5 things a successful man should never talk about on a first date (and 3 things he should)

The truth is that there are many women who are more successful than I am. And of course, people are really only successful according to the standards they set for themselves.

But it doesn’t change the fact that over the last few years, my businesses have grown. I’m starting to feel like an accomplished person.

So it raises the question:

To what extent is it appropriate to share my accomplishments on a first date?

You don’t want to brag, but you also don’t want to hide who you are. It’s a tricky balance, and I’ve learned some lessons the hard way.

That’s why I decided to write this article. 

It’s all about what to say and what not to say when you’re getting to know someone. It’s for guys like me who’ve done well but want to get it right on a first date.

1. You should never talk about money

Let’s get straight to the point: talking about money on a first date is a no-go. Sure, you’ve worked hard for what you have, and you’re proud of it. But bringing up your bank account, investments, or how much you make can really put a damper on the conversation.

Imagine sitting down to dinner, and the first thing someone tells you is how much they earn. It’s awkward, right? It can make the other person feel uncomfortable, or even worse, like you’re trying to show off.

Now, don’t get me wrong. If you’re asked a direct question about your job or your financial situation, it’s okay to be honest. Just keep it simple, and don’t go into details.

Here’s the thing: a first date is a chance to get to know each other, not a time to talk shop. Focus on shared interests, hobbies, and what makes you tick. That’s what really builds a connection. Save the money talk for later, once you’ve gotten to know each other a bit more.

In my experience, keeping money off the table has made for much better first dates. It sets a relaxed tone and leaves room for the fun stuff. After all, isn’t that what a first date should be all about?

2. You should never talk about your business strategy

So you’ve got big plans for your business, and that’s of course great. But when you’re on a first date, it’s probably best to keep those plans to yourself.

Here’s why: Your business strategy might be super exciting to you, but the person you’re on a date with probably won’t understand all the ins and outs. They don’t know your business like you do, and it might just end up feeling like a lot to take in.

I’ve been there before, and trust me, holding back on the business talk can make the date a lot more fun. Instead, focus on things you both might enjoy chatting about, like hobbies or favorite movies.

Down the road, if things go well, you’ll have plenty of time to share your big business dreams. But for now, keep it simple, relaxed, and focused on getting to know each other. It can make all the difference in having a successful first date.

3. You should never talk about your success stories

Having a successful career is something to be proud of, but on a first date, it’s not all about you and your achievements. Instead, it’s about getting to know someone new and finding common ground.

If you spend the whole date talking about your success stories, your date might feel left out of the conversation. It could come off like you’re more interested in talking about yourself than in getting to know them.

I’ve learned that a successful date means making it a two-way conversation. Sure, share a success story if it’s relevant, but also make sure to ask about their life, their interests, and their dreams. Show that you’re interested in them as a person, not just interested in talking about yourself.

It’s those shared moments and mutual interest that can turn a first date into something special.

4. You should never make the date feel like a job interview

Success often comes with being detail-oriented and wanting to know all the facts. It’s normal to be curious about the person you’re on a date with, but asking too many probing questions can turn a fun evening into something that feels more like a job interview.

I know, you’re used to getting all the information you need in business, but on a date, it’s different. You want to get to know each other, but not like you’re checking off a list of qualifications.

I’ve found that it’s better to let the conversation flow naturally. Share stories, laugh together, and let the evening take its course. You don’t have to know everything about each other on the first date. In fact, leaving some mystery can make things more exciting.

Instead of grilling your date with questions, focus on building a connection. Talk about what you both enjoy, your favorite places, or even what makes you both laugh.

5. You should never give unsolicited advice

Being successful often means you’ve navigated many challenges and learned valuable lessons along the way. While it’s natural to want to share your wisdom, offering unsolicited advice on a first date is a path best avoided.

Your date may have their own ideas, beliefs, and ways of doing things. When you jump in with advice they didn’t ask for, it might feel like you’re telling them they’re wrong or that you know better.

I’ve been in that situation, and it can make the conversation awkward real fast. What seems like helpful guidance to you might come across as patronizing to them.

Instead, focus on understanding and listening. If they ask for your opinion, that’s your cue to share. If not, enjoy the conversation without feeling the need to direct or guide it.

A successful date is about connecting and learning about each other, not a chance to show off your expertise. Save the advice for friends who ask for it or for later in the relationship when you know each other better.

The things to talk about on a first date

When I started feeling successful, it wasn’t just about hitting goals or making money. It was a growing confidence, a feeling that I was on the right track. But success isn’t just one thing, and that’s something I had to learn.

I started to realize that people might be more successful than me in ways I hadn’t even considered. Or they might define success differently, and that’s okay. What really started to matter was understanding others, respecting their stories, and learning from them.

So when I’m on a first date, it’s not about bragging or showing off. It’s a chance to connect with someone else and find out what makes them tick. What do they love to do? What’s important to them? Where have they been, and where are they going?

I’ll ask about their hobbies, their family, their dreams. We’ll laugh about shared interests or explore our different viewpoints. I’ll listen, really listen, with an open mind, even if we see things differently.

I’ve learned that this approach leads to more enjoyable and meaningful connections. It’s not about measuring success in dollars or achievements. It’s about connecting with someone else, learning from them, and respecting their journey.