If you're a guy in your 20s and going on dates (or 30s we don't discriminate here) this is definitely one you should listen to. This is Part 2 of my interview with Luke Lenny so if you haven’t heard Part 1 yet, go back and listen and then come back... or just listen to this on its own, that's cool too. This is one of the episodes that really captures the mission of this podcast.

Luke and I talk about his favorite first date, how to wrap up a first date, what to say at the end, when to text them after, a recent bad first date, what to wear on a date, and anything else you can imagine around this topic. We talk about how to find confidence and the differentiation between confidence and cockiness. We talk about relationships and his first breakup. Luke recently bought his own apartment and is living on his own for the first time so he takes us through that process and his feelings. 

I can't thank Luke enough for his vulnerability and honesty in this episode, I know it's going to be one that resonates with many.

The Complete Guide to First Dates: What to Do, What to Wear, and How to Handle the Awkward Moments

Real advice from someone who's learned from both great dates and terrible ones

First dates are nerve-wracking for everyone. You're trying to make a good impression while figuring out if you actually like this person, all while navigating the unspoken rules of modern dating. In Part 2 of our conversation with Luke, a 24-year-old living in NYC, we dive deep into the real challenges of dating in your twenties - from planning memorable first dates to handling breakups and building genuine confidence.

Here's what we learned about navigating the dating world with authenticity and grace.

Planning First Dates That Actually Work

The Food Tour Success Story

Luke's most memorable recent first date wasn't dinner and drinks - it was a curated food tour through the East Village:

"We walked around the East Village. We got a 7th Street burger... We got one sandwich from each and then we went to Ray's Candy Shop. Got some fried Oreos."

His strategy was thoughtful: "She lives in Little Italy. I don't think she tried a lot of East Village places, so I was like, I'm gonna take you to a couple of my highlights."

The original plan included sitting in Tompkins Square Park with a bottle of wine, but when it got dark, they adapted and found a brewery where you could bring your own food.

Why this worked:

• Personal curation - he shared places he genuinely enjoyed

• Activity-based - walking and trying different foods kept conversation flowing

• Flexible planning - when the park didn't work out, they had alternatives

• Thoughtful preparation - he brought a towel and planned ahead

The Safe Backup: Drinks with Strategy

For more standard first dates, Luke recommends finding a spot with good deals if you're going to be dating regularly:

"I do a wine bar that I really like, it's called BB wine bar 4th Street. They do $30 bottles from 5 to 8 p.m. every weekday. If you're somebody that's gonna go on a lot of first dates like you want to just meet some people, it's a good spot... find a spot with a deal cuz you will go broke."

His cautionary tale: "The second first date I went on in New York, I spent $140 on espresso martinis... We had like four espresso martinis each. I didn't go to sleep five hours after."

The lesson: Budget-friendly spots aren't just about money - they remove financial stress so you can focus on getting to know each other.

The End-of-Date Playbook

The Golden Rule: No First Kiss

Luke's stance is clear: "Do not lean for the first kiss after the first date."

His reasoning: "It could have gone really well in your head, might not have gone really well in her head. You don't know. So I think that the best way to go about it is just like, I had really great time, I would like to do something again sometime, I'll let you know."

Why this approach works:

• Takes pressure off both people

• Leaves room for anticipation if there's mutual interest

• Avoids awkward misreading of signals

• Shows respect for boundaries

The Proper Send-Off

"Give a hug... I'll walk her to the subway, we're at whatever subway she's taking. I think that that's just respectful to do."

This demonstrates basic courtesy while keeping things appropriate for a first meeting.

When Dates Go Wrong: Survival Strategies

The Worst-Case Scenario

Luke shared his most challenging date experience: someone who had recently gotten out of a relationship and wasn't ready to date yet. Mid-date, she ordered another bottle of wine without consulting him (while he was paying), and the conversation turned to her ex for the rest of the night.

"At this point I'm like just slamming cups of wine trying to like finish this bottle very quickly."

The Respectful Exit Strategy

Even when dates aren't going well, Luke believes in basic courtesy: "If you ask somebody on a first date, like I think it's just, you kind of owe them that time... if it's not going well, like suck it up."

His timeline: An hour to an hour and a half is appropriate for a first date, even if it's not clicking.

How to end gracefully:

• "Great meeting you"

• Reference something specific from the conversation ("Good luck with that work thing tomorrow")

• "Get home safe" or "Have a great rest of your night"

• Only say "Let's do something again soon" if you actually mean it

The Follow-Up Game

Timing Your Next Move

Luke's evolved approach to post-date communication:

"Unless they text you after the date, I think you should not text them... that night. Maybe check in to make sure they got home safe."

His recommended timeline:

• Same night: Only safety check-in if appropriate

• Next day or two: Follow up with something specific from your conversation

• Within the week: Suggest concrete plans if you want to see them again

"I think you could wait till like the day after work like honestly, you could probably wait a little bit longer. In fact, I would argue it's like not the worst thing in the world to wait till you want to see them again, like maybe the next week."

The Quality vs. Quantity Approach

"I think texting frequency means different things to different people... you kind of have to gauge it out by person."

The key is finding the balance between showing interest and not overwhelming someone you've just met.

Building Authentic Confidence

The Post-College Confidence Crisis

Luke was honest about his own journey: "I actually... feel like I went through a crisis of confidence last year after college... I feel like I kind of lost the like persona I had in college because we weren't in college anymore. I like wait, like what am I?"

This transition period is normal - your college identity doesn't automatically translate to adult life.

The Confidence vs. Cockiness Balance

Luke's strategy for walking this line: "I think that I will make a cocky comment, but then follow it with like kind of like a laugh... and then acknowledge that that was a little bit too much."

Example: When someone compliments you: "Like yeah, I know" (with a laugh) "I'm just messing with you, like thank you."

This approach lets you accept compliments confidently while showing you don't take yourself too seriously.

Building Real Confidence

Luke identifies several key factors:

Physical Health: "Gym routine. I think just being confident in your like physical appearance, like feeling really healthy, I think is important for confidence."

Self-Knowledge: "The more you know about yourself, I feel like the more confident... I think the more time you spend with yourself, the more you become more confident."

Successful Experiences: Having positive interactions where you feel like you came across authentically builds confidence for future encounters.

Internal vs. External: "I genuinely believe that confidence comes from you... I think that's where cockiness comes from, honestly. Is like how you think others perceive... I think that like confidence is between you and you."

What to Wear on First Dates

Luke's Evolution

"I'm sure you've noticed I've become jeans guy. I never wore jeans, I just thought they were uncomfortable. Then I went to Levi's and I got straight jeans because I just didn't like the skinny jeans."

His current go-to: "Jeans and a shirt that I bought on Etsy... I wore my Justin Bieber mugshot on my date today."

The Philosophy Behind Bold Choices

"If they don't laugh at that shirt and make a comment on it like we're probably not gonna get along... I think it comes down to... looking in the mirror before you go out and be like this is how I want to present myself. I look good. Let's go get it."

The key insight: Wear something that represents who you actually are. If someone doesn't appreciate your authentic style, they're probably not right for you anyway.

Seasonal Adjustments

For fall/winter first dates, Luke might choose a button-down shirt instead of a t-shirt for slightly more formality, but still maintains his personal style.

Learning from Breakups

The Retrospection Process

Luke emphasizes the importance of honest self-reflection after relationships end:

"You need to do some retrospection on... what went wrong. What did you do wrong. Because every relationship anyone's ever been in both people have done something... There are things that both people did incorrectly that led to it."

Filling the Void

"I spent so much of my time talking to this person and like having this person in my life. Like how do I fill that time? Cause it's like, it's like a void there."

His recommendations:

• Physical activity - gym, running, anything that benefits your health

• Passion projects - rediscover what you care about

• Self-improvement - work on areas you want to develop

The Time Factor

"It's so cliche... but it's the most true thing ever. The only thing that heals the pain of a breakup is time. Like literally that's the only thing."

The cliché exists because it's true - but you can use that time productively to become a better version of yourself.

First Date Red Flags and Green Flags

Red Flags to Watch For

• Talking about exes extensively - especially getting emotional about past relationships

• Not respecting boundaries - like ordering expensive items without asking when someone else is paying

• Being completely unprepared - showing up without any thought or consideration

• Inability to have conversation - constantly interrupting or not listening

Green Flags to Look For

• Genuine curiosity about your life and interests

• Respectful behavior toward service staff and others

• Ability to go with the flow when plans change

• Authentic personality that matches their dating app persona

Your First Date Action Plan

Before the Date

1. Choose a location you know well - somewhere you can share genuine enthusiasm

2. Have a backup plan - in case your first choice doesn't work out

3. Dress authentically - wear something that represents who you are

4. Set realistic expectations - you're just meeting someone new, not your future spouse

During the Date

1. Be present - put your phone away and focus on the conversation

2. Ask genuine questions - show real curiosity about their life

3. Share authentic stories - don't try to be someone you're not

4. Stay flexible - if something isn't working, adapt

After the Date

1. Make sure they get home safely - basic courtesy

2. Wait before texting - give both of you time to process

3. Reference specific conversations - show you were listening

4. Be honest about your intentions - only suggest future plans if you mean it

The Bigger Picture: Dating in Your Twenties

Managing Expectations

"Don't take it too seriously... you don't know this person. If it goes horribly, it doesn't matter at all... Really, like, you're just meeting somebody for the first time."

This perspective removes pressure and allows for more authentic connections.

The Learning Process

Every date, whether successful or not, teaches you something about:

• What you're looking for in a partner

• How to communicate better

• What authentic confidence looks like

• How to handle social situations gracefully

Building a Dating Life That Works

The goal isn't to become a dating expert - it's to become comfortable being yourself in new situations. When you approach dating from a place of genuine curiosity rather than desperation or performance, you're more likely to find meaningful connections.

Final Thoughts

Luke's approach to dating emphasizes authenticity over perfection. Whether it's wearing a Justin Bieber mugshot t-shirt on a second date or planning a thoughtful food tour, the key is being genuinely yourself while showing consideration for the other person.

The best relationships start when both people feel comfortable enough to be authentic from the beginning. By focusing on genuine connection rather than trying to impress, you set the foundation for relationships that can actually go somewhere meaningful.

Remember: the right person will appreciate your quirks, not just tolerate them. Your job is to show up authentically and see if there's mutual interest - not to convince someone to like you.

Want more practical dating advice for your twenties? This is Part 2 of our conversation with Luke. Check out Part 1 for insights on Hinge profiles, meeting people in real life, and building post-college routines that support your dating life.

Listen to the full episode on all major podcast platforms by searching "Guyset podcast" or watch the video version on YouTube for visual elements including Luke's actual dating app profile.

Thank you for listening! Send in any questions, things you want me to talk about, or things that should be talked about for guys in their 20s to josh@guyset.com  

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See you next Tuesday.