#18 - Guyset Toolkit #1 (Ask Me Anything)
Oct 10, 2023
Welcome to the first segment of Guyset Toolkit (also known as Ask Me Anything). These questions are all from you guys! from my email (josh@guyset.com) Instagram, or TikTok. Send me anything you want answered for the next one.
Guyset Toolkit #1: Your Most Asked Questions About Dating, Work, and Life Answered
Welcome to the first-ever Guyset Toolkit - my new "ask me anything" segment where I answer your burning questions about dating, work, hygiene, and everything else guys in their 20s are thinking about but not talking about. These are real questions from real listeners, answered honestly and without filter.
This is a new type of episode for me - instead of one big topic, I'm answering the questions you actually sent to my Instagram @theguyset and email josh@guyset.com. Think of this as your personal toolkit for navigating your 20s. These aren't rigid rules, just tools you can pick up when you encounter these situations.
Social Media and Breakups: The Ex Photo Dilemma
Question: "Should you leave up pictures from an ex or with an ex on your Instagram?"
This is such a good question because literally everyone goes through this. Here's my take: No, definitely not. You want other people to know that you're available.
Before you delete everything, ask yourself: Is there a chance you're going to get back together? If you think you might reconcile soon, then maybe leave them up because you don't want people thinking you're on the market. But if you're really breaking up and want to move on, you need to archive those photos.
Use Instagram's archive feature instead of deleting permanently. This saves the photo with all the likes and comments intact, but removes it from your profile. If you get back together, you can put it back up exactly where it was. If you never get back together, the photos are safely stored away.
The bottom line: If another girl is stalking your Instagram and sees you with your ex, she's not going to pursue you. Your social media should reflect your actual relationship status.
Dating and Pickup Lines: What Actually Works
Question: "What's your best pickup line?"
I'll be honest - my last episode about talking to girls at bars was pretty bare minimum advice. Basically "just go talk to them," which is really asinine advice. But I've learned more since then.
Here's what actually works: A girl friend gave me this line that I tested on three different girls the next night, and it was incredibly successful:
"Hey, can you settle a debate between me and my friend? What movie is better - Shawshank Redemption or Good Will Hunting?"
Why this works:
It starts an actual conversation
It involves their friend and your friend, making it group-friendly
It gives you something to debate and discuss
It's not sleazy or aggressive
The psychology: You're not complimenting their appearance or being overtly flirtatious. You're asking for their opinion, which people love to give. Then you can playfully disagree ("You don't think Good Will Hunting is better?") and keep the conversation rolling.
Adapt the formula: Think of any good question that could start a debate. "What's the best pizza spot in the city?" or "What bar has the best drinks around here?" The key is giving them something to respond to beyond just "Hey."
Pro tip: Think about where you are when talking to girls. Some bars are more conducive to conversations than others. A sports bar with shuffleboard might not be the right vibe if you need a dancey atmosphere to feel confident.
Work Happy Hour Survival Guide
Question: "How many drinks do you have at a work happy hour?"
This is such a smart question because it shows you're thinking strategically about your professional image.
My rule: Two to three drinks maximum - and that's for big company events where the CEO, your boss, and people who could judge you are present.
Why this matters: I know free alcohol is tempting, but you're having conversational drinks, not "let's get fucked up" drinks. You're holding it, sipping it, not chugging. These are business conversations with alcohol, not a party.
The exception: If you're just with your immediate team and the vibe is more casual, you have more flexibility. But for holiday parties, company-wide events, or anything where senior leadership is present, stick to the limit.
Remember: You can always go get drunk with your actual friends later. Don't let free alcohol ruin your professional reputation, especially in your first or second year.
The "How Often Do You Wash?" Section
This might be my favorite new segment because these are questions guys actually think about but never discuss.
How Often Do You Wash Your Sheets?
Honest answer: Not often enough. I'd love to say every two weeks, but that would be a lie.
My actual system:
If I've gone out over the weekend and was super sweaty, they get changed Monday or Sunday
If I've had a girl over, they're getting washed immediately - let's not be disgusting
If I've had a particularly dirty day (subway, gym, etc.), I'll think about it (but probably won't do it)
Rule of thumb: Every couple weeks (meaning two to two and a half weeks). And yes, I always shower after the gym before getting in bed.
Duvet cover confession: I couldn't tell you the last time I washed mine. Don't judge me. I don't even know how you're supposed to wash a comforter.
How Often Do You Wash Your Pants?
The truth: Not a lot, and I think every other guy is the same.
My system:
If I spill something on them, they get washed immediately (I spill a lot)
For jeans or work pants: 4-5 wears before washing
I rotate between a couple pairs throughout work weeks, then wash them all together
The golden rule: If you sweat in them, they're done. Wash immediately. No ifs, ands, or buts. If you don't wash after you sweat, you're disgusting.
How Often Do You Wash Work Shirts?
T-shirts: Every single time. No exceptions.
Button-downs: Every couple of times (1-2 wears), but in summer when it gets sweaty, it's every time.
Summer rule: If a shirt gets sweaty, it's done. Period. No second wear.
Pillowcase tip: Wash these more often than your sheets. If you sleep with greasy hair or don't wash your face, dirty pillowcases can cause acne.
Halloween Costume Ideas That Actually Work
Question: "What should I be for Halloween?"
Easy go-to: Your favorite current TV or movie character. Think Spider-Man, Iron Man, any Avenger.
Trending options:
The Bear - Get an apron, white t-shirt, maybe pump some iron
Ken (from Barbie) - Very popular this year
Ted Lasso characters - I did Jamie Tartt one year with friends
Mario and Luigi - Cheap and easy with a friend
Funny options:
Whiteboard - Wear a white t-shirt, carry markers, let people write on you
Yearbook - Same concept, people write "HAGS" and yearbook messages
Shrek - Always gets laughs
Couples costumes: If you have a girlfriend, coordinate something cute.
Most important rule: Don't wear something you can't go out in. You will sweat and look like a buffoon. Comfort over creativity - people don't care that much what you're wearing, especially at 23.
Random but Important Questions
Best Condoms
My choice: Trojan blue ones. They get the job done and don't break. That's literally the only criteria that matters - do they break and do they protect you? Stay protected.
Budgeting Going Out vs. Saving Money
Honest answer: I'm very bad at this, but I'm working on it.
Tools that help: Mint Intuit app (not sponsored, but they should sponsor me). It tracks expenses and helps with budget planning.
Date strategy: Look at menus before going out. I went on a date once without checking and ended up at a place with $18 cocktails. The date didn't go well and I spent $75. Always check drink prices beforehand.
General approach: Balance cooking and going out. If you're cooking most nights and going out once or twice a week, that's reasonable.
Skincare Routine
Full transparency: I didn't wash my face until like a year ago, which is gross. If you're in the same boat, don't panic - you have to learn somehow.
My current routine:
Wash face every night with cold water
Apply cleanser/face wash
Rinse off and pat dry
Moisturize
Use acne cream on any problem spots
Key point: If you don't currently wash your face, start now. We have skin and faces too, not just girls. I'll make a video demonstration and put together a product list.
New iPhone 15?
Yes, I'm getting it. Currently holding an iPhone 11 and it's time for an upgrade.
Donna Kelsey Rating
10/10. She's everybody's mother and it would be a disservice to rate her anything less.
The Bottom Line
These questions prove we're all thinking about the same stuff but not talking about it openly. Whether it's social media etiquette, work situations, basic hygiene, or dating strategies, these are the real issues guys in their 20s face daily.
The goal of Guyset Toolkit is to give you practical tools for navigating these situations. Not rigid rules, but options you can use when you encounter these scenarios.
Keep the questions coming - this was really fun and I'll do another one next month. Send anything to josh@guyset.com or DM @theguyset on Instagram/TikTok.
Want more honest advice on the stuff guys actually think about? Follow @theguyset on social media and check out guyset.com for more content on dating, work, wellness, and everything else that should be talked about in your 20s.
The questions are timestamped below:
1:42: Should you leave up pictures with an ex on Instagram
4:49 Best pick-up line
9:26 How many drinks should you have at a work happy hour (full episode on work happy hours coming soon)
11:26 First Ever Question Section: How often do you wash?
This section features:
-How often do you wash your sheets
-How often do you wash your pants
-How often do you wash your work shirts
16:48 What should guys be for Halloween
20:32 What are the best condoms (full episode on this coming soon)
21:25 How do you budget going out vs saving money (full episode on budgeting coming soon)
24:29 Rank Donna Kelce 1-10
24:46 Are you getting the new iPhone 15
25:06 What is your skincare routine (full episode on guys skincare coming soon)
27:53 End of Guyset Toolkit but I give a message about what’s going on in Israel- please listen!
Thank you for listening!
Send in any questions, things you want me to talk about, or things that should be talked about for guys in their 20s to josh@guyset.com
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See you next Tuesday.
