The episode where you guys ask me anything and I answer off the cuff. These questions are truly some of my favorites you guys have asked so far. The topics range from balding and tipping to hangovers and family vacations, the possibilities are truly endless... so sit back, relax, and enjoy.

Guyset Toolkit #3: Your Dating, Style, and Life Questions Answered

Welcome to the third installment of Guyset Toolkit - my take on "ask me anything" where you send in questions and I give you the unfiltered, honest answers. These are real questions from real guys (and girls) in their 20s, and I'm answering them off the cuff, straight from the heart.

This episode covers everything from dating timeline dilemmas to family vacation anxiety, plus my controversial take on tipping etiquette. I don't prepare these answers - whatever comes out in the moment is what you get. So let's dive into the questions you sent to my Instagram @theguyset, TikTok, email, and even my new Reddit community r/guyset.

Dating Questions: The Real Talk You Need

"I got a girl's number but won't be in the city for a few weeks. Is it weird to schedule a date so far out? I'm not sure I want to text her for two weeks."

My honest answer: Texting for two weeks before you've even met someone is really hard. You're basically having conversations with a stranger every day asking "How was work? What'd you have for dinner?" - and what the fuck do you talk about for that long with somebody you don't know?

The solution: Wait about a week, then text her to schedule the date. A week out is totally normal and fine. A week and a half of texting is manageable. But anything above two or three weeks is really far out, and I've had experiences where the conversation just dies out because it's such a long time.

Exception: If the text banter is going really well and you're both into it, then keep it up. But otherwise, don't feel obligated to maintain daily conversations with someone you haven't met yet.

"Hookup culture: What is the ideal amount of dates to wait?"

I've talked about this before in previous toolkits, but here's the thing: there is no set number of dates to wait.

If you feel comfortable with the person and they feel comfortable with you, and it's consensual and you're both down - go for it. Life's short, have a good time. But if you feel nervous or you're not sure if it's right yet, then it's probably not.

Don't rush yourself into anything because you feel like there's some societal standard or timeline you're supposed to follow. Do what feels right in the moment for both of you. Rushing can make things awkward and set a weird tone for future dates.

Style and Grooming Dilemmas

"Is it weird to wear pajama pants in public? Can we normalize it?"

My take: Do whatever the fuck you want. Who cares?

Is it a little collegey? Yeah, we all wore pajama pants to class in college. Is it a little weird out of college? Maybe, but it depends on the situation.

Going to get a bagel on Saturday morning? Fuck it, who cares. Running errands at the supermarket? Still fine. If you're trying to impress somebody, maybe put on real pants. But if you're just living your life and running errands, wear whatever you want.

"Yay or nay to a shirtless Hinge pic?"

It's a fat nay from me. Here's why:

First, I don't have a six pack (maybe that'll be my 2024 goal), so I'm not posting a shirtless picture because I leave something to the imagination. But even if you do have abs, I think it gives off a douchey vibe right off the bat - kind of like a fish picture.

A picture of you looking dressed up or nice gives off more of who you are than just a shirtless picture where people can only analyze your body.

That said, if it works for you and you're getting results, then epic and awesome. I'm jealous of you in that respect. This is just my opinion.

Family and Social Situations

"Is it weird to go on family vacations at this age?"

Absolutely not - I think it's awesome. If you're lucky enough to have parents who want to take you on vacation, have the money to do it, and you're close enough as a family to enjoy that time together, then you should be very grateful and take full advantage of it.

Looking back now, I'm so much more grateful for the family vacations we went on when I was younger. I took them for granted at the time. If you're lucky enough that every member of your family is able to go explore and take a trip together, that's amazing.

There are definitely families that don't want to go on trips together, and the fact that you're close enough to even consider it is really awesome. Don't take it for granted - it's something not a lot of people get to do.

The Fast Question Section: Tipping Etiquette

Welcome to the fast question section where I answer questions quickly and not expertly because I'm just saying them right off the bat.

Someone asked if I tip on beer, which inspired this rapid-fire tipping breakdown:

Do I tip on tax? Yes, mostly because I don't want to pull out my calculator and do math at a restaurant like a loser.

Restaurants: 18-20% every time. Waiters and waitresses work really hard.

Uber: A dollar or two, but not 15-20%. (Let me know if that's bad - I'm not sorry yet.)

Taxis: Always tip because I had one awkward experience where I didn't tip and the driver called me out. Plus they're usually cheaper than Uber anyway.

Cocktails: 15-20% or a couple dollars to even it out.

Draft/bottled beer: A dollar or two. (Please tell me if I sound like a dick here.)

Coffee: 50 cents to a dollar, especially at smaller coffee places.

My philosophy: If someone is just handing me a beer they opened, a dollar's fine. But if they're shaking a cocktail, pouring a drink, or making coffee - yeah, you should tip for that effort.

Life Management Questions

"I'm an impulse buyer and like to treat myself a lot. How can I discipline myself and save?"

I struggle with this too. I'm Josh, I'm an impulse buyer - welcome to Impulse Buyers Anonymous.

Living in a city makes this worse because everywhere you walk, there's something you want - coffee, treats, sandwiches. I could save so much money by making coffee at home instead of buying $6 coffee every time.

What I've learned: We as a generation get everything we want immediately without waiting, which makes things feel less valuable. When you have to wait for something (like I do for my Friday coffee), it feels more rewarding and exciting than getting it every single day.

My solution: Set certain days or times when you can treat yourself. Otherwise, make yourself wait. It's literally a discipline thing - you have to tell yourself "No, I should save money right now" or "I can wait a couple days for that."

"What do you do for a hangover?"

My secret weapon: Take a metal mixing bowl, fill it with cold water and tons of ice, then dunk my face in it. There's science behind this - when cold water shocks your nervous system, it calms you down. This also works for anxiety.

Other hangover helpers:

• Drink tons of water

• Coconut water or sparkling water (lemon and sparkling water is underrated)

• Carbs like bagels and pretzels

• Time and sleep

My face gets puffy and bloated after drinking, and the ice water trick helps with all that. I feel 10 times better immediately.

Content Creation and Goal Setting

"How do you keep up with content and have so many ideas?"

Honest answer: I don't sleep. I've sacrificed a lot of sleep to make this happen, which is something I'm working on changing in the new year.

My brainstorming process: I sit down with a blank piece of paper and think about all the things that are bothering me, making me anxious, problems in my daily life, questions I have, things that aren't talked about enough. I make a big list and work through it.

Week by week, new things come up. Like last week I quit my job, so I knew I had to talk about that. Friends text me ideas too.

The key insight: You need time to brainstorm and self-reflect. I heard someone say that when you're building something, one eye should be a magnifying glass (focusing on immediate tasks) and one eye should be a telescope (thinking about the future). Right now both my eyes are magnifying glasses because I'm thinking week to week.

Setting Goals: The Assessment Method

I recently discovered this amazing goal-setting technique from motivational speaker Mel Robbins: You have to figure out where you're at first in order to move forward.

Here's what you do:

1. Take a blank sheet of paper

2. Write down categories: relationships with friends, dating, money, health, happiness, career, sleep

3. Rank each category 1-5 and write why next to each rating

4. Note what you're happy with and what you're not happy with in each area

This assessment was incredibly helpful for me and gave me tons of ideas for future podcast topics. You need to understand where you are before you can set meaningful goals for yourself.

What's Coming Next

Based on these questions, I'm planning several full episodes:

• Hair loss and balding (something so many guys face but we don't talk about)

• Acne and my Accutane experience

• Staying in touch with friends (it's harder than it seems and can get overwhelming)

• Book club revival (coming back next week!)

The Bottom Line

These questions prove we're all thinking about the same stuff - dating anxiety, money problems, style choices, family dynamics, and life management. The whole point of Guyset Toolkit is to talk about things that should be talked about but usually aren't.

I love doing these episodes because I get to be completely unfiltered and answer whatever comes to mind. If I get canceled, I get canceled - that's that.

Want your question answered in the next Guyset Toolkit? Send it to josh@guyset.com, DM @theguyset on Instagram/TikTok, or ask on Reddit at r/guyset. These are some of my favorite episodes to make, so keep the questions coming!

Thank you for listening! Subscribe. follow, and like the podcast, give this episode 5 stars, and leave a review! Click HERE to connect with Guyset on Instagram, HERE to connect with Guyset on TikTok, HERE to check out Guyset.com, and HERE to watch the full episode on YouTube. You can reach me on Instagram DMs HERE or email josh@guyset.com. See you next Tuesday!