If you are going on first dates, this one’s for you.

I went on a first date recently and it… wasn’t the best date. I was in a position where I wanted to leave but didn’t know how to end it. Listen to the episode for what I decided to do and my thoughts on the whole experience.

I want to emphasize that I would never go on a date with the intention to talk about it on this podcast but if or when something comes up that I would have wanted to hear before as a guy in my 20s, I’ll talk about it. This is exactly the reason I started this podcast in the first place because I couldn’t find anything like this or anyone talking about these types of experiences.

I also share my takeaways from about a year of going on first dates and how to spin a bad date into a positive experience. Enjoy and thanks for listening!

How to End a Date Respectfully When It's Not Going Well (Without Being a Complete Dick)

The awkward conversation no one teaches you: what to do when you're stuck on a first date that's going nowhere

You're 45 minutes into a first date. She's telling her fourth story in a row without asking you a single question. You've already finished your drink while she's barely touched hers. The conversation has shifted to astrology, and you're mentally calculating how much this evening is costing you.

Sound familiar?

We've all been there—trapped on a date that started with promise but quickly turned into a one-sided conversation marathon. The problem? No one teaches you how to gracefully exit a date that's not working without looking like a complete asshole.

Here's everything you need to know about ending a date respectfully when it's just not clicking.

The Reality: Not Every Date Will Be Magic

First, let's get this straight: Having a bad first date doesn't make you shallow, and wanting to leave early doesn't make you a dick. Dating is a numbers game, and sometimes the chemistry just isn't there.

"Every single first date is a great experience," Josh explains after his own recent dating mishap. "Even something like this where I had this realization of like, fuck, I need to learn how to end this respectfully."

The key insight: Learning how to handle these situations gracefully is a crucial dating skill that no one talks about.

Red Flags That Signal It's Time to Plan Your Exit

1. The Conversation is Completely One-Sided

• She's telling story after story without asking questions

• You've become the "question master" just to keep things moving

• There's no natural back-and-forth dialogue

2. Basic Date Etiquette is Missing

• She orders a second drink without consulting you

• She's not reading obvious social cues that you're ready to wrap up

• The energy feels forced rather than natural

3. You're Both on Different Pages About the Date's Direction

• You're ready to leave after one drink; she's settling in for the evening

• The conversation topics aren't connecting with either of you

• You find yourself mentally checking out during her stories

Respectful Exit Strategies That Actually Work

Strategy 1: The Work Day Out (Most Effective)

What to say: "I just realized how late it's getting. I have an early morning tomorrow and need to get some sleep."

Why it works:

• It's honest (you probably do have work tomorrow)

• It's not personal or insulting

• It gives a legitimate reason for leaving

Pro tip: This is why Wednesday and Thursday first dates are perfect—you naturally have a work day the next morning.

Strategy 2: The Phone Check Method

How to execute:

1. Steer conversation to something that requires showing a photo or taking notes

2. "Wait, let me write that down" or "Let me show you a picture of that"

3. Pull out your phone and "discover" how late it is

4. "Oh wow, I didn't realize it was already 10:30. I should probably head out soon."

Why it's effective: Gives you a natural reason to check the time without seeming rude.

Strategy 3: The Honest but Gentle Approach

What to say: "This has been really nice, but I'm pretty tired from my day. Should we call it here?"

When to use it: When you want to be more direct but still polite.

What NOT to Do (Common Mistakes That Make You Look Like a Dick)

Don't Split the Check Out of Spite

Even if the date is going terribly, if you asked her out, you should pay. "I think that if I asked her out to go on a date, I should be the one to pay for it, at least for the first, second, third date."

Don't Make Obvious Excuses

• "My friend is having an emergency" (unless it's actually true)

• "I just got really sick all of a sudden"

• Fake phone calls from roommates

Don't Just Disappear

Going to the bathroom and never coming back is the coward's way out and will definitely get you a reputation.

Don't Be Brutally Honest in the Moment

Save the "I don't think we're compatible" conversation for later via text.

The Graceful Exit: Step-by-Step

During the Date:

1. Finish your current drink rather than ordering another

2. Use one of the exit strategies mentioned above

3. Get the check and handle payment

4. Walk out together rather than having an awkward goodbye inside

The Goodbye:

1. Keep it brief and friendly: "This was really nice. Great meeting you."

2. Go for a quick hug rather than anything more intimate

3. Head in your respective directions without lingering

The Follow-Up (Within 24 Hours):

Send a respectful rejection text: "Hey, I had a nice time meeting you last night, but I don't see this going any further. Hope you're enjoying getting settled in the city!"

Why this matters: Ghosting feels terrible. A quick, honest message shows you're a decent human being.

The Psychology: Why This Happens and How to Handle It

Common Reasons Dates Go Sideways:

• Nerves (she might be talking non-stop because she's anxious)

• Inexperience (new to the city/dating scene)

• Incompatible communication styles

• Simply no chemistry (it happens)

Your Mental Game During the Exit:

Accept that you can't save every date. Sometimes the kindest thing you can do is end it early rather than prolonging the awkwardness.

Don't take it personally. A bad date doesn't mean there's anything wrong with either of you—just that you're not a match.

Learning from the Experience

Questions to Ask Yourself After:

1. What did I learn about my own communication style?

2. How did I handle the awkward moments?

3. What would I do differently next time?

4. What positive skills did I notice in myself?

Building Your Dating Confidence:

"Feeling like I could leave those silences tonight... I was like, okay, I've improved in that. That's a conversational thing and a date thing that I'm happy I've learned."

Track your progress: Notice what you're getting better at, even on bad dates.

Dealing with Dating Fatigue

The reality check: "This shit can be so exhausting. It can be just very treacherous when you've gone on a slew of bad dates."

Signs You Need a Dating Break:

• Feeling unmotivated to set up new dates

• Going through the motions without genuine interest

• Becoming cynical about the whole process

How to Reset:

1. Take a conscious break (a few weeks to a couple months)

2. Focus on other areas of your life (friends, hobbies, work)

3. Come back when you feel genuinely excited about meeting someone new

The Money Factor: Don't Let Cost Cloud Your Judgment

The mindset shift: "I spent $90 on drinks... I could have spent that on US Open tickets. But you can't look at things like that because had it gone amazing, I would have spent that in a heartbeat."

Remember: The cost of a few bad dates is nothing compared to finding someone you actually connect with.

Setting Yourself Up for Success

Pre-Date Strategy:

• Choose Wednesday or Thursday nights for easy exit opportunities

• Pick venues with a natural time limit (not all-night spots)

• Have a realistic mindset about first date expectations

During the Date:

• Stay present but trust your instincts

• Don't check your phone frequently, but don't be afraid to check the time when appropriate

• Be genuinely interested in giving the date a fair shot

The Bigger Picture: Dating is a Skill

Every bad date teaches you something valuable:

• How to handle awkward conversations

• When to trust your gut feelings

• How to be respectful even in uncomfortable situations

• What you're actually looking for in a partner

The goal isn't to avoid bad dates—it's to handle them with grace and learn from them.

Key Takeaways for Ending Dates Respectfully

1. Have an exit strategy before the date starts

2. Use work obligations as your go-to respectful excuse

3. Pay the bill if you initiated the date, regardless of how it went

4. Send a follow-up text within 24 hours to avoid ghosting

5. View every date as a learning experience, even the bad ones

The Bottom Line

Learning how to end a date respectfully when it's not working is a crucial life skill that will serve you well beyond your twenties. It's about treating people with dignity while also honoring your own time and energy.

Remember: You're not obligated to suffer through a bad date, but you are obligated to handle the situation like a decent human being.

The right person is out there, and learning to gracefully navigate the wrong ones will make you a better partner when you find them.

About Guyset

This post is based on an episode from Guyset: A Guy's Guide to What Should Be Talked About - a weekly podcast for guys in their twenties navigating dating, relationships, and life's awkward situations. New episodes drop every Tuesday.

Listen and connect:

• Email: josh@guyset.com

• Instagram, TikTok, YouTube: @theguyset

• Website: guyset.com

Have your own dating disaster stories or exit strategies that worked? Submit them through the website or slide into the DMs.

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!