#85 - Frequently Asked Dating Questions
Jan 14, 2025
I answer frequently asked dating questions sent in by you guys:
When should you confirm that the date is on before the first date?
How do you actually get a first date?
How do you greet someone on a first date?
I feel like I should have gone in for the kiss after the first date but didn’t, what do I do now?
Is it weird to kiss on a first date?
What do I talk about on the second date?
What do I talk about during the talking stage?
Dating FAQs for Guys: Real Answers to Your Most Common First Date Questions
Based on real questions from guys who aren't afraid to ask for advice
Let's address the elephant in the room: guys have dating questions. Lots of them. And despite what some people might say in the comments, there's absolutely nothing wrong with wanting advice on first dates, conversation topics, or when to go in for that first kiss.
At Guyset, we believe everyone deserves honest answers to their real questions – especially when it comes to dating. After posting dating advice on social media and receiving thousands of responses (both positive and negative), one thing became crystal clear: guys are hungry for practical, shame-free dating guidance.
Why Guys Need Dating Advice (And Why That's Perfectly Normal)
Before diving into the FAQs, let's address the criticism head-on. When dating advice for guys goes viral, there's always someone ready to comment "It's crazy men need a list like this" or "How do they not already know this?"
Here's the reality:
Not everyone has been on dozens of dates
People are on different timelines (and that's okay)
There's no dating manual that comes with adulthood
Even experienced daters encounter new situations
The same people who shame guys for seeking dating advice are often the reason guys stay silent about their insecurities in the first place. Breaking that cycle starts with honest, judgment-free conversations about real dating challenges.
The Most Common Dating Questions Guys Actually Ask
1. When Should You Confirm the Date Before a First Date?
The Answer: Confirm twice – once the day before, once the day of.
Day Before: Send a text like "Hey, checking to see if we're still on for tomorrow. Looking forward to it!"
Day Of: Around 12-2 PM, send something like "Hey, really excited to see you tonight. Looking forward to getting drinks later!"
Why This Matters: Nobody wants to be left wondering if the date is still happening. Confirming shows you're reliable and considerate – two qualities that never go out of style.
2. How Do You Actually Get a First Date?
The Two Best Approaches:
Dating Apps (Easiest Route):
Hinge consistently gets the best results for serious dating
Consider upgrading to premium – think of it as investing in yourself
Tinder tends to skew more casual
Bumble gives women control of initial contact
The League requires payment but has success stories
In-Person Approaches (Higher Confidence Required):
Still highly underrated and effective
Requires reading social cues and choosing the right moment
Having a wingman helps with group dynamics
Confidence and genuine compliments go a long way
3. How Do You Greet Someone on a First Date?
The Formula That Works:
Stand up when you see them approaching
Smile and make eye contact
Say: "Hi, how are you? It's so nice to meet you. I'm [your name]."
Go in for a hug (sets a warm, friendly tone)
Add a genuine compliment: "You look really nice tonight"
Transition smoothly: "How was your day so far?"
Pro Tip: That 5-10 minute waiting period before they arrive is awkward for everyone. Stay attentive but not glued to your phone, and remember – they're probably just as nervous as you are.
4. Should You Kiss on a First Date?
The Real Answer: You'll know when you know.
If the date goes amazingly well and the vibes are undeniable, trust your gut. If you're unsure or the moment doesn't feel right, there's absolutely no shame in waiting.
What to do if you think you missed your chance:
Don't overthink it for hours afterward
Talk to a friend about it (guys need to normalize this)
Remember there will likely be a second date
A hug or kiss on the cheek is perfectly fine
Bottom Line: There's no timeline or pressure. If it's meant to happen, it will happen naturally.
5. Is It Weird to Kiss on a First Date?
Short Answer: Not at all, if both people are into it.
The key is reading the situation and respecting boundaries. If the connection is strong and the moment feels right, go for it. If you're getting mixed signals, err on the side of caution.
6. What Do You Talk About on a Second Date?
The Goal Shift: First dates are about general vibes and chemistry. Second dates are for going deeper.
Good Second Date Topics:
Build on conversations from your first date
Ask about things mentioned in your texts between dates
Explore their interests, hobbies, and passions
Discuss future plans, career goals, and dreams
Share more personal stories and experiences
Remember: You don't need to know everything about someone after the first date. Use the second date to genuinely get to know them on a deeper level.
7. What Do You Talk About During the "Talking Stage"?
The Challenge: Maintaining conversation momentum when you barely know each other.
The Strategy:
Don't try to sustain deep conversations for weeks before meeting
Set an actual date rather than endless texting
Use this time to plan future dates and build anticipation
If you're not great texters, that's okay – focus on in-person connection
Pro Tip: If there's a long gap before you can meet, let the conversation naturally fade rather than forcing awkward small talk. Pick it back up closer to your date.
The Bigger Picture: Building Confidence Through Community
These questions matter because dating confidence comes from preparation and practice, not from pretending you already know everything. The guys asking these questions aren't "behind" or "inexperienced" – they're smart enough to seek advice instead of stumbling through trial and error.
Breaking Down Dating Stigma
Every time a guy asks for dating advice and gets shamed for it, it reinforces the toxic idea that men should just "naturally" know how to navigate complex social situations. This stigma keeps guys from:
Talking openly about dating challenges with friends
Seeking advice when they need it
Building genuine confidence through learning and growth
Creating supportive communities around shared experiences
Your Dating Questions Deserve Real Answers
Whether you're going on your first date ever or your fiftieth, having questions is normal. Seeking advice is smart. And there's a whole community of guys figuring it out together.
Remember:
Everyone is on their own timeline
Confidence comes from preparation, not perfection
Your dating questions are valid, regardless of your experience level
Real friends will support your growth, not shame your curiosity
What's Next?
Got more dating questions? You're not alone, and you shouldn't have to figure it out by yourself. The most successful people in any area of life are the ones who aren't afraid to ask for help and advice.
Ready for more dating advice and real talk about guys' issues?
Listen to Guyset: Available on all podcast platforms – new episodes every Tuesday
Get Personalized Advice:
Email: josh@guyset.com
Social: @theguyset across all platforms
Anonymous questions: Google form on guyset.com
Join the Community: Thousands of guys are already part of the conversation. Your questions could help someone else going through the same thing.
Have a specific dating situation you need advice on? Submit your question and it could be featured in an upcoming episode and blog post. All submissions can be kept anonymous.
Send in anything else you want me to answer below:
See you guys next Tuesday.
