyn]

I don't. I can't imagine him living many days past this.

[Jamie]

I don't think so either. Yeah, imagine, like he's got to do other crazy shit too, right? If this is. This isn't just the only. So this reminded me of a thing from ymh, a clip from YMH that makes me laugh every time. I hope you've never seen this, Jamie, because it gets me every time. So while everyone else is just.

[Robyn]

Everyone's okay and hers is not. No. Is it because of how big she is? Is it.

[Jamie]

I don't know. I'm not a ride technician. But she looks a little.

[Robyn]

This is so bad. Why didn't they stop it?

[Jamie]

I think she's having fun.

[Robyn]

No. Is there audio? There's no audio.

[Jamie]

Oh, no. But they would have alerted her before getting on the ride if she was too big. They tell you if you're too big. I don't think she's too big.

[Robyn]

The alarm, the lights are. Oh, good, they're stopping it. Oh, my God.

[Jamie]

See, she needs to do what the other guy didn't. Go back the other way. Oh, I love that.

[Robyn]

Wow. Yeah, that was.

[Jamie]

Sorry. For any listeners, we're watching clips, but let's. Do we have a. A memory lane to cleanse the palette a little bit here?

[Robyn]

Oh, I remember this. Robbie, you look so good.

[Jamie]

Oh, thank you. I almost looked tall.

[Robyn]

I was very newly pregnant with Jack there. Really wasn't telling anyone. Yes.

[Jamie]

Oh, did I know.

[Robyn]

Tiny, little bumpy under my jacket. Yes. You probably know this was like the ca. It was something like the Cable hall of Fame or something.

[Jamie]

Yeah.

[Robyn]

So this had to been 2017, because I gave birth in 2018.

[Jamie]

Tony Sirico. Is this the last time we saw Tony?

[Robyn]

Maybe.

[Jamie]

Yeah, it might have been. Yeah.

[Robyn]

No, he was at. Yeah, yeah. No.

[Jamie]

Yeah, yeah. Right.

[Robyn]

Yeah. And this was in Washington, D.C. david.

[Jamie]

Chase was getting an award.

[Robyn]

Or HBO was David.

[Jamie]

Or the Surprise.

[Robyn]

Or the show. David and the show, maybe.

[Jamie]

Yeah. Yeah.

[Robyn]

Are we right? Maybe this was. So if this was newly pregnant, maybe this is like June. April, 2017. April. Okay. So I was just. Just pregnant.

[Jamie]

Do you have the name of the award show thing?

[Robyn]

It just says Cable hall of Fame.

[Jamie]

Damn, James, she's so good. Yeah.

[Robyn]

Yep. That was us there.

[Jamie]

Yeah, this is us, Rob.

[Robyn]

I like that hair.

[Jamie]

Oh, thank you. So you're how many months pregnant?

[Sponsor Voice]

Weeks.

[Robyn]

Like, not even. I got pregnant early April or late March.

[Jamie]

Wow.

[Robyn]

It was. I was like. I remember we were trying. We didn't try the first time, so we had never experienced that. It was like my first month trying. We were at a wedding and I was like, cut her. Today's the day. He, like, hated, like, the appointment sex. Like, whatever about it.

[Jamie]

Now, now he'd love it.

[Robyn]

He would.

[Jamie]

He would do anything for some appointment sex.

[Robyn]

And I swear to God, when we finished, I felt like a light switch go off inside my. But I was like, I'm pregnant. He's like, you're fucking crazy. I was like, I'm telling you, it literally felt like. And I was like, I'm pregnant.

[Jamie]

What position? How do you let people want to know out there? People want to. People want the light switch to go off to get pregnant.

[Robyn]

I. I'm not sharing the position that we were in. I don't think that's what did it.

[Jamie]

I just knew it was some crazy position you don't want to talk about. Huh?

[Robyn]

It definitely wasn't crazy. It's pretty much on the standard top three positions.

[Jamie]

It was doggy, guys. It was doggy. Come on. Yeah, Jamie didn't want to say doggy. It was doggy. Listen, it's the doggy dog world out there, you know?

[Robyn]

Yeah, that's Jack. So. Yeah.

[Jamie]

Oh, Jack. Yeah. I didn't even put it together.

[Robyn]

Well, you don't track.

[Jamie]

You don't. You don't know it tracks. Yeah. You don't know. You know, because I'm sure you had other sex around there. But.

[Robyn]

But, you know, it was the night. It was. No, we knew because it was like, then. And then I got I knew it. Found out I was pregnant. Yeah. Like a few weeks later.

[Jamie]

And how long after, like, if you feel like a woman, a light switch go off like that. How long before a test says, yes, you are? Four weeks.

[Robyn]

But I knew that whole time.

[Jamie]

Wow. And you're like, I gotta stop smoking weed. Right.

[Robyn]

I think I stopped by then.

[Jamie]

That light switch was just so much guilt. Right. You're like, well, I don't know for sure how. Yeah. Like three days later, you're talking yourself out of it. You're like, I don't know.

[Robyn]

Before I stopped. Like a month or two before.

[Jamie]

Yeah. So they say before you try and get pregnant, you should stop smoking weed. Yeah, but what about alcohol? They say it's fine.

[Robyn]

Well, I don't drink alcohol, so I don't know.

[Jamie]

But other people. But they don't give you advice on that.

[Robyn]

I mean, many people get drunk and get pregnant.

[Jamie]

I think most.

[Robyn]

Yeah. Yeah, yeah. Yeah. I don't think there's. I mean, I think. I'm not a doctor, but maybe if you're having fertility issues, you just want to be, like, as clean as possible. But I don't think. I don't know if alcohol plays as much of a part in worrying about a fetus as weed does.

[Jamie]

Yeah. All right, well, listen, that's. You learn. You learn things.

[Robyn]

We talked about dating, getting pregnant.

[Jamie]

Doggy. We talked about doggy style. Overweight ladies spinning out of control on rides. What else did we cover today?

[Robyn]

What you're gonna do next time somebody says I love you. Yeah.

[Jamie]

How to. How to let them down. Let them down gently.

[Robyn]

Let them down easy.

[Jamie]

Yeah. All right, we'll see you guys. How do we say goodbye? I don't.

[Robyn]

What did Chuck. Hillary used to say at the end?

[Jamie]

Two and two. No, but that was a commercial.

[Robyn]

No, how do you used to end Love connection? Can we look it up and I'll do it.

[Jamie]

You guys keep out there. I think he said something like that, right?

[Robyn]

Keep.

[Jamie]

Keep up the doggy.

[Robyn]

We'll be back in two and two. You were right.

[Jamie]

Yeah, but I think that's for a commercial. He would say that. Yeah. Commercial break.

[Cutter]

See you again real soon. Goodbye for now. Reminding you to make that love connection.

[Robyn]

I'll just say we'll be back in two and two.

[Jamie]

Well, this really sputtered out. Sorry, guys. Yeah, hopefully we'll be back next week.

[Robyn]

We'll be back in two and two.

[Jamie]

Oh, wow. That was good. Thank you. Sounds good. It Capone one time at hat, one of the stocks, Ripper at New Jersey Battery.

[Robyn]

Capone one time at hat one of.

[Jamie]

The Stars river at 2J Z.