What to Say When Approaching a Woman at Work

It depends which kind of work. If she is a coworker, say something short and honest, make it easy for her to decline, and never press. If she is a woman working a shop, cafe or bar, you step out of the customer role first, keep the exchange brief, and respect that she is on the clock. In both cases the aim is a friendly invitation, not a campaign.

Men type "approaching a woman at work" and mean either one. This article covers both, because the right words differ.

A coworker is the harder case. You will see her again on Monday whatever she says, so the cost of a clumsy ask is higher than with a stranger.

Know the rules first. Your company may have a policy on relationships between coworkers. If you are in her reporting line, the risks are higher, so get your situation clear before you ask anyone anything.

Ask once, in private, and keep it small. Do not ask in front of others, and do not make it a speech. Something simple works: "I'd like to take you for a coffee outside of work sometime. No pressure if you'd rather not."

Make no a comfortable answer. If she says no, say "No worries" and mean it. Then go back to being a pleasant colleague. Do not ask why, and do not ask a second time.

Watch how she has been with you. If she is warm and easy, an invitation is natural. If she is distant or brief, accept that and leave it.

This is a different situation. She is a stranger, and she is at her job. a dating coach's first rule for it is to get out of the customer frame. If she is treating you like the next customer, she is not in the right headspace for anything else. She may also feel awkward flirting at all, since it could cost her the job.

So make it clear, gently, that you are a person talking to a person, not a customer being served.

Do not make it a sales exchange. If you are actively browsing or buying, the frame is mixed. Finish what you came for first, then say something once you are free.

Keep it brief. She has other customers and may get called away. A short, warm exchange is considerate and much more likely to go well.

Be honest about why you stopped. For example: "I'm not trying to hold you up. I just wanted to say you seem like someone I'd enjoy talking to. Would you want to get a coffee sometime?" That is plain and clear, and it gives her an easy out.

a dating coach also points out an advantage here. She has to talk to you, so you do not have to do the opener. That removes one of the harder parts of an approach.

Some workplaces do not let employees give out a number or leave with a customer. She may say she cannot. Take that at face value and do not push. You can leave a friendly line, like "No problem, I'll let you get back to it."

• Do not lead with a comment on her body or looks.
• Do not use a line you got from the internet.
• Do not keep her talking when she is busy.
• Do not ask in a way that puts her on the spot in front of coworkers or customers.
• Do not keep coming back day after day to the same place. One honest ask is plenty.

Whether she is a colleague or a clerk, give her room. Be clear about your interest, keep it short, and make an answer of no easy to give. A man who does that is remembered kindly, even when the answer is no.

The words are simple. The hard part is saying them while your pulse is up. That is a skill, and it improves with repetition and feedback. The workplace is a high-stakes place to practice it, which is a good argument for building the skill in lower-stakes settings first.

Cold Approach Bootcamps are in-person coaching in the field, in Miami and New York. Each training day is two four-hour blocks, with daygame and nightgame mixed to suit you, and a coach beside you for every approach. You leave with a written practice plan and access to the community Slack.