How to Flirt With Customers at Work

Decide first whether you can afford to lose the job. If you cannot, don't. If you can, keep it to the moments where there is no line, you are alone with her at the counter, and the vibe is already clearly good. A student on one of our live calls works in a big-box store and asked this exactly: customers say hi to him, so should he go for it? The coach's answer was that it depends on how much you care about the job, and that you do not have to choose between always and never.

A retail job is easy to underrate. The coach pointed out that losing one is not just losing a paycheck. A bad word from the people you worked with can slow a promotion or follow you to the next application, or leave an odd mark on your work history that you will have to explain.

So the first step is to ask whether you would accept that risk. If the answer is no, there are plenty of women who are not your customers, and you can meet them somewhere else. If the answer is yes, the next question is how much risk you actually want to take.

The coach was blunt about the frequency. If you hit on women all the time, it will get back to you, and you will probably lose the job. A man who is known for flirting with half the store is a man with a problem at work.

That does not mean you have to live like a monk. It means that you pick your moments, the way you would pick a venue.

The coach laid out a narrow version that carries much less risk:

• No line. If other customers are waiting, you are on the clock, and she is being watched. Do nothing.
• One on one. You have been helping her, the conversation is private, and nobody is waiting behind her.
• A clearly good vibe. She is smiling, lingering and asking you questions, or she is plainly the one making the running. It should be almost silly not to say something.

If you do not have all three, wait. You are not waiting for a perfect chance. You are waiting for one where the risk is small compared to the chance of it going well. The coach said you do not want the dicey ones, where the risk of losing your job is higher than the chance she says yes.

A woman at your counter is not like a woman in a park. She came for something else, and she may feel she has to stay polite until she has what she wanted.

That is why the bar is higher at work. Keep the conversation light and brief, and make sure any friendly thing you say can be answered with a smile and nothing more. If she gives you a short answer or looks toward the door, that is a no. End the topic right there, finish the transaction, and treat her the way you would treat any other customer. Her comfort comes before your interest.

Matthew and his team of coaches describe a different approach for jobs where you spend time around customers, like a tour guide. If you are giving a tour, you obviously have to do it for everybody. But when a woman shows interest in something specific, you can tell her quietly that there is more to show her and she should find you afterward. The coach called this a bridge: it moves things out of your working role and into your own time.

A similar rule applies where a job comes with a code of conduct. A man working on a ship can say he cannot have a drink on board because it would be unprofessional, but that if they are both in port, he would be glad to. That keeps you completely professional while you are on duty. It also gives her a clear place and time to take you up on it.

A related warning comes from our dating coaches on venues. If you work at a bar and you take date after date to that bar, you build a reputation at work, and it may not be a good one. It can also limit whom you can date, because coworkers will know about it.

The same logic applies to customers. If you take women you met through work out to the same places, people notice. Keep your dates in places that have nothing to do with your employer.

Some jobs bring women to you without you doing anything. One of Matthew's coaches notes that staff at a bar or nightclub get approached because of the venue. If you work somewhere like that, your best move is often to be friendly, relaxed and interesting, and let her come over.

For everyone else, a counter job is a place to be good at your job. If a woman is interested, she will make it obvious, and that is your signal to take the one careful step above.