Your Valentine’s Day Questions, Answered!

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In this special Valentine’s Day episode, Sarah shares a sex fantasy gone awry. Plus, she helps a heartbroken New Yorker move on, weighs the pros and cons of telling your manager you like them, and offers tips on how to meet people IRL.

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Sender 10, Carrie, Sender 2, Sarah Silverman, Sender 6, Diana, Lizzy, Vanessa, Amy, Maya, Pepsi, System, Tyler

Sarah Silverman  00:00

Hey everyone, it’s your old pal Sarah. And today we have something very special for you. It’s a Valentine’s Day show because Valentine’s Day is coming up. We thought it would be fun to put a whole episode together where I try to answer your questions about love. All the good and bad and ugly in between. My Valentine’s Day is going to be very romantic. I am going to get fitted for hearing aids. Um, but maybe we’ll have a romantic dinner or something after you know. And it’s, you know, Rory and I, it’s funny because I talk about worrying a lot here. And Rory, and I have, you know, we’ve been together for a while now it’s been, it’s been three years. And you know, we make love and it’s, we, we always try to keep it fresh. So like, I’m pretty sure this is normal. I mean, what’s normal, but every once in a while, we’ll like when we’re doing it well, like slip into fantasy talk to like, freshen it up, you know, like, keep it fresh. So a while ago, we were we were like starting to fool around. And then I went to do something like that. And I just go, you just showed up at my camp. And then it was just kind of quiet. And he goes, but you like own the camp, right? And I’m like, yeah, yeah, you own the camp, I own the camp. It’s weird getting older and, and like having sex, it’s really fucking weird. So then another time, we were having sex. And he goes, this is so crazy, like, I don’t even know your last name. And it’s so hard being a comic because you want to be in the moment with sex. But then your mind thinks another way, and I’m trying to stay in it, and I just said it’s Hitler. And it, you know, it broke things up for a little while, but we focused and finished. As matter of fact, he immediately came right, right between my nose and my upper lip, like right in a little Hitler mustache area. All right, maybe that’s not true. But the first part is, alright, let’s take some calls.


System  02:26

You left me a message, now I’m playing it for the world.


Carrie  02:39

Hey, Sarah, it’s Carrie. So I’m recently single and I want to start dating again. And I really want your best advice about how to approach strangers in bars or restaurants or even in the elevator at my building. It’s just such a tricky navigation out there. I don’t know who is single, I don’t know if their what their sexual preferences. I just know who I’m attracted to and who I want to talk to and, like, what is the best advice to approach strangers without coming off crazy, needy or? Weird?


Sarah Silverman  03:25

Okay, well, you know, you really can’t force a meet cute. You just have to be open. But I didn’t know as you were talking, I was thinking of like, let’s say you’re in the elevator and you think a guy is cute. I say be bold, you know? Like, go, hey, I like your style. And then if he goes, thanks, if he doesn’t say anything else, just go. Nothing about me, that could be funny. I don’t know if it’s romantic but or, you know, nagging. I think that was the big thing in the game that men would read about picking up girls. That’s when you’re like, kind of put him down in a flirty way. There’s that I guess, but I always like just something that’s truthful that you don’t usually blurt out loud, is cute. And it shows that you’re confident. And I actually think men are attracted to confident women. I mean, first you, you should just present as you are, because that’s who you’re getting. God, you know, you always get like the best of a guy in the beginning. And then he gets comfortable, and he feels comfortable being a dick. I don’t know women are that way too, I’m sure so try to just be your whole authentic self and because if that’s a match, then you’ve got a real match. Also by the way, the internet you know, people don’t meet so much in bars anymore but maybe, you know, but the internet is nothing to be ashamed of, it’s like that’s what people meet now and you get to really say like it’s almost like you go I like I want this you know like, I want someone with these general politics these this religion or not no religion or cares about this likes doing this isn’t into this like you can get so specific with what you’re looking for. But um, you know just be your adorable self or your kick ass self or your silly self, whatever your self is, good luck. What else?


Sender 2  05:51

Sarah, I’m hella single. This is […], by the way. And I did a bunch of different people and everybody wants to go out on Valentine’s Day, and I I’m not trying to have five dates in one day, and I feel it would be unfair to all the people I do see the to, to pick one person and what caused me a lot of problems, what should I do?


Sarah Silverman  06:12

I know […] hi well, you can’t help that you know, when you’re that hot, and that desirable. You gotta share yourself. I um, oh, my god, I love […] so he’s a comic. And he books comics. I don’t know if he still does. But boy back in the day, we would all do shows for […], and he’d be on it too, and we got paid in weed, which was not legal at the time. But it was like always kind of kind of legal. Maybe were we in Canada? No, we definitely did some here too. Yeah, you know, when you’re a comic, sometimes you get paid in weed. And you know what you say to that? Thank you, sir. Hi, […] Hi yeah, you want to go out on Valentine’s Day but you don’t want to pick just one of the women you’re dating. So you have to go out with just one. You can invite all of them and just say, hey, I’m dating four women, and I’m inviting all of you. But you should probably just invite one. And then if she’s not available, go to the next one. All right, what else?


Pepsi  07:25

Sarah, it’s your best friend, Pepsi, okay, I’m calling about the Valentine’s call. I just want to know whether or not you’re okay with me and my Valentine’s and birthday and every other holiday where your dude thinks that the only way it can be awesome is if you do the deed that day. And to me during the deed on any of these days, anniversaries, birthdays, Valentine’s Day, it’s just all cliche. But if I have to do the deed, how about I do it before the big dinner or the wine or whatever. It’s like alcohol does nothing to me besides make me sleepy. And typically, I’m not a big drinker, because every time I achieve the perfect buzz, all my drinking partners are tapped out and ready to go to sleep. And then I ended up sitting in some dark room, unable to go to sleep because the bed won’t stop spinning. So Valentine’s Day, don’t over consume and just do the deed before you take your shower to go out for your romantic dinner. And then when you get home.


Sarah Silverman  08:57

Well, one I find it a little I know sad isn’t the word melancholy. That’s not the word, I don’t know that it’s like a job you have to do. But I will agree hard agree with you. Not because I want to get it quote out of the way but I do like having sex before we go out to dinner or before the big party or whatever, because I want to come home and like pass out. You know, you can’t always plan that or it doesn’t always happen, but it is. I do like the earlier sex or the like on weekends. I like some afternoon delight. I really enjoy that, so that I can like pick out and not feel like too stuffed to like be naked or like you know, I mean, it’s all in my mind. You know, Rory couldn’t care less if I’m like my stomach is distended from from food or whatever you know, like, but sometimes you just don’t feel sexy and like, after eating, I don’t always feel like hey, let’s, you know, shove something more inside me from the other side. But I’m sorry, Charles. I see our engineers face like right in front of me, and let’s it really honestly helps to like I love how you react and listen, but it’s so funny because some things I say, I guess, are disgusting, and are as evidenced by his human face. Yeah, I’m all for it. I love an afternoon moment. All right, what else?


Maya  10:49

Hey, Sarah, my name is Maya and I want your input on my love life. Because I, over the past three years have lost 195 pounds, which does result in excessive amounts of loose skin, more than the average person. And I’m dating a fella who we are so compatible sense of humor, personality, everything. We frequently talk about the future and having kids together. The issue is he is not attracted to me because of my loose skin, and he won’t sleep with me. I’m getting a tummy tuck and breast augmentation in February. And I don’t know if he’s grooming me for that or if I should even be dealing with this man, because he’s vocal that is a problem. Thank you.


Sarah Silverman  11:48

He’s vocal that it’s a problem. You know, it’s refreshing that he’s being honest. And speaking face value. I don’t know if how that makes you feel. And I’m guessing not great. By the way, congratulations, if that was if you lost weight, because you were trying to lose weight, that is 195 pounds is quite a feat. And, you know, we all are given one bag of skin to live in for our entire lives. And Charles somebody’s looking at himself like good. Yeah, we live in, you know, this is very shrinky to say, like therapist talk, but we were in skin suits, man. I mean, can you believe you’re in the same skin suit that you’re in when you were born? When you came out of your mom’s beef curtains, I’m dry I was just trying to think of the grossest thing I could say and that was something that I remember Todd berry once calling a vagina. Um, you know, it’s amazing what our bodies do. They stretch they grow, they heal. They they all I mean, it’s fucking crazy. I’ve been in this bag for 53 years. That’s fucking crazy oh, you have loose skin? Fuck him or you’ve got loose skin from like, doing something very few people are able to do fuck you, bro. Just be friends with them, does he even deserve you? You’ll get that little talk, and hopefully everything will go as planned and when you have that tighter body that he prefers. Then you can decide if you want to share it with him or if he fucking blew it. But you know, you should be with someone who deserves you and there’s more than one. I can Guaran fucking tee you that? Let me guess he’s a perfect specimen of a human body of a man. Just this perfect, yeah, I’m sure he doesn’t have like tits or backcare or low hanging balls. I’m sure he’s incredibly tight, good grief, as your friend I say fuck him, he doesn’t deserve you. If you want to be friends with them fine, but like, he doesn’t get that, unless you want to. That’s up to you, I support you either way, I’m on your side.


Lizzy  14:51

Hi, Sarah, I’m Lizzy. I live in New York City. And I have this great love in my life, or had not sure yet. I was a senior in college, and he was a freshman. And so we were phone pals for four years. When I was in the city, and he was in LA. Then there’s he graduated this summer from college, and he moved to New York, and we started to date and we were so in love. And then we took a trip to visit our parents. And New York City is the first place that he’s lived that’s not his home and he just loved being home, and I felt like I wasn’t really a part of that world, and I think that’s why we started to fight and when we got back to the city, he broke up with me. He said his heart said yes, but his head said no so that’s why he did it. And I was mad, and we’re just, I don’t know, I just so messed up, and I don’t know whether to reach out to him or not. He asked me to call him at some point but should I? Thank Sarah.


Sarah Silverman  18:17

Oh, Lizzy, I’m sorry you’re heartbroken. I just don’t have enough information, he asked you to call him but he broke up with you. You know, I my instinct is, you know, don’t call him respect that he broke up with you, and you got to just try to move forward and live your best life and meet more people. I mean, listen, you’re not going to be able to understand this now. But you’re so young, you’re going to meet so many more people, you’re going to fall in love a million more times, you’re going to think back at him and you won’t have these feelings you have right now. If you’re meant to be you will meet again. But I don’t know why he asked you to call him so there’s information I’m not that I don’t have that, that I need to give you good info to give you good advice. You know, you’re young, you live in New York City. I know you feel like this is your person. But he probably is not your person. And it’s hard to be broken up with, you know, a lot of times people get broken up with somehow they get back together with the person and then they break up with the person. And so the truth ultimately is you weren’t meant to be together, but you needed to be the one to break up, you know, and I think that that happens a lot for some reason. Try to separate ego and hurt feelings from the actual love. You know, maybe you’re very fond of him. Maybe you like things about him, but a lot of this might be the ego and the hurt feelings of being broken up with that if maybe you broke up with him, you would not have these feelings. Obviously, if you broke up with him, you don’t want to be with him, but what I’m saying is, with everything going the same, and you’re both fighting a lot, maybe you would have said that, listen, let’s take a break, you know, we’re fighting. And you would be more open to meet new people and to move on maybe quicker. I could be right, imagine it see if I am. But you know, unfortunately, both people have to be interested in having a relationship to have a relationship and it only takes one person to not want to be in the relationship to not have a relationship. And that’s just simply the case, it means nothing. I’ve been broken up with everyone’s been broken up with and has broken up with people. I’m sure you’re gonna meet people whose like, I’ve just never experienced being broken up with bullshit. Please try to make it not affect your self worth. Not everyone is made for everyone. You’re going to find someone who is crazy for you. And hopefully you will find that attractive and not be turned off by it. But I promise you’re going to have a lot more experiences, you’re going to have many more experiences. You’re going to fall in love, you’re going to fall out of love, you’re going to pine first people you’re going to all this all the things and I know it sucks to be broken up with it hurts so much, and it feels like love. And maybe it is maybe it isn’t irrelevant, because your feelings are your feelings and that’s your truth. You know, I remember my mom, I was heartbroken, this total fucking asshole like looking back, I can’t relate to it on any level, broke up with me, and I was heartbroken, and she said, don’t let this have you build a wall where you don’t have love anymore and you don’t you know, you’re too afraid of being heartbroken to ever fall in love because it’s worth it. It’s having love in your life is worth the pain of it no longer, you know, existing of being broken up with or losing that love it’s worth it. You have to be willing to experience heartbreak, love is worth that but the people come and go all right, I promise. All right, good luck, what else?


Sender 6  22:40

Hi, Sara, you had such great advice for the young man whose boyfriend was going to be living abroad. You had tips for how they could stay in touch and stay close. And I wanted to add to that by saying you know, a great thing to do is to take advantage of good old fashioned U S mail. Write him a love letter, like actual paper with a nice pen or write or a card or a postcard from the city that you live in or city you’ve been too together. Make him a care package with the things from your area that he loves and that he might not be able to get when he’s abroad. Getting something physical, in the mail that was sent with care and love and actual handwriting is really romantic and a wonderful way to kind of feel the person in your presence. And so I just wanted to add that and send my best wishes to him and his boyfriend and every couple who is living apart. With that extra effort. I think you can make it actually a really sweet romantic time. Speaking with experience, okay, thank you.


Sarah Silverman  24:09

Thank you, that’s good advice […] about they’re listening. Alright, what else?


Tyler  24:17

Hi, Sara, my name is Tyler, I’m from South Carolina. So I’m bald look, I don’t have a lot of time, I’m just gonna get right into it with you. I’m bald, and I’m okay with it. It doesn’t bother me. What bothers me is the amount of people online in real life that just think that they can pick on me about it. I didn’t choose this you know, I can’t afford to hop on a plane and go to Turkey and get the implants. Which you know, you maybe you’re asking me how do I know? That one would do that? I don’t mind your business. I am I’m not someone that comments on people’s bodies, online in person. I never even made fun of Trump, you know, everyone was constantly talking about how orange he is in the hairpiece and everything. I’ve always just judged people based on their character. My question is, am I just too sensitive? Am I mad that other people don’t play by my rules? Or do we just live in a in a terrible society? And, you know, I need you to do a PSA, telling everyone to stop picking on me specific.


Sarah Silverman  25:44

This is strangers online, that that’s yeah, that’s the world we live in, that’s why, like, you have to just not be on Twitter, you know, or limit your comments or something. I mean, even reading comments is at your own risk, you know, but you’re bald and beautiful if it doesn’t bother you that’s all that matters. But the comments bother you. I don’t know if it bothers you, because you’re embarrassed that you’re bald, but it doesn’t sound like you are I mean, extremely cool, gorgeous. All sorts of people are, are bald, as you know or maybe they’re teasing you and they think you’ll laugh I don’t know, if you know other people’s intentions kind of can’t be your business because what it Rory told me something. And I’m not gonna I think I’m saying it wrong or it’s I’m people are inferring the wrong thing from it but it’s something like you are, who you think other people think you are. Meaning you’re projecting who you think you are, or your biggest fears of who you think you are onto other people, but you can’t read their minds, and it has nothing to do with them. You’re putting it on others. And that’s what so many of us do. We are, who we are, is what we think other people think we are not what they think we are what we think they think we are. So we might as well cut out the middleman and just be okay with ourselves and not be, you know, involved in what other people may or may not think of us. Because it’s never going to be what is true. It’s just what you’re, it’s you’re projecting your biggest fears onto them. Now, if someone makes a joke that you’re bald, they might think you think it’s hilarious like they’re trying to make you laugh. If they’re just being mean, block them. Yet they’re strangers or friends do it. Hopefully, it’s because they love you and they think that you will just feel like oh, that that’s funny they love me. You know the you that you feel it with love, I don’t know, I don’t have enough information but good luck. You’re balding, you’re beautiful.


System  28:07

Here’s some ads. And we’re back.


Vanessa  28:12

Hi, Sarah. I love the show my name is Vanessa. I live in Los Angeles, and I just have to tell you that you’re like my porn soul sister, and that just makes me laugh so much. Because anytime you talk about what you like, I’m like exactly the same, I didn’t think anybody else women liked watching men have sex with Vic vaginas and sex dolls and all that. But I do totally into the whole, like, really verbal ecstasy expression as well and like talking to the inanimate object. And also, but for the same reason like watching the women in those contexts, it just a start to be like, oh, you know, and wonder about her and so I love the fake, the fake version, and then also, I used to be really into, like, cartoon porn for the same reason, wondering if that’s true for you, too. Okay, bye.


Sarah Silverman  29:24

Um, well, hello soul, soul porn sister. Um, yeah, it’s interesting. I wonder what would that comes from or what it means but hey, the heart wants what it wants the vagina, the libido? I don’t know. Um, yes, the anime kind of animated porn. I like some of that too, especially because if it’s like kind of hardcore, you know that nobody is getting hurt or anything or being taken advantage of or being you know, any  of the bad stuff that can happen in that industry it, but it’s pretty well regulated industry in general. But because so much of it is amateur I’m sure that isn’t, although a lot of the amateur isn’t amateur. It’s like professional porn made to look like amateur. It’s funny that like, every kink exists every it’s like trying to think of a new app, like I had a friend where we would go let’s try to think of a new app. And every time you think of something it exists so you know, and that’s the same with porn we were in the writers room for I love you America. And you know, in writers room, you go off on many tangents because you want to fuck around and not work. But we were googling all this different, like animated porn and stuff. I mean, it’s insane what people are into, and I say this as someone who’s into like, weird shit, I guess but it’s all weird shit. But there’s like, I don’t know if you were there, Amy. I mean, we were looking up. There’s like, airplane porn. And it’s literally like, animated airplanes with like, big tents. Like fucking other airplanes.


Amy  31:14

Wasn’t that on schoolhouse rocks?


Sarah Silverman  31:17



Amy  31:18

I’m kidding.


Sarah Silverman  31:21

It’s, first of all, I believe there’s no ask for that Schoolhouse Rock. But anyway, um, yeah, it’s an Amy should know that because her uncle wrote I’m just a bill. But isn’t that right?


Amy  31:34

Yes, Dave […] and there is no s on it. You’re always right about that shit.


Sarah Silverman  31:40

So you were right or wrong?


Amy  31:44

But my uncle is Dave […] wrote that song so boo.


Sarah Silverman  31:47

I’m just a bill. But isn’t that crazy? It’s just like, everyone’s into something. And it’s it probably is like created in our formative years. You know, like, so as you raise your kids. You know, basically, I think Nora Ephron said something like just raise them to be able to afford therapy. You know, but like, you don’t know what it what you’re doing that’s going to affect their weird kinks in adulthood.


Amy  32:18

Everyone in here thought that that was going to be like the Mile High Club and then it took a real left turn.


Sarah Silverman  32:23

No, yeah, no, yeah, I bet there is Mile High Club porn, although I call fucking bullshit on this. Like, I’m not a big person. And you couldn’t fit to have me in a airplane bathroom. Give me a break. If you’re having sex in a bathroom. You’re touching so much. bacteria and germs like, can you imagine touching anything in the bathroom? Like, the only thing I hold? Is that handle so I can like, sit? You know, like crouch enough and not touch anything.


Amy  33:00

I touch nothing but on my way back from New York this last time? There was like a standard poodle. Like a lot, it was a sizable dog. It wasn’t like a heavy dog just a sizable, standard poodle.


Sarah Silverman  33:12

Where is this going?


Amy  33:13

And every time the owner went, got up to go to the bathroom. I think that she didn’t want to leave the dog unattended. So she brought it with her. And I was so amazed, like, where is that dog sitting in there when she’s in there? There’s clearly not enough room unless it was for him to go.


Sarah Silverman  33:33

Hold on, oh. Poodles are very smart. Maybe she taught them to go on the seat.


Amy  33:39

Yeah, I mean, cats can do that. I’ve seen a couple of dogs do it on videos, but it was the dog Blake standing up would have been taller than me.


Sarah Silverman  33:48

You know it did you see or take the dog in because maybe she brought it up to give the like the leash to flight attendant.


Amy  33:57

No she went in. The proximity from where I was was close enough that I could see the dog enter the bathroom with her.


Sarah Silverman  34:06

Okay, this is how I’m picturing it. If it’s just like she brought him in while she peed. She would have to sit down and take him and put his arms around her neck facing her. This is a new type of airplane porn to me. Google it I’m sure it exists. All right, what else?


Diana  34:30

Hi, Sarah. My name is Diana. I love your podcastsm, so here’s my question. It’s been six months since I’ve started working. It’s my first job experience. And the thing is, I have a crush on my manager. He’s not the CEO, but he’s my manager. I work as a legal specialist, and he’s the legal manager. It’s been months and I can’t stop thinking about it. So, I’m planning on telling him. Do you have any advice on how I should tell him? Or maybe you want to convince me that I shouldn’t? So, let me know what you think.


Sarah Silverman  35:18

Oh, this is a little bit of a tough one. Um, hmm. You know, it’s not appropriate for him to have a relationship with someone who works for him. So it’s a sticky situation, you have to maybe weigh what’s more important to you this particular job or a potential relationship with this person? If you’re going to tell him it puts them in a very complicated situation? And I guess there’s not really any way you’re, you know, you didn’t mention that he has signaled to you that he feels similarly, but I think maybe is it worth kind of getting feelers out for another job? Before you even now, maybe not right? I don’t know this, I don’t know how committed to this job you are. But if it’s important to you, I don’t think you can date your manager. Gee, I don’t know what the right answer is, because I love love. And people fall in love at work. I know, long time married couples who met at work and weren’t supposed to date people at work and did. But it can go very badly, too. And he’s probably in a position where he does not want to do anything inappropriate. There’s really a hard lines now with that stuff. So if you tell him, you have to be prepared to have it be a little uncomfortable at work if he does not feel the same, or to get another job, or him get another job if he’s willing to but you know, if you’re listening, and you know what the right thing to do in this scenario is please call in because it’s very interesting. I love love, but there are hard lines now with work. So be interested to hear what other people think. Hmm, think kind of what you did tell them. But I there are consequences, potential consequences to it that you have to be prepared for. Not consequences to telling him but certainly, well, even that, yeah because if he doesn’t feel the same, and now you’re working together, it’s gonna be a little awkward. And that’s kind of on you, right? But gee, I don’t know. I just don’t know what the right thing is, so somebody call in and tell us. What else?


Sender 10  38:08

Hi, Sarah. I’m old, I’m married, I have a heart condition. I’m not doing anything to anybody. But happy Valentine’s day anyway, bye.


Sarah Silverman  38:19

Well, thanks for letting us know. Don’t ever say you’re too old. Just say you don’t feel like sexual anymore, which is fine. I have a girlfriend who’s 10 years older than me. And she just said she just hit a wall where she just has zero sexual desire anymore. And she’s not lamenting it at all, she’s like, I’m getting so much shit done it’s crazy. I have no man distractions. I’m not trying to get fucked. I’m not trying to be in a relationship. I don’t want anything. I just want to do my work in my life and she’s loving it. I could see how like having zero sexual desire can be amazing because it’s wildly freeing. You have so much more time to like get shit done, but it’s also nice to still love making love. Dad wherever you are in space and time, I miss you so much and I’m telling you we are winding down. This is the part of the podcast when I say send me your questions, go to speak. That is and subscribe rate and review wherever you listen to podcasts. Really hear me when I say it, it changes. It makes it good for us, we can keep going, and it’s good when you do that, or some chips. And there’s more of the Sarah Silverman podcast with Lemonada Premium subscribers get exclusive access to bonus questions like one from a poker player in Boston, who’s often the only woman at the table. Subscribe now in Apple podcasts. Thank you for listening to the Sarah Silverman podcast. We are a production of Lemonada media, Kathryn Barnes and Kryssy Pease produce our show. Our mix is by James Sparber. Additional Lemonada support from Steve Nelson, Stephanie Wittels Wachs and Jessica Cordova Kramer. Our theme was composed by Ben Folds and you can find me at @SarahKateSilverman on Instagram. Follow the Sarah Silverman podcast wherever you get your podcasts or listen ad free on Amazon music with your Prime membership.

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