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Dating Again

Why do I feel like I have to prove myself on every first date?

You walk in with a whole career's worth of proof and walk out wondering why nothing sparked. Let's talk about the résumé you keep handing across the table.

A Black woman and man in their early fifties share a relaxed conversation across a restaurant table.
Illustration: Melanin Mermaid

You know the moment. The server has just taken the menus, there's a little gap in the conversation, and your mouth is already moving. Somehow you're telling a man you met an hour ago about the team you run, the house you bought, and the time you handled a flat tire, a sick kid and a deadline on the same Tuesday.

He nods. He says "wow." You drive home feeling oddly tired, like you just finished a presentation nobody asked for.

I have done this. More than once. I once told a perfectly nice man about my five-year plan before the bread basket arrived. He didn't call back. I couldn't tell you why, but I realized I barely knew whether I'd wanted another date myself.

After my divorce, I was proud I could keep a household moving and still get my teenagers where they needed to be. I also got used to explaining how much I could handle. As a Black woman at work, I knew what it felt like to walk into a room already prepared to prove I belonged. On a date, though, I wanted something different: a conversation where I could laugh, listen, and find out whether I even liked the man across from me.

Why the résumé always comes out first

Let's be kind to ourselves here, because there's a reason. You've spent years being taken seriously only after you proved you deserved it. At work, in meetings, at the school, at the bank. Somewhere along the way, listing what you've done became how you walk into a room safely.

So when you sit across from a stranger and feel that tiny flutter of nerves, your whole body reaches for the thing that has never failed you: your competence. It fills the silence. It says, don't underestimate me. It says, I'm fine on my own, so don't you dare think I'm desperate.

That doesn't make you cold or hard. You learned to speak up for yourself, and you have every reason to be proud of what you've built.

It's just that the list was never going to get you what you came for, which is a little spark and a good conversation.

You were never supposed to win the first date; you were supposed to find out who showed up.
A Black woman points out a sculpture detail as her date turns toward her with an interested smile.
Illustration: Melanin Mermaid
Quote card: You were never supposed to win the first date; you were supposed to find out who showed up. (Imani Brooks)
Melanin Mermaid

Are you leaving room to be curious?

You don't have to hide what you've built. You also don't have to recite it all before the appetizers arrive. If you catch yourself filling every silence with another accomplishment, pause and ask him something you actually want to know. His response is his to own; you're there to see whether you enjoy being with him, too.

Here's the quiet cost of performing. While you're busy being evaluated, you're not noticing much about him. You came to find out who this man is, and you ended up giving a speech.

Try being curious instead of impressive

You were never supposed to win the first date; you were supposed to find out who showed up. That one sentence changed how I walk into restaurants.

Curiosity is a much better use of your energy than proving yourself. It's lighter, too. You don't have to defend anything. You just have to wonder about him out loud.

Ask the question underneath the question. Not "What do you do?" but "What part of your week do you actually look forward to?" If he mentions his kids, try "What are they like?" instead of moving straight to the next question. Then listen the way you'd listen to a friend who's finally telling you something real.

Pay attention to how he talks about the people in his life. Can he describe a disagreement without making everyone else the villain? Does he ask you something back, or does he wait for his turn to talk?

One story won't tell you everything about a man. But how he tells it can give you something worth asking about, beyond what looked good on his profile.

And about the quiet moments: my sister laughs at me because I can't stand a silent table. But a pause gives both of you a moment to think. You don't have to fill it on your own. Give him a chance to pick up the thread, and notice whether the conversation starts to feel like something you're sharing.

Take a sip of your drink. Look around the room. Let a few seconds go by. Some people fumble when it gets quiet, and that's human. Others lean in. Either way, you've learned something without doing any extra work.

Maybe the quiet bothers you because you're used to keeping everything moving. A pause can feel like you're dropping the ball. But conversation belongs to both of you.

And being curious doesn't mean making the whole evening about him. Tell him what made you laugh this week, what you're looking forward to, or something you love about your work. See whether he follows up. You're making room for a conversation, not giving him the floor for the rest of dinner.

And you aren't spending your best energy on a stranger who hasn't earned it. You're sitting back and letting the evening show you what it is.

Try this, this week

  1. Pick two questions you're truly curious about before your next date, and ask them in your own words.
  2. Let one pause last a few extra seconds. Sip your drink and see what happens.
  3. Notice how he talks about the people in his life, and make a mental note afterward.
  4. Accept a gesture you welcome without feeling you owe him anything.
  5. Talk about work if you want to, then ask about something you'd enjoy learning about him.

Between us

Between us, you have nothing left to prove. The woman sitting at that table already did the raising, the working, the surviving and the rebuilding, and she did it well. A first date can't add to that list, and it can't take anything off it either.

So leave the résumé in the car. Keep it for the job, where it belongs. On your next date, pick two questions you're honestly curious about, let one pause run a little longer than feels comfortable, and see how the two of you do with it.

You might feel bare without your credentials for a minute. You can be proud of everything you've done without making it your opening argument. Give yourself a chance to enjoy him—and notice whether he gives you that same chance.

You might be wondering

Should I avoid talking about my career on a first date?
No. Tell him what matters to you; your work is part of who you are. Just notice whether you're enjoying the conversation or trying to pass a test. If it feels like a test, that's your cue to get curious about him.
What if he doesn't ask me anything back?
You don't have to carry the whole evening. Notice the imbalance without making excuses for it, and then decide whether you want a second date. One lopsided night is information, and it's yours to use however you like.
What if I'm nervous and talk too much?
Take a breath and ask something you're genuinely curious about. Nerves make everybody ramble, and a grown woman can laugh at herself. You don't have to deliver a flawless first date, you just have to show up as you.