How to Ask Out a Coworker You Do Not Know

Meet her before you ask her out. At work, a woman who has never spoken to you has no reason to say yes and every reason to feel watched, and her friends in the building will hear about it. So find a real reason to introduce yourself, have a few short conversations over a couple of weeks, and only then ask for a coffee or a drink. If she works for another company and you rarely see her, you can be more direct.

On the street, a man walking up to a stranger takes very little risk. If she decides he is not her type, she walks on and never thinks about him again. Inside your own company the same move works differently. She sees you in the elevator next week. She has friends on her floor. And a man she has never spoken to asking her out tells her he has been noticing her from a distance, which is the part people repeat.

You can still date someone from another floor. The order simply changes: first a colleague, then a date.

Large offices are full of small, ordinary openings. The coffee machine. The elevator. A company event, a training day, a cross-team project, the charity run. A mutual colleague who could introduce you. Start with the setting and your name: "I don't think we've met. I'm Sam, I'm on the finance team."

Go to the events that mix departments, and volunteer for the project that puts you in her meetings. A sociable person does these things at work anyway, and they give you a reason to be in the same room.

Think of your workplace as one big social circle. If you are warm with the whole office, men and women alike, saying hello to her is just you being you. If she is the only person on her floor you ever talk to, people notice, and so does she.

The same goes for social media. Where your company is relaxed about it, connecting with colleagues lets people see your life outside work, and it gives her an easy way to react to something you post. Some workplaces are strict about this, so know yours first. Connecting only with the women would look odd anywhere.

After the first hello, keep the exchanges short and easy over two or three weeks. Remember one thing she tells you and ask about it next time. Leave while the conversation is still going well instead of stretching it out.

Watch how she responds. If she starts conversations, stops to talk when she sees you, and asks about your life, she is glad to know you. If she gives polite one-word answers, keep it friendly and go no further.

When you have had a handful of good conversations, ask in private and keep it simple: "I've liked getting to know you. Want to grab a coffee after work on Thursday?" Name the day. Do not ask on the company chat, and do not ask in front of her team. If she says no, say "No worries" and treat her exactly as before.

Before any of this, check your company's policy on dating colleagues. Leave alone anyone above or below you in the reporting line, since that is where most of the real trouble starts.

Some women count as coworkers only loosely. Someone from another company who shares your building. A contractor who visits once a week. A partner company's employee you see at the same site on Wednesdays. With less shared ground, the stakes drop, and you may not get two weeks of casual hellos before she is gone.

Here a more direct approach at a natural moment makes sense. Introduce yourself, talk for a few minutes, and if it goes well, ask for her number or Instagram so you can keep talking outside work. Plenty of workplace couples started exactly like this, seeing each other once a week and connecting online before the first date.

If she works for a client, take more care. A bad moment there can cost your company business, so the work relationship comes first.

Walking up to a woman you do not know is the core skill here, and the safest place to learn it is with strangers in coffee shops, bookstores and on the street. A Cold Approach Bootcamp puts you in those places with a coach, in Miami or New York. Group runs three consecutive days at three students per coach, and Private is 1-on-1 for one, two or three days. You get live coaching on every approach, feedback after every set, and a written practice plan to take home. No experience is needed.