April 24, 2026 • 20 mins
Chelsea and Catherine deal with an awkward etiquette situation. Then: A caller follows up about making out with her boss. And a couple is in trouble when their parents start dating each other. And a powerbottom needs Chelsea’s help.
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Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com
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Executive Producer Catherine Law
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Episode Transcript
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Speaker 1 (00:00):
Okay for the High and Mighty Tour people, we are
rocket and rolling. These are the shows we have coming up.
April twenty third is Kansas City, Missouri. April twenty fourth
is Saint Louis, Missouri. April twenty fifth is Minneapolis. April
thirtieth Nashville. May first, Charlotte, North Carolina. May second is Durham,
North Carolina. May sixth in Los Angeles at the Sabon
(00:22):
Theater for Netflix as a joke. May fifteenth, I will
be in Saratoga May sixteenth, Monterey, May seventeenth, Modesto.
Speaker 2 (00:31):
I will be in port Chester on June fourth, and
we added two new dates to the High and Mighty Tour.
On June third, I am coming to Saratoga Springs, New York.
Speaker 3 (00:40):
So pre sale has.
Speaker 1 (00:41):
Begun for that, and then on June twenty eighth, I
am coming to Nantucket and presale has started on that.
June fifth, I will be in Boston, Massachusetts. June twelfth,
I will be in Portland, Oregon. And June thirteenth I
will be in Seattle, Washington. June twenty seventh is going
to be Hyenna's, Massachusetts. August sixth is Red Bank, New
Jersey August seventh. I'm coming home to Montclair, New Jersey
(01:05):
August fifteenth. Is Calgary, Alberta, Canada, September eighteenth, Santa Barbara
September nineteenth, San Diego September twenty fifth. I will be
at the Beacon in New York City September twenty sixth.
I will be in Philadelphia September twenty seventh, New Haven, Connecticut.
October second, Atlanta, Georgia, October third, Baltimore, Maryland, October fourth, Saginaw, Michigan,
(01:28):
October ninth, Pittsburgh, Pennsylvania, October tenth, Toronto, Canada, October sixteenth.
I'm coming to Boise, Idaho, October seventeenth, Spokane, Washington, November seventh.
I will be in San Francisco and November thirteenth, Salt
Lake City November twentieth, Austin November twenty first, Houston, Texas,
(01:50):
November twenty second, Irving, Texas.
Speaker 2 (01:52):
December fifth.
Speaker 1 (01:53):
I am adding a second show in Denver for those
of you who can get tickets to the first one.
And on December sixth, I will be coming to Vancouver, Canada. Okay,
those are all my dates for the Hide Mighty Door.
Go to Chelsea Handler dot com for tickets.
Speaker 2 (02:08):
Hi there, Hi Catherine.
Speaker 3 (02:10):
Good morning, Chelsea, Good morning.
Speaker 4 (02:11):
Hi.
Speaker 3 (02:12):
We're back in your house.
Speaker 2 (02:13):
My house has tried to be we would let a candle.
Speaker 1 (02:16):
Look, guys, we're in my home. It's nice. I supped
in about thirteen hours last night.
Speaker 2 (02:20):
I lost you and crab a say Sianto in crable
or Ciano in krable.
Speaker 3 (02:27):
Yeah, Santo, yes, you have something in.
Speaker 1 (02:30):
Your tooth right there, to the left of your to
the left of your big tooth.
Speaker 2 (02:34):
This one, Yeah, we get it. No, it's right that one.
Speaker 1 (02:40):
I think it's gone. That should be on camera for sure. Yeah,
that's gone now.
Speaker 3 (02:46):
I mean, listen, I do think like a real friend
will be like, you have smoothie in your teeth, which
is exactly.
Speaker 2 (02:50):
What's going on there.
Speaker 1 (02:50):
Yeah, you have to tell people. I don't even think
it's about being a friend. It's just about seeing it's respect.
Speaker 3 (02:56):
It's like it's more embarrassing for the person in the moment.
But then I mean, I want.
Speaker 2 (03:00):
Someone to tell me when I have a fucking food
in my tooth, or a teeth or a tooth.
Speaker 3 (03:05):
I was actually talking to Yamanika's folks yesterday.
Speaker 2 (03:09):
She's got Comedica's moving in, you guys.
Speaker 1 (03:11):
I led her sleep with me one night on the
road because she fucked up and double booked herself into
two hotel rooms in the wrong city. So we were like,
say we were in Chicago, she booked them in Minneapolis,
two hotel rooms, so she lost all that money, and
so I let her sleep with me one night.
Speaker 2 (03:26):
Then the next night she's like, that was fun. I
was like, it was fun because it was one night.
Speaker 1 (03:29):
It's not fun for you to be fucking sleeping in
my bedroom with me two nights in a row. So
then now she's sleeping here for Netflix as a joke festival.
We'll both be performing you guys May six. Tickets available
at Chelsea dot com, Chelseahandler dot jam, Chelseahandler dot jam.
And she'll be staying here. And then I fear she'll
never stay anywhere.
Speaker 3 (03:48):
I don't think she's gonna leave.
Speaker 2 (03:50):
Yeah. I just got a text from her.
Speaker 1 (03:52):
We're doing shows this weekend and she said, oh, I
fucked up with my hotel room in Mesa, Arizona.
Speaker 3 (03:57):
I mean that's on purpose.
Speaker 1 (03:59):
At this point, she wants to be with me, and
we've discovered that she'll take sex from a man or
a woman.
Speaker 2 (04:04):
So she's fluid, she's not. She doesn't care. She just
wants action.
Speaker 1 (04:08):
And I think she gets so much affection from me
that she's confusing that with some sort of like sex.
Speaker 3 (04:12):
You don't have Doug there, so you just have to like.
Speaker 2 (04:15):
Yeah, well that's racist.
Speaker 3 (04:18):
Oh I have an update for her collar and this
is a little bit of a disappointing one.
Speaker 2 (04:23):
They took my advice and all ship. She chickened out.
Speaker 3 (04:27):
So Stephanie, who had called it on our Josh Radner episode,
the one who wanted to make out with her boss.
Speaker 1 (04:32):
I just have to tell you now, the thing that
was on the left side of your tooth is on
the right side of your You.
Speaker 3 (04:36):
Have a toothbrush. I got it, and I want to just.
Speaker 2 (04:38):
Be on the record. It's more uncomfortable for the telee.
Speaker 3 (04:42):
It is.
Speaker 1 (04:42):
It is for the teller, for the teller than the
teley because then you have to bring it up.
Speaker 3 (04:46):
Twice, especially when it moves, and it can.
Speaker 1 (04:49):
Sound like you're kind of like you know, like, uh,
what's the word You're like yeah, yeah, or like you're
trying to make someone feel feel bad.
Speaker 3 (05:01):
And I'm good as Chelsea likes you, bra.
Speaker 2 (05:03):
Do you think that's the first time I've been called
a bitch? Yeah? You're fine. Now there you go. You
did it teams.
Speaker 3 (05:12):
Okay, so Stephanie says, Hi, Chelsea, well I probably still
have a crush on my boss. Nothing ever happened after
I talked to y'all. He left on a work trip
for a couple of weeks and returned only to leave
for more travel about every four to five days. This
allowed me to reflect, as it was all quite literally
making me go crazy. I think she was just maybe
very horny at the moment. He had stopped drinking, and
(05:33):
this actually changed our dynamic a ton, not as much
flirting or texting. We stopped going to dinners or events.
He did randomly invite me to go watch his favorite movie.
Then the next day he told me he met someone.
I'm not hurt by it. This is his third girlfriend
in nine months. He texted me last night at twelve
thirty eight am saying he liked my new hairstyle. Wtah,
I know he's like dragging her along annoying. Yeah, anyway,
(05:56):
he loves very hard and honestly, I'm not interested in
love bombing. Too independent for that. So there's a little
relief it's not me. Also, I still love my job
and I don't want to leave it to even explore
this option. I'd for sure still like to make out
with him at least once. I mean, why not, But
for now it's boundaries and being a supportive friend slash coworker.
Stephanie Great's noting that's probably best.
Speaker 2 (06:16):
She probably saved herself.
Speaker 1 (06:18):
Yeah, like drama and whatever other words go with drama.
Speaker 3 (06:23):
Yeah for sure.
Speaker 2 (06:25):
Yeah, yeah. Yeah. Also, when somebody texts you at twelve
thirty in the morning, we all know what that means.
Speaker 3 (06:28):
We all know what that means. That means you up. Yeah, Okay,
it's time for some couples counseling with Chelsea. So this
is my.
Speaker 2 (06:40):
Having a lot of heat by the way, for my couples.
Speaker 3 (06:42):
Oh good dating instagrams.
Speaker 1 (06:45):
Yeah, a lot of heat between gay guys and gay girls,
gay girls and gay girls or guy gay girls, and
a lot.
Speaker 2 (06:51):
Of heat between gay guys.
Speaker 1 (06:52):
But were still having problems personally before I put the
men up, because I didn't really want to put women
up and just have men like the just men are
not to be trusted. So but I did do some
finagling on the side before I started broadcasting people, and
there's like two people that are on straight couple that
are on their like third and one is on their
fourth date.
Speaker 3 (07:12):
Well do you know if you you probably do know this,
if you introduced three couples who get married, it's like
a mitzvah or you're a mensch something very good.
Speaker 1 (07:23):
Well, that's all right, that's already.
Speaker 2 (07:25):
I don't I need that. And I thought you were
gonna say I'm become a.
Speaker 3 (07:29):
Fairy or something straight to heaven.
Speaker 2 (07:31):
Oh well, I wish I believed in that.
Speaker 3 (07:34):
Well, Miles and Natalie. This is Natalie writing in. She says,
Dear Chelsea, my boyfriend and I recently moved in together
and blended our families. We've been together almost three years
and have had no major issues until now. Recently, my
dad lost his partner and his mom lost hers this
past summer. We invited both of them to join us
as past Thanksgiving, so they weren't alone. A few weeks ago,
(07:55):
my boyfriend's mom reached out to me for my dad's number.
All I thought was how nice a friendship is blossomed.
I'm getting texts from my dad with pictures of them
gallivanting around little small towns in the Midwest and teaking,
meeting for coffee, drinking wine, and going to museums, all
things you would expect old people dates to look like.
My boyfriend doesn't like this whatsoever. It's nothing personal toward
(08:16):
my dad, but he thinks it's selfish of them to
do this to us. My sister and I, however, find
it awkward and weird, but think it's actually kind of funny.
We're very close with our dad since we lost our
mom unexpectedly five years ago. We have the type of
a relationship where my sister and I call him a
hoe bag and tease him about all of this. It
is weird, but we're supportive. My boyfriend and his mom
are not quite as close. They haven't communicated much about
(08:38):
this at all, since she knows he's not supportive. Here's
the thing. I normally tell my boyfriend everything I want
to be able to come home and laugh that his
mom spent the night at my dad's, that they went
to a museum today, etc. He gets pretty weird about it.
I totally understand his viewpoint, but you only live once
and it really doesn't affect our life, is what I
say help Miles and Natalie.
Speaker 2 (08:57):
Hi, Miles and Natalie? Oh, Hi, Hi? How's it going good?
How are you two doing good? So your parents are
are hooking up? Yeah? Yes, and Miles, you don't like that.
Speaker 4 (09:14):
I'm not a fan, No, not at all.
Speaker 5 (09:16):
And I'm a little bit more on the supportive side.
Speaker 2 (09:20):
Right.
Speaker 1 (09:20):
Well, Luckily, it's really not either one of your business,
you know what I mean, Like, it's really not up
to you guys what your parents are going to get
up to. And while I understand your discomfort, Miles, I
can relate. I just think that, like, let they've got
to do their thing and they're happy, and you know, like,
what are you going to do about it?
Speaker 3 (09:41):
I think it's so cute.
Speaker 1 (09:43):
It is cute, but I understand the reluctance in wanting
to know the details. And Natalie, you don't have to
tell Miles everything you know about their relationship, like it's not.
Speaker 2 (09:53):
If he's interested, he'll let you know.
Speaker 1 (09:55):
And other than that, you've got to just kind of
like have a great, nice, loving attitude towards them for
doing their thing. It's not like they're having sex in
front of you and you have to sit there and
watch it, like it's not that's not happening, so be
grateful for small blessings.
Speaker 2 (10:12):
Yeah. Yeah, So is it.
Speaker 3 (10:15):
Just the ick factor or is there anything else?
Speaker 4 (10:17):
No, No, it's not even that. I think it's how it happened,
not that it happened, if that makes sense, Because they
both recently lost somebody, very very within a couple of
weeks of each other. He lost his significant other, my
mom lost her significant other, and so they it's kind
(10:40):
of like trauma bonding which has then evolved into something else.
And also she was not honest about it, where he
was telling Natalie everything that was going on, and my
mom was not telling me anything that was going on
and not being honest about it even when I asked
her about it. So I think that's where.
Speaker 5 (10:59):
But then he also came across like that he wasn't
as supportive, So then I was like, well, why is
she gonna want to tell you anything?
Speaker 3 (11:08):
Yeah?
Speaker 1 (11:08):
I mean, first of all, Miles, you're like kind of
like setting her up for failure, because she obviously consents,
as your mother and as a woman, we all have intuition.
She consents that you're there's a level of disapproval coming
from you, whether or not you're exhibiting that or not.
Speaker 2 (11:24):
Like a mother will know.
Speaker 1 (11:25):
How her son feels about something, especially her personal life,
and especially like this this kind of sensitive issue. But
something that's really important to remember is like, listen, we
want people to be happy, period, don't we We want
the people in our lives to be happy. Don't make
excuses for why you should be unhappy for them or
you should be unsupportive of them. Be happy that they
(11:47):
found each other. Who cares if it was two weeks,
at least they have each other to like console and
confide in and spend time together. And isn't that what
you would want for any single person in your life
that you cared about?
Speaker 4 (11:59):
Yes, I would agree with that.
Speaker 3 (12:01):
Do you think they should like address this with mom
and dad or that he should with mom? Just be like,
I'm happy for you.
Speaker 2 (12:07):
Or it's already been addressed, okay.
Speaker 5 (12:10):
And one awkward thing that I got in the middle
of is they both called me and had me on
speaker because my dad wanted to go to his kids
sporting event that his mom was going to and I'm like,
why would you be going to that? Like I'm not
even going to be there, And so we.
Speaker 4 (12:31):
Haven't told the kids not thers, and.
Speaker 2 (12:35):
So they didn't.
Speaker 5 (12:37):
That's socially awkward, and you know why Miles is having
an issue with it. And then I was just like, you.
Speaker 4 (12:45):
Know, so my kids were pretty attached to their grandpa
that just passed, so introducing this so quickly. So that's
another aspect of this is that I don't It's not
that I don't want her to be happy, but my kids,
he pass from a long, hard disease and so it
was long deterioration of watching this and then all of
(13:06):
a sudden they're at his funeral and then all of
a sudden this is going on. So we have not
broken this to the kids yet.
Speaker 2 (13:13):
Okay, how old are your kids?
Speaker 4 (13:15):
Minor ten and twelve, minor seven and nine?
Speaker 1 (13:20):
Okay, wow, good for you guys. That's nice. Yeah yeah
half the time, so thank you. Fit Yeah, well even better,
that's reasonable. That's totally reasonable not to want to introduce
this relationship to your children.
Speaker 2 (13:34):
That's a separate issue.
Speaker 1 (13:35):
So like, while you work on your acceptance, you guys
can both have like a conversation with them, and I
would do it together just to make sure they know
you're a united front, so they're not playing you off
of each other like children would do, because you know
what I mean, like, let them know you guys both
are supportive and Miles, you can use this as an
opportunity to be like, yeah, we're supportive. We want you
(13:56):
both to be happy. It's the timing is a little quick. Well,
while we're going we are in full acceptance mode and
working on our acceptance, we do have to take some
time to be sensitive to the children and what they
are learning. And you guys, coming out as a couple
so soon after doesn't feel right.
Speaker 2 (14:14):
So let's give it some time.
Speaker 1 (14:15):
And we just want to make sure you guys understand
where we're coming from and that you can be respectful
of that.
Speaker 2 (14:20):
And that's not a tall order. Yeah.
Speaker 5 (14:22):
Yeah, they did come over for Easter and we told them,
like that's fine, just arrive separately and no flirting.
Speaker 1 (14:31):
Right, Well, so then they can they can follow the program,
right If you set the rules down for interaction, and
you only have the right to set rules around your
family and your children, that's it. You can't direct them
in any other way. Even if this blows up and
ends up being a real like dramatic something like breakup
or whatever, like all you can do is throw love.
Speaker 2 (14:54):
And support their way. That's it.
Speaker 1 (14:55):
You're not here to judge them, you're not here to
guide them. You're just here to support them.
Speaker 3 (15:01):
Okay, yeah, and now you can double date.
Speaker 2 (15:06):
Yeah, so that's cool.
Speaker 1 (15:08):
So yeah, just make sure that they know that they
have to leave their clothes on at all times, especially
around family members.
Speaker 3 (15:17):
Or maybe just like not kiss in front of you
two for no.
Speaker 4 (15:23):
Well if they get married, then we'll be step me
and now they step like. I'm like, no, I'm not
doing that kind of role playing nothing.
Speaker 1 (15:31):
No, I mean listen, take it for what it is.
It's pretty fucking entertainments, but you know what I mean. Yeah,
so look at it like that through the lens of
comedy and entertainment. Everyone could probably on both sides could
use a laugh right now.
Speaker 2 (15:45):
So let that be it. It's pret hilarious, which is yeah.
Speaker 5 (15:51):
I thought it was a good topic for your show.
Speaker 2 (15:53):
Thank you. Yes, it's perfect. We love it. You please,
all right, you guys.
Speaker 4 (15:59):
Take care all right, bye, thank you.
Speaker 3 (16:06):
That's maybe one of my favorite questions we've gotten in
a while.
Speaker 1 (16:09):
I just love those when older when people die, like
the old people just like cling on, not cling on
or they fast. Everything is quick because they have been
through life and they're like, fuck this waiting round. It's
like the opposite of girls not knowing whether to call
a guy or approach a guy. It's like they know
there's no time to lose and that they got to
(16:31):
get down to.
Speaker 3 (16:31):
Businessespecially if they just lost somebody. They're like, let's make
it happen. I like you, you and me, right.
Speaker 2 (16:36):
Right, that guy's dead. He took him a long time
to go. There was no sex probably, you know.
Speaker 3 (16:41):
Right right right, Okay, Well, speaking of sex, we have
our you want me to have sex. Don't make me blush, Chelsea.
Speaker 1 (16:48):
Sorry, I'm sorry for hitting on you in the top half.
Speaker 2 (16:52):
That's indefinite. No, no, no, no, no, you're.
Speaker 1 (16:54):
I mean it's that's why I can't have a real
job because I would be fucking evicted.
Speaker 2 (16:59):
From it, victim. Notice my use of conviction.
Speaker 3 (17:02):
That's what they do at jobs when you can't be
there anymore. So this question is our Wondering Question of
the Day and the title is Closet power bottom needs
your help.
Speaker 2 (17:12):
Dear Chelsea, I believe I'm a power bottom.
Speaker 3 (17:15):
Yeah.
Speaker 2 (17:15):
I like to be on bottom. I sometimes being on
top is too much work.
Speaker 3 (17:19):
I agree, like you're gonna to fuck me.
Speaker 2 (17:22):
Fuck me.
Speaker 3 (17:22):
Men have more muscle quote unquote use it.
Speaker 2 (17:25):
Yeah, I don't understand, like I want to just get fucked.
Speaker 3 (17:28):
Have you seen this thing online that's like men planking
till failure and it can they last? I think it's
less about that than just like hearing them struggle and
being in a playing position.
Speaker 2 (17:39):
Now I feel like, yeah, I'm yeah, I want to
get on top of you. I'll let you know. Yeah,
I'll tap you out.
Speaker 3 (17:45):
So Charlie says, Dear Chelsea. I'm a twenty seven year
old gay man living in Los Angeles with a little
bit of an odd situation that I need you to
weigh in on. I developed a large skin tag on
my butthole when I was around twenty one. As you
can imagine, this would interfere with my second I finally
had it removed when I was around twenty three. After
the removal, sex was amazing. I could finally bottom and
(18:06):
I was really enjoying it. Everything was good for about
a year or so, and then it started to grow back,
this time bigger and more painful. I know now I'm
single and in the best shape of my life. I'm
a true verse, but I absolutely love bottoming, which I
feel like is like the secret of a lot of
people who say their verse is like they really love
to be a bottom.
Speaker 2 (18:24):
Oh is that right? Yeah?
Speaker 3 (18:25):
I think that's Unfortunately because of the skin tag, I've
become a strict top.
Speaker 2 (18:32):
Does it hurt to have sex with Yes?
Speaker 3 (18:33):
Yeah, I think it's like because of this, it's like
getting in the way. I found a doctor who specializes
in gay men, but it's quite expensive and insurance won't
cover any.
Speaker 2 (18:42):
Of the cost to do what remove it again? M I?
Speaker 3 (18:45):
I guess like the last person, the last doctor was
not a gay man specializing doctor, and like could have
been done better. So I live comfortably, but this is
something I would have to take on some medical debt
for Is it worth it? Part of me thinks that's irresponsible,
but I also want to fully enjoy my sex life
as a single man. PS. I was at the Netflix
as a Joke show at the YouTube Theater. I'm a
(19:05):
big fan of Chelsea's and that was my favorite comedy
show I have ever been to.
Speaker 1 (19:08):
Sincerely, well you can come again Netflix A Jokes as
a Joke Festival starts again. Say I'm at the Sabam
Theater this year. Okay, yes you should. But why does
an insurance cover this? And maybe that's a stupid question
because he's a gay man and they know.
Speaker 3 (19:21):
There's a specialist, so it's like not under his insurance.
Speaker 2 (19:24):
Okay, so it's not under his insurance. I would say
it's worth the investment.
Speaker 1 (19:27):
I think if something you enjoy, yeah, yeah, that you're
being you're prevented from doing because of that, and it's removable,
I would say financially, just to take a bullet and
do it.
Speaker 3 (19:38):
Yeah, especially if you're like living comfortably and like you
can pay it off over time.
Speaker 1 (19:42):
And also to find out like how to get rid
of it. Is there a way to get rid of
it so that it doesn't come Is there a way
to ensure that it doesn't come back?
Speaker 3 (19:48):
Right?
Speaker 2 (19:49):
I mean no, maybe there isn't.
Speaker 3 (19:50):
Yeah, maybe there isn't. But also the specialist would probably
be the one to be able to answer that.
Speaker 2 (19:54):
So yeah, yeah, I want people to be enjoying themselves.
Speaker 3 (19:58):
Right, exactly like I think, I think it's definitely worth it. Yeah.
Speaker 2 (20:01):
Okay, Well we'll see you guys next week. Bye audios.
Speaker 3 (20:05):
If you want advice from Chelsea, write into Dear Chelsea
podcast at gmail dot com. Dear Chelsea is a production
of iHeartMedia. Follow Chelsea on all socials at Chelsea Handler,
and find Katherine on TikTok at flash Cadabra. Dear Chelsea
is edited and engineered by Brandon Dickert executive producer Katherine Law.
Find full video episodes and minisodes now on Netflix, and
(20:27):
get tickets to see Chelsea live at Chelseahandler dot com
Okay for the High and Mighty Tour people, we are
rocket and rolling. These are the shows we have coming up.
April twenty third is Kansas City, Missouri. April twenty fourth
is Saint Louis, Missouri. April twenty fifth is Minneapolis. April
thirtieth Nashville. May first, Charlotte, North Carolina. May second is Durham,
North Carolina. May sixth in Los Angeles at the Sabon
(00:22):
Theater for Netflix as a joke. May fifteenth, I will
be in Saratoga May sixteenth, Monterey, May seventeenth, Modesto.
Speaker 2 (00:31):
I will be in port Chester on June fourth, and
we added two new dates to the High and Mighty Tour.
On June third, I am coming to Saratoga Springs, New York.
Speaker 3 (00:40):
So pre sale has.
Speaker 1 (00:41):
Begun for that, and then on June twenty eighth, I
am coming to Nantucket and presale has started on that.
June fifth, I will be in Boston, Massachusetts. June twelfth,
I will be in Portland, Oregon. And June thirteenth I
will be in Seattle, Washington. June twenty seventh is going
to be Hyenna's, Massachusetts. August sixth is Red Bank, New
Jersey August seventh. I'm coming home to Montclair, New Jersey
(01:05):
August fifteenth. Is Calgary, Alberta, Canada, September eighteenth, Santa Barbara
September nineteenth, San Diego September twenty fifth. I will be
at the Beacon in New York City September twenty sixth.
I will be in Philadelphia September twenty seventh, New Haven, Connecticut.
October second, Atlanta, Georgia, October third, Baltimore, Maryland, October fourth, Saginaw, Michigan,
(01:28):
October ninth, Pittsburgh, Pennsylvania, October tenth, Toronto, Canada, October sixteenth.
I'm coming to Boise, Idaho, October seventeenth, Spokane, Washington, November seventh.
I will be in San Francisco and November thirteenth, Salt
Lake City November twentieth, Austin November twenty first, Houston, Texas,
(01:50):
November twenty second, Irving, Texas.
Speaker 2 (01:52):
December fifth.
Speaker 1 (01:53):
I am adding a second show in Denver for those
of you who can get tickets to the first one.
And on December sixth, I will be coming to Vancouver, Canada. Okay,
those are all my dates for the Hide Mighty Door.
Go to Chelsea Handler dot com for tickets.
Speaker 2 (02:08):
Hi there, Hi Catherine.
Speaker 3 (02:10):
Good morning, Chelsea, Good morning.
Speaker 4 (02:11):
Hi.
Speaker 3 (02:12):
We're back in your house.
Speaker 2 (02:13):
My house has tried to be we would let a candle.
Speaker 1 (02:16):
Look, guys, we're in my home. It's nice. I supped
in about thirteen hours last night.
Speaker 2 (02:20):
I lost you and crab a say Sianto in crable
or Ciano in krable.
Speaker 3 (02:27):
Yeah, Santo, yes, you have something in.
Speaker 1 (02:30):
Your tooth right there, to the left of your to
the left of your big tooth.
Speaker 2 (02:34):
This one, Yeah, we get it. No, it's right that one.
Speaker 1 (02:40):
I think it's gone. That should be on camera for sure. Yeah,
that's gone now.
Speaker 3 (02:46):
I mean, listen, I do think like a real friend
will be like, you have smoothie in your teeth, which
is exactly.
Speaker 2 (02:50):
What's going on there.
Speaker 1 (02:50):
Yeah, you have to tell people. I don't even think
it's about being a friend. It's just about seeing it's respect.
Speaker 3 (02:56):
It's like it's more embarrassing for the person in the moment.
But then I mean, I want.
Speaker 2 (03:00):
Someone to tell me when I have a fucking food
in my tooth, or a teeth or a tooth.
Speaker 3 (03:05):
I was actually talking to Yamanika's folks yesterday.
Speaker 2 (03:09):
She's got Comedica's moving in, you guys.
Speaker 1 (03:11):
I led her sleep with me one night on the
road because she fucked up and double booked herself into
two hotel rooms in the wrong city. So we were like,
say we were in Chicago, she booked them in Minneapolis,
two hotel rooms, so she lost all that money, and
so I let her sleep with me one night.
Speaker 2 (03:26):
Then the next night she's like, that was fun. I
was like, it was fun because it was one night.
Speaker 1 (03:29):
It's not fun for you to be fucking sleeping in
my bedroom with me two nights in a row. So
then now she's sleeping here for Netflix as a joke festival.
We'll both be performing you guys May six. Tickets available
at Chelsea dot com, Chelseahandler dot jam, Chelseahandler dot jam.
And she'll be staying here. And then I fear she'll
never stay anywhere.
Speaker 3 (03:48):
I don't think she's gonna leave.
Speaker 2 (03:50):
Yeah. I just got a text from her.
Speaker 1 (03:52):
We're doing shows this weekend and she said, oh, I
fucked up with my hotel room in Mesa, Arizona.
Speaker 3 (03:57):
I mean that's on purpose.
Speaker 1 (03:59):
At this point, she wants to be with me, and
we've discovered that she'll take sex from a man or
a woman.
Speaker 2 (04:04):
So she's fluid, she's not. She doesn't care. She just
wants action.
Speaker 1 (04:08):
And I think she gets so much affection from me
that she's confusing that with some sort of like sex.
Speaker 3 (04:12):
You don't have Doug there, so you just have to like.
Speaker 2 (04:15):
Yeah, well that's racist.
Speaker 3 (04:18):
Oh I have an update for her collar and this
is a little bit of a disappointing one.
Speaker 2 (04:23):
They took my advice and all ship. She chickened out.
Speaker 3 (04:27):
So Stephanie, who had called it on our Josh Radner episode,
the one who wanted to make out with her boss.
Speaker 1 (04:32):
I just have to tell you now, the thing that
was on the left side of your tooth is on
the right side of your You.
Speaker 3 (04:36):
Have a toothbrush. I got it, and I want to just.
Speaker 2 (04:38):
Be on the record. It's more uncomfortable for the telee.
Speaker 3 (04:42):
It is.
Speaker 1 (04:42):
It is for the teller, for the teller than the
teley because then you have to bring it up.
Speaker 3 (04:46):
Twice, especially when it moves, and it can.
Speaker 1 (04:49):
Sound like you're kind of like you know, like, uh,
what's the word You're like yeah, yeah, or like you're
trying to make someone feel feel bad.
Speaker 3 (05:01):
And I'm good as Chelsea likes you, bra.
Speaker 2 (05:03):
Do you think that's the first time I've been called
a bitch? Yeah? You're fine. Now there you go. You
did it teams.
Speaker 3 (05:12):
Okay, so Stephanie says, Hi, Chelsea, well I probably still
have a crush on my boss. Nothing ever happened after
I talked to y'all. He left on a work trip
for a couple of weeks and returned only to leave
for more travel about every four to five days. This
allowed me to reflect, as it was all quite literally
making me go crazy. I think she was just maybe
very horny at the moment. He had stopped drinking, and
(05:33):
this actually changed our dynamic a ton, not as much
flirting or texting. We stopped going to dinners or events.
He did randomly invite me to go watch his favorite movie.
Then the next day he told me he met someone.
I'm not hurt by it. This is his third girlfriend
in nine months. He texted me last night at twelve
thirty eight am saying he liked my new hairstyle. Wtah,
I know he's like dragging her along annoying. Yeah, anyway,
(05:56):
he loves very hard and honestly, I'm not interested in
love bombing. Too independent for that. So there's a little
relief it's not me. Also, I still love my job
and I don't want to leave it to even explore
this option. I'd for sure still like to make out
with him at least once. I mean, why not, But
for now it's boundaries and being a supportive friend slash coworker.
Stephanie Great's noting that's probably best.
Speaker 2 (06:16):
She probably saved herself.
Speaker 1 (06:18):
Yeah, like drama and whatever other words go with drama.
Speaker 3 (06:23):
Yeah for sure.
Speaker 2 (06:25):
Yeah, yeah. Yeah. Also, when somebody texts you at twelve
thirty in the morning, we all know what that means.
Speaker 3 (06:28):
We all know what that means. That means you up. Yeah, Okay,
it's time for some couples counseling with Chelsea. So this
is my.
Speaker 2 (06:40):
Having a lot of heat by the way, for my couples.
Speaker 3 (06:42):
Oh good dating instagrams.
Speaker 1 (06:45):
Yeah, a lot of heat between gay guys and gay girls,
gay girls and gay girls or guy gay girls, and
a lot.
Speaker 2 (06:51):
Of heat between gay guys.
Speaker 1 (06:52):
But were still having problems personally before I put the
men up, because I didn't really want to put women
up and just have men like the just men are
not to be trusted. So but I did do some
finagling on the side before I started broadcasting people, and
there's like two people that are on straight couple that
are on their like third and one is on their
fourth date.
Speaker 3 (07:12):
Well do you know if you you probably do know this,
if you introduced three couples who get married, it's like
a mitzvah or you're a mensch something very good.
Speaker 1 (07:23):
Well, that's all right, that's already.
Speaker 2 (07:25):
I don't I need that. And I thought you were
gonna say I'm become a.
Speaker 3 (07:29):
Fairy or something straight to heaven.
Speaker 2 (07:31):
Oh well, I wish I believed in that.
Speaker 3 (07:34):
Well, Miles and Natalie. This is Natalie writing in. She says,
Dear Chelsea, my boyfriend and I recently moved in together
and blended our families. We've been together almost three years
and have had no major issues until now. Recently, my
dad lost his partner and his mom lost hers this
past summer. We invited both of them to join us
as past Thanksgiving, so they weren't alone. A few weeks ago,
(07:55):
my boyfriend's mom reached out to me for my dad's number.
All I thought was how nice a friendship is blossomed.
I'm getting texts from my dad with pictures of them
gallivanting around little small towns in the Midwest and teaking,
meeting for coffee, drinking wine, and going to museums, all
things you would expect old people dates to look like.
My boyfriend doesn't like this whatsoever. It's nothing personal toward
(08:16):
my dad, but he thinks it's selfish of them to
do this to us. My sister and I, however, find
it awkward and weird, but think it's actually kind of funny.
We're very close with our dad since we lost our
mom unexpectedly five years ago. We have the type of
a relationship where my sister and I call him a
hoe bag and tease him about all of this. It
is weird, but we're supportive. My boyfriend and his mom
are not quite as close. They haven't communicated much about
(08:38):
this at all, since she knows he's not supportive. Here's
the thing. I normally tell my boyfriend everything I want
to be able to come home and laugh that his
mom spent the night at my dad's, that they went
to a museum today, etc. He gets pretty weird about it.
I totally understand his viewpoint, but you only live once
and it really doesn't affect our life, is what I
say help Miles and Natalie.
Speaker 2 (08:57):
Hi, Miles and Natalie? Oh, Hi, Hi? How's it going good?
How are you two doing good? So your parents are
are hooking up? Yeah? Yes, and Miles, you don't like that.
Speaker 4 (09:14):
I'm not a fan, No, not at all.
Speaker 5 (09:16):
And I'm a little bit more on the supportive side.
Speaker 2 (09:20):
Right.
Speaker 1 (09:20):
Well, Luckily, it's really not either one of your business,
you know what I mean, Like, it's really not up
to you guys what your parents are going to get
up to. And while I understand your discomfort, Miles, I
can relate. I just think that, like, let they've got
to do their thing and they're happy, and you know, like,
what are you going to do about it?
Speaker 3 (09:41):
I think it's so cute.
Speaker 1 (09:43):
It is cute, but I understand the reluctance in wanting
to know the details. And Natalie, you don't have to
tell Miles everything you know about their relationship, like it's not.
Speaker 2 (09:53):
If he's interested, he'll let you know.
Speaker 1 (09:55):
And other than that, you've got to just kind of
like have a great, nice, loving attitude towards them for
doing their thing. It's not like they're having sex in
front of you and you have to sit there and
watch it, like it's not that's not happening, so be
grateful for small blessings.
Speaker 2 (10:12):
Yeah. Yeah, So is it.
Speaker 3 (10:15):
Just the ick factor or is there anything else?
Speaker 4 (10:17):
No, No, it's not even that. I think it's how it happened,
not that it happened, if that makes sense, Because they
both recently lost somebody, very very within a couple of
weeks of each other. He lost his significant other, my
mom lost her significant other, and so they it's kind
(10:40):
of like trauma bonding which has then evolved into something else.
And also she was not honest about it, where he
was telling Natalie everything that was going on, and my
mom was not telling me anything that was going on
and not being honest about it even when I asked
her about it. So I think that's where.
Speaker 5 (10:59):
But then he also came across like that he wasn't
as supportive, So then I was like, well, why is
she gonna want to tell you anything?
Speaker 3 (11:08):
Yeah?
Speaker 1 (11:08):
I mean, first of all, Miles, you're like kind of
like setting her up for failure, because she obviously consents,
as your mother and as a woman, we all have intuition.
She consents that you're there's a level of disapproval coming
from you, whether or not you're exhibiting that or not.
Speaker 2 (11:24):
Like a mother will know.
Speaker 1 (11:25):
How her son feels about something, especially her personal life,
and especially like this this kind of sensitive issue. But
something that's really important to remember is like, listen, we
want people to be happy, period, don't we We want
the people in our lives to be happy. Don't make
excuses for why you should be unhappy for them or
you should be unsupportive of them. Be happy that they
(11:47):
found each other. Who cares if it was two weeks,
at least they have each other to like console and
confide in and spend time together. And isn't that what
you would want for any single person in your life
that you cared about?
Speaker 4 (11:59):
Yes, I would agree with that.
Speaker 3 (12:01):
Do you think they should like address this with mom
and dad or that he should with mom? Just be like,
I'm happy for you.
Speaker 2 (12:07):
Or it's already been addressed, okay.
Speaker 5 (12:10):
And one awkward thing that I got in the middle
of is they both called me and had me on
speaker because my dad wanted to go to his kids
sporting event that his mom was going to and I'm like,
why would you be going to that? Like I'm not
even going to be there, And so we.
Speaker 4 (12:31):
Haven't told the kids not thers, and.
Speaker 2 (12:35):
So they didn't.
Speaker 5 (12:37):
That's socially awkward, and you know why Miles is having
an issue with it. And then I was just like, you.
Speaker 4 (12:45):
Know, so my kids were pretty attached to their grandpa
that just passed, so introducing this so quickly. So that's
another aspect of this is that I don't It's not
that I don't want her to be happy, but my kids,
he pass from a long, hard disease and so it
was long deterioration of watching this and then all of
(13:06):
a sudden they're at his funeral and then all of
a sudden this is going on. So we have not
broken this to the kids yet.
Speaker 2 (13:13):
Okay, how old are your kids?
Speaker 4 (13:15):
Minor ten and twelve, minor seven and nine?
Speaker 1 (13:20):
Okay, wow, good for you guys. That's nice. Yeah yeah
half the time, so thank you. Fit Yeah, well even better,
that's reasonable. That's totally reasonable not to want to introduce
this relationship to your children.
Speaker 2 (13:34):
That's a separate issue.
Speaker 1 (13:35):
So like, while you work on your acceptance, you guys
can both have like a conversation with them, and I
would do it together just to make sure they know
you're a united front, so they're not playing you off
of each other like children would do, because you know
what I mean, like, let them know you guys both
are supportive and Miles, you can use this as an
opportunity to be like, yeah, we're supportive. We want you
(13:56):
both to be happy. It's the timing is a little quick. Well,
while we're going we are in full acceptance mode and
working on our acceptance, we do have to take some
time to be sensitive to the children and what they
are learning. And you guys, coming out as a couple
so soon after doesn't feel right.
Speaker 2 (14:14):
So let's give it some time.
Speaker 1 (14:15):
And we just want to make sure you guys understand
where we're coming from and that you can be respectful
of that.
Speaker 2 (14:20):
And that's not a tall order. Yeah.
Speaker 5 (14:22):
Yeah, they did come over for Easter and we told them,
like that's fine, just arrive separately and no flirting.
Speaker 1 (14:31):
Right, Well, so then they can they can follow the program,
right If you set the rules down for interaction, and
you only have the right to set rules around your
family and your children, that's it. You can't direct them
in any other way. Even if this blows up and
ends up being a real like dramatic something like breakup
or whatever, like all you can do is throw love.
Speaker 2 (14:54):
And support their way. That's it.
Speaker 1 (14:55):
You're not here to judge them, you're not here to
guide them. You're just here to support them.
Speaker 3 (15:01):
Okay, yeah, and now you can double date.
Speaker 2 (15:06):
Yeah, so that's cool.
Speaker 1 (15:08):
So yeah, just make sure that they know that they
have to leave their clothes on at all times, especially
around family members.
Speaker 3 (15:17):
Or maybe just like not kiss in front of you
two for no.
Speaker 4 (15:23):
Well if they get married, then we'll be step me
and now they step like. I'm like, no, I'm not
doing that kind of role playing nothing.
Speaker 1 (15:31):
No, I mean listen, take it for what it is.
It's pretty fucking entertainments, but you know what I mean. Yeah,
so look at it like that through the lens of
comedy and entertainment. Everyone could probably on both sides could
use a laugh right now.
Speaker 2 (15:45):
So let that be it. It's pret hilarious, which is yeah.
Speaker 5 (15:51):
I thought it was a good topic for your show.
Speaker 2 (15:53):
Thank you. Yes, it's perfect. We love it. You please,
all right, you guys.
Speaker 4 (15:59):
Take care all right, bye, thank you.
Speaker 3 (16:06):
That's maybe one of my favorite questions we've gotten in
a while.
Speaker 1 (16:09):
I just love those when older when people die, like
the old people just like cling on, not cling on
or they fast. Everything is quick because they have been
through life and they're like, fuck this waiting round. It's
like the opposite of girls not knowing whether to call
a guy or approach a guy. It's like they know
there's no time to lose and that they got to
(16:31):
get down to.
Speaker 3 (16:31):
Businessespecially if they just lost somebody. They're like, let's make
it happen. I like you, you and me, right.
Speaker 2 (16:36):
Right, that guy's dead. He took him a long time
to go. There was no sex probably, you know.
Speaker 3 (16:41):
Right right right, Okay, Well, speaking of sex, we have
our you want me to have sex. Don't make me blush, Chelsea.
Speaker 1 (16:48):
Sorry, I'm sorry for hitting on you in the top half.
Speaker 2 (16:52):
That's indefinite. No, no, no, no, no, you're.
Speaker 1 (16:54):
I mean it's that's why I can't have a real
job because I would be fucking evicted.
Speaker 2 (16:59):
From it, victim. Notice my use of conviction.
Speaker 3 (17:02):
That's what they do at jobs when you can't be
there anymore. So this question is our Wondering Question of
the Day and the title is Closet power bottom needs
your help.
Speaker 2 (17:12):
Dear Chelsea, I believe I'm a power bottom.
Speaker 3 (17:15):
Yeah.
Speaker 2 (17:15):
I like to be on bottom. I sometimes being on
top is too much work.
Speaker 3 (17:19):
I agree, like you're gonna to fuck me.
Speaker 2 (17:22):
Fuck me.
Speaker 3 (17:22):
Men have more muscle quote unquote use it.
Speaker 2 (17:25):
Yeah, I don't understand, like I want to just get fucked.
Speaker 3 (17:28):
Have you seen this thing online that's like men planking
till failure and it can they last? I think it's
less about that than just like hearing them struggle and
being in a playing position.
Speaker 2 (17:39):
Now I feel like, yeah, I'm yeah, I want to
get on top of you. I'll let you know. Yeah,
I'll tap you out.
Speaker 3 (17:45):
So Charlie says, Dear Chelsea. I'm a twenty seven year
old gay man living in Los Angeles with a little
bit of an odd situation that I need you to
weigh in on. I developed a large skin tag on
my butthole when I was around twenty one. As you
can imagine, this would interfere with my second I finally
had it removed when I was around twenty three. After
the removal, sex was amazing. I could finally bottom and
(18:06):
I was really enjoying it. Everything was good for about
a year or so, and then it started to grow back,
this time bigger and more painful. I know now I'm
single and in the best shape of my life. I'm
a true verse, but I absolutely love bottoming, which I
feel like is like the secret of a lot of
people who say their verse is like they really love
to be a bottom.
Speaker 2 (18:24):
Oh is that right? Yeah?
Speaker 3 (18:25):
I think that's Unfortunately because of the skin tag, I've
become a strict top.
Speaker 2 (18:32):
Does it hurt to have sex with Yes?
Speaker 3 (18:33):
Yeah, I think it's like because of this, it's like
getting in the way. I found a doctor who specializes
in gay men, but it's quite expensive and insurance won't
cover any.
Speaker 2 (18:42):
Of the cost to do what remove it again? M I?
Speaker 3 (18:45):
I guess like the last person, the last doctor was
not a gay man specializing doctor, and like could have
been done better. So I live comfortably, but this is
something I would have to take on some medical debt
for Is it worth it? Part of me thinks that's irresponsible,
but I also want to fully enjoy my sex life
as a single man. PS. I was at the Netflix
as a Joke show at the YouTube Theater. I'm a
(19:05):
big fan of Chelsea's and that was my favorite comedy
show I have ever been to.
Speaker 1 (19:08):
Sincerely, well you can come again Netflix A Jokes as
a Joke Festival starts again. Say I'm at the Sabam
Theater this year. Okay, yes you should. But why does
an insurance cover this? And maybe that's a stupid question
because he's a gay man and they know.
Speaker 3 (19:21):
There's a specialist, so it's like not under his insurance.
Speaker 2 (19:24):
Okay, so it's not under his insurance. I would say
it's worth the investment.
Speaker 1 (19:27):
I think if something you enjoy, yeah, yeah, that you're
being you're prevented from doing because of that, and it's removable,
I would say financially, just to take a bullet and
do it.
Speaker 3 (19:38):
Yeah, especially if you're like living comfortably and like you
can pay it off over time.
Speaker 1 (19:42):
And also to find out like how to get rid
of it. Is there a way to get rid of
it so that it doesn't come Is there a way
to ensure that it doesn't come back?
Speaker 3 (19:48):
Right?
Speaker 2 (19:49):
I mean no, maybe there isn't.
Speaker 3 (19:50):
Yeah, maybe there isn't. But also the specialist would probably
be the one to be able to answer that.
Speaker 2 (19:54):
So yeah, yeah, I want people to be enjoying themselves.
Speaker 3 (19:58):
Right, exactly like I think, I think it's definitely worth it. Yeah.
Speaker 2 (20:01):
Okay, Well we'll see you guys next week. Bye audios.
Speaker 3 (20:05):
If you want advice from Chelsea, write into Dear Chelsea
podcast at gmail dot com. Dear Chelsea is a production
of iHeartMedia. Follow Chelsea on all socials at Chelsea Handler,
and find Katherine on TikTok at flash Cadabra. Dear Chelsea
is edited and engineered by Brandon Dickert executive producer Katherine Law.
Find full video episodes and minisodes now on Netflix, and
(20:27):
get tickets to see Chelsea live at Chelseahandler dot com
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