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How to get to know a coworker you like before you ask

6 min read

To get to know a coworker you like, talk to them the way you'd talk to anyone at work you wanted to know better: short, friendly chats about things that aren't tasks, repeated over a few weeks. Pay attention to whether they start conversations and ask you questions back. If they do, and the policy and reporting line allow it, you can ask them to do something outside work, with an easy way to say no.

The rest of this post is how to do each step without making the office feel strange for either of you. How to ask a coworker out covers the ask itself. This one is about the weeks before.

Start by checking two things

Before you invest in the friendship, check the basics, because they decide whether this is even an option.

Neither check stops you from being friendly. They tell you what's allowed if it turns into something more.

Build ordinary contact first

You don't need a special approach, just more normal moments. A few that cost nothing:

Work-neutral topics are the easiest ones: food, a show, a trip, a hobby, where they live, a pet, how their commute went. You can get through most of these without asking anything personal. How to make small talk has more questions and ways to follow up.

One finding is worth knowing. In a 2018 set of five studies in Psychological Science (Boothby and colleagues; strangers in a lab, college dorm mates and workshop attendees), people underestimated how much their conversation partners liked them. The researchers called it the liking gap. These weren't coworkers and the studies weren't about romance, so don't stretch it, but the awkward feeling after a chat may be more about your own replay than about the other person.

What to watch for over a few weeks

At work, almost everyone is polite. "They're nice to me" tells you very little, because they're probably nice to everyone. A better test is what happens when work isn't forcing the contact. Over a few weeks, notice whether they:

One of these means little. Several, repeated over time, make a decent pattern. They can also just mean you're friends. How to tell if someone is interested goes through the cues in more detail, and friendly or flirting? covers how to tell them apart. If you still can't tell, that's useful information too: you can't tell yet.

Signs of the opposite matter as much. Short answers, a headset going back on, never joining anything social, or turning toward the person they came in with are all signals to back off. You're trying to find out whether they'd say yes, not to wear anyone down.

Keep it low-key at the desk

A few habits keep the early stage comfortable:

When to ask, and how

There's no fixed number of weeks. A rule of thumb is that you're ready when you've had several relaxed conversations, they've shown some interest back, and you can picture the next day being fine whichever way it goes. If nothing has moved after a few weeks, you may just be good coworkers, and that's fine.

When you do ask:

If it's a no, don't ask again, don't ask other people why, and don't start avoiding them. The U.S. Equal Employment Opportunity Commission (EEOC) says harassment is "unwelcome conduct" based on traits such as sex, and that the law doesn't prohibit "simple teasing, offhand comments, or isolated incidents that are not very serious." Repeated asks after a no are a different matter, and a no at work is final. A coworker said no: how to act at work afterwards covers the days after.

How common is this?

In a January 2023 SHRM survey of 632 working Americans, 40% said they had flirted with someone from their workplace and 27% were in or had been in a workplace romance. In SHRM's December 2025 survey of 1,243 workers, 47% said they were or had been in one. These are self-reports, and the two surveys aren't directly comparable. The 2025 survey also found 57% of workers comfortable with colleagues dating, which SHRM's release describes as down from 81% in 2025, so colleagues may feel differently about it than you expect.

What to do next

  1. Check the reporting line. If either of you manages the other, drop the plan.
  2. Read the policy this week or ask HR a general question that doesn't name anyone.
  3. Have three small conversations this week that aren't about work, each under five minutes, each with one follow-up question.
  4. Say yes to one group thing (lunch, coffee run, team drinks) in the next two weeks.
  5. Keep a simple note each week: did they start conversations, and did they ask you questions?
  6. Write your ask with a day, a place and an out, and use it only if the pattern is there.

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