The Conversation Mistakes That Ruined My First Dates (And How I Fixed Them)

I used to be TERRIBLE at first dates. Like embarassingly bad. I'd go on dates and they'd never lead to second dates, and I couldn't figure out why.

Then my friend sat me down and was like "dude, you're making some major conversation mistakes." She broke down everything I was doing wrong and honestly? She was right about all of it.

Here are the conversation mistakes that were ruining my first dates and how I fixed them.

Mistake #1: Turning Dates Into Interviews

I would just fire off question after question without really engaging with their answers:

"What do you do?"

"Where are you from?"

"Do you have siblings?"

"What are your hobbies?"

It felt like I was conducting an interview, not having a conversation. No wonder my dates felt stiff and awkward.

How I Fixed It

Instead of rapid-fire questions, I started:

Now conversations feel more like an actual exchange instead of an interrogation.

Mistake #2: Talking About My Ex... A LOT

Oh god this one was bad. I didn't even realize I was doing it until my friend pointed it out.

Me: "Yeah I love hiking, me and my ex used to—"

Me: "That restaurant is great, my ex and I went there—"

Me: "Funny story, one time my ex—"

NOBODY wants to hear about your ex on a first date. It makes you seem hung up on them, or bitter, or just generally not ready to date.

How I Fixed It

I made a conscious rule: don't mention my ex unless directly asked about past relationships. And even then, keep it brief and neutral.

Instead of "my ex and I used to do that," I just say "I've done that before and really enjoyed it."

Simple change, huge impact.

Mistake #3: Making Everything About Me

I would share too much about myself without checking if they were actually interested. Like I'd go on these long tangents about my job or my opinions and not notice their eyes glazing over.

Classic self-absorbed behavior, even though I wasn't trying to be selfish. I was just nervous and filled silence by talking about myself.

How I Fixed It

I started paying attention to:

The rule I follow now: for every thing I share about myself, I ask them something about themselves.

Mistake #4: Getting Too Deep Too Fast

I have this problem where I skip small talk and go straight to really heavy topics. On a first date I'd ask things like:

"What's your biggest fear?"

"What's your relationship with your parents like?"

"What's the worst thing that ever happened to you?"

These are interesting questions but they're way too intense for a first date with someone you just met.

How I Fixed It

I learned there's a middle ground between boring small talk and therapy-level deep conversation:

These are interesting enough to have a good conversation but not so heavy that it scares people away.

Mistake #5: Not Reading The Room

I would barrel ahead with conversation topics even when it was clear the other person wasn't interested.

Them: *gives short answer*

Me: *asks another similar question instead of changing topics*

I wasn't picking up on social cues that they wanted to talk about something else.

How I Fixed It

Now I pay attention to:

If I notice they're not engaged with a topic, I just switch to something else.

Mistake #6: Trying to Impress Them

I would exaggerate stories or try to make myself sound cooler/smarter/more successful than I actually am.

This always backfired because:

How I Fixed It

I decided to just be myself, even the boring/awkward parts. If someone's not into the real me, then they're not my person anyway.

Turns out being genuine is way more attractive than trying to be impressive.

Mistake #7: Monopolizing The Conversation

Similar to making everything about me, but specifically I wouldn't let them finish their thoughts. I'd interrupt or jump in with my own similar story before they were done sharing.

Them: "So last summer I went to Japan and—"

Me: "Oh I've always wanted to go to Japan! I almost went last year but—"

Super annoying behavior and I didn't even realize I was doing it.

How I Fixed It

I practiced actually shutting up and listening. When they're talking:

This was hard at first but it made such a difference.

Mistake #8: Neg-ing or Being Critical

Sometimes I thought I was being funny or playful but I was actually just being kind of mean:

"You actually like that band? Really?"

"Interesting choice of restaurant..."

"Wow you're really into [hobby]? That's so random."

I thought I was teasing in a flirty way. In reality I was just being judgmental and rude.

How I Fixed It

I stopped commenting negatively on anything they shared, even as a joke. If they mention something they like, I either:

No more sarcastic or critical comments, even in jest.

Mistake #9: Not Being Present

I would be physically there but mentally somewhere else. Thinking about work, checking my phone, looking around the restaurant instead of focusing on them.

Obviously this made dates feel like I wasn't interested even when I was. I was just distracted and anxious.

How I Fixed It

Before dates now I:

It's amazing how much better dates go when you're actually paying attention.

The Results

Once I stopped making these mistakes, dating got SO much easier. I started actually getting second dates. Conversations flowed better. I enjoyed dating more.

Not every first date leads to something, but now when dates don't work out it's because we weren't compatible, not because I sabotaged it with bad conversation.

Quick Reference Guide

DON'T:

DO:

The Biggest Lesson

The common thread through all these mistakes was: I was so focused on myself (my nervousness, my image, what I wanted to say) that I wasn't actually connecting with the person across from me.

Once I shifted to being genuinely curious about them and present in the moment, everything improved.

One More Thing

Even after fixing all these mistakes, not every first date is going to be great. Sometimes there's just no chemistry or compatibility.

But at least now when dates don't work out, I know I showed up as my best self and had a real conversation. That's all you can do.

What conversation mistakes have you made on dates? What did you learn?