Advice Guy: Real Questions from Guys in Their 20s (And the Honest Answers)

Welcome to the fourth installment of Advice Guy - the rebrand of the Guyset Toolkit where I answer all your burning questions about dating, work, and everything in between. These are real questions from real people (mostly sent to advice@guyset.com), and I'm giving you my honest, unfiltered answers.

Let me be clear: these aren't questions I wrote myself. These all came from you guys - real people dealing with real situations. And honestly? I don't prepare for these. Whatever comes out of my mouth and heart in the moment is what you get.

The Money Question: Venmo Etiquette with Couples

Question: "If you go out to dinner with a bunch of friends and there's a couple, do you Venmo request the guy for both of them or request them separately?"

This is trickier than it seems, but here's my solution: just ask them. Text the guy and say, "Hey, do you want me to request you for both of you guys, or should I request you and her separately since I know her too?"

This works universally because it's the least offensive approach. You're not making assumptions about their relationship dynamics or financial arrangements. Simple communication solves the problem.

Dating Red Flags: When Someone "Gets Sick" or "Is Seeing Someone Else"

Question: "What does it mean when you are texting a guy for a date and he suddenly gets sick or texts you an essay that he is seeing someone else and it's getting serious?"

I've been on both sides of this, so let me be real with you. These are often polite exit strategies, not actual circumstances.

My experience: I went on an amazing first date - we even ran into Dylan O'Brien and Suki Waterhouse (random but true). Two days later when I asked for a second date, she said she was "seeing somebody else and wanted to see that through." A friend later asked if I actually believed she was seeing someone else. Honestly? Probably not.

The reality check: Whether they're "sick" or "seeing someone else," it's often code for "I'm not interested but don't want to hurt your feelings." It's a 50-50 shot on whether it's real, but either way, let them follow up. If they don't, you have your answer.

Work Wardrobe Anxiety: The Same Outfit Rotation Problem

Question: "I have a lot of work clothes, but I end up wearing the same outfits in a cycle. I worry that I wear the same clothes too many times too often. I feel like people notice, especially my immediate team members who I'm in a room with all day."

First off, this isn't a stupid question. I literally had a coworker tell me I was wearing the exact same outfit as my LinkedIn photo. It happens to all of us.

The solution is two-fold:

1. Mix and match your existing pieces - if you're wearing a shirt a lot on Mondays, pair it with different pants on Wednesdays

2. Add a few new items to your rotation - buy a couple new shirts that you feel comfortable in and can add to your "top of pile" rotation

We all have those clothes that end up at the top of the pile that we reach for again and again. It's normal, but if you're noticing it, your coworkers probably are too.

The Nuclear Option: When Someone You Hated in High School Dates Your Sibling

Question: "Someone you hated in high school starts dating your sibling. What do you do? Is it the right move to step in or stay out?"

You should absolutely step in - but not the way you might think. This isn't about controlling your sibling's dating life. It's about having a conversation.

Ask your sibling: "Did you know they were a piece of shit in high school? Why are you dating this person? What have they done to change since then?"

If you're close with your sibling (which I'm assuming you are if you're asking), they deserve to know your perspective. Just keep it conversational, not confrontational.

Winter Bar Strategy: The Coat Dilemma

Question: "When going to a bar with friends in the winter, do you wear a coat? There's nowhere to put it, no coat check. Do I carry it? I feel like a bitch."

I usually don't wear a jacket out if I know I'm going somewhere I'll have to hold it all night. Hot people don't get cold, right? (Just kidding - everyone gets cold.)

Here's my strategy:

• If it's a dive bar where you can put it down safely with other coats, wear one

• If you're walking a far distance in freezing weather, wear one and deal with carrying it

• Don't pay for coat check - that's just stupid

• If you're going somewhere sketchy where you might lose it, skip the coat

It's circumstantial, but generally I'd rather be a little cold than deal with carrying a coat all night.

Work Flirting: The Morning After Dilemma

Question: "If a female coworker was being super flirty with you the night before and you want to remain professional, how would you approach seeing them in the morning? This is hypothetical, but you would totally flirt with this person if they weren't your coworker."

Work relationships are wild territory. I had two coworkers at my last job who were secretly dating for a year - we all suspected it, but it was still shocking when they finally told us.

My advice: be careful. If you're on the same team and things go south (which hookups often do), it's going to be weird. There's no way around that.

The work waters are wild. If you're both feeling it and you're willing to take the risk - life's short, we're young, take risks. But tread carefully, brother. Be safe out there.

What I Look for in a Relationship

Someone asked what I look for in a relationship, and honestly, I want someone who understands that this podcast means something to me. I'm passionate about answering these questions because there are so many things guys in their 20s are thinking about but not talking about.

What I'm looking for:

• Someone who understands that passions are important to have

• Someone who is passionate about something themselves

• Someone confident and independent who doesn't need someone else at all times

• Someone who likes going out and having fun but can also chill and hang out

• Someone with a good sense of humor who understands that life isn't so serious

• Someone who can have really good conversations

Yeah, I'm blushing writing this, but those are the basics.

The Invisible String Theory

Question: "Do you believe in the invisible string theory?"

I had to Google this one. Apparently it's based on an ancient Chinese proverb that "an invisible red thread connects those who are destined to meet regardless of time, place or circumstance. The thread may stretch or tangle, but it will never break."

That's actually a lovely allegory for life. Maybe I've already met my soulmate and don't know it, or maybe I've crossed paths with them. But there are also a lot of people I haven't met in the world yet.

My answer: yes and no. I don't want to put myself in a box and say I've already met the love of my life, so... I don't know. Ask me again in a few years.

The Ultimate Dating App Mistake

Question: "I got excited when I saw a match on Hinge, turns out he was asking about my friend in the picture, not me. What do I do?"

GUYS, LISTEN UP: If you see a hot girl in someone's friend group on their Hinge profile, DO NOT ask about the friend. That's insane. That's a crazy fucking move.

Imagine if a girl reached out to you and said, "Hey, I don't think you're cute, but your friend's hot." What the actual fuck?

I've seen hot friends in people's profiles before - we all have. But you don't reach out and ask about them. Work around it: Take a screenshot, figure out mutual connections, find her Instagram through mutual friends. Go through the window, not the front door.

The girl who sent this question put that guy in his place, and he deserved it. Don't be that guy.

Hinge Opening Lines That Actually Work

Question: "What do you say when you match with somebody on Hinge? Like a template but not a pickup line?"

Look at their specific prompts and respond to those. Here are my current Hinge prompts that get responses:

1. "Favorite Jonas Brother" - People usually respond with Joe, or if they're unique, they'll say Frankie (the bonus Jonas)

2. "What if I told you... I'm actually five nine and three quarters" (when my height says 5'10") - Gets a lot of responses

3. "Will you... sit front row at Comedy Cellar with me" - It's a New York thing that works

The strategy: Use their prompts as response mechanisms. If they mention something specific, respond to that. Don't use generic pickup lines - be specific to their profile.

Fast Question Section: What I Actually Eat

Since someone asked what I eat for lunch at work, here's my daily breakdown:

Breakfast: I don't usually eat breakfast (don't recommend this, I'm not a doctor). I go to the gym before work, then have a protein shake, protein bar, or banana at the office.

Lunch: Sweetgreen, Cava, or Taim (none sponsored). I love a good hearty bowl - salads, sandwiches, bowls. I don't prep enough the night before, so I usually buy lunch. Plus it gives me a reason to leave the office and take a walk.

Dinner: Wild card because I'm still not a great cook (working on it - New Year's resolution). Usually salmon, chicken, ground beef, tacos occasionally. I'll experiment with random stuff and usually fail. Sometimes I'll grab Trader Joe's chili or go out with friends.

I'm working on getting better at cooking, but that's where I'm at right now.

The Bottom Line

These questions prove we're all thinking about the same stuff - dating anxiety, work situations, relationship dynamics, and daily life decisions. The whole point of this advice series is to talk about things that are on our minds but we're not discussing openly.

Keep sending your questions - they're not stupid, even if they feel stupid when you write them out. We're all figuring this stuff out together.

Want your question answered? Send it to josh@guyset.com, DM @theguyset on Instagram, or submit anonymously at guyset.com. I answer questions every episode now, so you won't have to wait long for a response.

Guyset Toolkit is now called Advice Guy and here I answer questions that you guys sent to my email (advice@guyset.com), my DMs (@theguyset), or my website (guyset.com) to get my take on. They are always the first thing I think of from the heart. Below are all the questions timestamped:

Timestamps

2:40 If you go out to dinner with a couple, do you request the guy for both him and his girlfriend?

4:59 What does it mean when the person you are texting says they are sick and can't go out or texts you that they are seeing someone else?

8:42 I feel like I wear the same outfit all the time to work, do people notice or care?

12:31 Someone you hated in high school starts dating your sibling, should I step in?

14:05 Do you wear a jacket to the bar?

15:45 What should I do if my coworker is flirting with me... and I'm down?

17:46 What do you look for in a relationship?

19:58 Do you believe in the invisible string theory?

21:17 A match on Hinge asked about my friend and not me... (My favorite one!)

24:16 What do you say when you match with someone on a dating app?

26:56 Fast question section!

Thanks for listening! Subscribe and follow Guyset, 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.