Home
Creators
Search Recent Random
Posts
Search DMs Popular Hash Lookup Tags Random
Importer
Import FAQ
Register Favorites Keys Review DMs Logout
Community
Telegram ThePornDude
Home Creators Posts Import Register Favorites Logout

"If I Were You" Advice Questions (Patreon)

Published:
2026-01-26 18:17:30
Imported:
2026-01

Content

We are dusting off our advice pod for a few episodes but need more questions! Got any relationship/work/life quandaries that are ailing you recently? Leave them as a comment below and we'll do our best to answer them "IF I WERE YOU" style -- that's with a little bit of salt.

Thank you!

Files

Comments

Michael Gumption

This came at a great time because I’m in a particular pickle. Here’s my quandary: My dentist is a really handsome Latin man, and he always has his shirt buttoned down pretty far and he has a lot of chest hair so whenever he leans in, I’m reeeaally close to his chest hair. As a straight man I don’t like this, but he is handsome. Should I get a new dentist? His chest is really really hairy

bradley miller

I host bingo at a local bar and struggle to get tips from people who play. I feel like i do a good job and regulars definitely say they enjoy the game. What are the best ways to make absolute bank on the day?

Don Kianian

My girlfriend was an ER nurse working 3-4 12-hour shifts every week, often nights, in SF. Long story short, it was a supremely toxic environment. Now, she works in a private clinic (and is MUCH happier) but took a 25% pay cut to do it. So, she's debating picking up some one-off shifts at the ER to make back some of that cash. I feel like this is a bad idea for her mental health, but so is being poor. I've been trying to convince her to ask her boss for a raise, but she hasn't been there a year yet so I don't think she feels confident asking for that yet. What do you think? Also, I took her to come see you guys at the Headgum SF Sketchfest show - it was her first comedy show ever and she loved it! <3 Don Kianian

Carter

The band that I play drums in is extremely volatile. Long story SHORTS the bassist is getting fed up with the guitarists lack of motivation, which led to him almost breaking up the band a couple of months ago. He agreed to keep it going on the caveat that the guitarist writes all the music from here on out. Since then, the guitarist has not written a single song, despite me several times offering to help him. This has led to the bassist going back on his word and he plans to write a bunch of new songs to fill an album with. I recently talked to the guitarist and he said that if the bassist doesn’t let him write a new song, he’s planning on leaving the band. With that being said, he still hasn’t shown any progress on it, and the bassist has told me he is not interested in recording anything he wrote. If the guitarist leaves the band, the band will pretty much be over, in my eyes at least, because the guitarist also shares singing duties with the bassist, but I also worry about that because the bassist has told me recently that he’s interested in letting me sing a bit too. Which makes me think he’s not going to write anything for the guitarist to sing, which will probably make him upset. How do I keep the band together?

Chris H

I'm a 37yo dude with a Master's degree and 7+ years experience in marketing... stuff. I've been unable to land a job in my field for almost 1.5 years now and it's really getting annoying having to spend hundreds of hours sending applications to companies all over the country (Germany). I'm looking for a remote position which has the advantage that I don't need to limit myself to companies in the immediate vicinity but at the same time most companies are run by conservative old men who think that only office time is actual work time (I'm exaggerating a bit but that's what it feels like looking at their job listings). Self-employment isn't an option for personal reasons (i.e. not wanting every waking hour to be consumed by the nagging feeling in the back of my mind that I should probably be doing more work right now). I would prefer to stick to my area of expertise (creating / optimizing web pages, creating 2D video animations, SEO, all that crap) but many companies now think this can be handled by AI or by newlygrads making minimum wage. I'm not desperate enough to just take any job as I'm currently not paying rent and I can live off of my savings for quite a while. Still, I hate spending / wasting so much time on the job hunt without any results. What would you suggest I should do, seeing how the two of you have basically tried out every type of employment out there?

Noemi

Damn, the questions I have as a thirty-something are NOT interesting. I just want to know how to get enough fiber.

Shaun H

How do you decide what to feed yourself three times a day seven days a week? Feels like this is a scam from big food company

Sarah Hunt

First Time Long Time. I'm a 24 year old woman living in the midwest and I am having the typical career decision issues. I graduated with my MSW in May 2025 and had my first job doing student services in Dublin for 4 months. Now I am back in America and I took a job doing school social work and it has been less than ideal. I took this job while in Dublin because there were no macro research jobs due to the current climate. Now I feel like I've stuck myself in a job I am not passionate about because it is "safe". How did you both decide to take the leap to pursue comedy when it was not a sure thing? How long do I stick it out and do my best with what I have before something has to give? How do I not feel like a quitter? Thanks!

Gavin The Goose

Hey guys. Im 29 and the big TREY CERO is about a year away. Though I’m in a happy, long term relationship, i dont feel 100% ready to move things forward. Don’t get me wrong, she’s a dime and my dream girl. Problem is, i dont feel like i ever really got my life together. I did a 9 year Bachelor’s degree and i am about to finish my masters in opera. Ive been really depressed for that entire time, And I have struggled to overcome various bad habits (smoking, porn, unhealthy foods and drinks etc.). Steady work is hard to find with my mornings packed with classes and my evenings filled with rehearsals/shows. She’s so wonderful but I’m afraid if we take the next step while I’m still like this, it may all be for naught. Any advice on overcoming personal demons and becoming a better, successful member of society? I identify a lot with some of the crazy stories Jake would tell on the pod in the early IIWY days. Seeing you both become happy married guys makes me happy and hopeful. Thank you goys, Gavin The Goose

Jackson Morgan

Did I mention that Gavin was a goose ?

Noemi

You guys should ask the subreddit for questions, too.

John Coogan

I'll echo advice Jake gave a few hundred episodes ago and say: Overnight oats. You can make it in big batches and eat it for days, it's cheap, and depending on what you put in it (I use peanut butter and protein powder) it can give you great macronutrients to start the day. In other words it gets you made, paid, and laid.

John Coogan

Segments had a perfect game going but they just made it myspace.

Zarina Munoz

What's the best way to keep the intimacy in a long distance relationship? We've been together for 5+ years but now we're looking at maybe a couple years apart.

Urqu-DC

Hey guys, 28-year-old male here living in South Florida, and I have recently broken up with my ex. I think I'm average looking but the second that the news broke that my relationship with my ex was over. I had gotten a couple of ladies who were interested in dating me. I know the right answer is to generally process what had gone down, but I fear that I may lose these opportunities with some choice bachelorinas if I do. What do I do in this scenario and can I speed run processing a breakup, keep in mind that we had been together for 5 months. Jake, what would you do in this scenario? Amir, what would you wish you did in this scenario?

Adrian

Hi, I have a question! I am a 31 year old guy who just moved to a new city, and have been going to community-organised events to make new friends. I met a guy who is also new to the city and shares an interest in video games. We exchanged contact info, and a few days later met up online to play games and get to know each other a bit better over voice chat. An hour into the gaming session, we were having a good time and enjoying each others company until I made a cultural reference that he didn't understand. It was here where we realised that there was a 10 year difference between us. He is 21 and assumed that I was in my early-mid 20s, I am 31 and assumed he was in his mid-late 20s. It was a bit awkward, but we laughed off my unc status, kept playing the game, and had a good time. My question is this: Do I continue pursuing this friendship? We genuinely got along well, and I am happy to have found someone that is down to play games, but it also feels weird being an old man hanging out with a child. Would love to hear your thoughts!

Ace and Jocelyn

Here's one deeper than the pencil in amir's neck in Fish Scroll. Is it ethical to have children if I have autism and they likely would too?

Chimpman

Speaking as someone with autism, you would just be making some new friends to discuss Bionicles with. Completely ethical.

Joseph W

I moved from Winnipeg to Melbourne and learned that I prefer "the Peg" for heaps of reasons. My best friends, all family, girlfriends, and cat live there. Hard to mention that my fav jacking spot is there too. They say Melbourne is better, and I feel stupid, ungrateful, and like I forgot something. Any advice for some guy who prefers blizzards to heatwaves? Thanks Eskimo Joe

polyrain

My current job is pretty good on paper; remote work, flexible hours, and so on. Despite all that, I don't enjoy it the way I used to; the works changed, leadership is more punitive, in general I dread more and more going in. I've been working here for a few years now, and in the last year or so many of my co-workers have left to different companies, or even entirely different fields. I feel like I'm at a crossroads; I don't know if I should stay, leave, or do something more radical like looking into a different career that's not in front of a computer all day. What would you do in my position, or what would you be considering? Thanks guys!!

AlaskanEmily

I live in a quadplex, and one of the neighbors has been absolutely stuffing the trash bins every single week. I'm not sure who it is, but it seems to be something new that has happened. The landlord basically said they aren't going to do anything about it and we can't get any more bins to increase capacity. I really don't want to confront my neighbors or have some kind of witchhunt about it. I'm on the verge of having a come-apart over this. What should I do? Please remember to give me actual advice. Love, me.

Zane Carnie

I recently broke up with my girlfriend of four and a half years. The relationship wasn't perfect, due to some drinking issues and things from her, and ultimately ended because she cheated. However, her and I are still friends, and I'm aware my friends and family find it weird. They think I should cut my losses and leave her be, but we still get along, have deep love for one another outside of the relationship, and often I will be her support person still as her family and friends kinda suck. What should I do? Should I keep being there for her while she's in this tricky period? Or is it better to prioritize my healing and moving on? (which I'm not sure I wanna do yet but that's what I'm told is normal). Please help you advice kings! Love, Zealand Zane

Shaun H

You are a prophet and a cool. Thanks John, I’m going to give them a try

AFPT

Hey oldies! I’m a 23 year old lady! I work for a nonprofit where we help people struggling to pay off their debt. I’ve been working at this nonprofit for a few years so I’m not new but this is definitely my first “big girl job”. A few months ago, my executive director promoted two people to managers. My executive director also had a really serious meeting with us where he told us that we aren’t doing enough and that we need to take on more clients. Well, cut to now. We are taking on more clients but the extensive ( AND REPEATED) training that we’ve ALL participated in has not stuck with some of my colleagues. Clients are being told misinformation, procedures aren’t being followed, cases aren’t being worked on for weeks at a time. We’re taking on more clients but we aren’t providing an adequate level of care. Not me of course, I’m amazing at my job. One of my new managers (a 54 year old woman) is constantly screwing up cases as well. But there’s one case that she messed up BAD. The client has now taken on more debt as a result of her mismanagement. And she didn’t even care. I HAD to say something to her. So I did. I politely told her that this client’s situation was made worse because of her and that she could’ve done a lot better on this case. If I messed up a case THAT bad, I would want someone to tell me. Anyways, now I’m getting a clear vibe that I’m going to be spoken to about this, maybe by my executive director. And that maybe I’m going to be told to respect my manager and trust her work. There’s no way my executive director has all the details. There’s no way he knows that people have been fucking up this badly for months. I’m not trying to lose my job or get any else fired, but I’m tired of people doing less than the bare minimum when people’s lives are at stake. It’s our job to help people and my own manager is falling tremendously short. Should I bite my tongue or I can I find a professional way to stand for what I believe in?

Scampersand

I'm a 32 year old guy. I just moved back to my home city after 4 years in grad school and have been wanting to clean out my closet. My question: what is a good amount of clothes to have? How many suits? Pairs of socks? Blue jeans? I'm good on underwear (thank you for the discount off a monthly subscription). (Optional) Context: I work as a researcher and analyst for a non-profit, mostly remote from my home, with the occasional office/formal meeting (briefing state legislator or official). I did find out last week that one of my coworkers was an If I Were You fan but never really watched Jake and Amir. I live in Kentucky which sees most seasons every week. P.S. You answered a question of mine in Ep 178 with UTK if you're interested in doing a follow up pup. I'm so glad I didn't take Jake's advice.

Logan Stewart

Hey y'all. Hopefully I'm not too late for a submission - just recently migrated over from the Headgum patreon. I'm a 22 year old guy, and I've been in a long-distance relationship (7hr drive) for about 8 months at this point (i moved away for grad school, we went to college together). We're nearing our 4 year anniversary, and on the drives i've been listening to old IIWY episodes (on like ep. 150 or so atp). To spice things up (as we've only seen each other 1-2x a month over the past 8 months) we recently got in a situationship with a mutual friend of ours (as my girlfriend recently came out as bisexual). We've had a couple of three-ways, and really avoided all of the problems that come with having a three-way with your significant other (the jealousy, the possibility of leaving the S.O. for the other person), so it's been a good situation overall. The problem? The girl we've been hooking up with recently started seeing my best friend from back home. I was his roommate for three years during college and I've known him longer than I've known my girlfriend. The most recent time the three of us hooked up was after I was told that they were exclusive (definitely an issue). Here's my question: Do we still see this woman? They're not technically dating yet, and I'm supposed to come in soon for some celebrations (our anniversary and my birthday). I know it's a bad idea because my friend doesn't know about the extent of the situation (really all he knows is that we are friends with the girl), but I'm literally always down for whatever happens.