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It's a mailbag Monday. 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 you live from Delray Beach, Florida. That's right, every Monday is a mail bag Monday where listener email me the comedian for advice you can ask about anything, anything. Friendship, dating, family, roommate. We have a roommate question today, so send in your emails. Jtrain podcast gmail.com Send anything you'd like. Title it Mailbag Monday. So that we know because the inbox we get lots of emails. I, we, we get a lot of emails. I listen, I don't want to miss it. Mailbag Monday. Title at Mailbag Monday. Jtrain podcast gmail.com if you want to come to a show. I'm going to be in Doral, Florida this weekend. Red Bank, New Jersey. Foxwoods Casino, Portland, Maine. Huntington, Long Island. More dates to come. We have three emails from you, the listeners and then we have one ad. So we'll do email, ad, email, email. You can go and join. You know, go check out the YouTube. I'm putting up stuff from the book talk and standup and ick shows. So go to the YouTube, check it out. We got some thick emails today. Thick again. I read these with you and I, you know, happy July 4th. Some of your podcasts might be on break. You know who's not on break? Your dear old uncle J Train. So I'm here for you always. So listen for that. Why don't you share it? Tell a friend, Tell a friend. Tell a friend. Tell a friend. Friend, friend. Tell a friend. Tell a friend. Friend, friend, friend, friend. Tell a friend. Friend, friend, friend, friend, friend, friend. Tell a friend. Maybe review the show. Longtime listener, Feather, Feather and all the things. I'm a U up subscriber too. Thank you. So I figured if anyone could help untangle this mess, it's you. I'm a 25 year old woman. It really does make me feel good that young women are engaging with this show. That means a lot because, you know, 25 year old woman, I'm a 40 year old, 41 year old man. We, we're from two different generations. We have nothing in cop. We have something in common. We have a mentality. We have a, we have a, a an ability to open up our minds. You know, now I sound like I'm a, a cult leader. We have an ability to open up our minds to other worlds. No, we share a perspective. We share a curiosity. I would Say so. It is very nice though. 25 year old woman, good for you. I'm, I'm happy to have you. I'm happy to have you aboard the J train. Okay, so I'm a 25 year old woman who recently got engaged to my boyfriend of six years. Congratulations. Six year boyfriend. 25, you got together when you were 19. So college sweetheart, no judgments. I'm just giving you the facts. 19 years old, met your boyfriend. 25. And I get it. It's time we, we, we've dated, we figured this out. The next step is here. He's also 25. We met as French, we met as freshmen in college, survived our early 20s together, went through grad school together, and have lived together since we were 23. On paper, everything is great. He's kind, supportive, loyal, and genuinely my best friend. We have a very stable, loving relationship. No major drama, no horror stories, no secret second family that I'm aware of. The problem is I can't shake the feeling that, that I missed out. Huh? This is tough. You know, 25 is the quarter life crisis that everyone talks about. 25 is a tough age. 25, you know, especially when you've gone to grad school. You know, 23, you get out of grad school, then you live together. Now two years settled into, is this it? And I, I, I understand that. I understand that feeling. I was 25, selling life insurance and doing cold calls and wondering, is this the direction my life is going to go? Now I feel older than I am. You know, looking back, I just did a whole speech on 41 and 25 and I don't feel like I'm old. But then I felt like I was old. I felt like life had begun. And when you're not sure the direction, that can be tough. So I, I feel for you. None of this is, I don't want to underrate any of this. It's, it's, that's a tough age. Tough for anyone. Hey, I'm engaged to my college sweetheart. Is this it? Did I miss out? Hey, I'm in a job at 25. Do is this the job I'm gonna have? Is this who I am? While my friends were downloading dating apps, going on terrible first dates, getting ghosted, making bad decisions, and collecting stories they'd eventually laugh about over brunch, I was building a life with one person. I would say you've painted this in the way that, you know, it's funny that you're like, well, my friends are having all of these horrible things that they Laugh about over brunch. Yeah, but they're also, you know, they're also. I, I. It is funny that you only look at being single as this, like, horrible issue they have to deal with, but that they can laugh about. I don't know. Just reading your words. I was building and you're building a life. They're doing these fun, inconsequential things, and you're building a life. You know, it is all on how you look at things. And now that we're engaged, Instead of feeling 100 excited, I find myself and now that we're engaged, Instead of feeling 100 excited, I keep finding myself wondering what I never got to experience. I don't necessarily want someone else. What I want is the version of my 20s where I got to be single. Well, you don't get that. You don't get both. I want the dating apps, the first date, butterflies, the weight. Did he text me back? Group chat, the, the Wait, what? Did he text me back? Group chats, the flirting, the uncertainty, and the feeling of being chosen by someone new. Oh, that. That's tough. All of those things are fun. All of those things I look back at, as, you know, I, I from the other side too. From the male side too, like, oh, meeting someone out and going on a date with them and having that will they, won't they feeling. I, I, I enjoyed all of that. But I also don't want to lose what I have. My fiance hasn't done anything wrong. If anything, he's done everything right, which almost makes me feel guiltier for having these thoughts. Sometimes I wonder if I'm choosing him every day or if we've just been together so long that staying feels like the default setting. The thing that makes this confusing is that I don't think this is engagement panic. These feelings started months before he proposed. In fact, I'd be wrestling with them for. In fact, I've been wrestling with them for a while. And then about a week later, he got down on a knee. The proposal didn't create the questions. It just made them harder to ignore. This is tough. So my question is there any way to have both? Is there a healthy way to explore these feelings without blowing up my relationship that is otherwise loving and stable? Or is this simply the unavoidable grief of the road not taken that comes with committing to one person? Signed mourning my hot girl era with registering for china patterns? I. Because I, you know, the answer. The answer sometimes is in the email. And, you know, I listen, I'm in a relationship now. And I feared commitment for so long. And the thing I was looking for when it came to committing was to not look at the logical. You have to be more romantic than logical when it comes to committing. I, I really do believe that you have to be a little delusional. You have to be a little stupid. You have to be a little bit. You gotta. It's like starting a business. You know, so many things shouldn't work out, but you're the one that's gonna work out. You know, so many things can go wrong. Life is so long, but you're the one that's going to have the happy marriage and wonderful future. I. It is a little bit to get into a relationship to, to marry someone is saying it won't happen to us. And you wrote something very specific in your email. I'm not saying break up. I. You ask, is there any way to have both? I don't believe there is. I think there's a way for one of you to be happy and the other one to feel like they're getting something they didn't want. You know, I don't think, you know, what, are you going to open up the relationship at 25 at that point? Break up at that point? You know what, you're using some sort of morality. In my belief, yes. Morality of like, oh, well, we're on the same page. And it's an open relationship. I get. I guess if there's someone listening within an open relationship there, they might be upset to hear that this is my opinion of their relationship. At a certain age. I think it takes someone that's like two people that are wildly weird to do an open relationship. They have to really be open and communicative in a way that is beyond anyone that would email in. You have to kind of be this. You're looking for an alternative lifestyle. You're living so far the opposite of an alternative lifestyle that it's almost from another era. To me, college boyfriend turned into, you know, your fiance is like a little bit old school. You wrote something in the email that I just want to point out. And I don't know, I would say, is there a way to have both? I don't think so. Considering the level of communication that you currently have with your partner, considering you are writing to me and not going to him and letting him know every weird thought in your brain and how sometimes you think about another man licking your. And that kind of gets him hot and he's into it. Like, it would have to be that type of relationship to then say well, let's have it all, because right now, you can't even communicate these feelings you're having, you know, for the relationship and for the upcoming marriage. And so I would say you're way far away from being able to be like, hey, we'll be in an open relationship, and you and I will, you know, pray to our dream catchers that we put up in our homes and, you know, every time we come home from a date, we'll talk about the date to each other, and that will turn each other on, and then we'll make love. No, it's not going to work out that way. I. I just don't. Chances are slim. You wrote something. You're you in your email, which is beautifully written. You wrote something when you got to the fiance, you said, but I also don't want to lose what I have. And when you mention what you have, it wasn't the love of my life. You wrote it. My fiance hasn't done anything wrong. I don't think I want a partner who is with me because I haven't done anything wrong. If anything, he's done everything right to me. I hear that as he's checked all the boxes. I don't think anyone, regardless of gender or orientation, sexually wants to be a bunch of boxes that got checked. I think you want a certain level of romance, and that's why you're going into it. You're going into it. I would say he might be going into it. I would assume he's going into it with love will conquer all. Yes, life is tough. Yes, we're getting married young, but I love this person. And that's why I can stay delusional and ignore the dating apps. I never went on the dating stories. I never got the butterflies. I never experienced. Like, I think that's where your email tells me the answer, which you are settling for fine for fear that there's nothing better than fine, which. And the way you describe single life is all negative. So it sounds like, based on the full email, I never got to have. I never got to go on terrible first dates and be ghosted. But I have this guy who does everything right. That's someone who's playing it safe. That's someone who's upset that they never took a chance. And honestly, I'm not saying you should. I'm not saying you can. I'm not saying I'm. And this isn't, like, me challenging you. I'm not trying to, like, be mean to you. I'm just saying you wrote the email the words are written a specific way. Single, downloading dating apps, going on terrible dates, getting ghosted. How about you ghosting someone else? How about, you know, why is the perspective. I never got to get treated horribly by all these men and then laugh about it with my friends, but at least I got this guy who doesn't treat me horribly, so I don't want to leave him to me. There's a lack of belief in myself that's going on in this email. And listen, I can notice that because I have. That I have a lack of belief in myself. That's why I stayed single for so long. There's a. That's a good part of the reason I talk about it in the book. Confidence. I told Emily, I wish I had the confidence to dig in. The first time we dated, I didn't have it. So that's my perspective. That's. That's me being personal and vulnerable with you and telling you, I. I think step one is to communicate this to your partner. He might be on the same page. He might be like, yeah, I've thought about missing out on those apps. And you might hear him say to you, you know, the best thing that could happen in my opinion? Hey, I'm having all these thoughts. I have these insecurities. I never got to date, and it's, like, weighing on me, and the question keeps getting louder in my head, and I don't know how to deal with these things, and I need to include you in that conversation. He might say, I, I have those thoughts, too, but I love you so much, and we will conquer all together. And then you might see in his eyes what you lack in yours. And that might be a easier answer. Wow, he really loves me. And I don't feel the same way. This is a box that I'm checking to get me to the next step. And maybe I'm with someone so I'm not lonely. So that's my thought. Tough one. Listen, if it's 10 years from now and you're happily married with two kids, and. And that's the other thing to look at it from the other side. I have friends that got married at 25, beautiful family. They're now having this, like, they're going to be young and with kids that are older, so I'm missing out on that part of life, too. There's another. There's another side of the coin here. You know, you starting life now, you're gonna have friends that are gonna go, ah, I missed out on growing a life with someone that I met When I was very young and, and. And having this bond that no one can understand. So there's other things that get missed out, but it's just more. I'm answering this based on how you wrote the email because that is a fair point would be to bring up. You're getting. Other people are missing out on things that you get, but you're not even looking at it that way. J train podcast gmail.com j train podcastmail.com we're sponsored. You want your morning toast without the guilt? Just pull out the hero bread. Hero bread is high, high in fiber, low net carb with zero grams of sugar. Hero bread has been with this podcast for a long time. I am a huge proponent of it because I think it fits into how I live my life, which I'm assuming is the way you live your life. I want efficiency. I want the Uber to show up right. Right when I'm like, right when it says I want to see the Uber, you know, come up to my door and then I don't want to break stride, then go on my way and not have to say the directions. You're like, well, what does that have to do with bread? 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For your toast in the morning, you get the crunch. You can make an egg sandwich. I do it. It's great. Herobred is offering 10 off your order. Go to Hero Co. Use code feather at checkout. That's code feather at Hero Co. So we got two more emails on a Mailbag Monday Happy Summer. I'm here with you all summer, every day. Tell a friend J Train Feather Feather Big fan of the book. Thank you and congrats on all your success over the last few years. I've been a fan for a while. You up Subscriber all the great things. Say hi to Emily for me. Hi Emily. Now to my dilemma. About a year ago, my friend Emma was desperately looking for housing after being kicked out by her mom. At the time, I was living with a friend of a friend who wasn't my ideal roommate. Emma knew this and repeatedly encouraged me to ask him to move out since I'm the sole leaseholder. I was hesitant because it's New York City and I didn't want to put someone out. But after months of telling but after months of her telling me how badly she needed a place, I eventually did. He moved out. Nema moved in. So let me start. I haven't read the rest of this. Your friend is a pain in the ass. That's all. That paragraph tells me you had a situation that worked for you. Not your ideal roommate, but having a roommate where the money is set is like a big win. And she gets kicked out by her mom. So let's keep that in mind. Her mom was like get the fuck out of here. And now this woman is pushing another human being onto the street. It's a little shitty. We've been friends for about three years and met at work. Living together has been more of an adjustment than I expected. Again, the devil you know. That guy before sounds pretty good. She brought her dog, works long hospitality shifts, and despite her efforts to make it work, I still regularly come home to a dog smelling and the realities of having a pet in a small NYC apartment. Yeah, this is why the mom kicked her out. She also got a boyfriend shortly after moving in. We had to have a conversation about how often he was staying over because it started to feel like I had another roommate. She was receptive, but between the boyfriend, the dog, and our different lifestyles, our friendship has definitely taken a hit. Man. I mean, the mom might be listening right now. Like, could have told you this was coming. Here's where I need your help. I want to ask her to move out. It's not that she's a terrible roommate. I've just realized I don't enjoy living with friends. I miss when my apartment was quiet, clean and fully my space. I think I'd rather live alone or with someone I don't know because it's easier to have roommate conversations when friendship Isn't involved. I, I understand that. I mean, this is why it was easy to live with my brother. You just have it out, you know, my brother and I were gonna be fine. A friend you go. I gotta make sure I dance around them. My concern is that she won't take it well and it could affect our small friend group. I also don't want to put her in a bad position. Although I suspect she and her boyfriend could eventually find a place together. Am I being a total jackass here? No, I don't think you are. Is it reasonable to give her six months notice, tell her I'd like to live differently when the lease is up or should I stick it out because finding a sane roommate in New York City is hard enough? Am I being too much of a tidy Tiffany? Looking forward to insight. Your insight best your type a bestie. There's an easy solution and it's I'm moving out. But I understand that New York City, if you find a place, you kind of hold on to it because you have your neighborhood and you are good with the bills and moving costs are very high. Also broker fees and all those things that work into it. Here's the thing you have on her on your side. The thing you have on your side is that she pushed out the last roommate so she kind of gets how this whole thing works. Live by the sword, die by the sword. I don't think it's unreasonable to say, hey, I've been thinking a lot and I have the lease under my name and I'm looking to make a change here in six months. I'd like to have this place to myself. I think that's pretty reasonable. I mean, again, you have in your back pocket. This is kind of what happened with my last roommate and we've hit the end of the road here. I wouldn't get into her situation with a boyfriend because that's not for you to decide. You don't know how the relationship is going. The friend group thing, it's gonna, it's going to. To me, my concern is that she won't take it well and it could affect our small friend group. The friend group is already done. Like the idea that you and her are roommates and it hasn't gone as well as you'd like and the friend group has just stayed the same is crazy. That didn't happen. So I think the thing you're worried most about is already happening. So if anything, this can only make the friend group better because now you're getting this kind of out you're having this out right now. This is a hang now. You know you have. The friend group is in flux because you live with this girl and you guys probably talk about each other to the friend group and you're kind of on the doorstep of one final battle. But once that's done, then the friend group can be freed and maybe everyone works out. But I wouldn't bet on it. But I don't think you're being a jack. I think things change and the way you wanna live changes. And I think you could say, hey, I'm looking to have the place to myself. And the next round I think I'm gonna go in my own direction and I'd like you to move out. That's tough to do though. That's really tough to do because once they're in, they say, nope, I don't wanna go anywhere. And then you're like, well, can you please move? And they're like, ah, gonna be a no for me, dog. I'll be sitting here on the beanbag chair. Good luck to you. The best move is to move out. But I get that that's not what you asked for. Um, am I being a total jackass here? No, you're being prudent. Hey, I. I think you could even say, hey, this has been tough. I'm just going to give you how I feel. I like you. And it's tough because this roommate situation has made our friendship not as great as it was before you moved in. I'd really like to stay in this place and I'd also like to live alone. How do you feel about that? I think that's the way. How do you feel about that? Keep it open ended. This person is not new to being a bad roommate. The mom kicked them out. So like when the mom kicks her out and then she pushes another person outta your apartment, like they're ballsy too. Ballsy respects ballsy. So I think you're okay. This is really tough though. I love this email. I think you gotta let her know. Listen, how do you feel about our rooming situation? Well, I wouldn't start with that. Hey, I've been thinking about our room situation. There's six months less on the lease. I'd really think it'd be better off if you moved out for the next part of the lease. I kind of want to live alone or figure out my own thing and then I don't. You. I don't think including her in who's moving in next or if anyone will move in next is I Think that's a mistake because then they start to say, well, once you find someone, no, no, no, no, I'd like to live alone. And then when, if you bring in another roommate, you know, she'll, you'll deal. You'll be fine. It'll be easier to deal with that when she's out of the house. You want her out. That's, that's priority one. J train podcast@gmail.com J train podcast@gmail.com. last one. We do three every week. Send it in. J train podcast gmail.com Keep sending in your emails, title it Mailbag Monday. This one was from the book tour. We've, we've taken a couple of the book tour emails and we've brought them over here. So if you were at the book tour, maybe your question that didn't get answered will get answered here. I met an Irish gentleman in a bar a month ago. I had to rejoin my group, but at the end of the night, he approached me again as I was closing out and we talked for 20 minutes. He asked me out and we exchanged numbers. We texted pretty consistently for the next week and set a date, and then three days later before the date, and then we texted pretty consistently for the next week and set a date, and then three days before the date, he stopped texting. And I've never heard from him again. What was the point of wasting my time? My response to this is to your languaging wasting my time. I, I think we have to be okay with a pre. You met a guy at a bar, had some texting, didn't end up going out. Did they waste your time? I don't believe so. Is it annoying to have a date and then set in the calendar and then the person just drifts away? Yeah, it's annoying. Is it childish? Of course it is. Did your time get wasted? Nah, I, I, I think, I think you know something Jordana was told on the UF podcast and has become, you know, your words are your spell. Words are spells to me. If you're taught, if you use, I think using the phrase wasting my time flippantly and like, not really taking it seriously, it will make you more miserable. It will make you a miserable dater. Anyone using the phrase wasted my time seems to be worse off in dating than the people who don't use that phrase. I, I try to stay away from that phrase, I think, because people will waste your time and you'll need to use that and you'll need to be appropriately angry about that and you'll want people to go, what a piece of shit. This is not time wasted. Time wasted is two years of dating and then they said they're going to get engaged to you and they didn't do it and they broke up. That's a, that's a version of time wasted to me. This isn't. They wasted your time. They acted childishly. So why, what's the point? Here's the thing. They met you in a bar, I think meeting in a bar and then you reassess and then here's what I also will say. And this isn't, this isn't comfortable to admit and this will be very easy for someone to say isn't true or say that the person is weird or whatever. When you are used to a dating app and a world where you have a full album of photos of the person that you're going to go out with and then you meet someone in a bar and you don't have access to that. I do think the longer you go before that first date, the less excitement there is. And what did they really look like and who were they? And I don't know if I want to go. The whole I don't know. And forcing yourself out of the house is a little bit tougher. I do think dating apps take away the excitement, but I also think they keep you on the hook. So that's a theory of mine. That's a working theory, I would say. So why would that happen? I think that's why you had a lot of people more, you know, stood up before the Internet way more because he just didn't have anything to reference. Who am I going out with? Oh yeah, she's cute. Okay, yeah, yeah, I'll go out. Of course you do need these like gentle reminders. I, I just think you texted pretty consistently for the next week and then set a date. So now we're like a week and a half away from when they saw you blurry eyed in a bar after a few cocktails and you're like, ah, do I want to go out? And then it also becomes more organized. The bar meeting is for disorganization and casual. The minute that day gets planned. Oh, now I'm really okay, we're going on. We're doing a real thing here. Okay. I guess again, that's getting ahead of himself. But these are all reasons, you know, the, the, but the point, like to bring it back to your question, what was the point of wasting my time? The point was feeling good about yourself. That was the point. Sometimes getting the Date. Making the date is all you really need. And then you go, ah, do I need to go out? I got everything out of this that I wanted. I don't want a relationship. I don't want to go on a date with them. I'm fine. The chase is intoxicating. And so, like, again, there's no point. Their own insecurities, their own, you know, voids that they need filled by attention from a woman. And maybe, just maybe, if there's someone that met someone at a bar, you. Then there's someone that could meet someone else at a bar. Maybe they made a connection between when you met and when you were supposed to go out and they went out. It doesn't matter. This is all to say it doesn't matter and stop calling it your time getting wasted when no time was wasted. And I'm. I'm not trying to give you. Again, I'm not saying it's nothing, but I'm. I'm not saying they're not childish. I'm just saying when you speak in terms of, you know, what's not. When would they have not wasted your time? Let's say you went on a date and you had a fun time, and then they never called again. Did they waste your time? What was the point? I. I just think your question is the problem here. More. These things happen. I can't give you. I could give you a million reasons why the date didn't happen, why they didn't, why they ghosted, but your perspective is the only one I can actually speak to. Your perspective of what was the point of wasting my time. That's a miserable perspective. That's my feedback. Never heard someone who says, my time was wasted. That doesn't seem a little tinge of miserable, that is. Again, stay away. Take those words seriously. That's my advice. Mailbag Monday, every Monday, back next week, boom.
Host: Jared Freid
Date: July 6, 2026
In this jam-packed Mailbag Monday episode, Jared Freid dives deep into listener emails covering classic dilemmas around dating, relationships, friendships, and the big question of “missing out.” He reads and responds to three thoughtful listener queries, offering both empathy and comedic realness. Topics include: engagement doubts and FOMO over single life, the perils of living with a friend as a roommate, and the sting of being ghosted after a bar meet-cute. Jared balances candid advice with relatable humor, often reflecting on his own experiences to help listeners see a broader perspective.
[01:44-24:39]
“To marry someone is saying, ‘It won’t happen to us.’ … You have to be a little bit delusional. You have to be a little stupid.” (Jared, 14:22)
“Step one is to communicate this to your partner. He might be on the same page ... and then you might see in his eyes what you lack in yours.” (21:20)
[28:05-46:44]
“You had a situation that worked for you. Not your ideal roommate, but having a roommate where the money is set is a big win.” (31:12)
“Live by the sword, die by the sword. I don't think it's unreasonable to say…‘In six months, I'd like to have this place to myself.’” (35:29)
“Ballsy respects ballsy. So I think you're okay. This is really tough though.” (41:29)
[49:39-59:58]
“Did they waste your time? I don't believe so. Is it annoying? Of course. Is it childish? Absolutely. Did your time get wasted? Nah.” (50:25)
“Sometimes getting the date, making the date, is all you really need. And then you go, ah, do I need to go out? I got everything I wanted out of this.” (54:38)
“When you speak in terms of, ‘what was the point, why did they waste my time?’ that's a miserable perspective. That's my feedback.” (57:29)
On engagement and fear of missing out:
“To marry someone is saying, ‘It won’t happen to us.’ …You have to be a little bit delusional.” — Jared (14:22)
On living with friends:
“You had a situation that worked for you. Not your ideal roommate, but having a roommate where the money is set is a big win.” — Jared (31:12)
“Ballsy respects ballsy. So I think you're okay. This is really tough though.” — Jared (41:29)
On modern dating flakiness:
“Did they waste your time? I don't believe so…Did your time get wasted? Nah.” — Jared (50:25)
“When you speak in terms of ‘what was the point of wasting my time?’ that’s a miserable perspective.” — Jared (57:29)
Comic highlight on friend drama:
“The mom might be listening right now, like, could have told you this was coming.” — Jared (34:12)
Big-picture advice:
“Step one is to communicate this to your partner. He might be on the same page ... and then you might see in his eyes what you lack in yours.” — Jared (21:20)
Jared brings his trademark blend of compassion, honesty, and dry humor to classic (and thorny!) relationship and life issues. His core advice: communicate openly, be wary of negative perspectives like “wasting my time,” and recognize that “missing out” is a part of every path—not just the one you didn’t choose. Whether it’s wrestling with engagement doubts, untangling roommate drama, or bouncing back from being ghosted, Jared gently steers listeners toward self-assurance, honest connection, and a little less self-inflicted misery.
For more, submit your dilemmas to jtrainpodcast@gmail.com and catch Mailbag Monday every week!