Brooke and Jeffrey: Second Date Update - Second Date Update: Food Court Cutie

Episode Date: October 19, 2026

Susan said her date asked her a STRANGE question at the end of the night and was VERY disappointed by her response… You’ll hear the question and her answer in your Second Date Update!See omnystudio.com/listener for privacy information.

Lisa, tell them about our new show. We have a new podcast. It's called Don't Lie to Me. I'm Lexi Youanu. We're two best friends, 22 years apart, but so close at heart. And I'm Lisa Di Giulio, the old one, which means we have wildly different references, occasionally different opinions, and at this point in my 50s, I've lived it all. Now in my 30s, being the founder of new shoes, good taste is my business.

Listen on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. If anyone wanted to commit a murder, up here would be the greatest place in the world to hide the body. But no one will find it. He acted friendly. He talked friendly. He sounded friendly. They all knew that I did the scary boogie stuff. And I said, maybe she'll find out where this girl is.

I saw him violent. Backhanded a pow! Listen to the devil's quarry season two in the Bone Valley Feed on the iHeart Radio app. Apple Podcasts, or wherever you get your podcasts. The WNBA playoffs are here, and Good Game with Sarah Spain is the only daily podcast that'll keep you up to date on all the action. We'll make sure you're the smartest fan at the bar

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We get it. You have a lot of podcasts to choose from. So many. Too many. But low key, this is not your typical podcast. We want you to listen if you want to. We won't make you. That's why it's called listen if you want to.

And here's why you'll want to. We'll be your BFFs to tell you what to watch. We'll tell you who you need to care about when it comes to celebrity stuff. Sometimes we'll just talk about random things and you'll actually give a shh. Listen to. Listen if you want to on the IHeart Radio. Apple Podcasts or wherever you get your podcasts. Why have so many crop circles appeared around Britain?

How did thousands of people demonstrate powers of telepathy? Can the dead suck the life from the living? Join me, Tim Harford, for a trip into the paranormal throughout Halloween month on Cautionary Tales. Listen to Cautionary Tales on the IHeart Radio app, Apple Podcasts, or wherever you. wherever you get your podcasts. All right, it's Monday.

We have a brand new second date update for you. But first comments, I am JJ as me. So just clarification there. That's kind of redundant. I've been sick for the last two days. And all I've been listening to while I've been battling this ailment is your full episodes. Who needs health insurance when you have Brooke and Jeffrey?

It depends. Are we making you feel better or worse? Right. I think JJ, you might need to. Uh-oh. That's why the sickness is lasting so long, JJ. He's like, now I'm throwing up for some reason. It's Brooklyn influenza in the morning.

Yeah. Brooke and Jeffrey in the morning. Second date update. I appreciate when women email us for a second date, and they include a detailed physical description of the man that they met. Okay. You like that part? Yeah.

Like a police report. Caucasian male, six foot two. Last scene near the salad bar at Sizzler in a maroon flannel with the top two button's undone. Hold on. I'm sketching it right now. See, that's the mental image that I need to want to help you. Is that what you got from this last email? It's exactly the type of mental image I got from our listener, Susan, when she messaged dust. So first of all, Susan, thank you for being so thorough in your description and welcome to the show. Thank you. Hi. Okay. No, thank you. Usually I remember people that way because I actually think they're sketchy and I may have to make

a police report liner. But should we get her? her to describe herself in a belief report? We'll get to that. Let's still focus more on this guy you met. Tell everybody else the physical description that you gave of him. Oh, yeah. He was tall and dark and handsome.

That is the three most generic. Let a cook. No, no, no. But he had green eyes, which I thought was so interesting. Yeah. The green eyes were piercing. Oh, wow. Okay. Okay. And is this is this a description from the pictures

you saw on his bio or is this a description from when you got to see him in person? No, this is when I met him at the food board in the mall. Oh, that's how you guys met? Or is that your date? No, no, no, that was not our date. No. I work sort of nearby and, you know, every once in a while, I just hop over to the mall to pick up something to eat for lunch.

And I guess he was doing the same thing. Oh, nice. So I had gotten a salad and I couldn't find anywhere to sit. and there was an extra seat at his table. And he kind of just made room for me to sit. So he's beautiful and thoughtful. Wow, what a gentleman. He's like, would you like me to feed you by hand?

Piece of lettuce by piece of lettuce. That's hot. So did we learn his name yet? His name is Tim. Okay, Tim. Okay. And what's conversation like during this lunch? We kind of just asked like, oh, come here often.

Yeah, I just found out that he works in marketing. He also works nearby. And again, we were both on lunch. We didn't have a ton of time. So, as I, you know, we were finishing up. He asked her by number. When did the hotness come in? Like, when did you guys start flirting or when did you move to a?

Well, she said that this wasn't the date. She said this was just a meeting. Maybe that happens. Like, what did you consider as your date? Well, okay. So it wasn't really like a planned date. Nate, he just kind of texted me later on, like a few days later, and said, hey, I'm out with friends. We're just out for drinks.

Do you happen to be free? Would you want to join us? Oh, interesting. Is that, I mean, in the ladies' minds here, is that a better thing to do to act like, hey, just join me in something I'm already doing? Or would you prefer a guy, like, plan something specifically for you? I don't know. Going out with someone's friends is pretty fun.

Yeah. I mean, I think you can see all their friends, which tells a lot about them. Okay, good. Or see if they have hotter friends that you'd rather do. instead of that person. All right. Well, cool. Yeah, I mean, I actually

liked the idea because it just felt very casual and low pressure. And so I just joined in. I was like, yeah, sure, let me. Did you go by yourself or did you bring a girlfriend with you? No, I just want by myself.

Brave. Oh, that is brave. It was great. That's awesome. So tell us about it. How did it go? I mean, it was fun. Like, he had two guy friends with him

and there was another girl there. I couldn't really tell. like one of the guys might have been with that girl. They might have been dating. It was like not totally clear. One of the guys as in Tim may have been dating the other girl? No, no, no. No, one of Tim's friends.

Got it. But I actually, you know, Tim and I actually really did talk a lot. Like I didn't really connect with a girl and the other guy, like all that much. But, you know, things got a little flirty. What does that mean? You know, just he was very complimentary, you know, about my. hair and I was wearing, yeah, I was wearing like a blue dress and he said, oh, like, brings out your eyes. That means he made a point to compliment you. Yeah, he noticed you have hair and you

he noticed the color of your dress. He was looking at me. He was totally looking at me. That's huge. Yeah, it was good. Okay. I mean, how does this night end? Okay, so this is where things get a little bit confusing. He walked me to my car and he kind of just like hinted like, what do you think, like of my friends? Yeah. And I said, oh, they're really nice. It was a fun night. Thank you for inviting me. And then he repeated, do you like them?

And I looked at him and I was like, yeah, like they seem nice. Like, you know, like I spent like an hour and a half with these people. I don't know them that well. But I didn't know what else to say. I just said, yeah, they were really nice. But he kind of looked at me really skeptical. Like he didn't believe you, you mean? Like he was expecting something else.

It was just very confusing. Maybe there's a chance he was reading your body language differently during the date than the words that came out afterwards. Did you roll your eyes after every time another one of the guys talked? No, no, definitely not. No. Sometimes I do that. I don't realize it's happening. No, I was genuinely having a good time.

I did not roll my eyes at anybody. I swear you guys. And then it just ended. He gave me a hug. Then we said goodbye. And then honestly, I thought. I would hear from him again, and I haven't. Wow.

Well, the way you're describing it, it sounds like maybe he was trying to kind of test this as an initiation process to see if you would mesh with his friend group well, and you weren't giving the right. I mean, why would. It sounds like the way she's describing it. Why wouldn't he be calling her back after that? Well, I could see the friends like talking crap about her for sure.

Oh, yeah, because of a blue dress, maybe. Let's find out. We'll come back. It's a nice blue dress. Nobody ever says anything bad about it. Yeah, sure. his friends were nice too, weren't they? So let's find out what's really going on while Brooke rolls her eyes about it.

Did I do it again? I didn't mean to. It's going to happen a lot when we come back and do your second date update right after this. Brooke and Jeffrey in the morning. Second date update. We don't hear about these a lot on this segment where a first date happens in a group setting. Oh, yeah. Especially when our listener went by herself.

She didn't even bring a friend to the group setting. Right. That's brave, man. Because our listener, Susan, told us she got invited. at the last minute to join a guy where he was like, hey, you want to grab some drinks with me and my friends? Yes. And this is a dude she just met at the mall food court.

But a hot dude she just met at the mall food court. Tall, dark, and handsome, with green eyes. Yes. I remember. I want to say, it was a genuine meetup. We don't hear that a lot either. All green flags and green eyes. So she was fearless.

Well said, Jeff. And she said yes, and ended up having a great time. But afterwards, as the two of them walked to her car, he asked not once but twice. So, what do you think of my friends? You like him? And I guess he seems skeptical when Susan said, yeah, I like him. Man, I have a feeling that he planted one of his, like, crazy friends that normally isn't invited to stuff and was like, let's see if she can handle it.

Okay. If it's a guy that does weird tests like that, you don't want to go out with a big guy, you know. But if she can handle the weird guy, I think that's a good sign. I mean, Susan, what are you thinking? Where is your head out before we make the call? I don't know. I just, I find it really strange. Totally. Because he was the one that was initiating all of this.

He asked you out first. He suggested a friend group first. And then he drops off. Come on. Totally. I thought he liked me. I really, like, that's the message that I was getting. Yeah, he did like you. He wouldn't invite you to meet all of his friends.

Totally. Totally. So what change. That's what we have to find out. Yeah. And there is a chance that if we can get him on, you might need to lay it on a little thicker, Susan, about how great his friends are. You think you can do that?

I mean, they were okay between us, but sure. But with him on the phone, I would do a little more gushing about it. Maybe he's insecure about the people he hangs out with it. It's possible. Some people are like that. But let's find out. I'm going to dial this number. Here we go. Hello?

Hey, is this Tim? Yeah, who is this? Hey, Tim. My name is Jeff from a radio show called Brooke and Jeffrey in the morning. Hey, welcome to our friend group, Tim. Hey, that's our weird friend. We all got a weird friend. Just ignore her.

Focus on us. Wow. Yeah. We're a lively bunch. We're already awake, by the way. Sorry. And we're hoping that you'll be a part of this segment we're doing. It's called a second date update.

And we're reaching out to you on behalf of one of our listeners that you went out on a date with recently, a woman named Susan. Okay. That was a long pause. Yeah. Do you remember Susan? It wasn't that long ago. Yeah. Are you sure?

Maybe he's just one of those guys that does the weird pause at the wrong time. Brooke, I don't want him to hang up. Let's not start calling people weird. I don't know. He's weird. I just said the pauses. The implication was there. So again, I apologize for her, Tim.

But this girl, Susan. You know we just called Brooke weird? Yeah. Well, that's justified. So this girl, Susan, you met her at the food court at the mall. And then you took her to like a group thing with your friends and she had a blue dress on. So she had you guys call me. Right, because she told us about your hangout, had a lot of nice things to say, but she just doesn't know why there hasn't been a second meetup afterwards.

So she likes me? What? Wasn't that obvious? Yeah, bro. Yeah, like you guys met at the food court, you asked for her information, and then you asked her out to drinks. It's a big deal when a woman drops everything that she's doing to come meet up with you and your friends. like out of the blue. Maybe you're just insecure and you didn't realize it.

Like that's... Weird and insecure. No, I just... What are you doing? I'm saying, like, maybe he's one of those guys that doesn't realize how hot he is, you know? Because she described you as very attractive. It's kind of like Jeff. Not.

I was trying to set her up with one of my friends. Oh, my God. Oh, you weren't? Wait. Why would you tell her that? Yeah. It was obviously not clear to her. I guess I didn't say that explicitly, but I sat her next to him and he was trying to talk to her.

Oh, God. Oh, this makes so much more sense. No, he's the worst wingman ever. Yes. Tim, it totally came out that you were interested in her. She's not my type, but. Oh, what's my buddy. My buddy's a he just has a lot of trouble with women.

And that's why I hang out at the mall because I see a lot of business women there, chat them up, and then I just go from there. Wait, I think you'd be better at this thing. I'm sorry. You've done it before. This isn't your first time meeting a woman at the mall and setting them up with your dud of her friend. Oh, my gosh. Brooke, careful. Hey, if it works, it works.

Well, it didn't work. But that is where the if comes in. It's good to tell the woman. Okay, listen. This is clearing a lot of. I could see where, like, that is a really nice thing to do for your friend. Honestly. Stop rolling your eyes, Brooke.

Keep going. The problem is you're not being very direct with your intentions. Well, I'm not going to ask her what she thinks of him right in front of him. You had a chance with you. You and her at the food court one-on-one to say, I have a friend. And you've seen perfect for him. No, she hadn't met him at that time. She met him later.

Yeah, I get that. I get that. It's when you show a photo. You say, this is my friend. Oh, my gosh. I can't explain we manning. I feel like we're making backwards process. We're mansplaining.

wingman. Yes. May I. Let's try to just normally explain to him this situation that Susan is currently on the other line of this phone call right now, Tim. And she was waiting to talk to you. Great. Did you ask her if she likes my friend?

Oh, my God. No, we thought it was for you. Susan, talk to him, please. Oh, my, oh, my God. What the? I just, I'm sorry, guys. I'm speechless. Like, what kind of dumb ass are?

are you? Whoa. Whoa. Okay. I'm here with Brooke. This is a rose. That one was a little low, Susan. Yeah.

I mean, no, but like this, this is like a really good reminder of why I've taken a break from dating because guys are just so dumb. Oh. We are. No. Susan, if I wanted a one-on-one with you, I'd have asked you for a one-on-one day. If a date with a group of friends is code for I want to set you up with someone. Code?

What? Wait, what? That's a code. I'm going to tell you on behalf of women everywhere, it's not. Is it a guy code that I just haven't heard about? I think it's a tip code. We're not in on that. I just don't understand, like, why couldn't, I don't understand why you couldn't just say to me,

hey, I'd love for you to meet my friend. Would you want to come out with us? Yeah. I did say that. And I asked you twice by the car, wink. Wink. Wink. Wink.

Wink. It's too subtle. a secret. Is he weenking now or did he wink then? Oh, goodness. Yeah. Well, get out of here. I don't think Susan should maybe pass up this opportunity.

What if the friend is an upgrade? Yeah, honestly. You might be a more direct communicator than Tim is. Not even direct, just uncommunications. Just speak more than five words all in a row. Uh-huh. So maybe that's something you should consider. Look, Dave is very shy.

And he doesn't go on the apps much. But I mean, if you're interested, I mean, I saw you kind of ignore him, but maybe if you got to know him, he likes pickleball. Maybe he's not a total bozo like you are. Yeah, okay. Wait, his highlight is he likes pickleball? He has a good job. Okay.

He actually works at the mall. He's clean. He wears deodorant. Oh, wait, he works at the mall? Yeah. He was the one that texted me that day because he was watching you from the door. Oh, God. He was in Spencer's gifts. You don't say that out loud, too. It's like a security camera. You're the worst weak man ever. No, don't do it. Oh, wow. I mean,

it must mean a lot that a guy went through the trouble to get his friend to go pick you up in the food court and bring you out to the bar just for you to ignore him the entire night. Dude, that poor guy was so just disappointed after your guys' group pay. This is like in middle school. How would I know? You shouldn't. You didn't. But now that you do,

maybe you could give Tim's very quiet friend a chance. Dave, I heard his name was Dave. And if you did, we would pay for it, Susan. Well, he probably gets a discount at the food court. Done? No, listen. Listen, Dave's got to grow some bulls though and text me himself.

Oh, you're so open to it. I mean, how could it get any worse? Right, Susan? I mean, yeah, if you guys are paying, fine, I'll go on the date. Okay. Hey, there is. That's the same of the opportunity that we needed our help. Tim, you are a great wingman. Good job.

You pulled it out. See? You got to do it this way sometimes. You're wrong. You're the master, man. Well done. Brooke and Jeffrey in the morning. Pride is like love.

You feel it in your heart. IR. Radio. Canada's number one streaming app for radio and podcasts, including IHart Pride Canada, your favorite hits, and must-have party. Proudly presented by the PTP Pink Awards on November 5th. Come together, celebrate, love. Take pride with you anytime, anywhere.

Loud and drop. Just ask your smart speaker to play IHeart Pride Canada. Stream us on your phone or listen now at iHeartRadio.ca. Lisa? We should tell them about our new show. Oh my God, Lexi. We have a new podcast. It's called Don't Lie to Me. I'm Lexi Youan. We're two best friends, 22 years apart. So close at heart.

And I'm Lisa Di Giulio, the old one, which means we have wildly different references, occasionally different opinions, and at this point in my 50s, I've lived it all. I'm not going to get anyone you fighting. That is wild. I learned that about you today. Now in my 30s, being the founder of new shoes, good taste is my business. And I've always got something to say. If men were just honest about this, there would be so much more peace in the world.

We're going to talk about dating, relationships, beauty, getting older, and a little wiser. We're best friends, but we don't always agree. Because you told us how accommodating you are. Obviously, I would do what I think I could do to fight the fight, but there's only so much fight I can fight. Don't lie to me. Don't lie to me. Don't lie to me. Don't lie to me. Don't lie to me. Liar. Listen on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. I don't really care. man when's the last time a guy came on our show got roasted for his romantic approach and still ends up accomplishing his mission yeah that's true you know you're right it's smoother than we thought i mean i get it though his poor buddy's so busy piercing 12 year old's ears and clairs all day you think that's the job at the mall he just never gets a chance to meet women his age so he needs a friend to help him out okay yeah you think he was watching from clays

I hope that it's not that. Forever 21. Who knows? Forever 21 closed years ago, Jeff. Get with the time. Wow. We've been in the mall. Come on.

Maybe he works at Nordstrom. I mean, that would be a sweet hookup. That, oh, that'd be nice. Northstrom is not in eye shot of the food court. There's no way that that happened. Yeah, they have their own restaurant usually. They do. They have a cafe and a bar.

Oh, man, I love Nordstrom. Yeah, I know. It's good. I'm going to go back there today. What are we talking about? Oh, yes. We're talking about how he did good. And we want an update from Suzanne if she actually goes out with his buddy.

That's right. We need to find out what happens. And we want to find out what's going on in your love life. If you need a little help with it, email the show. We'll call that person who's not calling you back or that person that didn't know they were on a date with your friends secretly. All of it. Go check out all of our second dates. They're up online wherever you get your podcast at Brooke and Jeffrey.

Lisa, tell them about our new show. We have a new podcast. It's called Don't Lie to Me. I'm Lexi Wanu. We're two best friends, 22 years apart. but so close at heart. And I'm Lisa Di Giulio, the old one, which means we have wildly different references,

occasionally different opinions, and at this point in my 50s, I've lived it all. Now in my 30s, being the founder of new shoes, good taste is my business. Listen on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. If anyone wanted to commit a murder, up here would be the greatest place in the world to hide the body.

But no one will find it. He acted friendly. He talked friendly. He sounded friendly. They all knew that I did the scary boogie stuff, and I said, maybe she'll find out where this girl is. I saw him violent. Backhanded a bow!

Listen to the devil's quarry season two in the Bone Valley Feed on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. The WNBA playoffs are here, and good game with Sarah Spain is the only. daily podcast that'll keep you up to date on all the action. We'll make sure you're the smartest fan at the bar by bringing you interviews with some of the best minds in basketball, including your favorite coaches and players. No one cares what we did last year, if anything, that's a bigger target on our back. Want to know what's really going on in the WNBA?

We got you. Listen to Good Game with Sarah Spain on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. We get it. You have a lot of podcasts to choose from. So many. Too many. But low key, this is not your typical podcast. We want you to listen if you want to.

We won't make you. That's why it's called listen if you want to. And here's why you'll want to. We'll be your BFFs to tell you what to watch. We'll tell you who you need to care about when it comes to celebrity stuff. Sometimes we'll just talk about random things and you'll actually give a shh. Listen to. Listen if you want to on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

Why have so many crop circles appeared around Brow? Britain? How did thousands of people demonstrate powers of telepathy? Can the dead suck the life from the living? Join me, Tim Harford, for a trip into the paranormal throughout Halloween month on Cautionary Tales. Listen to Cautionary Tales on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts.