#44 - Your Money Questions Answered With Brian Matthews
Apr 2, 2024
Real Life Advice for Guys in Their 20s: Dating, Work, and Everything In Between
Honest answers to the awkward questions you're too embarrassed to ask your friends
Your twenties are full of situations no one prepared you for. How do you split the bill when there's a couple in the group? What does it mean when someone suddenly "gets sick" before a date? Should you ask your coworker out? These are the real questions guys face but rarely discuss openly.
Here are honest, practical answers to the most common dilemmas that keep guys up at night.
The Venmo Dilemma: How to Handle Couples at Group Dinners
The 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?"
The Answer: Always ask first. Text the guy in the couple: "Hey, do you want me to request you for both of you, or should I request you and [girlfriend's name] separately?"
Why this works:
Shows respect for their relationship dynamic
Avoids awkward assumptions
Lets them handle it how they prefer
Prevents any potential offense
The key insight: When in doubt about social etiquette involving couples, just ask. It's less weird than guessing wrong.
Decoding Dating Excuses: When "I'm Sick" Really Means "I'm Out"
The Question: "What does it mean when you're texting a guy for a date and he suddenly gets sick or texts you an essay that he's seeing someone else?"
The Real Talk: Both scenarios usually mean the same thing—they're not interested but trying to let you down easy.
The "Suddenly Sick" Pattern:
What it often means: They're looking for an easy out without confrontation
Why people use it: It's less harsh than saying "I'm not feeling it"
How to tell if it's real: They'll suggest rescheduling if they're genuinely interested
The "Seeing Someone Else" Essay:
What it often means: They want to end things but make it sound like it's not about you
Why this excuse is popular: It's definitive and hard to argue with
The reality: They may or may not actually be seeing someone else
Your move: Don't chase. If someone wants to be with you, they'll make it happen. Accept the soft rejection and move on.
Workplace Wardrobe Anxiety: The Same Outfit Cycle
The Question: "I feel like I wear the same clothes too often at work. I wash everything consistently, but I worry my coworkers notice I'm not rotating enough."
The Solution: This is way more common than you think, and it's totally normal.
Why This Happens:
Top-of-pile syndrome: You grab what's easiest/most comfortable
Favorite outfit bias: Some combinations just work better
Decision fatigue: Who wants to think about clothes every morning?
How to Fix It:
Mix and match existing pieces - Wear your favorite shirt with different pants
Add 2-3 new work pieces to break the cycle
Prep outfits the night before to avoid grabbing the same things
Remember: Most people are too focused on themselves to track your outfits
Reality check: Your coworkers probably haven't noticed as much as you think. But if it's bothering you, it's worth addressing.
The Dating App Response Strategy
The Question: "What do you say when you match with somebody on Hinge? Like a template but not a pickup line?"
The Strategy: Respond to their specific prompts, not generic compliments.
Examples That Work:
If they mention comedy: "That's a dream of mine too. Let's go get made fun of together."
If they have a height joke: Mirror their humor with your own honest twist
If they mention travel: Reference a specific place they've been
Why This Approach Works:
Shows you actually read their profile
Creates natural conversation starters
Feels more personal than copy-paste lines
Gives them something specific to respond to
The key: Use their prompts as conversation bridges, not just opportunities to compliment them.
Office Romance: Navigating Workplace Attraction
The Question: "If a female coworker was being super flirty with you and you remain professional, how would you approach seeing them in the morning?"
The Honest Answer: Workplace romance is complicated and risky, but here's how to navigate it.
The Risks:
Same team complications: If things go south, work becomes awkward
Professional reputation: Office relationships can affect how you're perceived
HR considerations: Know your company's policies
The Approach:
Stay professional at work - Don't let personal feelings affect your job
If you're interested, suggest something outside work - Coffee, drinks after work
Be direct but respectful - "Would you like to grab drinks sometime?"
Have an exit strategy - Know how you'll handle it if things don't work out
Bottom line: Proceed with caution, but don't let fear of workplace drama stop you from pursuing genuine connections.
What to Look for in a Relationship
The Question: "What do you look for in a relationship?"
The Real Answer: Someone who gets that you have passions and priorities outside the relationship.
Key Qualities:
Understanding of your goals - Whether that's career, hobbies, or personal projects
Their own passions - Someone who has their own life and interests
Independence - Doesn't need constant attention or validation
Balance - Can go out and have fun but also chill at home
Sense of humor - Doesn't take everything too seriously
Good conversation - Can talk about real stuff, not just surface-level topics
The insight: Look for someone who enhances your life rather than someone who needs you to complete theirs.
Winter Bar Strategy: The Coat Conundrum
The Question: "When going to a bar with friends in the winter, do you wear a coat? There's nowhere to put it, and I feel like carrying it around."
The Strategy: Depends on the situation and your tolerance for cold.
When to Skip the Coat:
Short walk to the venue
Crowded bar where you'd lose it
Dive bar without safe storage
When to Bring It:
Long walk or public transit
Bar with coat check (if you don't mind paying)
Place where you can safely put it with other coats
The Compromise:
Tie it around your waist when you get there
Coordinate with friends to create a coat pile you can all watch
Choose bars with coat storage when possible
Reality check: Everyone deals with this problem. No one's judging you for carrying a coat or being cold.
Hinge Horror Story: When They Ask About Your Friend
The Situation: Someone matches with you but asks about your friend in the photo.
The Response: This is incredibly rude and you should call it out.
Why This is Unacceptable:
It's insulting - Essentially saying you're not good enough
It's tactless - Shows poor social awareness
It's hurtful - Makes you feel like second choice
How to Handle It:
Call them out directly - "You should never do that again. It's hurtful and makes people feel terrible."
Don't help them - Don't connect them with your friend
Block and move on - They've shown their character
The Workaround (If You're Interested in Someone's Friend):
Screenshot and research (carefully and respectfully)
Find mutual connections through social media
Ask around your social circle - Someone might know them
Never go through their friend first - It's always awkward
Fast Questions: What to Eat When You're Figuring Life Out
Breakfast:
Protein shake after gym
Protein bar for convenience
Banana for quick energy
Keep it simple - You don't need elaborate morning meals
Lunch:
Bowl places - Sweetgreen, Cava, or local equivalents
Good salads or sandwiches
Get out of the office - Use lunch as a break from work
Don't stress meal prep if you're not there yet
Dinner:
Salmon or chicken - Classic, simple proteins
Experiment with recipes (and expect some failures)
Trader Joe's prepared items when you need easy options
Cook tacos - Easy way to practice cooking skills
The Dating Red Flags You Need to Know
Immediate Red Flags:
Asking about your friends instead of you
Constantly canceling last minute (without rescheduling)
Not asking questions about you during conversations
Only talking about themselves on dates
Green Flags to Look For:
Asks follow-up questions about things you've shared
Suggests specific plans for future dates
Remembers details from previous conversations
Shows genuine interest in your life and goals
Building Confidence in Your Twenties
Work Confidence:
Address wardrobe anxiety by adding new pieces strategically
Mix up your usual combinations to feel fresh
Remember most people aren't tracking your outfits as much as you think
Dating Confidence:
Don't take rejections personally - they often have nothing to do with you
Focus on having good conversations rather than impressing people
Be honest about your interests and goals - the right person will appreciate them
Social Confidence:
Ask questions when you're unsure about social situations
Set boundaries at work about personal relationships
Trust your instincts about people's behavior and intentions
The Bottom Line: Your Twenties Are For Learning
The truth about your twenties: You're supposed to be figuring things out. The awkward situations, the dating mistakes, the work wardrobe anxiety—it's all part of the process.
What matters most:
Being honest about what you want and need
Treating people with respect even when rejecting them
Learning from each situation rather than beating yourself up
Building confidence through experience, not perfection
Remember: Everyone else is figuring it out too. The people who seem to have it all together are just better at hiding their uncertainty. Focus on being authentic, kind, and open to learning, and you'll navigate these years just fine.
The awkward questions don't stop coming, but you get better at handling them. And that's really what your twenties are about—not having all the answers, but getting comfortable with the process of figuring them out.
About Guyset
This post is based on the "Advice Guy" series from Guyset: A Guy's Guide to What Should Be Talked About - a weekly podcast for guys in their twenties navigating dating, career, and life's everyday challenges. New episodes drop every Tuesday.
Send your questions:
Email: advice@guyset.com
Instagram, TikTok: @theguyset
Website: guyset.com (anonymous submission box)
Have a question you're too embarrassed to ask? Submit it anonymously—chances are, other guys are wondering the same thing.
Certified financial planner Brian Matthews is here to answer all of your questions about money and investing. We go back to the basics so you can leave this episode feeling like you know exactly where to start since this can all be incredibly intimidating.
We talk about where to start with investing, how much money you should have in your bank account, stock market, 401k vs Roth IRA, what percentage of your paycheck you should be saving, how much risk to take, budgeting, the cost of dating, overspending, and so much more.
Subscribe, give this episode 5 stars, and leave a review!
Ask Guyset:
https://forms.gle/qLrRqQxrZKwcToYk6
Follow me here:
https://www.instagram.com/theguyset/
https://www.youtube.com/channel/UC1FF1Et_x4dnGoa-eyv4sXg
https://www.tiktok.com/@theguyset
Website:
Email:
See you next Tuesday!
