10 Things to Talk About on a First Date With a Coworker

Dating a coworker can be awkward; you know him but you don’t know him. These first date conversation starters for coworkers will decrease your anxiety and increase your confidence. They’re geared towards couples who know each other through work, but haven’t spent much time together outside off the job.

When I wrote 6 Tips for Dating a Coworker Without Losing Your Job I just assumed that the first date conversation would flow easily. But the more I think about it, the more I realize how weird it is to date someone you work with. You like him as a person (and I mean like him) and are attracted to him as a potential mate…and that makes you nervous. Which makes it harder to think of things to talk about on your first date.

Here’s one of the most interesting, relationship-building, ice-breaking conversation starters: talk about how hard it is to find things to talk about on your first date with someone you work with. This is the “elephant in the room” conversation starter. When you talk about the very thing that’s making you uncomfortable, you immediately relax. You uncover the pain point, dig up the weeds, and shed light on the problem.

If you talk about how awkward you feel about dating a coworker, you might find that he’s thinking the exact same thing. After all, conversation was easy in the break room, after meetings in the board room, and in the elevator! And if you share the fact that you searched the internet for first date conversation starters, you might even laugh about it.

Something to remember when you’re wondering what to talk about: one of my most popular articles for a long time was 10 Conversation Starters to Help You Talk to Your Girlfriend. Men, too, find it difficult to get a conversation going with someone they like. Know that you are not alone on this date; it is not your job to make all the conversation and ensure there are no moments of silence. Let him do some of the heavy lifting.

What to Talk About on a First Date With a Coworker

Don’t stress yourself out. Dating is about becoming comfortable with each other and easing back into the same dynamic that first attracted you. You already like each other – after all, you’re going on a date. Don’t try too hard, or try to be someone you’re not.

At the end of this article you’ll find a quick list of 10 Questions to Ask Your Coworker on a First Date. First, though, a few thoughts about things to talk about…

1. Talk about the event or activity you’re doing

What to Talk About on a First Date With a Coworker
What to Talk About on a First Date With a Coworker

The best first date involves some sort of activity. Avoid a first date that involves coffee, a restaurant dinner, or even a walk in the park. Go to the horse races, a dog show, art exhibit, or a wine-and-paint event (where you drink wine and paint!). Do something together that forces you to talk about the thing you’re doing. When you were at work you had no problem talking, right? That’s because you had built-in conversations starters. Doing an activity on a first date with a coworker will give you plenty to talk about.

2. Know what men usually talk about

“We usually talk about what we’re engaged in at that moment,” says Esquire editor in chief David Granger in “Frequently Asked Questions About Men” in an old issue of O magazine. That’s why men do stuff together: fixing cars, playing soccer, hiking, playing video games. They don’t normally just sit down and talk.

3. Get comfortable with silence

I used to rush to fill in even a moment’s silence when I was with others. I thought silence was a bad sign and that it should be avoided at all costs. Now that I’m praying and meditating silently every day, I am so comfortable that I barely notice when several moments of silence has passed. Now other people make conversation, which is great! Instead of worrying about what to talk about on a date with a coworker, learn how to be comfortable with silent pockets. Let him bring up stuff he wants to talk about.

4. Ask about his previous experiences dating a coworker

Admit it: you’re dying to know about his last relationship, aren’t you? Especially if he dated someone at work. What was the most difficult thing about dating a coworker? What would he do differently? What did he learn? Talk about your own past experiences with dating coworker or boss. Tell him what you learned, and what you’d do different.

5. Remember that he already likes you

You can relax! He likes you. He wants to go on a date with you. You’re his coworker; he knows the potential for problems dating someone at work. He’s willing to take a risk and go on this first date with you. Relax into the knowledge that he already knows enough about you to like and you want to date you. The more comfortable, open and curious you are, the more likeable you’ll be.

6. Know when and why men talk seriously to each other

“The only time we really talk seriously with each other is when we fear we might be failing,” says Granger. “But that’s rare, and it usually passes quickly. We’d rather tell each other stories of embarrassment or triumph. We grew up telling each other stories, and we’ll never stop.” You know what? Your coworker — if he’s a typical male — is probably more worried about what to talk about on the first date than you are. Ask him to tell you about his biggest triumph or most embarrassing moment. He’ll like that.

7. Talk about whether you should talk about work on your first date

The most interesting first date conversation starters are often work-related because they break the ice. But should you talk about work when you’re dating a coworker? It depends on your job and how interesting it is. Here’s a tip: ask him if he wants to talk about work or if he’d rather pretend you weren’t coworkers. Make it a game; imagine you’re meeting for the first time and have to describe your workplace. I suspect you’ll be surprised at both your and your coworker’s job descriptions.

8. Ask my favorite question

Here’s my favorite thing to ask new people: “What do you think I should know about you?” I love this question; it always surprises me to learn what people think I should know about them. I also enjoy surprising people with my own answer, which is that I’d much rather be alone than with anyone. I could be a hermit and live happily ever after! I’m also not scared to die.

9. Talk about the pros and cons of dating a coworker

Some workplaces frown on romance between coworkers. In fact, some even have serious rules against that type of employee fraternizing. What is your company’s policy on coworkers dating? This is worth talking about – and there is no better time than the first date. It’s not the most engaging topic of conversation. It may even be painfully embarrassing and uncomfortable to talk about your company’s policy on dating when you’re on a first date with a coworker! But this is a good test. If you can talk about embarrassing, uncomfortable things this early in your relationship, you’re laying good track for the future.

10. Get Table Topics

first date conversation starters with coworker

Couples Table Topics is a great way to start a conversation – especially on a first date with a coworker, when you don’t know what to say.

10 Questions to Ask Your Coworker on a First Date:

  1. If I gave you $5,000, how would you spend it?
  2. Has your greatest fear ever come true?
  3. What gives your life meaning?
  4. What is the stupidest thing you’ve ever done?
  5. Who is the happiest person you know? What makes her so happy?
  6. How would you define a toxic coworker? (be careful not to gossip about your colleagues)
  7. When you think of ‘home’, what specifically do you think of? Is there a person who represents home to you?
  8. Where do you find peace when you’re stressed or worried?
  9. What’s your favorite way to spend a weekend? Family holiday? Vacation?
  10. What is the last new thing you learned how to do? How did it go?

Those are good questions to ask when you’re dating a coworker – and they’re all from the Table Topics box. Before you ask him those questions, though, be prepared to answer them. Some of them are hard.

Here are a couple questions for you: how do you feel about dating a coworker? Do you want to talk about work on your first date…or would you rather pretend you met somewhere else?

You might also want to read How to Deal With a Difficult Breakup at Work. In fact, the wisest, most mature people would actually talk about that on their first date with a coworker.


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4 thoughts on “10 Things to Talk About on a First Date With a Coworker”

  1. That’s awesome, Diego, that you had a good first date. Sometimes its our nervousness that makes us come up blank when we’re trying to figure out what to talk about on the first date – but it sounds like you and your date found a great place to start a relationship!

  2. I met a girl in an online dating website, and we were both nervous about talking in person. We met at a fair and had a great time looking at the rides and trying different types of foods. I did have a list of 5 things to talk about on our first date but didn’t need to look at it. We only ended up dating for a few months because she moved to a different state but we’re still friends. It was a good experience though.

  3. My favorite topics for a first date are your passions, your career and travel. Why? Because there is a lot to say about them and these topics offer an excellent opportunity go find out about his interests and priorities in life.