More Than A Business Dinner?


My female boss has invited me out for dinner. She says that it is to thank me for landing a big client. I’m a single guy and she has kind of flirted with me in the past. How can I make sure that the dinner is all business, as I don’t want to be dessert?


It is important that you approach the evening with the attitude that it is just a thank you for a job well done. That doesn’t mean that you won’t be on your guard it just means that you will be professional in your behavior. Dress as you normally would for a business dinner. Avoid colors or materials that might appear casual or sensual.

Watch your alcohol consumption.It is difficult to talk about business for an entire evening. However, choose other topics carefully. Stay away from discussing relationships. Talk about trips, hobbies, books, music; anything that is neutral.

You bring the evening to an end at the restaurant. Be gracious; thank her for the dinner and leave. Don’t do the ‘let’s go for a nightcap routine’. The invitation was only for dinner and you cannot be blamed for staying within those boundaries.

If you are really uncomfortable with the whole dinner idea you could suggest a lunch instead and ask if certain members of your team who helped you in land the client be invited. This will also help to illustrate your leadership qualities.

You didn’t mention your boss is in a relationship or not. There is a chance that the flirting she did was meant to be innocent and fun and you have nothing to worry about. However, an ounce of prevention is worth a pound of cure.

Be the one to steer the conversation. If your boss is already thanking you for landing a big one then this can be an opportunity for you to score points by offering her up some new business ideas. If you landed a new big account then you can sell. Use those skills to pitch your ideas to your boss. If she listens intently then she is interested in business. If she tells you that the evening isn’t for work then you know exactly where you stand.

If by chance it should come right down to it and she propositions you don’t hesitate to tell her that you enjoy working for her and how much you respect her as an employer and that you don’t believe in inter-office dating as you’ve seen others who have done so and found it to interfere with the company’s bottom line. This way she sees you have loyalty to the company and she doesn’t feel rejected.


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