Writing Stand-Up vs. Writing a Book (feat. Josh Gondelman) – You Up w/ Nikki Glaser


– I really love the effort
you’re making to see me again and I think you’re so hot, and I had a lot of fun with you
until the chaos that erupted at the end of our
hang last time. That awkwardness
and how weird I felt has stayed with me
a little too much and I’m sorry but I
don’t think I can hang. It’s just the way I feel and
I wanna be honest with you. But again, you’re super cute
and nice and smart and funny, and I hope to run into
you down the road. – That’s great, so honest. – So honest and
all that is true– – [Josh] So kind. – But I couldn’t get rid
of that feeling of hating the situation that we were in. – You can’t make yourself, like, want to hang
out with somebody. – I can’t make you love me
but that’s not the same song. – But the opposite, I
can’t make me love you. What an insulting song
that would be to hear. I wrote you a song. It’s Linda Ronstadt, right? – I can’t make.
– Make you. – No, Bonnie Raitt. – Bonnie Raitt, excuse me. – Make me love you
if I won’t (laughs). – I just think, you brought
me here to sing that to me? (Nikki laughs) – Just wanted to not ghost you. – Just text, Bonnie. – Bonnie.
– Send a voice memo. – Ah Josh Gondelman Oh by the way that guy
wrote back, “LOL gotcha.” (all laughing) – No love lost. – Took it I stride,
took it I stride. – No love lost, exactly. (upbeat rock music) There’s like 60
episodes at this point, online on YouTube, Comedy
Central’s YouTube channel. Just type in Nikki Glasser. – Wait did you tell them? – This is my Kaitlin
Jenner impression ’cause she told me how
to Google Rob Kardashian on Dancing With the Stars. – That’s so funny. – I’m all over the place
this morning but yeah. – She told you how to Google? – Well she was telling me
when we were during the roast in between commercial segments. She came up to me after hearing that I was voted off
Dancing with the Stars from several jokes
that were made. She goes, “You were
voted off first “On Dancing With the Stars? “That’s the worst thing that
can happen to a celebrity.” (Josh laughs) And I was like, “Oh my God.” First of all, it’s
not the worst thing. – The worst thing that can
happen to a regular person is you hit ’em with a car. (all laughing) – Precisely, Josh. – Ding dong. – I know, or that your
wife’s ex-husband defends a murderer who
murdered his wife. Like there’s a lot of things– – But when you’re famous
the worst thing that happens is voting off Dancing
with the Stars. – Or your daughter
has a sex tape which is like, you know– – A huge scandal. – That your wife
released and produced and did re shoots on but– – I wanna circle back
briefly to the she told you how to Google the footage. Like she thinks Google is a thing only rich
people know how to use. Like she’s like, “It
can search anything.” – [Nikki] Yeah ’cause she does– – They’re givin’ it away. – You know what? It’s almost kind
of her to do that ’cause you’re right, I think she understands that her life is this
privileged experience. – [Josh] It’s different, yeah. – And so because
Bonnie McFarland was in the writer’s
room with her, and said that Kaitlin came
in to go over her jokes and that Kaitlin got a
call about her plane. Like the maintenance
on her plane and she goes, “Oh,
it’s my plane guy.” She goes, “Okay, you guys can
all relate to that, right? “Who’s working on your planes?” And Bonnie goes, “I
actually fix my own plane.” And she was like, “There’s a lot of new women
coming up in aviation.” And Bonnie’s like,
“I’m kidding.” But you’re right. She probably extends that
little caveat after everything because she doesn’t know if
it’s a rich thing or not. – She doesn’t know if
it’s rich or normal. – Yeah so she was like,
“You gotta see Robert.” She literally goes,
“Go to YouTube.com. “Click on the search button, “and then type in
Robert Kardashian, “and then type in
Dancing With the…” I was like, “I know
how to do this.” She goes, “Go to the third one, “there’s a great compilation
of his fox trots.” (Josh laughs) She was like… It was so cute,
she was so proud. – That’s really cute. – We gotta get
him dancing again. – To be fair,
YouTube is confusing. – You think? – Yeah, I mean I tell people
how to find my web series and it really is like,
“Go to YouTube.com, “type in the Warner Sound, “go to the third thing
on the playlist.” – And there’s a great
compilation of my fox trots. (all laughing) – But Josh Gondelman is here and he has a new book out. I’m so excited about his book. I have so much to say
about Josh Gondelman, I mean, I could just like, I mean, let me go
in to like my… Okay, Josh Gondelman
to me is just, I mean, I love you so much and
everyone loves you so much and you’re the
kindest person I know, one of the smartest
people I know. Such an amazing writer. Such an amazing comedian. Just truly one of
the best people. – Oh thank you. – And I think you top
most people’s lists. I mean you’re just
one of these people, and you know that
about yourself. – That’s very sweet. I really appreciate
you saying so. Thank you. – I know you appreciate it. And you’re sincere like you do but you must hear
this all the time. You’re one of the
kindest people, the nicest people I know. And he does these things on… This is like Josh
Gondelman in a nutshell. He will do this thing on Twitter where you’re like, will you explain it to people? – Sure.
– How do you phrase it? – So I say, usually
it’ll be at night, often when I’m on the road, sometimes just if I get home and my wife is already asleep. And I’ll say, “If anybody
needs to hear a kind word “or a pep talk I’ll be
here for five minutes, “just let me know.” – Five minutes. – It’s usually
people respond with a lot medium
specific stuff, like, “Hey I have a job
interview this week.” Or like, “I don’t know
man, the world just seems “really stressful.” And I try to just
say a nice thing to help people feel
a little better before they go to bed. It’s like, I don’t
think I’m doing therapy but it is like, I don’t know, I feel like sometimes
if you’re like, “Well, it’s too late “to text anyone so I guess
I’ll just stew online”. – Yes. You’re bringing some
positivity to that platform. – [Josh] I try. – And I always miss it. – Yeah I miss the window too. – I mean, I love that you
give such a short window and I honestly might
steal that idea from you, because there’s
sometimes where I’m like I want to interact but I don’t want this to go
on longer than five minutes. – I think if you put a
window to it honestly, ’cause I always
go past the window but if you don’t, then I think people understand
that you’d set a boundary. – Yes boundaries. – [Josh] Yeah I’m
very bad at that. – We just heard of those. – Oh yeah. – I’ve heard rumors. – I love Amy Schumer’s joke about I took my mom
to a soccer game to show her what
boundaries were. – That’s incredible. – I loved it.
– Oh that’s so good. – I remember that joke
’cause I remember being like, “What are bound, I don’t
even understand that joke.” That’s how far removed
from the concept of having boundaries with
your family was to me, that I remember
hearing that joke and it stood out to me because
I didn’t understand it. And then years later I’m like, I mean I understood but I didn’t understand
showing your mom boundaries. Like why would you do that? Why is that funny? And now it’s like click. – I used to shower
and my Russian mom, would just come into the shower to have a conversation
with me when I was like 14. And I’m like, “Mama you
can’t do this, boundaries.” And she was like, “I’m
from communist Russia. “We have no boundaries,
everything is we. “There is no I.” – That’s a good point. – There is no me, my and yours. – It’s cultural that
I’m watching you shower. – Get over it. – I go home and I
have no boundary. I pee with the door open. I just wanna like keep
talking to people. – I also wanna keep
talking to people. I have that impulse too. – Well, Josh Gondleman so
much to get to with you today. Josh has a new book out. He’s the nicest man on Twitter. He’s the nicest man in comedy. He’s done so many things. I mean, are you currently
working at Desus and Mero. – I am, yeah. – [Nikki] You’re a EP. – No just supervising producer. – [Nikki] Supervising producer. – And writer, yeah. – I love that you
are on that show ’cause those guys are
two of the nicest. – They’re so nice and so funny. – It’s just when there’re
nice people in this business you gotta say
something about it. People say that a lot, “Like
this is the nicest person.” But it’s usually true because we need to call
it out when we see it because it’s so few
and far between. – I always love to hear it too. Like, whenever we have a friend
that works on a big movie and they’re like, “I
worked with whatever star “and they were just
like so considerate.” I like a good gossip I like a good like,
“This fucking dick.” It’s fun to talk about.
– Love it. – But it really
heartens me when someone is a kind person despite
every opportunity to not be. – Yeah I wish we had
more of those stories, like gossip stories about
people being super nice on set. – It’s great, I love it. It’s like the opposite. I almost started a podcast
that was just the opposite of talking behind
someone’s back, where you just go on and
say nice things about people that you would never
tell them to their face. – Yes, so behind their back but talk about them
on the podcast? – Yeah, like positive stuff. – [Nikki] Oh my god,
that’s really good. – Thank you. It’s so fun– – Yeah like Kimmel doesn’t
he have a great reputation as being really
nice and certain– – Oh yeah, Kimmel. Kimmel, Fallon, Adam Sandler. – Adam Sandler is
like legendary. – Legendary.
– Seth Meyers also. – [Nikki] Seth Meyers so nice. – Has like a great reputation and has always been nice
when I’ve encountered him. And he had like a long
Twitter thread like a year ago just about how kind Sarah Silverman and
Adam Sandler were to him when he started comedy. Like from the SNL family
and like two people who are also from New
Hampshire where he’s from. And so he had that long thing and I was just like, “That’s
so nice to see that.” – Josh Gondleman,
you wrote a book, that is why you’re here today.
– I did. – I mean like you’re here
today ’cause I love you but and it’s been
a long time coming. I can’t believe it’s your
first time on the show. – [Josh] I’m so excited. – Is it your first
time on the show? – It is my first
time on the show. – That seems crazy to me. – I’ve really wanted to. I’ve been so excited to do it but I always have to be at work. – You’re at work,
you’re working. Josh Gondleman wrote a book, it’s called “Nice Try: Stories of Best
Intensions and Mixed Results” I didn’t get a
chance to read it– – That’s okay.
– Yet. I can’t wait to though because I mean you’ve
written for the New Yorker. Have you written for the Times? – [Josh] Mm hmm. – Yeah, you’ve written
all over the place. I love your pieces.
– Thank you. – You’re such a great writer. How did this book come about and what are we
to expect from it? – So it’s an essay collection. Just stories from my life. I’d co-written just a
straight up humor book a few years ago with
my fried Joe Berkowitz, who’s super great and talented. And the book ended
up just kind of being like a publisher
wanted a kind of book. And we were like, “Sure,
we’ll write that for you.” And I’m really happy
with the job we did on it but I still feel like it
was someone else’s project that we were executing for them. And this one, I was like you
know I really liked the process of writing a book, and I really want to
put something out there that feels more like me. And at the time, I was
at Last Week Tonight and I felt like I was
working really hard and working on a project
I was really proud of, a TV show that I
was really proud of as part of a bigger team. And I was like, I really
just want something that I can work on
and really dig in to and share that just feels like, “Hey I did this, check it out.” – Just you. – And so it took me a while to come up with a proposal
that felt just right, that felt like, oh I’m gonna… Because writing a book
and putting out a book and pitching a book and
editing one, takes so long. – So long. Talk about when did
you first start, sit down to do your proposal? What month are we talking? – Summer 2017, so June 2017. – Wow! Okay, and then the proposal, for those of you who don’t know, which I didn’t know
this until recently to put together a book, or to pitch a book, you have to write a proposal which is about like at
least 50 pages, right? – Yeah so it was
like a long essay. Probably a 20 page sample
essay that was new. And fortunately, I had
like written enough stuff that they didn’t need like,
“Okay, write four of those.” – Right, so you had
enough stuff going in but generally it’s
just a big chunk. You have to write the
big chunk of the book. – Plus like a pitch that’s like
here’s what my book will be, and here’s why I’m great
and should write it. – It’s a whole… It’s like a class project, like the biggest
class project ever and there’s no
guarantee, obviously. – No, you’re doing
it all on spec and there’s no like… I had a hunch that it would sell but it could have also been the only deals I got offered were to worth two years of work. And so it would’ve been a
really tough place to be. – How did you pick your editor? – This is a great question. Part of it was money and part of it was
my editor, Stephanie, who is amazing from the jump off did not fall for my bullshit. And it made me– – What’s your bullshit?
– Yeah what is your bullshit? – It made me crave her
approval desperately and trust her so much, because I was like,
“If she doesn’t like me “she must know what’s going on.” So my bullshit is I
have stand up instincts as an essay writer, and so if instead of
digging into like– – Every other sentence you go, “Hey you guys can you
quiet down over there?” – Yeah, yeah, yeah. – Can I get another club soda? Like you’re that kind of stuff? You’re interjecting. – I don’t come to your book and knock the pages
out of your hands. – Okay, sorry. So you wanted a
joke, joke, joke? – [Josh] So a joke, joke, joke. – ‘Cause that’s why
I love your stand up. It’s very similar to mine where it’s like because
I’m saying I like you ’cause you’re like me but I mean generally isn’t
that why we like people? They remind us of ourselves.
– Sure. – But no, I like it
because it’s just… I like comedy that’s
like joke, joke. – [Josh] Me too. – I don’t want fat, no fat. I just get the jokes. – Literally she hates fat.
– Don’t be vulnerable. Literally no periods. And that’s how I
like my writing. One run on sentence, one period. – I would literally turn
in a 4500 word essay and there’d be like 800 words that were just about
a pair of big jeans I saw when I was 14. And she’d be like,
“Josh that’s nothing. “That like distracts
from the point.” – So like let’s get into
who you are as a person? – [Josh] Yeah, and
she would be like– – Stop with the little bits. – Yeah the flourishes. And she’s like lets
thin out the jokes so the stuff that’s
there really hits and it doesn’t like when
people are reading it, they don’t get distracted
from the story you’re telling. And the jokes are there
to enhance the story rather than like you
don’t have to get laughs because you’re not telling
a worthwhile story. – God, I struggled with
the same thing, Josh. when I was putting together
my special, Banging, which comes out
tonight at midnight. – I am so excited.
– Woo. – [Nikki] Thanks Josh. – I’m like setting myself ’cause I have a train ride
tomorrow up to Boston, I’m setting myself
a calendar alert to download it to
Netflix on my phone so I can watch it on the train. – Thank you, dude,
that means so much. – I’m so psyched. – It is incredible. – Check out Josh
Gondleman’s new book, “Nice Try: A
Collection of Essays” by one of the funniest writers
in the biz, Josh Gondleman, long time old friend. You’re married now. – I’m married now. – How long have
you been married? A year or some? – Two years.
– Two years, wow, okay. How did you meet your wife? Can we talk about that? – Of course. We met at a party
that she was throwing. A mutual friend brought
me to this party. And I had just had a break up like five weeks before probably. And I was like, “I’m just
gonna say yes to fun things” And so I was on my way home
from a show in Brooklyn, I lived in Harlem at the time, and a friend texted me and
was like, come to this party, do you know Maris? It’s crazy that you
don’t know each other. You guys should meet. – Oh my God a little
light shade just fell down and Anya screamed. – I thought it was an
entire light fixture, sorry. – Oh my God that’s so funny. – I thought it was like
a prehistoric moth. (all laughing) I don’t know how that
would have happened. I was just like big moth, cool. – That does look like… I mean it’s falling
from a light, so that’s often what moths do. – And it had like a
fluttery vibe to it. – And it was huge. That is the size of one of
those moths that you go, “Oh my God, I can’t
believe they get that big.” Yeah that was hilarious. That’s what you’re gonna find
in Josh Gondleman’s book. – Prehistoric moths. – It’s like a little
cover for the light ’cause they’re
filming this episode. So it looks legit. You could have worked on
writing what that could be all day long and nothing as
funny as prehistoric moth. – The problem that I have
is I’m so self-satisfied with the first thing, there might be a better
joke but I’m like, “Prehistoric moth, I’m a genius. “Time to take the
rest of the day off.” – No, you’re right because sometimes the first
thing is the best thing. – Often yeah in music too. I just recorded a song
for Nikki by request and I was working
on it last night– – Will you seriously
dedicate it to me? Like can we just say
you did it for me? – I just did, I literally did. – Okay, can that be a thing
though that you say every time? – I’m doing a Taylor Swift cover and it’s 100% because Nikki
introduced me to the song, and then I played it
at Hotel Cafe in LA and a couple weeks later
I got home from tour and she’s like, “Are you
gonna record that song? “Please record it,
please record it.” So I just did. That’s how you talk. Wasn’t that a great Glasser? – Wasn’t so bad,
was pretty good. – What you’re gonna do is
you put in the YouTube. – Go to the search bar. But anyway I did four
takes of the vocal and the first take and we
did 95% of the first take with a couple little fixes. It’s weird. – And I often feel,
you’re so right. It’s not always the first
time that you get it right, there’s something to be said
about trying and trying again. – [Josh] Yes, the whole
premise of the book. – Yes, nice try.
– Nice try. – But often times, and you
do this with stand up a lot where you have a joke that
you’ve written and it works, and you know every
time you do it you go, “I should
go back to that.” But then you never do
and it stays at a C plus when it really could be
an A if you worked on it for I don’t know, two minutes. – For sure. Or, sometimes you
dress it up too far and you go, “The kernel of
what I originally thought, “that’s the important part. “I’m gonna go back to that.” – Well, I just taped
the Degenerates, this special that’ll come
out at the end of the year and I was tempted, I did a bunch of
new material on it just because I was
like, you know what? I’m excited about this stuff. It’s what I wanna say now. Fuck it. So I ended up putting a lot
of brand new material in it. And I’m like, “Yeah, I know
this is gonna be better “at some point and
that it sucks that…” Josh just accidentally
spilled seltzer when he was opening it
and it fell into his palm, and he was holding
it like a baby bird and then he sipped the
water from his palm instead of dumping
it on the ground like everyone else would do. – [Josh] Yep. – I love you so much. I once saw Big J in
another studio here drop a seltzer on the
floor and then he was like, “Should I clean it up?” And I go, “The thing to
clean up anything is seltzer “so keep it goin’.” And we just let
the can spill out and it probably
cleaned the carpet. But I appreciate that that’s a– – It got out there was a
red wine stain underneath. (Nikki laughs) – So I did these new jokes and I was toiling over
it for a little bit because they were good and I was happy with them. And I go, “You know what,
I’m gonna take these jokes “and in the next couple weeks “and I’m gonna regret not having
the tags that I developed.” So I’ve taken these
jokes out since then. I mean I taped this special
two and a half weeks ago and since then been
doing ’em every night. I’ve worked on the harder, they’re exactly what you wrote– – [Josh] That’s so funny. – I over wrote them
and they’re less funny than the ones I put down and so I’m grateful that I put
them down in their infancy. – That’s awesome.
– Nice. – Because that’s when they
should have been put out, because they’re not
killing as hard. – Right, you were psyched. It was the most excited
you’ll ever be to tell them. It was the cleanest
version of the vision. My big problem with a comedian other than deeply unfunny
is that I over write. I’ll have one thing that works and I’ll be like,
“This 90 minute bit “should be like a
four minute bit.” And then I do a four
minute version of it and it’s like,
“Nope, it wasn’t.” It’s like but it’s not that
I didn’t need to work on it, it’s like a lot of it is the
archeology and paleontology of getting trimming out, right? It’s not like I
need to write more, it’s like I need to get
everything that’s not essential away from this gore. – Yes, over writing again, what we were
talking about before, about you just derail the
premise that you’re trying to, and oh man, I had some
awkward moments on stage because the joke
I’m talking about is about my dad DMing me when I’m waiting
for a guy to DM me, and it just gets really gross. And this weekend,
I put so much fat in between my dad DMing
me and the punch line which is really disgusting and like telling my
dad about like jizz. My dad’s like, “What’d
you have for breakfast?” and I’m like, “You
wanna really know?” And they just were disgust, they got so far away
from the original premise that I could have it that it was like
I alienated them and pushed them away. But what were we just
talking about before that? Oh, what? – [Noah] How he met his wife. – Oh how I meant my wife. – [Nikki] Thank you Noah,
producer Noah, killin it. – Thank you. I went to this party and we
met and got along immediately and we had– – What attracted you
to her immediately? – She’s just like
very smart and funny. I knew of her– – [Nikki] Of her. – Excuse me. So I knew that she
was a smart literary kind of outspoken
political person, and she’s obviously very pretty. And we were talking
and it was her party. So I was like, I will
talk to this person and that’s great I’ll
make a new friend. I was just like I’m
out to have a good time at this party. And so we met and just
got along immediately and I said the only cool
thing I’ve ever said in my whole life, yeah. I had just booked
a gig in Sweden. And she was like, “How
are you, what’s new?” And I was like, “Oh today,
I just booked this gig “in Sweden, I’m really excited. “I’ve never really
traveled outside “of North America before.” And she goes, “Well,
I wanna go to Sweden.” She had a couple
drinks and was like, “Well, I wanna go to
Sweden,” very bold. And I said, “Well,
come to Sweden.” This is like when we just
met like 15 minutes before. I go, “Come to Sweden but
we should hang out once “in the United States first “to make sure we
don’t hate each other. “Give me your phone number.” – [Nikki] Oh my god. – So I got her phone number, and she did not come
to Sweden with me which was probably
like for the best. My whole family came. Which I didn’t tell. It would have been
a mess (laughs). A real true disaster case. – But that was a
hot, confident move. – I felt, I don’t know why– – So hot. – I felt so confident
about doing that and saying that. I’ve never felt that way, like those instances like that kind of
crystal clear confidence, I so rarely have had
in my whole life. – Wow.
– Yeah. – And that’s interesting because that’s usually
what people say when I’m like how
did you guys meet when I’m talking to
people about the one. And they’re like,
“It was just easy. “I hadn’t ever acted
that way before.” Everything fell away, the
stuff I that I had approached relationships with before
wasn’t there anymore. It was just easy. – There was no pretense
of playing it cool. I was just like,
oh why not say this and if she’s into it great, and if she’s not then
that’s okay nothing is lost. And so I texted her the
next day and I said, “Hey very nice to meet you. “Lets hang out before it’s weird “that we exchanged numbers
but haven’t hung out yet.” ‘Cause you know how
sometimes you do that. You like meet someone and then it’s like
three weeks of planning and you’re just like, “Well, I don’t think either
of us are that interested “in making this happen.” – Yes dating apps. – Yeah, yes, and so we went out for a stone cold
sober breakfast. – Love it.
– Like three days later because I was about
to go on the road and I was like, “I’ll come to Brooklyn
before I like drive up “to Rhode Island for this gig.” And much less
glamorous than Sweden. She wasn’t like, “I’ve always
wanted to go to Rhode Island” (all laughing) And we just had a great time, and we were dating
like immediately. It was just like
off to the races. – Wow, when was your first kiss? That brunch? – Our first kiss was at the bar. Which again, very
unusual for me. – Oh wow.
– Which bar? – So that night. – At the bar that
her party was at. Yeah, we just like really got– – Oh wow. Did you lean in? How did that happen? – I think I must have. – Confidence,
confidence, confidence that’s what I’m
hearing Josh Gondleman. – And like that’s maybe happened
two times in my whole life. – Well what I wanted
to ask you about was you’re such a nice guy that I feel like a
lot of women might… Have you been
friend zoned before? How do you shift
between those two? – Sure I think you have to– – ‘Cause a lot of guys
listening are nice guys and gettin’ friend zoned. I myself get friend zoned. What would be your advice? – One, it’s very
nice to have friends. I’m very pro-friendship. That’s like a thing. And being married is a very
liberating thing for friendship because I’m never trying
to hook up with someone, I mean other than my wife.
– Sure – I’m never like trying to
hook up or flirt with strangers so when I meet someone, I feel this incredible
clarity of purpose, of this is either
business or friendship and there’s no weird
ulterior motive. So I love friends. – [Nikki] But before? – Yes, so before
it was different. And I think when I was younger
in my teens and early 20s when I was dating, I had people tell
me I was too nice. I say it in the book too but it’s like that’s
just a euphemism for I’m not really
interested in fucking you but you seem sweet. And that’s totally fine but I also think I got that less as I became older
because I was nice but not nice in a
boundary less way. Nice in like a comfortable way. And I feel like I have got
increasingly comfortable with who I am as a person and that’s made
it a little easier and it reads less as too nice and more just like if you’re… And you also kind of like this is what you’re
signing up for. I’m like a very soft man with with the posture
of a croissant. (Nikki and Anya laughing) It’s like if that’s
not what you’re into, if you’re not into
a very gentle person who’s also a wise ass, then it’s okay that
I’m not for you. It’s been that way. And so I think being nice but having a sense
of this is who I am and it’s like I don’t need
this other person, right? If I’m nice and they’re
not into it, that’s okay because I am sufficient. – That’s great. – That’s just healthy. – You sound incredible healthy. – If you don’t want me
I don’t want you either. Not saying I don’t
want but it’s okay. I’m not gonna take
it personally. – [Josh] Yeah it’s okay
that you don’t have the same interests. – It’s like he trusts
the process of his life. You’re not like, “I’m doomed.” It sounds like
you see this whole leading up until Maris,
is that her name? – Yeah.
– Yeah, leading up until her it sounds like you
were just sorta like, “Okay, well that didn’t
work out, that’s all right.” It’s not like this is
the end of my life. – I got a lot better at that. I had breakups like you do when you’re in
your teens and 20s. Breakups that are not
like they don’t alter the course of your life, but they feel like
you’re are going to. And I just had less
of that as I got older where I was like man,
this is really sad but I also got
better at being like, “Well the time we spent
together was very worthwhile “and it’s okay that
we’re not together now.” – Yeah, yeah. It’s just trusting that
it’s just gonna work out the way it should and reflecting on your
life and realizing… I was talking to
someone last night who’s going through a pretty
bad breakup right now. And I’ve seen him go
through other break ups and I reminded him, and I had forgotten about it but I was reminded of it
watching how sad he was. I was like, “I have
seen you this sad.” But I was like, “Remember
your last break up?” And he was like, “Yes.” And I was like,
“Remember that it passes “and that you were so
grateful for that breakup now “because it lead to this girl “that you’re now upset about.” Now, I mean, can’t you
project into the future and know that–
– That this could, this would happen
– Literally every rejection I’ve ever had and every rejection
anyone’s ever had, leads to a million things
that wouldn’t have happened had that not happened. – [Josh] Totally. – And it’s so hard in
the moment to know that but it’s good. – And I feel really grateful that the really painful
breakups in the past were like, I can look back and be like,
“Oh that’s not a person “that wanted to be with, “I could have been
compatible with forever.” – Yes. – Or even longer
term than we were. And now I’m with
Maris, who’s my wife, and I love her so much, and we’re so compatible and I just love being
with her every day and it doesn’t… I think if she left it
would certainly destroy me but you know. – Can I ask how did you know
when you wanted to marry her? – The rubric that I developed, which is so fucking hot to say. (Nikki and Anya laughing) Just like nothing
gets people horny like the word rubric but a thing that I tried to
ask myself in relationships as I was more of an adult is, “Do I want this person
around as much as possible?” And that was it. It was like I just want to
be with her as much as I can. Like when I’m hanging out at
home on the couch and working, it’s nicer when she’s there. And when I’m going
out with friends, it’s more fun when
she’s also there. And going to movies,
like all that stuff. – That’s great. That’s the rubric. – It’s the rubric.
– It’s so great, yeah. – So you always knew you
wanted to get married, or did this rubric
come into play as you were meeting her
and hangin’ out with her? – We’re talking
rubric play now, okay? (Josh laughing) – Some guys are marriage guys other guys are whoa, marriage. – I was always open to it
but I wasn’t seeking it out. I didn’t have like a
ticking clock or anything which I think is
easier for a guy because it’s like
there’s just less to think about on a
timeline biologically. But when we got engaged and we basically
decided very quickly that we weren’t going to
have biological children. So like that also took
a lot of pressure off. Where it’s like we
can just be together and if that feels
like all we need, then that’s wonderful, and if it feels like
there’s something missing we can like think about
ways to acquire a child whether adoption or kidnapping, or some kind of Frankensteiny
child experiment. – And you have a
pug, a famous pug. – We do have a pug. Oh, she’s so good. She’s just a fat
little dumpling. – Is she famous? Can you follow her? – Instagram. – You can follow
her on Instagram. Maris manages her account. It’s @bizzythepug. – Bizzythepug – I used to get in
my old neighborhood, when we lived in Williamsburg, people would recognize
Bizzy when I was out and it was like
nothing makes you feel like a nobody in entertainment than someone
recognizing your dog and not knowing your name. – I actually just saw
some Buzz Feed article about people not knowing that paparazzi taking
pictures of people noticing famous people’s dogs and not noticing them. – [Josh] Oh, that’s so funny. – Yeah, so it is a
thing that happens. – Your first kiss was like
when you were in 10th grade. – Yeah, like yeah
end of 10th grade. 11th grade, beginning
of 11th grade. – That’s insane, French?
– Yeah. – Did you peck
before you Frenched? – No. – You went right to
the French you slut. (upbeat rock music) – He raped my face, Andrew. – Did he really? He threw his tongue
how deep in your mouth? – It was so awful. It just, he leapt
across the room but I felt like it was my fault. Like I had asked for that so
I felt really bad about it that I didn’t want to kiss him, and that’s what
screwed me up with guys for so long is that if I
tell the guy I like them, I feel like then I
owe them everything. I owe them sex, I
owe them kissing. I don’t ever feel comfortable
letting a guy know I have a crush on him unless
I’m absolutely 100% sure I would want their penis in me. So I will not– – Okay but a first kiss– – Because this guy it was after the football
game in high school, we were both on the pep squad. We came back to his place. – He was on the pep squad? – Yeah it was like the cool
guys ad the cool girls. And I was–
– I don’t know about that. I don’t think a guy on the
pep squad is the cool guy. – You don’t understand
what the Kirkwood pep squad was back then.
– Okay, my bad. Did he play on the team? – No. – Okay, so he wasn’t that cool. – No he was so hot. Girls in my school weren’t
into the football players. It was like a separate thing. There were certain
girls that were, those were the cheerleaders but girls like me
we were into… Like he was a cross country guy. He was so hot. – Okay, so he was
ripped, he was skinny? – He was like skinny
but he was tall and tan and had bleached blonde hair like naturally from the sun.
– So he looked like you? – Kind of.
– Yeah (laughs). – And he was so hot. But one time we were hanging out and watching TV after the
football game and he was like, “Nikki, I like you.” and I was like, “Oh my
God, I like you too.” ‘Cause we were just friends but I liked him so much, I thought he liked
my friend Taylor. He goes, “So, can I ask you
out on a date sometime?” And I was like “Yeah.” and I was just like, “Oh my God (beep) likes
me, I can’t believe this.” I was so excited. I remember Mitch Hedberg
was on Letterman. We were watching Mitch Hedberg,
for the first time ever. It was the first time I saw
Mitch Hedberg was this moment. And we were just
sitting there in silence and I was just like so excited. I was like I’m gonna
have a boyfriend and it’s (beep). And then he out of
nowhere leapt across. I mean he was sitting
like across the room, ran at me and just
attacked my face. And I just started making out, and I just go, (beep) “Stop.” And I pushed him off and
then he went into the kitchen and started slamming cabinets and being like,
“Fuck, I fucked up. “I fucked up.” And then it was just like
throwing shit around, and I was just sitting there. And he was my ride home, I think I didn’t have
a license at the time or didn’t have a car that night. And I was just sitting
there annoyed like, “Are you okay? “It’s fine (beep) it’s fine.” And he’s like slamming
cabinets and being like, “I fucking fucked
up, I fucked up.” And I was just like okay. – I’m fucking captain
of the pep squad. I’m better than this. – Yes and so finally I’m like,
“Will you drive me home?” And he did and what I
didn’t know in the kitchen he was chugging vodka,
chugging his parent’s vodka. – Before– – Driving me home. – Oh my god. – And he drove like 60 in a 30. He was speeding. I thought I was gonna
die on the way home ’cause he was so mad at me. And so he drove me home. I was terrified the whole way. I got out of the car. This is like me now but when I was in high school
I was meek and mild and timid, and it was just a little taste of what I was gonna be someday but I stepped one
foot out of the car and he took off and I
fell out of the car. He almost ran me over. And I’m all, I get up and
I go, “Fuck you, fuck you.” – [Andrew] Jesus. – And I went inside and
I called all my friends and told them what happened and the next day I had to
go be on a parade float with this asshole the whole day. And then– – And that was your first kiss? – That was my first kiss. – How awkward was the parade? He must of been hung over. – He was hung over. Did he pretend like
that all didn’t happen? – Yep. And then he called
me later to apologize which was nice. But yeah, that was my first kiss and I think that really
like traumatized me forever. – And my first kiss I think
was my camp counselor. No, no it was in fourth grade. – Make out? – I kissed a sixth
grader, (beep). We were on the bus. I was new at the school. I was in private school
and I was so small but I was a cute kid but I was
like the smallest kid ever. And this girl, she
was a head taller and she was the hottest
girl in sixth grade and she liked me. I don’t know why
but like whatever. – Whoa, a fourth
to a sixth grader? Like in fourth grader?
– Like a fourth grader. – Whoa, May December. – So I’m on the bus. We’re in the back of the bus. Everyone saying (beep)
likes you, (beep) likes you. So then I guess we’re
going out some how. I don’t know if it was
ever talked about– – My gosh why didn’t this last? Her career got in the way. – Well I think I just. I was very timid and
so when we kissed, I remember everyone
was watching on the bus and I’ve never kissed
and I didn’t have any gum and I slammed my
nose on her nose. I didn’t turn my head. – Yeah you just straight her. – And everyone just
fucking laughed at me. So it’s kind of
similar to yours. Like where it was just like, “Okay, well that
didn’t go well.” – Yeah. – I fucked that up. And then I think
I kissed her again but I don’t think I ever
kissed her with tongue. I don’t know if I
kissed her with tongue until like, seventh grade, I remember (beep)
and she liked me and she was an eighth grader, the hottest eighth grader
liked me when I was I don’t know.
– Wow. – And she dumped me because I wouldn’t make
out with her with tongue. – Why wouldn’t you? ‘Cause AIDS?
– Maybe ’cause of AIDS, yeah.

21 thoughts on “Writing Stand-Up vs. Writing a Book (feat. Josh Gondelman) – You Up w/ Nikki Glaser

  1. Hey I’m a 16 yr old streamer just trying to make a living it would be greatly appreciated if y’all would drop a sub

  2. Caitlyn Jenner told Nikki how to YouTube: 1:14

    Josh Gondelman is a really nice guy: 4:00

    Nikki asks Josh about the process of writing his book, β€œNice Try”: 9:29

    Josh asked his future wife to come to Sweden the first time they met: 20:23

    Friend zoning has pros and cons: 24:00

    Off Air, Nikki and Andrew discuss disastrous first kisses: 30:46

  3. https://en.wikipedia.org/wiki/Polo_Polo

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  4. Astounding Work, I Liked it a lot, See this New Album 'Monish Jasbird – Death Blow', channel link www.youtube.com/channel/UCv_x5rlxirO-WKjLIyk6okQ?sub_confirmation=1 , you may like it πŸ™‚

  5. I find most people to be very nice and sweet if you are nice and sweet to them. It's people who go out of their way to do nice things for people who make this world go around. What a great episode! Thanks Josh!

  6. Im man with aspergers I am terrified of conversing with humans. Dogs and turtles are easiest. But I listen to Nikki Glaser speak on a show, podcast whatever I can nearly daily because she brings sunshine into my life. If only we all had a Nikki best friend we might all be happier people. I know i would. I love you Nikki. I can't believe i just said that

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