When I coach my private clients, I tell them NOT to ask a guy they just met online or in real life questions like “What kind of business do you have?” or the worst question ever “What do you do?”

The reason is because, besides being boring, predictable and dead-end (Where do you go with a response “I work in finance”, anyway? Talking about work is great…at networking events),
men assume what you really asking is “How much money do you make?”

He’ll assume what you’re really interested in is in his money—not him; it’s especially true for men who’re visibly wealthy or who you’d met at an upscale event. This question kills attraction, makes you come across as someone you’re not (e.g. a gold digger) and leaves no room for sexy things like flirting or creating an intrigue.

Back when I was single and dating, I made it a point not to talk about work at the first encounter (even though I could easily brag about my career when I worked throughout my 20s at a global consulting firm traveling all around sub-Saharan Africa on life-saving programs and, after moved to New York to earn my second Masters degree, got selected for a highly competitive United Nations internship program.) Yet, whether it was a speed-dating event or a first dinner date, when a guy asked “So, what do you do?”, I would shift a direction of our conversation.

Why? Because I wanted to flirt, be playful and create a deeper connection with my date. Because I wanted to create an intrigue about who I was and leave him wanting more. Because I wanted to stand out from many boring and predictable dates he’s been on before that sounded more like job interviews.

There are many ways to avoid this deadly question.

You can flirt (enter and own that sexy territory) by asking him a question right back like “Well, what do you think I do?” Let him guess and ask why he thinks you’re a CEO or waitress (by the way, his guess give you an awesome insight into his subconscious perception of you. For instance, when I met my now husband, he thought I worked at a beauty counter—not bad because he noticed and appreciated the way I took care of my appearance.)

You can create an intrigue by saying that you’ll share it with him later after you get to know him a bit better e.g. his passions and things that get his heart pumping (let him think whatever he wants about why you aren’t sharing what you do—a stripper?! Let his imagination run wild.)

You can comment on how this staple question can make a potentially amazing date like any other—boring, average and feel like you’re at a networking event. Get him to agree on that and instead start talking about what you would do if you could wake up anywhere in the world tomorrow. Where would you be? What would you do? Why? Having this kind of conversation will give you enormous insight into who he’s, what drives him, what’s important to him and why.

A guy who wants to wake up in Las Vegas so that he can party and gamble is very different in his values and passions from a guy who wants to wake up in Tanzania so that he go on safari and help build a school for impoverished kids.

Both can live in New York and work in finance, by the way….

Test it for yourself. Next time you meet a guy at a happy hour or go on the first date with a guy you met online, stay away from the deadly question “What do you do?” and see how it goes.

Let me know about your experience and results.

I would love to hear about your  experience. Have you had something similar happen to you? How did you handle it? Please respond by leaving a comment below.