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It's a mailbag. Munder, you got problems there? I'm gonna help you from the comfort of my chair. It's a mailbag Monday. Hello and welcome to the J Train podcast. This is J Train Jared Freed coming alive from Delray Beach, Florida. That's right, Monday. It is a mail bag Monday, where you, the listener, email me the comedian with your advice questions. I've been doing advice podcasts for 13 years. 13 years. So I, I guess my, my experience leads me to being, I think I would hope better at dissecting the email, finding the interesting part of the email, and also giving you an unbiased response to whatever you're going through today. Our producer V has put together a theme week. It is work themed. And who better to ask your work questions than a guy that hasn't been in an office in 15 years? But I will say this is an entre. This is an entrepreneurial endeavor I'm doing. I. And yeah, it's, this is. You might be like, ah, you know, funny clown guy. You make your jokes and you have your fun and you, you dance on stage and you, you make your funnies and it's all fun and games. No, this is a business. That's right. I would love to go on Shark Tank and like, I want to like present 10% of me. Jared Free, the comedian. I always wondered. Cause I think there was a band that went on once. But I digress. We want your emails. So today's work themed I'm gonna go through. I got three emails in front of me. I got. Do I have more than three? I think I got. Oh, one is a long one. I, I read these. So my creative listen, if your feedback is. I wish you would read them before and then give the advice, then I would listen to that feedback because I. It is a creative choice I've made. I am an artiste and my creative choice is to read these as you hear them. You're getting me reacting in the way I would react, like you listening. So I have three emails that I'm gonna go over and they're all work themed, put together by V. And I also have one advertisement. Advertisement, advertisement. I got one ad and that's the show. So we're gonna do the emails. We're gonna go to the ad. If you have a question, it doesn't have to be work theme. We're gonna do. You know, this isn't now a work themed advice podcast. This is a advice show every Monday. So if you have a question and if you're new Here and you clicked on the link in wherever you found the link or a friend send it to you. Thank you for joining us. It's a daily show, the J Train podcast. We have different themes every day. My ask of you to pay for the show. Yeah, I'm gonna bring up money. I know it's uncomfortable, but we're gonna bring up money. How do you pay for this great show, for this experience so that, how do you pay for it? So it keeps going. Because I can't lose money doing this. You know, after 15, 13 years, I, I can, I'd like to not. There is costs associated. I know it comes to your phone and I, I could go on and on about how our relation to paying for things. But like you can use the promo code in the ad, which I think is a perfect relationship. The company pays me, they give you some free money, you use the code, you get a discount and it's all. We're all tugging each other off now. There's some other ways to pay for this show that have nothing to do with money, but they are a currency. Liking the Instagram post is a form of payment. Sharing the clip that we put out, subscribing to the show, just hitting subscribe, that's a payment. Joining the patron Patreon is every Friday. That gets you the fifth day. And it's my diary. Every Friday you get my diary. This Friday I, I'm taping this before. I'm taping this Tuesday, September 23rd, for the next Monday, September 29th. So you will have a new coffee with J. Tron on Patreon. And all these links are in the, the description of the episode. I will definitely be talking about. Oh, I had like a whole, oh, driving home. I mean I, I had a whole incident in the parking lot at Palm Beach International Airport. I'll talk about Rosh Hashanah. I'll talk about a little bit about a review of the kind of. I wouldn't even call it political, but I, Everything's political these days or everything's political always. I, I do believe that. But there was a, you know, I talked about Kimmel. There was a little bit of feedback from that that I'll probably get into or touch on. So sign up for the Patreon if you want to get into that. And that's a great way to, you know, pay for the show. So, okay, we have three emails, one that's a little bit longer. All work related. Also, you can come to a show. The shows have been really wonderful meeting you guys on the road and is the greatest pleasure. It's so nice. And especially when someone says, I'm a J Train listener. I'm like, whoa. You're like in. That's cool. So I'm gonna be in Richmond, D.C. i got all these dates. I added Miami on. Miami is going to be during Thanksgiving weekend. So if you're coming to Florida during the holiday, Fort Lauderdale during Thanksgiving weekend. I'm doing these off the top of my head, but there's a ton of cities and buy them early. That's my, my ask of you. I'm. I'm asking for a lot. You're right. It's Monday. Jared, chill out. Entertain us. You're right. You're right. This has gone a little long. Let's do an email. Jared, my fiance and I are both big fans, have been to multiple shows of yours together. That makes me. That's another thing that makes me happy. I love that, like, there's couples that, like, enjoy what I do together. Like, I, I, again, these are all things I didn't. It would be douchey of me to say this is what I got into comedy for. It's not. I got into comedy for a very selfish thing. I want to be funny for a living. And selfish would be me being harsh on myself. But you, when you're starting a business, when you, when you're. You have to keep your eyes on the, you know, the bottom line. The bottom line is I want to have. I want to live a good life while doing something that I truly love to do. And when I hear that couples like what. I would never think that you. You along the way, you find out, oh, that makes me feel good. I didn't expect that. And that is one thing I really do enjoy, especially because comedy is. Is tough to share with someone you really have to like. I always find it a little bizarre when the couple doesn't agree on the comedian they like. I don't know. I'm always like, do you guys even talk? Do you even like each other? We recently got. Someone's listening right now. Their husband hates me. They're like, Jared, it can happen. Okay. We recently got engaged. Congratulations Are in the midst of all these all things wedding planning. With that, the guest list is something that is a struggle. And we could use the wise words of J Train. I would love to weigh in. I would love to weigh in on your guest list. Yeah, this, this seems to be. Here's the one thing I'll say before we get in the email having. Having not read it here's what you hear from everyone. The guest list is a problem. No matter good couple, bad couple, great couple, they all have this issue. So I think in a sense that should make you feel better. Like I would, I would feel better. Everyone has this problem is something that makes me go, oh, good, I'm not a fucking idiot. I'm not a loser. I'm not being a baby. I'm not with this horrific fiance that I'm seeing in a new light. Like this happens on the other side of that, you go. When you go, oh, this happens to everybody. You kind of like give people leeway that maybe you shouldn't. You know, there's pros and cons. For some background, we decided on a mid size, about a hundred people. Hundred people goes quick. You're hearing a hundred people, you go, who knows? 100 people. Well, let's talk about 10 aunts and uncles on each side. Now you're at 20. Now you got 80. Those, they got cousins, let's call it, let's go. You got 10 aunts and uncles. And then, you know, let's, let's say all the family all in, 35 people. Now you're at 75. Now your mom and the other mom, you both got friends you got to pay back. Okay, let's say it's five friends each. Now we're at 10. Now we're at 65. Okay, you got the people from work from both your side and his side. Let's call it 10 people. You got to invite them. Now we're 55. Now you got those people that invited you to their wedding, but you don't keep up with anymore, but you got to invite them. Okay, let's put 10 on that. 45. We have, we have now we've bled out a little bit here. So 100 is 100 goes quick. We decided on a mid size, about 100 people, local wedding based on our budget. This all sounds great. My family alone can cover this amount of people, so we have had to make a lot of this. My family alone can cover this amount of people, so we have had to make a lot of decisions on who to cut from the list, as I'm sure most couples do. You. Yes, most couples do. As I said, this is a, this is not a you problem. I don't particularly love my job or the people there and didn't have, I hope none of them. Listen, wait, is that, wait a minute. I just got her an engagement gift. She doesn't like us. I don't particularly love my job or the People there and didn't have anyone from work on the list. It's a company I started at. Oh, I thought you started the company. I started the. This is the problem with not reading it before. It's a company I started a year ago, and I hate everyone I've hired and I hate what I do. Oh, yeah, it's a company I started at under a year ago, so it's not like I've been there my whole life. That's important. However, the other day, my boss said something about being excited to receive our save the date. Hey, whoa, Johnny Assumptions with the assumes. Ah, well, who would ever say such a thing? That takes. I mean, this boss. No wonder you don't like work. This boss stinks. Who would do that? I. That's like you're pregnant. Oh, no, you're not. Okay, like. Like, I don't understand these people that just. Why would you say I would assume I'm invited to no weddings even, you know, my brother. So when's the wet? What are we doing? You send the end. Yeah, I'm not even asking. Why would you do this? Who wants to go to a wedding of someone they kind of half know? Those are crazy. That's a crazy person. It's a company I started at under a year ago, and it's not like I've been there my whole life. However, the other day, my boss said something about being excited to receive our save the date. Who's excited to receive a save the date? What kind of loser? Sitting at home waiting by the mailbox. Is it coming today? Will I get to see this person who I barely knows? Calligraphy? He has met my fiance before for some work events, so it's not like he's completely disconnected from us. But he's not someone I was envisioning at my wedding either. Am I a block? Am I obligated to invite people from work? If I do invite my boss, do I need to invite others? Thank you for any guidance here. Well, here's like the math you do. You don't have to do anything you don't want to do. There are consequences. There are pros and cons to all decisions. That's something you know. I know. We all know. Even when I went through my list of people you have to invite, I did say work people. So it is something we assume is. You know, sometimes I wish I had balls. Like, some people have cojones. Some people have the ability to say, these are my boundaries. Love me or hate me, and I will be fine no matter what. I wish I had a little bit of more of that in my Frappuccino. I wish I had some more of that in the smoothie that I call Jared Freed, because I don't. I'll admit to you, I wish I had it. I really do wish I had that gene. I think my brother has it way more than me not to say he's like this, like, piece of. Again, that's me saying that having boundaries makes you a piece of. No, it's just that it's, It's. That's who you are. That's what you do. So now I do believe in salesmanship in a, In a. In a work environment, you know, do you want your boss to think on the kinder side of things when there's a spectrum of ways to think of you? That's something I want do. I think, like, I have this with, like, comedy a lot. There are some people that are doing, you know, there are people that can't, say, sell a ticket in any town in the country. And I, I can. I'm very lucky. But also it's because of the work I've put in and the, and, and this podcast, and having done it for a long time, there's a lot of people that know me from years and years, and if they. Maybe they don't listen to the podcast, but, oh, I know them from that thing, I'll go to the show. So that's all kind of works into how a ticket gets sold, in my opinion. And there are some comics that I know that can't sell one of those tickets, and they act like they are the Rock, like they. And they walk with a confidence and a swagger, and it's something I genuinely envy. And they are doing well, you know, because. And I think it has to do with that. That. And I think it's this again, I'm, like, a little bit off the rails from your question, because I, I'm making this about me, which. This is the J Train podcast. But I, I do think the power of answering an advice email is. I think anyone can answer an advice email, tell you what to do. Not everyone will get personal with you. And I'm being personal in the way that I wish I had more of this. Like, he's my boss, we work together, and I know I'm not going to invite him. And that has nothing to do with how you view me as a coworker. Now, I am a person who doesn't have that type of confidence. So I think you say, am I obligated to invite people from work? No, I don't think you are. Now, are you trying to rise in the company ranks and having this, like, fun night with someone and having someone see you in this way amongst your friends and family, really at your wedding is the best someone. The. The best angle someone can see you at. First of all, physically, you're the best you've ever looked. You have your makeup, hair, exactly how you want to be seen in that sense. But also, mentally, you're with the people you love, and they see how you have fun with people. And in a work scenario, and this is your boss in a work scenario, when something comes along, there's. They're going to think of you fully now. So as far as marketing is concerned, the marketing of you, I think you are better off for having your boss at the wedding than you are for having them not at the wedding. But I would say to you also, the other math on that is who doesn't go instead of your boss? Like, who's the switch up? Because then at that point, you can kind of. If it's because I think with a hundred people, that makes it a little bit easier. You go, okay, it's boss or friend I haven't spoken to since college. Again, this is kind of like you're gonna do the same thing with the friend you're deciding to invite or not that your boss is gonna do with you. And I'm thinking this out right now. You're gonna go, okay, do I invite my boss, who I don't really particularly have a relationship with, but it will make me. It will make our relationship stronger. Will they'll think more positively. I would hope. Again, you have to. It's not. It's not definite. I would hope they would think of me in a more positive light the next time that comes around. Now you're. You're comparing them to a friend. Well, I haven't seen this friend since college. And now that friend has a brand and they haven't reached out. And you know what? They don't really dance when they go out, and they're not that fun, and they don't really bring it, and they're not, you know, or if it's another friend that you're like, they are the life of the party. I haven't seen them in five years, but whenever they're around, I'm just a happier person. You're gonna go, you boss in the same way when the trip comes up, that your boss has a choice between you and the other person at the company. And they go, well, I can choose, you know, person A or I can choose the person who had me at their wedding and they were so fun at their wedding. And oh my God, if we hang out at the bar, we'll, we'll have a good time. That's, we're all doing that stuff. So this is a marketing opportunity for you. And I would say that's my answer. I'm not going to tell you to invite your boss, but I'm going to tell you I think inviting your boss does. Here's the one thing that I think you're worried about that you're not. If I do invite my boss, do I need to fight others? No, that's. That to me, I think you go, I think it goes boss first good friend at work, which it doesn't sound like you have one. I think you can go boss on their own. Done. If, if you want. J train podcast gmail.com J train podcast gmail.com this is a perfect sponsor for this time of year. Hello Fresh. I just think a meal kit in the fall just makes a lot of sense. You're done with all the trips of the summer, you're done with all the events. You're trying to like, get on some sort of regular, consistent schedule. That's what a meal kit can do for you. And I've done the hello Fresh meal kit. It's great. I'll say this. It's also. I'm going to read the ad they gave. I think, what a beautiful mental Zen moment, cooking the meal. There's so few things and I, this is my go to. When it comes to these meal kits, it is satisfying to your brain to put together all the ingredients and, you know, finish it and take a picture of it and compare it to the picture they send with it and go, well, wow, I did a good job and it tastes good and I was a part of that. That, that'll make you feel good. If you haven't tried out HelloFresh yet, there's no better time. HelloFresh took it to the next level with a menu that's literally double the size. Choose from a 100 chef design meal options each week and fresh pre portioned ingredients show up right at your door. They've even added veggie packed recipes with two or more vegetables for that extra boost of greens and steak and seafood recipes that come at no extra cost. That's huge. Here's the other thing, portion size. You can have a great meal at the right portion. And now it's not like you're really going off your health regimen. I think portion matters way more than we want to really admit to. I mean, we want to admit to. I want to admit to. They even have bigger portions now. Okay. But I think cooking for one or two is really hard. This is less waste, this is more savings. Really. On top of the saving savings that we're going to give you. They even have bigger portions now. They'll keep everyone. That'll keep everyone satisfied. The best way to cook just got better. Go to hellofresh.com jtrain10fm that's J train 10 FM now. To get 10 free meals. Are you kidding me? Plus a free item for life. People come on. One per box with active subscription. One per box with active subscription. Free meals applied as discount on first box. New subscribers only, varies by plan. That's hellofresh.com j train10fm to get 10 free meals plus a free item for life. So you can have dinner on me 10 times. That's pretty unbelievable to be honest. All right, let's do. We got two more emails. Great email so far. I I mean that first one, I love that. Hi Jared, I need to know if I'm overreacting or just need some thoughts in general. I work with this guy for context. I'm 26, he's 24. I work mornings, he works nights. So we usually only see each other for about an hour. We banter all the time, just shooting the at work we hit it off but in my opinion it was just flirty banter. He's not ugly, but I don't know if we're compatible or if I even want to jump his bones, if you know what I mean. I get it. Cute guy, you have some banner, it's fun but you're not really looking to go the extra distance to make this whole thing happen. I get it. And that's me giving the most empathy. I kept saying I just wanted to be friend. I kept saying I just wanted friends to hang with since I I kept saying I just wanted friends to hang with since I moved here last year and don't know many people about I I will say this, listen, considering 24 year old guy we have FL and you're saying it's just flirty banter. When you say I'm looking for friends, he's not the friend. He's not looking for friends. I oh, he's just looking to cuddle the tiger. It's like no tiger is going to be a tiger all the time and I get it. Oh, why can't we just be friends? Why can't men and women be friends? Men and women can be friends, but if someone's making it clear that they're flirting with you, that is not something you are responsible for changing or you're gonna change. I kept saying, and you can't really tell. You can't tell someone how to feel. So, hey, we flirt all the time. Just be my. I. I haven't read the rest of the email, but, hey, we flirt all the time. Let's just be friends. That's you telling them how to feel. And the reason no one goes back at the person like, let's just be friends, because there's a morality thing. You're saying I want to be friends is a nice thing to say, but it's really not nice to someone to say to someone who's letting you know I'm. I have different intentions. I don't know. Nice, not nice. I don't know. That might not be the right wording, but. Okay. I kept saying I just wanted to be friends. I kept saying I just wanted friends to hang with since I moved here last year and I don't know many people. About two weeks later, he gave me his number and we started texting. This is like, one of those things that, like, I just want to be friends. Well, here's my number. He doesn't. He. A lot of people think, well, we'll be friends, and then they'll see how great I am, and then they'll want to be with me. Then they'll be so attracted to me once they see me as a friend. And then it becomes more insulting because it's like, wait a minute, you like me. It becomes more insulting because you're like, wait a minute, you think I'm funny. You enjoy my company, you respond to my text. So the only thing is, you don't wanna fuck me. And then it becomes like, a personal ego shot. He made a. Okay. So about two weeks later, he gave me his number and we started texting. He made it clear he was attracted to me and wanted to hang out. Okay. We ended up texting nonstop for four days, but he kept coming off flirty while I was only giving friendship vibes. I'm not blaming you. I get it. You're in a new town, you want to make friends, but he's telling you exactly what he's looking for at this. At a certain point, you have to say, we need to take a minute to let this cool, because I don't want the same thing as you. But okay. And I'm not blaming you. That's hard to do. I thought maybe I'd keep an open mind. This is kind of how it goes. You. Because you're probably doing what I would do. Well, they're nice and they're fun and why don't. But. But you know, there's no future for it. And maybe you're looking for something more serious. So you go, I gotta. Why do I have to be mean to someone? Which you're not. Again, this is about boundaries. Why do I have to end something with someone that I've never began with? That sucks. I hate that I. Happens to me a lot. I thought maybe I'd keep an open mind, but the more we texted, the more he made it obvious he was super into me. I figured if we hung out, he'd see it as a date, quote, unquote. You're right. He would. It never happened. And instead he started making things sexual. Like he just wanted to bang. That's. Yeah. Okay. I made it clear I only wanted to be friends and wasn't looking for anything serious. He said, oh, so we're on the same page. Oh, no. He's missing me. The message. And then let's take it day by day and see what happens. So he's trying to say, once you get to know me, I'm irresistible. Oh, you don't want to be in a relationship. Good. Me neither. Like, he's hearing. He's missing everything. He's hearing only what he wants to hear, basically meaning if something happens, so be it. That made me feel. Played like an object. Yeah, I. I can. I can't tell you how to feel as well. I told him I didn't think we should be friends anymore because I thought he genuinely. Because. Because I thought he genuinely wanted friendship. Okay, well, I'm happy he's told him we don't want to be friends anymore. He later apologized, said he was high all night, wanted to be friends and was 80. Joking. No, that's. He wasn't joking at all. He. He was joking to try and communicate to you that he wants to have sex with you. And when you came back at him and said, that's a no from me, and then you're making me feel bad, he backed off, but I just feel icky. We were vibing so well and I was excited about a friendship. Am I being dramatic? You're not being dramatic. He's just not going to be your friend ever. Ever. Over you. Tried to. He didn't listen. Time to go away. And this sucks that you have to interact with him at work, but this is one of those things where I think you gotta dump him. Even though there's nothing. There's never been a relationship. A dumping has to happen because he's not even listening to you. We still see each other at work and he tries to talk and text me, but I feel uncomfortable and bummed. I know it was just comments, but it still made me feel weird. Like he didn't come in with good intentions. It just went 0 to 100. Why can't girls and guys be friends without it turning sexual? They can, just not this guy. So I think what you're doing is what a lot of people end up doing, is you make this into a societal thing. You're not going to solve society. You're going to find people who are going to agree with you. They're going to go, yeah, you're right. Men never want to be friends with women without sex involved. And it's like, okay, now you're just a bunch of people screaming at a cloud. Like, I. I just don't think there's anything to be fixed. And you're not gonna improve your life. Let's be selfish for two seconds. You don't want to bang this guy from work. Good. That's your feelings. Sometimes knowing your feelings is really powerful. I think what you need to do is forget. Why can't girls and guys be friends without it turning sexual? They can. Everything can. Every scenario has happened. Every scenario will happen. The people who go, oh, why can't men and women be friends? Are wasting their time, energy and breath. I care about you getting to a better place where you're in a new town. As you said, you want to make new friends, let's make that happen. You know what won't help you make new friends? Wasting your time and energy on a guy who doesn't want to be your friend. He's attracted to you. He wants to be with you in some sort of way, but not in the way you're looking for. Time to say goodbye. I would text him, I would end it. I would say, hey. And I wouldn't get into changing his mind. That's why this keeps going. So, hey, I really appreciated the relationship that we had. It was a friendship to me. And that's something that I'm looking for in this new town. I need to end this with you. I'm going to be cordial at work and then again, get ahead. I'm going to be cordial at work. I'm always going to be nice to you, but it's obvious that we can't be friends and I need to stop texting with you. And I hope you can respect this boundary. You know, the theme today is work, but it's also boundaries, so. And his apology. I'm sure he's sorry. Ish. I, I just wouldn't get caught up on why can't men and women be friends. I think that is a waste of your time. You want friends, so let's go make them with people who want to be them. Now, if you come across a guy in the future who's trying to be your friend, it is a sad reality that you have to keep in mind. Well, maybe he's flirting with me and is trying to be more than a friend. And if you don't feel that way, I think continuing flirty vibes with someone in the hope that they realize that you won't be more than a friend with them is probably not gonna happen. They're not gonna realize that. So being upfront and communicating all the things we know to do that are just hard to do. And even harder when you say you're 26 and he's 24. I mean, there's no way I would be upfront and communicative. Upfront and communicative at 24 or 26. I, I, you're better than me or you're at least writing in to figure it out. I wouldn't be this mature. You're so, you're so. I want to, like, give you credit and I don't. I hope this doesn't. I don't think you're being dramatic. It's annoying. I think your time will be better spent worrying about you rather than why men and women can't be friends without sex being involved, because they can. It's just hard to find. J Train podcast gmail.com. j Train podcast@gmail.com. keep sending your emails. I mean, today's a work themed episode, but we'll do any theme. If you, if you kind of coming hot with whatever you're going through, I'm up for it. Jared, hope you're doing well. I am. I'm sitting here in Delray Beach. It's a beautiful day. I'm gonna go for a walk after. I'm gonna get on the bike after this. I'll go get a coffee. I gotta make breakfast. All right. You don't care about that. All right, here's my problem. I'm a 30 year old woman who dates women. Nice. And I have a Co worker around my age. I think she's gorgeous and I always enjoy working and chatting with her. We've had some good conversations that got sort of personal and we have plans to hang out, but with another co worker too. It's not against our job's policies to date a co worker, so I'm thinking of asking her out. However, I've been at the job for quite a while and a supervisor position just opened up. But it just so happens that if I got the supervisor, but it just so happens that if I got this supervisor position, I would be this woman's supervisor. I'm currently looking for the policy on this sweating emoji. I guess I just feel torn. Should I just forget about asking her out? Well, I think this is like one of those things. Even just by the way, you're a 30 year old woman who sounds very mature and you're thinking through this in a very like, rational way. So here's the worst advice in the world that I, that is the hardest to take. I think you can cross that bridge when you get to it. I think these two things happening are happening. I think you being attracted to a woman at work that you're going to get drinks with is happening on the left and you applying to a supervisor position is happening on the right. At some point those roads are going to cross. They haven't yet. I think when they do cross, you're a mature person who has gotten to this place on earth and done great and wonderfully and you've handled everything that's ever come at you. So why would this situation, if it happens, be any different than that? This is very woo woo. This is very spiritual and I'm encouraging you to push forward because what if it all works out? What if the woman at work becomes the love of your life and you get this supervisor position and you go to the love of your life and you say, hey, this is going to be a little weird, but I'm going to be your supervisor and let's figure out how to handle this. And if they're the love of your life, they'll go, we'll figure it out. It might have tough times, but we'll get through it because we can communicate. And what if it, what if it happened? What if you had everything you wanted, the woman of your dreams, the job of your job of your life? Wouldn't it be great? You know what, you know how that doesn't happen if you don't try. So I don't think there's something against trying to Again, this isn't to say it's going to be easy. You're going to have to be over communicative. Which more power to you if you can do that. Not a lot of people can, but you'll feel better for it. The, the rewards are, they're sweet. But what are the rewards of not trying? You're in the same job, you're single, you got nobody, and you're downloading a lesbian dating app, whatever that is. Maybe, I don't know. You can do Hinge. I, I, I, I'm sure you can do any app. This is where I start sounding like an old straight guy. Hey, you can do any app you want. I, I'm a hinge, a grinder. I don't know, whatever your pleasure is. I, I, I'm sorry, I'm sorry. I'm, I think you go for it because I, I again, this isn't. I'm her super again. The, the pemdas matters when it comes to issues, the order of operations. So if you wrote to me and said I'm the supervisor of a hot broad I'm trying to bang, I would be like, hey, you are in trouble. Back it up. But that's not what you wrote. You said, I have met this wonderful person at work. We're going to go get drinks. We have another coworker coming. Should I ask them on a date? And then you said, also, I'm applying to be a supervisor and if I get that job, I would be her supervisor at work. Okay, this is different. None of this has happened yet to me. I go out for drinks with the other co worker. We see how the vibe feels. If the vibe is good and feels like there's something there and there's someone you're interested in getting to know more, you have their number. Hey, I know this might be weird and I totally respect your boundaries at work if this is something you would never do, but I would love to get drinks with you sometimes. Then you go for drinks. You guys hit it off. Wow, this is great. All the while you're applying to a supervisor position. Maybe that works out. Hey, you're going to be the supervisor of this woman. Let me be up front. Her and I have gone on a date. We're starting to hit it off. We have date two planned. I just want to let you know that work comes back to you. They go, great. We're going to have to sign some contracts, but this happens, you know, we're working in close confines. You know, we all take a look at each other's. Titties from time to time. I'm sure they'll say something like that. And then you got to go to your person that you and have a you have to go to the person you've gone on one date with and have a conversation that is a little uncomfortable and might be a conversation that's a little more vulnerable than you'd have with a first date person. But it might be, it might all work out. Why wouldn't you try? So that's my advice. It's a little woo woo. I mean, let us know how it goes. I love a follow up Jtrain podcast. Gmail.com back next week. Boom.
Episode Title: Do I Have To Invite My Boss To My Wedding? – MONDAY MAILBAG
Podcast: The JTrain Podcast
Host: Jared Freid
Date: September 29, 2025
This special work-themed Mailbag Monday episode sees comedian Jared Freid answering listener questions about workplace dilemmas, boundaries, and the sometimes messy overlap between personal and professional life. Jared provides insightful, honest, and comedic advice to three work-related listener emails, covering topics from wedding guest list politics to workplace flirtations and dating colleagues.
A listener, recently engaged, struggles with whether to invite her boss to her 100-person wedding after her boss assumed an invite.
On the Guest List Dilemma:
Jared begins by normalizing the stress around wedding guest lists, especially with limited space:
“Everyone has this problem... it’s something that makes me go, oh good, I’m not a fucking idiot. I’m not a loser.” [07:45]
Work Invite Breakdown:
He humorously narrates how fast 100 guests get claimed by family, obligatory invites, and now, work people.
On Obligation vs Benefit:
Jared insists there’s no obligation to invite work colleagues, but acknowledges there are pros/cons:
“You don’t have to do anything you don’t want to do. There are consequences. There are pros and cons to all decisions.” [14:10]
On Bosses Who Assume Invites:
He calls out the boss’s entitled behavior:
“Who’s excited to receive a save the date? What kind of loser... is sitting at home waiting by the mailbox?” [12:49]
Jared jokes how out of line it is for a boss to expect to be invited after less than a year.
The ‘Marketing Opportunity’ Angle:
Jared frames it as a potential opportunity:
“As far as marketing is concerned, the marketing of you, I think you are better off for having your boss at the wedding than you are for having them not at the wedding.” [19:55]
No Domino Effect:
If you do invite your boss, Jared notes you’re not automatically required to invite all colleagues:
“I think you can go boss on their own. Done. If you want.” [21:54]
A young woman, new in town, wonders if she’s overreacting after workplace friendship with a male colleague turns uncomfortable due to his unwanted flirting and sexual comments.
Can Straight Men and Women Be Friends? Jared empathizes with the confusion and disappointment when friendly banter is misinterpreted, and stresses clear boundaries are necessary:
“When you say I’m looking for friends, he’s not the friend. He’s not looking for friends.” [26:20]
Communication & Boundaries:
He voices sympathy for how hard it is to assert clear boundaries, especially for younger people:
“Why do I have to end something with someone that I’ve never began with? That sucks. I hate that.” [31:16]
Jared prescribes a direct cutoff, with kindness:
“We need to take a minute to let this cool, because I don’t want the same thing as you.” [29:12]
Societal Narratives = Distraction:
Jared warns against generalizing:
“You’re not going to solve society. ...You want friends, so let’s go make them with people who want to be them. Now, if you come across a guy in the future who’s trying to be your friend... that is a sad reality you have to keep in mind.” [36:00]
Direct Advice:
Jared suggests proactively ending the personal relationship:
“Hey, I really appreciated the relationship... It was a friendship to me... I need to stop texting with you and I hope you can respect this boundary.” [35:41]
A 30-year-old woman is considering asking out a coworker she likes, but is also applying for a promotion that could make her this woman’s supervisor.
Cross the Bridge When You Get There:
Jared gently urges not to overthink hypothetical problems:
“These two things happening are happening... At some point those roads are going to cross. They haven’t yet. I think when they do cross, you’re a mature person... Why would this situation, if it happens, be any different than that?” [45:05]
On Taking (Calculated) Risks:
He calls it “woo-woo” but champions optimism:
“What if you had everything you wanted? The woman of your dreams, the job of your life? ...You know how that doesn’t happen? If you don’t try.” [46:32]
"PEMDAS" of Office Romance:
Only worry about policy and conflicts if you have both the relationship and the supervisor role.
Clear, Communicative Approach:
If both things happen, suggest radical honesty—with HR and the coworker.
Signature Jared-ism:
“If you wrote to me and said, ‘I’m the supervisor of a hot broad I’m trying to bang,’ I would be like, ‘Hey, you are in trouble. Back it up.’ But that’s not what you wrote.” [48:55]
On Weddings and Obligations (Jared, 13:00):
“Who wants to go to a wedding of someone they kind of half know? Those are crazy. That’s a crazy person.”
On Boundaries at Work (Jared, 32:58):
“This sucks that you have to interact with him at work, but this is one of those things where I think you gotta dump him. Even though there’s nothing. There’s never been a relationship. A dumping has to happen because he’s not even listening to you.”
On Optimism in Office Romance (Jared, 46:32):
“What if you had everything you wanted? The woman of your dreams, the job of your life? Wouldn’t it be great?... You know how that doesn’t happen? If you don’t try.”
On Cutting Off Wasted Energy (Jared, 37:27):
“I think your time will be better spent worrying about you rather than why men and women can’t be friends without sex being involved, because they can. It’s just hard to find.”
Jared’s approach remains self-effacing, direct, and highly relatable, often weaving in personal anecdotes and playful asides. He balances humor with empathy, especially when giving “tough love” on workplace hierarchies and the realities of adult boundaries.
This episode of the JTrain Podcast combines relatable advice with comic candor as Jared Freid tackles three distinct workplace dilemmas. Listeners walk away with actionable frameworks, permission to set boundaries, and a reminder that sometimes, the best thing you can do is to try—whether that’s inviting the boss, shutting down a flirt, or shooting your shot at love and promotion alike.