I talk about the mistakes I’ve made and lessons I’ve learned from the past year of dating. I don't hear any guys talking this openly about what they’ve learned from their dating experiences and how they are going to apply those lessons to change their ways and improve going forward, so hi guys welcome back to Guyset. I hope you can hear parts of this episode that you relate to or see yourself in and use those moments to reflect on your own dating life. It's not weird to reflect on this stuff and want to get better for future relationships. In fact, it's the opposite. 

The Unfiltered Truth About Dating: 5 Mistakes I Made So You Don't Have To

Dating in your twenties can feel like navigating uncharted waters. There's no manual, no perfect roadmap, and most guys aren't openly talking about their mistakes or what they've learned. That's why I wanted to share some personal reflections on my own dating journey over the past year.

These aren't just random tips – they're real lessons from real experiences that have shaped how I approach relationships. And while nobody's perfect (especially me), recognizing where you've gone wrong is the first step toward doing better next time.

1. Communication Matters More Than You Think

I'll admit it – I'm not always the best communicator. Sometimes I assume the other person knows what I'm thinking or what my plans are, when in reality, I haven't actually told them anything.

For example, I once went on a lunch date without mentioning I had plans right afterward. When I tried to leave, there was obvious tension because she expected we'd hang out longer. A simple heads-up beforehand like, "Just so you know, I have plans with a friend afterward" would have avoided the awkward situation entirely.

What I've learned: Set clear expectations upfront. Whether it's about your availability, your intentions, or your feelings, saying things directly prevents confusion and hurt feelings later.

And yes, I've been called a "bad texter" too. While I'm reliable with responding, I'm not one for elaborate messages with emojis and exclamation points. But communication style matters, and sometimes putting in that extra effort shows you care.

2. Only Commit When You Mean It

We've all done it – said "yes" to plans without fully committing mentally. You agree to something thinking it might not actually happen, then when the other person follows through, you're caught off-guard and either have to cancel or show up unprepared.

What I've learned: Be honest with yourself and others about what you're willing to commit to. It's either a 100% yes or it's a no. If you're not sure, say something like "Let's play it by ear" instead of making a commitment you might break.

Canceling last-minute is particularly damaging. When you're on the receiving end, it feels terrible – you've prepared, gotten ready, and mentally psyched yourself up only to have plans fall apart. I've been guilty of this in the past, and it's something I'm actively working to improve.

3. Set Boundaries Early

When you start seeing someone new, it's easy to get swept up and begin sacrificing other important parts of your life. Before you know it, you're canceling on friends, skipping family calls, or neglecting hobbies that matter to you.

What I've learned: Know your non-negotiables before getting into a relationship. For me, maintaining close friendships is a priority. Anyone I date needs to understand that these people are important to me, and I won't constantly cancel plans with them.

Setting these boundaries early prevents resentment later. It's much harder to reclaim your time and priorities once patterns are established than to be clear about them from the beginning.

4. Trust Your Gut About "The Spark"

That indescribable connection – the spark – is something you typically know pretty early on. It's when conversation flows effortlessly, when you're fully present in the moment, not checking your phone or thinking about anyone else.

What I've learned: No amount of advice from friends can override your own gut feeling. If you're constantly questioning whether you feel a connection with someone, that itself is probably your answer.

While it's worth giving someone a second or third date if you're unsure, ultimately you know how you feel. The spark can fade temporarily and come back, but you can't force it to appear where it doesn't exist.

5. End Things Respectfully (No Ghosting)

Ending relationships – whether they're hookups, situationships, or committed partnerships – is never easy. There's no perfect way to do it, but there are definitely wrong ways.

What I've learned: Ghosting is never acceptable. I've been on both sides of ghosting, and it feels terrible to be left wondering what happened. A short, kind text provides closure for both parties.

Put yourself in the other person's shoes. How would you feel receiving your breakup message? Something simple like, "I had a great time getting to know you, but I don't see this going any further" is direct but respectful.

Final Thoughts for Guys in Their 20s

We're young. Despite what previous generations might have done, there's absolutely no rush to settle down in your early twenties. If a relationship isn't adding value to your life, why continue?

I've also learned that I'm a one-woman man – I can't emotionally invest in multiple people simultaneously, even though modern dating culture often pushes for keeping options open. Know yourself and what works for you.

The dating world can be challenging, but the good news is that we have the ability to reflect, learn, and improve. Every mistake is an opportunity to become a better partner in your next relationship.

What dating lessons have you learned? Share your experiences in the comments below, or reach out to me directly with questions or topics you'd like covered in future posts.

Want to hear the full episode? Listen to "My Biggest Dating Mistakes" on Apple Podcasts, Spotify, or wherever you get your podcasts. You can also follow along on Instagram and TikTok @theguyset for more content.

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See you next Tuesday!