#96 - Dear Guyset 2
Apr 1, 2025
Dear Guyset: Real Answers to Your Biggest Questions About Dating, Relationships & Career Anxiety
Welcome to the second installment of "Dear Guyset," where we tackle the real questions guys in their 20s are asking—from relationship advice to career anxiety, dating dilemmas to fitness concerns. These questions came straight from DMs, emails, and online forums, and Josh provides honest, practical answers based on real experience.
1. "What are some nice things I can do for my girlfriend?"
Josh's Take: "Girls are much more simple than we make them out to be. Getting them flowers or doing something nice for them sometimes means so much more to them than it would to us."
Small Gestures That Make a Big Impact:
Stay Connected Throughout the Day
Send good morning texts consistently
Text her whenever you're thinking of her
Share memes, TikToks, or anything that reminds you of her
Use all the communication channels available—texts, DMs, calls
Plan Meaningful Dates
Take initiative in planning activities
Don't wait for her to make all the plans
Keep the element of surprise alive in your relationship
Ask "What are you doing next week?" and then plan something special
Regular Communication
Call her once a day or every other day
Find your optimal time—walking home from work, doing laundry, etc.
If you haven't talked by 6 or 7 PM, it's time to check in
The Bottom Line: "Keeping in contact with the person you're in a relationship with is probably the best way to do it. Most guys aren't really good at maintaining relationships like that."
2. "Do you ever feel anxious about your job?"
Josh's Raw Answer: "Yes, of course I do. Are you kidding me? I think everybody does."
The Layers of Career Anxiety:
Multiple Sources of Workplace Stress:
Uncertainty about whether you're doing what you want to be doing
Questions about job performance and competence
Concerns about job security and future prospects
Worries about raises, promotions, and advancement
Interpersonal dynamics with bosses and coworkers
Why It's Normal:
We're early in our careers and still figuring things out
Many of us feel lost or unsure about our professional path
It's natural to question your direction in your 20s
Josh's Perspective: "We are very early in our careers. I think it's normal to not know what the fuck is going on or if we're doing a good enough job."
Coping with Career Anxiety:
Acknowledge it's normal - Most people your age feel this way
Share with trusted friends - You'll likely find they feel the same
Remember you're early in your journey - Uncertainty is part of the process
Focus on what you can control - Your effort, attitude, and growth
3. "Can I go up to a girl at the gym and ask for her number?"
Josh's Honest Take: "Yes, you can... but I wouldn't do it. That's just me personally."
Things to Consider:
The Gym Environment:
Gyms are male-dominated spaces (roughly 80/20 split)
Women may be on high alert for unwanted attention
Most people are there to work out, not socialize
People often feel self-conscious during workouts
A Real Example: Josh witnessed an interaction where a guy approached a woman doing core exercises. Despite his attempt to be friendly, she politely declined by saying she had a boyfriend.
Better Alternatives:
Community fitness classes where interaction is more natural
Social gyms with a more communal atmosphere
Post-workout coffee shops or other venues near the gym
Josh's Recommendation: "I think there's better places to meet somebody than a gym. If you want to go up to her and it works out... let me know. Please let me know."
4. "I feel like I'm too small. How do I get bigger?"
Josh's Response: "I'm assuming you are referring to the gym... go back and listen to [Taylor's episode] specifically. He had really great insights to that."
Why Different Perspectives Matter:
Josh acknowledges this isn't his experience—he's dealt with the opposite issue of wanting to gain muscle while getting leaner. This highlights the importance of diverse voices in men's advice content.
For detailed advice on bulking up as a smaller guy, Josh directs listeners to his previous episode with Taylor, who shared his personal transformation story and specific tips for gaining size.
5. "I have been on two dates with this girl, but I don't know if I'm invested. Should I go on another date?"
Josh's Recommendation: "Yes, you should go on another date."
The Three-Date Rule:
Why Give It Another Shot:
You didn't mention any red flags or awkwardness
You're in the "unsure" zone, not the "definitely not" zone
A third date often provides clarity one way or another
What Changes After Date Two:
People become more open and honest
You see more of their authentic personality
Conversations tend to go deeper
You might discover something special you would have missed
Josh's Philosophy: "You may be able to find something that you never... there may be an opportunity here for something that you may be throwing away if you don't give it that extra chance."
Follow-up Request: "Please write back in after the next date and let me know if it went well."
6. "I feel like my hairline is receding. Has this ever happened to you?"
Josh's Honest Answer: "Yes, it has happened to me."
Understanding Hair Loss:
Potential Causes:
Genetics (Josh notes his dad has a similar hairline)
Medications (he mentions Accutane as a possible factor)
Natural aging process
Solutions That Work:
Rogaine (Josh's Experience):
Used it consistently for several months
Requires daily application (morning and night)
"It worked like it definitely did work"
Needs about a year of consistent use for best results
Other Options:
Consult a dermatologist for professional advice
Hair transplant procedures (including medical tourism to places like Turkey)
Strategic haircuts to minimize appearance
Various medications and treatments
Josh's Reassurance: "I think a lot of guys have it... There's ways to work around it."
7. "What should I text after my date?"
Josh's Go-To Formula: "Hey, I had a really great time with you tonight. Would love to see you again!"
Why This Text Works:
Hits Two Key Points:
Acknowledges you enjoyed the date
Expresses interest in seeing them again
Simple and Effective:
No overthinking required
Clear message about your intentions
Opens the door for their response
Advanced Tips:
Follow-Up Strategy:
If they respond positively, suggest a specific day and time
Reference something from the date for the next plan
Example: If she mentioned loving margaritas, suggest a great margarita spot
Personal Touch:
Add your own style with emojis or exclamation marks
Keep it genuine to your personality
Don't overthink—be yourself
Josh's Advice: "From that text, you'll be able to see everything. If they heart it, they obviously are into it and they want to see you again too."
Key Takeaways for Guys in Their 20s
On Relationships:
Small gestures matter more than you think
Consistent communication is key
Take initiative in planning dates
On Career Anxiety:
It's completely normal to feel anxious about work
Share your concerns with friends—you're not alone
Remember you're early in your career journey
On Dating:
Be mindful of context and environment when approaching women
The third date often provides clarity on compatibility
Keep post-date texts simple and genuine
On Personal Issues:
Hair loss is common and treatable
Different guys have different experiences—seek diverse perspectives
Professional help is available for most concerns
Want your question answered in the next Dear Guyset episode? Send your questions to:
Email: josh@guyset.com or dearguyset@gmail.com
Instagram DMs: @theguyset
Remember, these are real questions from real guys navigating their 20s. You're not alone in whatever you're dealing with, and there's no shame in seeking advice or admitting you don't have all the answers.
Want more honest conversations about the things guys actually think about? Subscribe to Guyset for weekly episodes covering everything from dating and relationships to career advice and personal growth.
The questions I answer:
What are some nice things I can do for my girlfriend?
Do you ever feel anxious about your job?
Can I go up to a girl at the gym and ask for her number?
I feel like I’m too small, how do I get bigger?
I’ve been on two dates with this girl but I don’t know if I’m invested, should I go on another date?
I feel like my hairline is receding, has this ever happened to you?
What should I text after my date?
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Contact: josh@guyset.com
See you guys next Tuesday.
