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Ryan Seacrest
AI.
Hoss
Had the time of my life a I never felt this way before.
Melissa
From building timelines to assigning the right people, and even spotting risks across dozens of projects, Monday Sidekick knows your business, thinks ahead and takes action. One click on the star and consider it done.
Host D
And I owe it all to you.
Hoss
Try Monday Sidekick AI you'll love to use on Monday.com hey, it's Ryan Seacrest.
Commercial Announcer
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Host D
The First Show all right, hoss, how you doing today, dude?
Hoss
I'm good, man. I'm good. I'm kind of nervous. I'm very nervous.
Host D
If I was in the hot seat like you right now, I'd be nervous also.
Hoss
I, I just, I don't know what to say. I mean, this is what I'm about to say right here has never been released to anybody except for this person. And it was only like a month ago.
Host D
All right, don't, don't reveal that just yet.
Hoss
I'm not going to, but the, the.
Host D
Deal with Relationship Report Card is this and askmen.com is one of my favorite websites. And it just so happens that they kind of have the same philosophy that we do. And if you go there, it actually tells you that men should actually really take a good hard look at their last 10 relationships. And I think this probably goes for women also. You take a really good hard look at your last 10 and do some real soul searching and find out where it all started to go wrong.
Melissa
Well, I think that you find in your relationships that if you don't face certain problems, problems or issues either with your usually with yourself, then you get into the same patterns in every single relationship. You end up fighting about the same thing or you end up breaking up over the same thing. And so that's kind of why Relationship Report Card. I mean, we had a lot of listeners who, when we started this who were like, you know what? I just can't get out of this rut. I date the same kind of people. I just don't understand why I can't get into a more evolved Relationship. And so we kind of take a hard look at it and see exactly what the pattern is.
Host D
What we do is we ask you to supply us with a whole bunch of names and phone numbers of your exes and then we put you on with them one by one throughout the week. And then by the end of the week you have a pretty good snapshot. Because like Melissa said, kind of like this, there's a common thread in between all the relationships. Sometimes it's gotten pretty intense. Like, remember that one girl that had like the drinking problem?
Co-host F
Mm, that's right. Oh, I remember that.
Host D
She didn't even realize it and all of her boyfriends were like, yeah, man, you just drink too much, party too hard, and that's it. She didn't realize it till the end of the week and it got really, really serious. So we thought we'd put Hoss under the microscope and he gave us a couple of different phone numbers of exes that we will call later in the week. But he doesn't have 10 x's to even call.
Hoss
No, only, I think I've only, I've only dated three girls. I mean all three girls have been. I mean there have been long term relationships. Like the last one I just got out of was a three year relationship. The one before that was two and a half years. And the one before that I think was a year, year and a half.
Ryan Seacrest
Now are you counting that girl on the show that invited you upstairs? Oh, she a girlfriend or she just.
Hoss
She was just a, a random on.
Co-host F
His last show that he was her name.
Ryan Seacrest
The co host against the name Madison.
Host D
Oh, yes. Yeah, that was a one night type deal.
Hoss
Yeah.
Host D
Right.
Hoss
So this is, that's not awkward.
Co-host F
Not a relationship, so to speak.
Hoss
Right.
Ryan Seacrest
That's like you might be able to do that same deal with no undies over here.
Co-host F
Dude, it's a. I have to fulfill the bet. It's not like I'm trying to.
Ryan Seacrest
I'm just saying you're lucky it's not an 11 week football season or else. Awesome to have you all sorts of ways.
Co-host F
Dude, I'm still married.
Melissa
What is wrong with you?
Co-host F
What is wrong with you? That's not funny at all.
Ryan Seacrest
Hey, bet's a bet.
Host D
Initially you said no pants. I really thought you. Or no underwear. I thought you were talking about Melissa because this is, this is commonplace for her. So this is a little bit of a different snapshot than what we've been painting of you. Because while you've been having a great time here in Atlanta, I think you were the One that said he's kind of like a serial monogamous. Monogamous, yeah.
Co-host F
But it sounds like those relationships were further apart.
Hoss
Yeah.
Co-host F
And there's times in betweens where you've been.
Hoss
Yeah. The year. The year, year and a half deal was like sophomore year of high school.
Melissa
Okay.
Hoss
The two two and a half year relationship was like senior to, like, freshman, sophomore year of college. And then the. The last one was pretty. Pretty recent. I mean, it's just. It was. The last one was right after the. The two and a half year one. Out of this, six months after, how.
Ryan Seacrest
Many of those three relationships were you completely. 100%. No holds barred. No, no. No question whatsoever. 100% faithful in God.
Hoss
This is where. I don't want to talk about it. 0.
Host D
0. Screwed around on every girlfriend you've ever.
Hoss
Had, but the ex girlfriend doesn't know. Yeah.
Melissa
This last one doesn't know.
Hoss
Yeah.
Melissa
Okay.
Host D
Yeah, well, she doesn't have to know. I mean, we're gonna get her on later in the week, but, I mean, it's not like you have to confess.
Melissa
To her because we're really asking them the question. So we're not asking you questions in front of them. We're asking them questions.
Hoss
Makes me so freaking nervous. I can't.
Ryan Seacrest
Maybe you should have kept it in your pants.
Hoss
That's where it goes wrong.
Co-host F
Well, I think you really do learn something about it. And the cool part about us doing this with you is that we all get to learn more about you.
Hoss
Yeah.
Co-host F
And listeners get to know you a little bit better by knowing, you know, getting to hear from your exes, sometimes.
Host D
That'S a good thing, sometimes that's a bad thing. How old are you?
Hoss
24.
Host D
Yeah, I'd have to be honest with you and say the same thing. Like, when I was 24 years old, there weren't too many relationships I had where I wasn't screwing around. Yeah, I'm not proud of it, but.
Hoss
Dude, I can do stunts. I can act like an idiot and do all these types of things. That doesn't bother me at all. But this right here is just freaking me out.
Co-host F
Welcome to the vert show.
Host D
Keeping it Real.
Hoss
Thank you. Oh, God.
Host D
What now? You have given all of those phone numbers of the X's to producer Tracy.
Hoss
I've only gotten in touch with one. One of the three.
Ryan Seacrest
Tracy, find them. You don't have to do that. Just give her names.
Hoss
I'm trying to get in touch with the other two. One I can definitely get in touch with. The third one is the One that. That might be the hardest one to get.
Co-host F
Why? Because you don't want to talk to her?
Melissa
Well, because enough that she doesn't want to talk to you?
Hoss
Well, yeah, I might have made a. Made a big mistake about a month ago and she's pretty much cut off all ties. Oh, yeah.
Co-host F
Is this the one you told us about in the post show meeting?
Host D
So when you're going to tell us about today?
Hoss
Yeah, yeah. I don't even know where to start. You want me just lay it out there.
Ryan Seacrest
Why don't you start the day. The day you met her.
Co-host F
What is she, though?
Host D
Settle in, get comfortable, cut off your underwear and tell us where it all started.
Hoss
How long?
Melissa
This is the last one, right?
Hoss
This is the one. This is the two and a half year. Right. Relationship.
Co-host F
Okay.
Host D
All right.
Hoss
Not the previous one or the recent one? Well, we. We dated in sophomore year of high school, and I just. I got out of relationship, like I said earlier, a couple about a year before, and this was the person that I had lost my virginity to. Well, me and her had a. Had a pretty serious relationship and everything. So I started dating this girl. Well, her name is. I don't know if I should even say her real name. We'll say her name's Allison.
Ryan Seacrest
Why don't we call her Virgin?
Hoss
Yeah. All right, let's call her Virginia.
Host D
Is she here in Atlanta?
Hoss
No.
Host D
Okay.
Hoss
No.
Co-host F
So this is girlfriend number one.
Hoss
Two. Oh, girlfriend.
Melissa
All right. Girlfriend number one you lost your virginity to, and then now we're talking about girlfriend number two.
Hoss
Yeah. Okay.
Melissa
Okay.
Co-host F
So girlfriend number one's Virginia. Who's girlfriend number two gonna be?
Hoss
We'll call her Alice or Alicia.
Melissa
Allison.
Host D
Oh.
Hoss
Okay, we got that.
Melissa
I think we got it. Virginia analysis are now.
Hoss
Okay, so lost my virginity to Virginia, started dating Allison. All right. Me and Allison dated for about two years, and we never. We never. We didn't have any problems. We didn't argue a lot or anything like that. We broke up because she said that we moved too fast. And in two years. In two years, all we did was hold hands.
Host D
That was too fast.
Hoss
Yeah.
Melissa
Okay, so you slept with Virginia, obviously, but you never were intimate with Alison.
Hoss
No.
Melissa
Okay.
Hoss
It's just she. She had never. She'd never made out with a guy before. Like, she had never done anything with a guy before.
Host D
And she was how old at this point?
Hoss
17.
Host D
Okay.
Co-host F
Did you guys kiss each other?
Hoss
No.
Co-host F
Nothing.
Hoss
Hands. Oh, man. Yeah. And I was like, yeah. She broke up with me because we were moving too fast because I. I tried to give Her a kiss in.
Host D
Two years, you tried to give her a kiss and she broke up.
Hoss
Yeah.
Host D
Are we going to talk to her? Because I wouldn't. I want.
Hoss
That's the one.
Ryan Seacrest
You can't come down on her, though, Bert.
Host D
No, I want to know her side of the whole thing, because we're here in one side here. But I don't know.
Hoss
No, I swear I'm not. I mean, I'm not lying to you, but.
Melissa
Yeah, it's a small town. North Carolina, too.
Hoss
Yeah. So Bible Belt and everything like that.
Ryan Seacrest
She ain't kiss nobody but family.
Hoss
I don't.
Ryan Seacrest
I don't know about that, Hoss.
Hoss
I just.
Ryan Seacrest
The only other person touched my boobies. A daddy.
Melissa
That is sick.
Co-host F
Dude.
Melissa
What is wrong with you?
Host D
Save that, by the way.
Hoss
So, yeah, so she broke up with me, like. Oh, yeah.
Host D
So for two years, you hang in there, she gives you nothing but kiss, and then she breaks up with you?
Hoss
Yeah. No, not even kissing.
Host D
Yeah, just holding hands.
Hoss
Holding hands. Exactly.
Host D
That hurts.
Hoss
So she broke up with me, and we basically went our separate ways. But ever since then, I've always had feelings for her, and I don't know why.
Ryan Seacrest
Cause you always want what you can't touch.
Hoss
That might be it.
Co-host F
You were thinking about it by yourself for so long.
Ryan Seacrest
Seriously, you know what it is?
Co-host F
It just kind of became routine to think about her when you're by yourself.
Hoss
She is.
Melissa
He never fulfilled that ultimate chase.
Commercial Announcer
Yeah.
Ryan Seacrest
You know what it is? She is sexual chick fil A. When is the only time you want a waffle cup fry?
Co-host F
Sunday.
Host D
Sunday afternoon when they're not open.
Ryan Seacrest
But you can't have it because they close.
Hoss
So she was close.
Ryan Seacrest
You couldn't have it. That's all you wanted.
Host D
So, 17 years old, she breaks up with you, and you still have thoughts and feelings about her for how long?
Hoss
Up until right now.
Host D
Right now.
Hoss
Right now.
Melissa
So you dated the third girlfriend?
Hoss
Dated the third girlfriend.
Melissa
It's still.
Co-host F
What are we gonna call number three?
Hoss
We'll call her Alicia.
Host D
We got. Allison is number two. Alicia is number three.
Co-host F
And Alicia was for how long?
Hoss
Up until.
Co-host F
But how long did you date her?
Melissa
Three years ago. We need the baby. We need the baby book of names that they always publish and just have that handy when we need the fake name.
Ryan Seacrest
Well, I've been bothered that Hoss is one of those people that names all their kids with, you know, names that start with the same first letter.
Host D
Gotta keep it simple, man.
Melissa
It's confusing as hell.
Host D
So now she obviously has moved on with her life. So what has her dating history been. Since you.
Hoss
She. She's dated a couple guys, and then we both went to the same college together, and we got drunk one night at a. At a party, and we ended up in the bathroom together, just talking about, you know, our relationship, stuff like that. Stuff that happened, you know, while we were dating.
Host D
That's where good college romance happens. Right there.
Hoss
Exactly. And I was, you know, you know, giving her. Giving her grief about her breaking up with me because we never made out.
Host D
And this was years ago.
Hoss
Years ago.
Melissa
And so. And you did something in the bathroom.
Hoss
We did.
Host D
You did?
Hoss
Yeah, we made out for the first time, and that's that. She had me hooked right there.
Melissa
That's all you do was make out in the bathroom.
Hoss
In the bathroom.
Host D
So now you can't stop thinking about her.
Hoss
Yeah.
Host D
Now, is she going out with anybody or was she going out with anybody at the time?
Hoss
I don't think she was going out with anybody at the time. I called maybe. Maybe like four or five days later to actually just ask her out on a date because she was single. I was single. Let's make it happen.
Ryan Seacrest
But let's take this beyond the restroom.
Hoss
But when I called, she was going out on a date with another dude. So I'm like, God. And then that. That ended up lasting for about a year, that relationship.
Host D
And who was that guy?
Hoss
Just. I don't know, Some dude. Yeah, just some random guy.
Ryan Seacrest
Okay.
Hoss
Yeah. So. So we kind of broke off conversations again, and we. We'd speak to each other very rarely. But it was about three, four months ago. I got wasted one night and decided to send a drunk email to her and proclaim to her my love for her and how I still think about her all the time, how I still want to be with her and, you know, everything about this girl that. Just that she's somebody that I would want in a wife or something like that, in a serious relationship. Yeah.
Co-host F
So you told her you're basically. You told her she's the love of your life?
Commercial Announcer
Yeah.
Hoss
Yeah.
Co-host F
Wow. In an email.
Hoss
In an email.
Melissa
Now, is she seeing anybody?
Hoss
I didn't know until. Until she called me a couple days later when she was drunk. But she is engaged with my best friend.
Co-host F
Oh, okay.
Host D
So we gotta back up.
Ryan Seacrest
You didn't know that?
Host D
That's. That's where the story gets a little muddy here. If he's your best friend.
Hoss
Well, he's not a best friend. He's a good friend from high school, but we haven't really talked since.
Commercial Voice
Okay.
Hoss
Since high school.
Host D
And in Guy's world. You can be best friend with a guy and not talk to him for a year and a half, you know?
Melissa
You had no idea they.
Hoss
No.
Melissa
Okay.
Co-host F
Okay.
Host D
Swear.
Co-host F
Question.
Hoss
I knew that they were dating.
T-Mobile Rep
When you emailed her.
Hoss
Yeah. Yeah.
Co-host F
And you were trying to stop it. You didn't know that?
Hoss
I wasn't trying to stop it. I knew. I knew that they were serious, but I didn't know that they were going to be engaged. I didn't know they were engaged. As honest, I didn't. I really didn't know that they're engaged, but I knew that they were serious. And I figured that now was. Now would be the best time to. To let her know before she got.
Melissa
Married because she's only serious with him because she doesn't know. And Hoss wants all going on in.
Hoss
My head right now.
Host D
Did your friend find out what you wrote to her?
Hoss
Yes.
Host D
Oh.
Hoss
When she opened up the email, he was right over her shoulder.
Ryan Seacrest
Oh, boy.
Co-host F
Oh, yeah.
Ryan Seacrest
How'd that work out for a minute.
Hoss
Yeah.
Co-host F
What did he do? Did he call you or.
Hoss
No, I just found out. I just found this out, like Wednesday or Thursday of last week. Like, I sat there and had an instant message conversation with her, like, telling her, hey, listen, I'm sorry, I didn't realize that you are engaged. You know, congratulations. But I had to let you know this is. I had to get this off my chest. I feel a lot better now. And she's like, yeah, she's like. I'm sorry to say. She's like, but, well, his name's Brandon. We'll say his name's Brandon. She's like, Brandon was. Was looking over my shoulder.
Host D
All right, well, first of all, I don't believe that Brandon was looking over her shoulder. I believe that that's what she told you.
Hoss
Yeah, I'm thinking so.
Host D
But I think that she went and she told Brandon.
Hoss
I'm thinking, so.
Host D
Exactly what you said.
Hoss
Yeah.
Melissa
Because then I'll get irritated if anybody's over my shoulder while I'm checking email. And why are you gonna just be standing there just like hovers?
Ryan Seacrest
What are you doing?
Host D
Who's that one from Jeff's over Jet Hobby shoulder right now?
Co-host F
Who's that screen name?
Host D
Yeah. So at this point, did she cut it off with you?
Hoss
I IM'd her. You know, we had this conversation last week, and then I tried to IM her Friday night about coming on and talking with us and everything, and I was like, listen, I got a. I got a question. I got a favor to ask of you has nothing to do about, you know, what we've been talking about and everything like that. I'm not trying to do anything like that. Swear. But, you know, and just told her that whole situation, and she didn't. I mean, back and just signed. Signed off right afterwards.
Host D
Now she's avoiding you.
Hoss
Yep. So I think.
Melissa
I think we should all talking to him. Even though, I mean, I just find it interesting that even after she gets the email of love and commitment that she and her and her fiance talk about it, that she still is in contact with Hoss.
Co-host F
How old is this girl?
Hoss
Same age. 24.
Co-host F
24.
Hoss
Yep.
Co-host F
To me, she may be using Hoss as hand in her relationship with guy with. What's his name?
Melissa
Brandon.
Hoss
Brandon.
Co-host F
And Brandon.
Host D
Well, he was. Never mind.
Co-host F
What?
Host D
Nothing.
Co-host F
Oh, you're gonna.
Host D
I was gonna get naughty. Go ahead. Yeah.
Commercial Announcer
Okay.
Co-host F
Well, my. My thought is from the girl perspective, it's flattering, I'm sure, to hear from her.
Hoss
That's what she said.
Co-host F
And I'm sure she is. You know, it gives her, like, the warm, fuzzy feeling to, you know, think about that. And if boyfriend's been ignoring her maybe a little bit, maybe he hasn't been super attentive, you know, like he proposed, but maybe he's been screwing up or whatever, like, using this email and going, look, what I got, you know what I mean, is kind of giving her a little bit of hand in the.
Host D
Yeah.
Co-host F
Her own relationship.
Hoss
I feel bad because, I mean, this is one of my friends. And, like, I didn't. I didn't. I wanted it, in a way to get out just because I didn't care anymore if people knew. Like I told some of my good friends before, but I just told him to keep it quiet, you know, don't mention anything about it. But, you know, once I sent. I sent her that email, I didn't really care anymore if it got out, but I. I didn't want it to get to him.
Host D
I guess the guy code, dude, I.
Hoss
Should give up my man card right now. But, I mean, I didn't want him to know, but I guess I knew he was gonna find out eventually. She sent me an IM saying, you know, that was the sweetest, sweetest thing that she's ever got before and everything. So I kind of felt good about that. But, like, I think we should all.
Ryan Seacrest
Start calling her and just saying we've been in love with her for years.
Melissa
I mean, I know that I grew up in Tennessee, and you grew up in North Carolina.
Ryan Seacrest
I heard about you, and I just want to let you know I'm in love with you.
Melissa
I'm a volunteer. You're a Tar Heel. But we can make this work.
Host D
Is this one of the girls that we. We can or cannot talk to you so far?
Hoss
I don't know if she'll go on the air.
Ryan Seacrest
She's ignoring him.
Hoss
Yeah.
Ryan Seacrest
He doesn't know.
Host D
Okay, so we gotta get producer Tracee on it.
Co-host F
She can convince anybody of anything.
Host D
Totally.
Melissa
So the third girlfriend, Alicia, did she ever know about your feelings for Alison?
Hoss
No.
Melissa
Because you dated her. You dated Alicia while you still had feelings for Alison? And probably. Were you dating Alicia when you. I don't know. I guess when you wrote that email, you weren't dating.
Hoss
No.
Host D
The first girl that we're going to talk to to do relationship report card is Virginia Ye. And she's gonna come on with us on Wednesday.
Hoss
Okay.
Host D
Okay, cool. And you'll start to get a snapshot of what it was like for her and your relationship.
Hoss
Oh, God, I'm not looking forward to this at all.
Co-host F
Oh, but you were a sophomore in.
Melissa
High school though, right?
Hoss
No, this was like senior year of high school.
Co-host F
Senior year of high school.
Melissa
Okay, still high school.
Host D
Still high school.
Melissa
Yeah.
Host D
I don't know how much you can learn from a high school relationship.
Melissa
And if you get crab, it's like.
T-Mobile Rep
Well, you know, it was high school.
Host D
And he's obviously matured since then.
Ryan Seacrest
So much. Boss, I just wanna let you know that I've loved you since the moment I've met you. Even though all we ever hold hands.
Hoss
Feelings are mutual.
Ryan Seacrest
Right here, buddy.
Host D
The first show.
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Melissa
Oh, hey.
Hoss
Welcome to gift wrapping. Whoa. So we Saldana.
T-Mobile Rep
Hey, can you wrap these, please?
Hoss
Wow. IPhone 17s.
T-Mobile Rep
You splurged at T Mobile. You can get four iPhone 17s on them. The new center stage front camera is amazing for group selfies. It's the perfect gift for everyone.
Hoss
I'm the worst. I only got my mom a robe.
T-Mobile Rep
Well, it's better than socks.
Hoss
So I have to trade in my old phone, right?
T-Mobile Rep
No @t mobile there's no trade ins needed when you switch. Keep your old phone or give it as a gift.
Hoss
Incredible.
T-Mobile Rep
In fact, wrap up my old phone too for my aunt Rosa.
Melissa
Forget that.
T-Mobile Rep
Aunt Liz will be jealous.
Hoss
Sounds like my family drama.
Melissa
Oh, I got it.
T-Mobile Rep
I'll give it to my abuela. I'll take reindeer paper with hey, where are you going?
Ryan Seacrest
To T Mobile.
Host D
The holidays are better. It's T Mobile.
Hoss
Get four iPhone 17s on us. No trade in needed when you switch plus four lines for just 25 bucks a line. And now T Mobile is available in.
Commercial Voice
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Date: November 24, 2025
Host: Pionaire Podcasting
Cast in Episode: Host D, Hoss, Melissa, Co-host F, Ryan Seacrest, Producer Tracee
This episode puts cast member Hoss in the hot seat with a “Relationship Report Card,” a recurring Bert Show segment. The premise: examine your past relationships to identify patterns, face uncomfortable truths, and encourage personal growth. The team walks Hoss through his limited but intense dating history, poking fun but also providing candid, sometimes awkward, support as he reveals secrets and regrets about his three serious relationships.
The Three Relationships: The cast adopts fake names for anonymity:
Anatomy of the Second Relationship (Virginia/Allison Story):
Lasting Feelings: Hoss admits he’s harbored feelings for Allison ever since, through other relationships.
Missed Connections & The Drunk Email:
The Engagement Reveal: Hoss finds out only after sending the email—his friend was reading over Allison’s shoulder.
Regrets & Rationalizations: The group debates whether Brandon was actually there; Melissa is skeptical.
Closure or Further Complication?
Being Used As “Hand”:
Guilt and ‘Man Card’ Surrender:
“Screwed around on every girlfriend you’ve ever had, but the ex girlfriend doesn’t know.” – Host D (05:04)
“I can do stunts. I can act like an idiot…but this right here is just freaking me out.” – Hoss (05:56)
“She broke up with me because we were moving too fast because I tried to give her a kiss in two years.” – Hoss (08:53)
“You always want what you can’t touch.” – Ryan Seacrest (09:55)
“She is sexual Chick-fil-A... When’s the only time you want a waffle cup fry?”
“Sunday.”
“But you can’t have it because they close.”**
– Ryan Seacrest & the Cast (10:10–10:18)
“I got wasted and decided to send a drunk email…proclaim to her my love for her and how I still think about her all the time.” – Hoss (12:30)
“When she opened up the email, he was right over her shoulder.” – Hoss (14:16)
“I should give up my man card right now.” – Hoss (17:23)
Listeners are drawn into a raw, entertaining, and at times cringey self-examination as Hoss lays bare his romantic missteps. The episode sets up a week of “Relationship Report Card” segments, with exes returning to share their perspectives—promising even juicier confessions and emotional insights to follow.