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Jeffrey
Your favorite artists in your library, your favorite songs in your playlist, but your favorite morning show.
Brooke
They're really funny.
Announcer
Or your favorite team in action.
Michael
Oh my goodness, he caught it.
Jeffrey
Or your live local news, traffic and
Medical Advertiser
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Announcer
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Jeffrey
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Announcer
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Jeffrey
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Announcer
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Jeffrey
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Michael
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Jeffrey
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Brooke
I asked for help.
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Brooke
All right, here it is. It's Brooke and Jeffrey. Thank you so much for finding the official second date podcast. And we have a new video up Today on our YouTube. Yeah, and it's one people have been waiting for for weeks, apparently. Oh, yes. It was when Brooke had to break up with a listener who started flirting with her. Oh, it was so uncomfortable. It was so uncomfortable. Oh, my God. So many people are commenting they couldn't wait to see your and see you blushing. Why are you so happy about that? I'm gonna go rewatch it even though I lived through it. Oh, my God. So go to our YouTube, Brooke and Jeffrey, please. Okay. All right. There it is. And subscribe while you're there, please. All right, here's your second. Here's your awkward. She's flustered again. I am.
Michael
What is it?
Brooke
Awkward Tuesday, right now.
Jeffrey
When it comes to your very best friend, that relationship is so strong. You would do anything, anything for them.
Brooke
Sure.
Jeffrey
You would bail them out of jail.
Brooke
Absolutely.
Jeffrey
You would help them bury the body.
Brooke
Absolutely.
Jeffrey
You would lend them thousands of dollars just because they asked. No questions needed. Reminds me, Brooke, I need to borrow 45 grand. So I'll text you my venue.
Michael
Okay.
Jeffrey
But no question. Well, what. Okay, 40 grand then.
Medical Advertiser 2
Fine.
Jeffrey
What if, though, the one thing that you needed them to do goes against any every unwritten rule of friendship ever? Oh, that's the reason one of our listeners needs our help today. He has to convince his best friend to do him an enormous favor. Even though it 100% goes against bro code. You're gonna hear it in a brand New awkward Tuesday phone call. Next. It's awkward.
Brooke
It's Tuesday.
Jeffrey
It's awkward Tuesday phone call. They say in life only three things are certain. Death, taxes, and having weird, awkward drama with your ex.
Brooke
That is a certainty.
Jeffrey
Definitely going to happen. Of course, one of our listeners is having an issue with one of those life certainties and wants our help today.
Brooke
God, I hope we're going to have a whole tax discussion.
Jeffrey
I'm guessing it's taxes. Let's open up our Quicken apps. Hopefully we're going to save some money for today's listener named Michael. Michael, you have your W9 form ready?
Michael
I can.
Brooke
We're going to do both. Sounds like you got another issue.
Jeffrey
Yeah. What's your drama about?
Michael
Yeah, I reached out because I've had this awkward. Have an awkward situation with my ex, April.
Announcer
Okay.
Brooke
Just. Even when you say her name.
Jeffrey
April.
Michael
Yeah. I mean, she's lovely, but I'll give you the whole story. We haven't been together for a few years.
Brooke
Oh, it's been a while.
Michael
Yeah, it's been quite a while. It was like five to six months that we actually dated. The thing is, it was. It was good overall. I mean, I was attracted to her. Just. We just didn't really mesh well. Our conversations were pretty dull or just disconnected. Okay.
Brooke
You guys just weren't the right fit.
Michael
Yeah, yeah, yeah. And then, like, towards the end of that time together, I just started. I mean, it was, like, subconsciously started listening to a lot of breakup songs. Then I started having dreams of breaking up with her. And when I'd wake up, I'd feel really positive and better about everything.
Jeffrey
Oh, man, that's a sign. Like, the universe is trying to tell you that something's wrong with your relationship.
Medical Advertiser
Yeah.
Brooke
Important to the story.
Michael
Yeah.
Jeffrey
What else?
Michael
Yeah.
Jeffrey
Let's spend five more minutes saying what you didn't like about it.
Brooke
Yeah.
Michael
Nothing really was. Other than just us not meshing well. We didn't cheat. There was no like. Like, we didn't argue anything like that, but we did. Like, the breakup came really weird and sudden, but, like, in a kind of like, as you said, like the universe telling us we broke down in. In this tunnel and we just were, like, stuck together waiting for a tow truck, and we just had a conversation, was sort of just blunt, and we decided to not be together. Okay.
Jeffrey
You broke up in a car stuck inside of a tunnel?
Michael
Yes.
Brooke
Well, sad time to kill. Yeah. Right. Let's pull the bandaid off here.
Michael
O.
Brooke
Can you imagine being that tow truck driver when he pulls up yeah, so
Jeffrey
you said that happened, you know, years ago. How does the drama happen today?
Michael
Well, we've remained friends because as friends, we work really well.
Brooke
That's awesome. That seems healthy and great.
Michael
Yeah. Overall. Yeah. Yeah. I'm sort of like. I would say I'm kind of her shoulder to cry on now in the dating scene.
Jeffrey
You know, you're the only guy who's ever happy with being in the friend zone now. Yeah.
Brooke
Yeah, it's good because you both want that.
Michael
Yeah. Right? Well, yeah, it's a good friend zone, but, you know, I just try to pep her up. I. A lot of times she'll go into that space where she's like, oh, I'm gonna die alone. And I'm just like, no, you're not. Just keep at it. You're great.
Jeffrey
Yeah. Maybe you should change that advice up and agree with her.
Brooke
Why do I feel like that's actually what you would do, Jeffrey?
Jeffrey
Well, maybe that would motivate her to actually find somebody.
Brooke
So where's the awkward part come in? In all this? It all sounds fine.
Jeffrey
Yeah, that's true.
Michael
Yeah. Okay. Just recently we were out drinking at a bar and she to confide to me that she finds my best friend Chris attractive. Oh, boy.
Jeffrey
And you find Chris attractive too?
Brooke
Yeah. You don't like her anymore? Oh, it's like they're both.
Medical Advertiser 2
Yeah.
Michael
Okay.
Brooke
I don't understand the issue.
Michael
I. When she told me this, I actually was quite excited because I think they'd be perfect together.
Jeffrey
Oh, wait, what?
Brooke
Chris also loves boring. Stalled out.
Michael
No, no, I don't think it would be boring. Installed out with this too.
Brooke
Okay.
Michael
Okay.
Brooke
Like they would click yes.
Michael
I mean, one, I mean, they're way better together.
Brooke
Okay, okay.
Michael
They mesh really well. And then two. Oh, I would just like to relieve myself of the burden about hearing her dating life anymore.
Brooke
Shifted over to Chris, shoulder to cry
Jeffrey
and my shoulder's wet. Yeah, but you don't think that that would be weird for you and Chris's relationship to have your ex dating him now?
Brooke
Well, they all know each other, right?
Michael
They all.
Jeffrey
But that's. I mean, that's so awkward.
Brooke
Even if you do claim that you're really just friends, it shouldn't be a big deal that they broke up.
Michael
It would not be awkward for me at all.
Brooke
Okay.
Michael
It's Chris that I know. I just know he has a bro code mind and it's going to be awkward for him. And that's the awkward thing is I need advice on talking to him and convincing him to ask her out oh,
Brooke
so we're going to call your best friend and try to play matchmaker now.
Jeffrey
Let me ask Alexis. You know, from a lady's perspective, if you were the ex girlfriend, how would you feel if your ex boyfriend was, like, pushing his best friend on you?
Brooke
Now, you don't want anyone to be pushed to want to date you, but gently nudged.
Jeffrey
Whatever you want to say, you wouldn't know.
Brooke
She. I wouldn't want her to know. Like, I wouldn't want to find out.
Jeffrey
Oh, you'd want it to be kept a secret. Like it was just a natural connection.
Brooke
He's just been waiting for me to actually be. You know, he's always wanted to date me.
Jeffrey
Okay.
Brooke
Secretly, he didn't have to be persuaded. Yeah, like, he's like, finally, we didn't have to offer him a prize at the end of this in order for him to go out with her.
Jeffrey
Sure. That could be part of the strategy that maybe we come back with when we give you advice before we do our awkward Tuesday phone call to your best friend and try to convince him to date your ex right after this.
Michael
Thank you.
Jeffrey
Hold on. It's awkward.
Michael
It's Tuesday.
Jeffrey
It's awkward Tuesday phone call. We do a segment on our show called say yes to the X. Oh, yeah. Where we try and convince someone to, you know, try things one more time with an old flame of theirs. See if it goes better the second time around.
Brooke
Usually works 2% of the time.
Jeffrey
Yeah, well, this is a little twist on that. It's say yes to your friend's ex because we're trying to help Michael call up his best friend and convince him to try dating Michael's ex girlfriend.
Brooke
That's right.
Michael
So weird.
Jeffrey
Which is a violation of every bro code that's out there.
Brooke
Come on. They only dated for, like, five or six months, and that was years ago.
Jeffrey
Okay, Most people don't gloss over relationships the way that Brooke does.
Brooke
Like, bro code is really not that strong. Yeah, you're being dramatic.
Jeffrey
I wouldn't expect any women to understand the value of bro code, but he thinks they would be a great match together. And he's also tired of hearing his ex complain about how she's gonna die alone to him. So there's two reasons for doing this. Now he just needs a little advice on how to convince his best friend to say yes. Brooke. Without hitting on him. What advice?
Brooke
Listen, you need to let your best friend know and remember that you're his best friend. You know him better than anyone, okay? You always have his best interest in mind, and that's why, although the idea may be crazy, you gotta listen to him. Does that make sense?
Jeffrey
So your advice is just trust him?
Brooke
Yeah. Yes. Because it's best friends.
Jeffrey
What do you think, Michael?
Michael
It's not really the detailed advice that I was hoping to get, but I'm happy to give him a call and tell him that. And remind him, I guess, that we're best friends.
Jeffrey
He may have forgotten. This call may remind him of your friendship. Yeah, we are best friends.
Brooke
Friends.
Jeffrey
I do trust you, Jose. What do you think? There's a lot more to Broco than just don't date. My ex and bros do each other favors. And this is what you need. Get him to agree to one date.
Brooke
Okay.
Jeffrey
And then your job is done. Okay. You know, so it's like a win win. You're doing favors for your friends here. Set it up like you're doing him a favor.
Brooke
The ex a favor.
Jeffrey
It is a favor. He. She said that? What do you think, Mike?
Michael
I mean, that sounds like clear advice that I can. You know, a goal in mind.
Jeffrey
My advice sucks.
Brooke
Yeah, I never liked it.
Jeffrey
My advice was just going to be toss him in a closet together with some candles and Barry Manilow and just like, let it happen. Just lock the door.
Brooke
See, that's what bro code always gets broken.
Jeffrey
Yeah, naturally. That's how babies are made. But anyway, that's what we got for you, man. We're going to wish you luck and dial up your friend and try and convince her.
Brooke
Friend.
Jeffrey
Best friend. Sorry.
Michael
Yeah.
Jeffrey
Thank you for reminding me. I'd already forgotten. But we're going to try and help you convince him to date your ex. Here we go.
Michael
Go.
Jeffrey
Good luck.
Michael
Hello? Hey, Chris. Michael. What is this number that you're calling from? Oh, I just. New phone, man. Sorry. I just like trying to get my contacts in here and I thought, why not call you check in. Dude, what's up? I was just calling check in. Like, me and April, recently, we went out, we got drinks together, you know, as we do. Nice. It was really a fun time. She's just so delightful and easy to get along with as you, you know. Dude, did you guys hook up again? Nice work. No, no, no, no. We didn't hook up. We're still really good friends and you know, you and me, our best friends. Yeah. I don't understand what you're getting out here. Dude. I'm just saying I. I know you better than anyone else and I know it's good for you hanging out with April. She brought up something that I think was also Good for you. Okay. You know, we're a couple rounds in and she told me that she's. She's attracted to you. She, like, digs you as your best friend. I think that would be great for you and her. Wait, what would be great? She finds me attractive. I don't know what you're like, what? Yeah, she sees something in you, you know, like. Like I do. Like, as a best friend. Why do you keep saying that? I'm just. Just reminding you, bro. I mean, you dated her, so I think that that's like a moot point at this point. Like, it's. It's off limits. But is it? It was years ago. Bro code, smoke code, who cares? Like, I'm just letting you know it would not bother me. And you would be doing me a huge favor by just. How would I be you? Like, how is that doing you a favor? Dude, I. I just want you to be happy. You're my best friend. Best friends look out for each other. I mean, if I can be straight with you about this, like, yeah, that's awesome that she finds me attractive. She's cute. I mean, you're right. She is really cute. Right. So I just gotta level with you. The short version has been there, done that.
Brooke
Oh. Oh.
Jeffrey
What?
Michael
What? What do you mean? April and I have. We've made out before.
Jeffrey
What?
Michael
Wait, when? I'm not proud of this. This was when you all were on the rocks.
Announcer
Awkward.
Jeffrey
Oh, my God.
Michael
Bro code.
Brooke
Smoke code. Right, Jeff.
Michael
Sorry, what? I mean, I can't believe she cheated on me with you. My best friend.
Jeffrey
Best friend. Oh, God.
Brooke
Oh, that's some news.
Jeffrey
Yeah, we need to. We need to jump in on this conversation. Chris, are you there?
Brooke
Yeah, hi, Chris.
Jeffrey
Yeah, we're a radio show called Brooke and Jeffrey in the Morning. You're. You're on our show right now on a segment called Awkward Tuesday. Phone call, man.
Michael
Whoa. Okay.
Jeffrey
Whoa to what you just said.
Michael
Oh, my God, Michael.
Medical Advertiser 2
Oh, man.
Brooke
Oh, God, is he breathing? Michael.
Michael
I was just having a hard a moment. But.
Jeffrey
Okay, wait, weren't you saying that you're completely over her though, bro?
Michael
Well, I'm just more bummed out about my best friend now.
Brooke
Alexis, you nailed it. Bro code. It never exists. No, it's a fake line.
Michael
Okay, seriously, I gotta be honest with you. It was like a very brief make out session. We were both buzzed. You at that point also had said to me like, you were kind of done with the situation. So that was another factor. Like, I am very sorry. That is not who I am.
Jeffrey
Well, that's hard to come back from.
Brooke
Sounds like, though. It sounds like Chris has a lot of guilt about it and knows he made a dumb decision.
Michael
100%. The reason I didn't even mention it before is because it was so inconsequential. I cannot emphasize. Like I said, it was nothing and it was stupid.
Jeffrey
I mean, clearly it wasn't stupid and nothing for your ex girlfriend because she's still interested in thinking about Chris. I'm sorry, I'm just wondering why, after three Long island iced teas, why wouldn't the girlfriend, like, admit to you, Michael, that she's already kissed him before at that point?
Brooke
Obviously, she's better at secrets than Chris is.
Jeffrey
Oh, yeah. Well, I guess she would have to admit that she cheated on him at that point, so. Okay, that makes more sense.
Brooke
She wants to be friends, you know,
Jeffrey
she wants to go out with. Good kiss Chris. Oh, my God. How you doing?
Michael
I'm doing all right. I mean, I want to. I want to forgive my best friend, but I need a favor from you.
Brooke
But you're still going to ask.
Jeffrey
Oh, no way.
Brooke
What is it?
Michael
What is the favor? Chris, can you just. Can you just agree to take her on one date?
Jeffrey
Oh, you still want this to happen?
Michael
Whoa, whoa, wait. I'm so confused. So you still want me to take her on a date? It's the least you could do. I mean, you cheated. She cheated, you cheated. Both cheated on me with. With each other. Just go on one day.
Jeffrey
You've already kind of done it. I mean, kiss it. Do it under, like, the proper terms.
Brooke
If you end up together, it makes it better. Cancels out.
Jeffrey
Yeah, that's what a best friend would do.
Michael
Dude, if I do that and we're still good, it would be the only reason that I'm doing it.
Jeffrey
Okay, Michael, he said that he would do it for your forgiveness. Do you forgive him?
Michael
Oh, I forgive you. Yes. Just go on that date.
Brooke
How whiny is this woman about her dating life?
Michael
Hold up. Is that why you're having me go out with her? You told me she complains a lot. But is this just, like, trying to get her off your back? Am I taking the bullet right here? That's what best friends do.
Jeffrey
Best friends and relationships saved here today. That was a successful, awkward Tuesday phone call. And if you have an awkward relationship going on with your best friend or your current ex, you can share this podcast with them, even if you're not. Even if you make them.
Brooke
Is this how you tell them you cheated on their.
Jeffrey
Yeah, what better way to deliver the news than by listening to Brooke and Jeffrey wherever you get your podcast or share a laugh. Exactly. Whatever you want to do.
Announcer
Brooke and Jeffrey in the morning, there's an app for your playlists, an app
Jeffrey
for your photos, even an app that
Announcer
helps you dodge traffic.
Jeffrey
But only one app brings you this live radio station anytime, anywhere.
Announcer
With the iHeartRadio app, your favorite radio station fits right in your pocket. Live shows, news, sports, exclusive music channels, and voices that don't just go viral.
Jeffrey
They're the voices of your local community.
Announcer
So if it's not already on your home screen, fix that.
Jeffrey
Download the number one radio app, the free iHeartradio app today.
Announcer
IHeartradio being there for those we love can be so hard for people with chronic migraine 15 or more headache days a month, each lasting four hours or more Botox Unabotulinum Toxinae prevents headaches in adults with chronic migraine. It's not for those with 14 or fewer headache days a month. It Prevents on average 8 to 9 headache days a month versus 6 to 7 for placebo. Prescription Botox is injected by your doctor. Botox effects may spread hours to weeks after injection, causing serious symptoms. Alert your doctor right away as trouble swallowing, speaking, breathing, eye problems or muscle weakness can be signs of a life threatening condition. Those with these conditions before injection are at highest risk. Side effects may include allergic reactions like rash, breathing problems, dizziness, neck and injection side pain and headache. Don't receive Botox if there's a skin infection. Tell your doctor your medical history, muscle or nerve conditions like als, Myasthenia gravis or Lambert Eaton syndrome and medicines like Botulinum toxins which may increase the risk of serious side effects. Why wait? Ask your doctor about Botox. Visit botoxchronicmigraine.com or call 1-844botox.
Brooke
Well I'm glad they're still buddies. You know, they really work through that. Would you date a friend's ex if they begged you just to help getting them off your their back?
Jeffrey
If they begged me still no. It'd be too weird I think.
Brooke
What if you had already made out with them? Yeah, exactly.
Michael
That does change.
Brooke
The comments were pretty positive about it. We got. Well that's an awesome best friend. Yeah, that's what best friends are for. Okay. Oh yeah, somebody did say nobody wants your friends leftovers. But you know I like a second hand store so what's the difference, right? I'll take habitans from my girlfriend.
Dr. Doug Lucas
Yeah.
Brooke
All right, there it is. Thank you so much for being here please. Again, go subscribe to our YouTube. You can watch a bunch of fun videos up there. We're we're working a lot on getting you new content, so it's BrookeandJeffrey. Subscribe and have a lovely day. Or if you've been with your friend's ex, let us know. Oh, oh boy. Let them know first or write it anonymously. Yeah, that's even more fun. All right, do it right now. It's Brooke and Jeffrey in the morning.
Dr. Doug Lucas
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Brooke
sleepover all week, but I think about her food allergies all the time. Fortunately, her doctor prescribes Olair Omalizumab. It's proven to significantly reduce allergic reactions,
Announcer
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Jeffrey
This is Matt Rogers from Las Culturistas with Matt Rogers and Bowen Yang. This is Bowen Yang from Las Culturistas with Matt Rogers and Bowen Yang. Hey Bowen, is it just me or does it feel like nothing is actually what it says it is anymore? Yeah, like when you order chicken fingers, you don't get fingers, you get mystery nuggets.
Medical Advertiser
Exactly.
Jeffrey
Well, except hotels.com I was gonna say hotels.com because they do hotels refreshing. And when booked as a member, rewards are earned every stay, not points that disappear. Rewards that work like cash and can actually be used so the name checks out and the perks do too. Yep, members can get up to 20% off tons of hotels with no blackout dates. Just works with real travel.
Michael
Okay, that tracks.
Jeffrey
Hotels.com, it's all in the name.
Dr. Doug Lucas
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Jeffrey
personalized care that understands the whole woman.
Dr. Doug Lucas
Join me Dr. Doug Lucas, clinical lead of Hormone Optimization and Longevity at lifemdash, along with other leading experts on the podcast. Here's something good on women's health and longevity. To learn more, go to lifemd.com iheart
Brooke
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Podcast: Brooke and Jeffrey: Second Date Update
Episode Date: July 28, 2026
In this lively and unpredictable "Awkward Tuesday" episode, the Brooke and Jeffrey team tackles a classic relationship dilemma: is it ever okay for a best friend to date your ex? Listener Michael seeks help to persuade his best friend, Chris, to ask out his ex-girlfriend, April—a request that threatens to break every “bro code” in the book. What starts as a matchmaking quest quickly unravels a tangle of secrets, awkward revelations, and surprising forgiveness, all delivered with the show's signature humor and bold honesty.
Michael shares his history with April
“We didn’t really mesh well. Our conversations were pretty dull or just disconnected… We broke down in this tunnel and just had a conversation, was sort of just blunt, and we decided to not be together.” – Michael (06:03)
Ongoing friendship post-breakup
“I would say I’m kind of her shoulder to cry on now in the dating scene.”
– Michael (07:54)
The catalyst: April confides she is attracted to Chris
Brooke, Jeffrey, and the team’s reactions
The hosts debate the seriousness of the "bro code" and if this situation really violates friendship norms.
Brooke downplays the drama:
"Bro code is really not that strong."
– Brooke (11:43)
Jeffrey sees it as a classic violation:
“Which is a violation of every bro code that’s out there.”
– Jeffrey (11:36)
Michael’s real concern
(11:36 – 13:44)
Brooke’s advice: Remind Chris of their close friendship and that his happiness is Michael's top concern.
“Although the idea may be crazy, you gotta listen to him. Does that make sense?”
– Brooke (12:28)
Jeffrey’s advice: Set it up as a favor; get Chris to agree to "just one date" and let the chips fall where they may.
Comic relief:
Jeffrey jokes about tossing them into a closet with candles and Barry Manilow, poking fun at the tension.
(13:27)
(14:01 – 18:15)
Michael reaches out to Chris, attempts a subtle pitch
Surprise twist: Chris confesses he already made out with April during Michael and April’s rocky period
(16:42 – 17:03)
> “April and I have… we’ve made out before.”
– Chris (16:47)
“I am very sorry. That is not who I am.”
– Chris (18:15)
(17:05 – 19:01)
Brooke, Jeffrey, and the team jump in, processing the double awkwardness with humor and support.
Michael is more upset at Chris than at April, but Chris expresses deep regret and emphasizes how insignificant it was to him.
(19:08 – 20:22)
Despite the shock, Michael asks Chris for a favor: go on one real date with April as a form of atonement.
Chris reluctantly agrees—mainly to maintain friendship and make up for the past indiscretion.
“If I do that and we’re still good, it would be the only reason that I’m doing it.”
– Chris (19:50) “I forgive you. Yes. Just go on that date.”
– Michael (19:59)
The team celebrates the (somewhat questionable) happy ending and jokes about “best friends and relationships saved today.”
| Timestamp | Speaker | Quote | |-----------|---------|-------| | 07:24 | Michael | "We broke down in this tunnel and just had a conversation, was sort of just blunt, and we decided to not be together." | | 09:02 | Michael | "When she told me this, I actually was quite excited because I think they'd be perfect together." | | 11:36 | Jeffrey | "Which is a violation of every bro code that's out there." | | 14:01 | Michael | "Hey, Chris. ...Me and April, recently, we went out, we got drinks—she told me she finds you attractive. I think that would be great for you and her." | | 16:47 | Chris | "April and I have… we've made out before." | | 18:15 | Chris | "I am very sorry. That is not who I am." | | 19:59 | Michael | "I forgive you. Yes. Just go on that date." |
If you've ever questioned whether friendship rules come before romance, or laughed (or cringed) at the messiness of dating within a friend group, this episode delivers the drama—and the laughs—you’re looking for.