- 5/27/2025
Dave & Chuck the Freak talk about someone who is having an issue after sharing a room with a coworker on a business trip. This leads to them talking about their personal experience when Dave had to spend one night with Chuck.
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00:21Well, business trips with co-workers can be dramatic.
00:25As we well know, lots of personalities to deal with.
00:28Not every roommate is a match.
00:31This guy is sharing his story online, looking for feedback.
00:35He was called out for sleeping in his boxers in a shared hotel room with a male work colleague.
00:42I'm sleeping in my underwear every time.
00:44I know, honestly, unfortunately I've lived through this with Chuck.
00:47I had to share a room with him.
00:49We were forced to share a room together.
00:51I'm not bringing PJs.
00:52Thank God it was too bad.
00:54Initially it was one.
00:55It was one.
00:56I was like, leave it!
00:57I was like, leave it like that!
00:58We would have had to share a bed.
00:59Can you imagine how awkward?
01:00That's how they booked it, though.
01:01We could have sued the company.
01:03That's how they booked it.
01:04We could have.
01:04We could have.
01:04But think about, I think about this.
01:06If you would not have done that, say you would have refused, right?
01:09Yeah.
01:10Whatever.
01:11We might not be here today.
01:12Your whole, everything could have took a different road.
01:14Yeah, that's true.
01:15Exactly.
01:15We had to sleep in the same room and order for us all to be together.
01:17I know, it's weird.
01:18Have you heard all those little crazy, stupid, ridiculous life moments you have to go through?
01:22You wouldn't believe the stuff I've made him go through.
01:26All right.
01:27You made it weird.
01:28Of course he made it weird.
01:29It's crazy, though, that that happened.
01:31Yes, I came out of the shower and he's standing there in his underwear trying to be seductive
01:34as a joke.
01:36That's not a joke.
01:37That's hot.
01:37I just can't imagine you guys in a room.
01:41That's so, it's so strange, right?
01:43I don't.
01:44No, it's like, unfortunately we worked for just a very, well, it's radio, so it's all
01:49getting really cheap, but.
01:50But it's always been cheap.
01:52It's always been cheap.
01:53And, and.
01:54It's crazy they made you guys get a room together.
01:56One room.
01:57We could only get one room.
01:58One room.
01:59And we couldn't afford another room?
02:01That's nuts.
02:02Yeah.
02:03We really tricked him into that whole thing, though.
02:05Oh, because it was really us wanting to go see you two in Boston.
02:09That's really what it was.
02:10Oh, so that's why you stayed in the same room.
02:11That's what it was.
02:12Why don't we take some posters?
02:13Oh, never mind.
02:14Let's make it a contest.
02:14Yeah, we had to, we had to make it work.
02:17Yeah.
02:17It would not have changed anything, then.
02:18You forced it.
02:20You wanted to sleep in the same room.
02:21I wanted a single bed.
02:23Oh, no.
02:23I wanted a small, twin-sized bed.
02:25Come on, it's awkward.
02:26It is awkward, but you did.
02:27Imagine sleeping with a co-worker.
02:28No, right.
02:28Yeah, it's not great.
02:30But you wanted to go, so.
02:31But we did want to go.
02:32And we were so exhausted.
02:33Thank God, I just passed right out.
02:35Yeah, thank God.
02:35Was it just one night?
02:36No, I didn't.
02:37Yeah, it was just one night.
02:38It was there.
02:39And of course, we had to get up in the morning and do the friggin' call into the show.
02:43Oh, yeah.
02:43You should write a book called, like, One Night with Chuck.
02:47Write it down.
02:48Remember that.
02:49Jesus.
02:49One Night with Chuck.
02:52This is my telling of it, and then Dave's telling of it.
02:56Yeah, the two stories.
02:58The two sides of the cat.
02:58It's like that Albuos album.
03:00There's like, there's two sides.
03:02One Night with Dave.
03:04Yeah.
03:05One Night with David.
03:07Oh, David.
03:07Don't call me David.
03:09Oh, that's funny.
03:11He passed out.
03:13I'm wide awake.
03:16He probably just stared at you.
03:18No, of course he made it weird.
03:19Of course he did.
03:21And he was joking about getting into my bed and all sorts of stuff.
03:23And he had to share a bathroom.
03:25Yes, yes.
03:26You showering in there, Dave?
03:28You're standing there.
03:29You naked, Dave?
03:30I'm against the wall.
03:31When you had to do your business, did you like leave the room?
03:34Like, how did you guys manage that?
03:36That's so embarrassing.
03:37I don't think we did any business.
03:39We must have had some kind of rule on that.
03:44Because I don't have a memory of either one of us like blowing out the bathroom.
03:50I don't even thank God I don't.
03:52We weren't there very long.
03:53We probably did it at the restaurant.
03:56And you had stuff to do.
03:57You probably did it.
03:58The weirdness was brief.
03:59It was so brief.
04:00Dave probably didn't sleep well.
04:02No, my God.
04:04Yeah.
04:05It's hard to sleep well when a man is standing at the edge of your bed.
04:08Yeah, I was just looking at him.
04:09Yeah.
04:11Yeah.
04:11My covers aren't working.
04:15Cold.
04:16My covers are cold.
04:18Oh, God.
04:19What a night.
04:19What a weird time.
04:21Well, the thing about, too, like, and I always think about, like, the Katrina thing where
04:26they tried, they were going to do the same exact thing again.
04:30They were like, well, we can get one room for Lisa.
04:32And then we would have had to share.
04:34We would have had to share.
04:35And then we looked into the hotel had been hit.
04:38And mold was growing inside of it.
04:41And that's why they got this incredible deal.
04:43Of course you got an incredible deal.
04:45But even with the incredible deal, they were only going to give us two rooms.
04:48Two rooms.
04:48Yep.
04:49They were like, we've gotten you a poisonous room.
04:51They did.
04:52They really did.
04:53No, honestly, a mold-filled room.
04:55And I think we said no to that, right?
04:57Is that how that all went down?
04:58I cannot remember.
04:59Well, Lisa looked it up online, of course.
05:01Lisa did the groundwork and was like, we can't stay here.
05:03Yeah, because we were like, me and Dave were like, we're going down there, I guess.
05:07With the titties and all that stuff.
05:09And Lisa's like, hold the phone.
05:13Wait a minute.
05:14There's mold everywhere.
05:15Look at the elevator.
05:16What is that place called?
05:17Well, that's this one, right?
05:19Check this out, Dave.
05:20Some people had done reviews and were like, there's mold on every wall.
05:23That's great.
05:23Oh my God.
05:24Yeah.
05:24Like, it was literally underwater.
05:26Yeah.
05:26It was after one of the biggest disasters.
05:28Yeah.
05:28It was underwater.
05:29History.
05:30Right.
05:30We still sent listeners, though.
05:31We just didn't go.
05:32But they put them up in a nicer hotel.
05:34They did.
05:35But they couldn't send us at that point.
05:37They couldn't afford it.
05:38They couldn't afford it.
05:39At a nice hotel.
05:40Anyway, back to this guy who had to share a room with a coworker.
05:45He said, I'm a 24-year-old male teacher at a charter school network.
05:50They sent me and some colleagues to a conference where they put us up for the night.
05:53We had to share rooms.
05:55And they matched us up with same-sex coworkers.
05:59Me and a guy named Blake, who's also in his 20s, room together.
06:04Um, we've actually hung out a couple times.
06:08Anyway, we do all the conference stuff.
06:10We're tired.
06:10We decide to hit the hay.
06:12To get into bed, I take my clothes off and I'm wearing boxer briefs.
06:16Blake said, what are you doing, man?
06:19And I said, I'm going to sleep.
06:21What do you mean?
06:22He said, well, you better put on more clothes.
06:25And I say, no, I'm going to sleep.
06:29I'm in my underwear.
06:30Yeah, that was weird.
06:31He said, this is a work event, buddy.
06:32You better be professional.
06:34And I say, well, I'm sleeping.
06:36That's not part of the work event.
06:38And I'm going to bed.
06:39He said, so I just went to bed.
06:40In the morning, I wake up.
06:43And let me be clear, I'm not flaunting anything.
06:45But I go quickly get a drink of water from the bathroom and check my phone before I walk to the shower.
06:51I notice Blake taking a picture of me.
06:54And I say, what are you doing?
06:56He's going to report it.
06:57That's what he said.
06:58He said, well, I have to show this to HR.
07:00I told him, absolutely delete that right now.
07:05He said he did, but he refuses to show me confirmation.
07:08Oh, he didn't.
07:09No, he kept it.
07:10Anyway, back at work, I know he was telling people I was being an exhibitionist.
07:14And he keeps telling people that he's going to report me.
07:17And I just don't know how to deal with it.
07:20He's probably worried about you giving him a massage in the middle of the night or something.
07:23That's it.
07:23Or his inability to stop from going over and putting his mouth on your pee pee.
07:28Jesus.
07:29Well, I'm just wondering, like, why are you so concerned about it?
07:32Are you supposed to wear, like, pajamas?
07:34Like, man pajamas?
07:35Yeah.
07:36Man pajamas?
07:37You are supposed to.
07:37When you sleep with another man, you get early 1800s pajamas and a hat and socks and slippers and a candle.
07:46No one gave socks and a hat and a hat is how you sleep.
07:48Slippers and a candle?
07:50You do.
07:50The full Monty.
07:52That's how you go in the middle of the night and go to the bathroom?
07:56Hart, who goes there?
07:58I am looking for my phone.
08:01Nobody massaging each other here, they say.
08:04It's impossible.
08:08Yeah, you get the buttons on the butt of your pants and all that.
08:10Oh, buttons all the way down, like the gown goes to wrinkles.
08:14Oh, yeah.
08:15Oh, yeah, the gown.
08:17Male gown.
08:18It's a male.
08:20You have to wear a male sleep gown.
08:21Yeah, during one night with Charles, those rules didn't apply.
08:24Nope.
08:26I wouldn't want you to be all nude either.
08:28I'd be like, just put a shirt on.
08:29What are you doing?
08:30I guess my whole thing, though, is like, it would be insane that someone would think, like, I would be an exhibitionist because I'm going to sleep in my boxer shorts.
08:40The picture's weird.
08:41I'm showing off or something.
08:42Yeah.
08:42Like, taking the picture's weird.
08:43Oh, it's definitely weird.
08:44You could just be like, hey, dude, put a shirt on.
08:46This is weird.
08:47We, I don't even want to remember it.
08:50We both slept in our underwear.
08:51I think so, yeah.
08:52Yeah.
08:52Yeah.
08:53It's like, whatever.
08:53You're in separate beds, right?
08:54Separate beds.
08:55Yeah.
08:56No, we were mouth to mouth.
08:58Okay.
08:58All right.
08:59I like as many.
08:59What's that?
09:00Said I'd still sleep naked.
09:01See that?
09:02Oh, my God.
09:02Get out of here.
09:03I would.
09:04Get the hell out of here.
09:04That's how I sleep.
09:05What do you want me to do, man?
09:06Get out of here.
09:07Trying to, time to book a show trip.
09:11Shot pick the room assignments.
09:14Come on.
09:14Snuggle up.
09:15Oh, my God.
09:15I love clothes between me and other men.
09:17Oh, yeah.
09:17You know, like, wearing, like, shorts and a t-shirt or something?
09:20Yeah, I mean, it's just a t-shirt.
09:23I can't sleep in a t-shirt.
09:24I really can't.
09:25And I don't want you to look at me.
09:26We don't know what this guy is actually wearing either.
09:28He's like, I like to sleep in bikini breezes.
09:31That's how I'm comfortable.
09:32It's my sleep thong.
09:33It's just my sleep thong.
09:34I like the breeze.
09:35It'd be tough to have someone nude in the other bed.
09:41Yes, it would.
09:41You know?
09:42That would suck.
09:43But at the same time, like, okay, so, like, you know, we've talked about it enough.
09:47We know Jason sleeps nude, right?
09:49So if this happened, and, like, it was like, you got stuck with Jason in your room, and
09:55Jason gets nude.
09:56None of us are taking a photo of Jason and then running to HR.
10:00Well, you would never see me nude.
10:02Right, exactly.
10:03I would get in, and then I'd pop him off, and I'd be under the sheets.
10:05Yes, exactly.
10:05And when I woke up, you'd never see me.
10:07That's right.
10:08You'd never know.
10:09Right.
10:09I'd be secretly nude.
10:10You rascal.
10:11Oh, God, you are a nude rascal.
10:13I might tell you I'm going to sleep in my boxers, but as soon as I get under the sheets,
10:16I'm popping him off.
10:17Yeah, that's what I did, too.
10:18None the wiser.
10:19Nobody gets hurt.
10:20Yeah.
10:20Dave thought I had boxers on.
10:23Oh, for God's sakes.
10:25You could tell by all the bed hair that he was rolling around.
10:28Bed hair?
10:29Oh, yeah.
10:30You could tell which bed was mine.
10:33I'll tell you that.
10:34I'll tell you that right now.
10:35All the hair.
10:37It's like Sasquatch.
10:37One night with Chuck.
10:41Yeah.
10:42Let me tell you.
10:44Wild.
10:44So, yeah, I hope.
10:46I mean, lots of guys here say they, you know, they have to share rooms on trips and it's
10:51not a big deal.
10:52But one guy said sleeping in shorts should be fine, too.
10:56Yeah, shorts.
10:57That's fine.
10:57I just don't want to sleep.
10:58I would do anything possible to not sleep in a room with another man on a business trip.
11:02Yeah, that's the best.
11:03I mean, it's just probably way to go.
11:04I would just like, I'd be like, oh, I'm going to go sleep in my car.
11:07Mm-hmm.
11:07You have fun?
11:09Yeah.
11:09No, like, it's worked out here.
11:11They haven't done that to us yet.
11:13It's an odd thing.
11:14Like, you just, like, a business should give you your privacy on a trip, you know?
11:19Oh, yeah.
11:20No, there was, I swear to God, there was initial talk of all of us having to be in, like,
11:27one suite.
11:29Yeah, they had, like, a two or three bedroom suite.
11:32Yeah.
11:32That they wanted us all to share.
11:33And we're like, no.
11:34No way.
11:35Like, no way.
11:36Come on.
11:37Lisa's got to get her own space.
11:38Like, we had to, I remember that.
11:39It was like a fight to make sure that Lisa was going to get her own room.
11:44It was.
11:45There was, like, behind the scenes.
11:46They didn't care about lawsuits, I guess.
11:48No, they didn't.
11:48No, they didn't.
11:50That's insane.
11:50It was cheaper to get, like, one suite.
11:51You have to remember, like, because who was the boss at that time?
11:55Yeah.
11:55You know?
11:55And he was.
11:56That wasn't going to happen.
11:57A little wild.
11:58Be no worries rooming with Court, because he's got his silk PJs.
12:02Oh, that's true.
12:03That is.
12:03Yeah.
12:04That's true.
12:04I'd bring matching pairs.
12:06Oh, that's nice.
12:08My kind of fella.
12:08Yeah.
12:08Oh, thank you.
12:09My kind of fella.
12:10Yeah, exactly.
12:11Head to toe.
12:12I'd appreciate that.
12:13The only time I'd appreciate Court's pajamas.
12:15Yeah.
12:16Be like, all right.
12:17Thank you, sir.
12:18Yeah, but what do you do in that situation?
12:19Do you get ahead of it?
12:20Do you go to HR and be like, hey, like, we had to share a room.
12:23I sleep in my underwear.
12:25I guess you just don't know.
12:27I don't know how HR works enough to be like, okay, well, like, which one of these is more
12:31of a violation?
12:33You went to bed in your boxers, or a man took a photo of you in your boxers?
12:40Like, what is the more egregious?
12:42Once you get into your underwear, it's not like a business trip anymore, and you're just
12:46wearing your underwear.
12:47It becomes a slumber party.
12:48I love a slumber party.
12:50What about a pillow fight?
12:51But if it's for business, not everybody's about it.
12:54Yeah.
12:55Someone said, my girlfriend invited me to her brother's wedding, new relationship, and said
13:00we're going to stay in a room with her sister and cousin and their significant others.
13:06I know this wasn't a business trip like you guys are talking about, but still crazy.
13:09I freaked out and said, no way.
13:11I'll pay for my own room, which I did.
13:12Yeah.
13:13I don't mind if I'm dating a chick, and then another couple, and nobody's all banging or
13:21anything.
13:22That's more of a buffer there.
13:24I don't know.
13:25I'm weird.
13:26I remember when I had my roommate, and me and her never had anything going on, but her
13:32dad was going to stay over.
13:34They were heading down to Florida, and the first stop was going to be stay over at our
13:40place, and this is like 8.30 at night, and I'm playing video games, and around the corner
13:48comes her dad, just in his tighty-whities.
13:50That's so uncomfortable.
13:51Just in his tighty-whities.
13:53And he's like, who cares?
13:55He didn't care at all.
13:58And I was like, this is nuts.
14:00That's a dad thing.
14:01My dad didn't care.
14:02But it was like, I feel like also sharing a room is like, okay, if you're in your 20s
14:08and you have no money and you need whatever job, that's one thing.
14:11Once you get in your 30s, you're like, I'm getting my own room.
14:13Yeah.
14:13I get my own room.
14:14No matter what.
14:15Yeah, radio in our ... I don't know how old we would have been there.
14:19It would have been maybe early 30s.
14:21Radio has just been like, you pay for your own room.
14:23Maybe even late 20s.
14:24Yeah, was it late 20s?
14:25It could have been late 20s.
14:26I went on a work trip with my female boss and had to share a room with her.
14:32I'm also female in my early 20s.
14:34She slept butt-ass naked as my boss.
14:38And when I kind of said something about it, she told me to deal with it.
14:42Two chicks?
14:43Two chicks.
14:44Getting cooler, huh?
14:46Whatever they want to do, man.
14:48It's different.
14:50It's different.
14:51Everybody.
14:51It's really weird.
14:52Oh, my God.
14:53I mean, I can't even imagine.
14:54One of the other weird things I've done is when I went to Toronto to play for the station's
15:02hockey team and realized, oh, God, I'm about to see every guy that I work with naked and did.
15:13Well, that's like a locker room situation.
15:15It's a locker room thing.
15:15It's just still so weird.
15:17It's still weird, but it's different.
15:18It's so weird.
15:19You don't want it to happen to Tennessee.
15:21No.
15:21You really don't.
15:22You don't want to see Coworker Dong?
15:23No, I didn't want to see.
15:24I saw a big boss naked and doing drugs that we didn't know.
15:29At the same time?
15:30Naked and drugs?
15:31No.
15:32Naked and then drugs.
15:34I was like, that's a what?
15:35And I was like, this has been a trip.
15:37Yeah.
15:38Someone said, who are we kidding?
15:39Jason would sleep in the cuck chair.
15:41The chair.
15:43You know, that's like making the rounds lately.
15:47Like they show the picture of a hotel room.
15:49There's always one chair in the corner.
15:50Yeah.
15:51That's called the cuck chair.
15:52Oh, yeah.
15:53Okay.
15:53I'll sit there while you guys bang in your same bed together.
15:56That sounds great.
15:57All right.
15:57I'll just be naked with my legs crossed.
16:00Naked with my legs crossed.
16:02How else would I be sitting in the cuck chair when I've been done?
16:05That does sound relaxing.
16:07That does sound relaxing.
16:07How else would I mind?
16:10I'm not trying to scare you.
16:11I'm not trying to cope.
16:12Want to?
16:12And I'm not going to be able to.
16:14I'mbring you.
16:14It's fine.
16:15I'm not going to be the police and someone separate.
16:15I'm sorry.
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