Business or Pleasure?


After finishing a year long project last Friday, Emily (recently single) and her boss invited their team and their client Jon (also single) out for celebratory drinks after work.  A couple of hours in, Emily’s boss paid the tab and left for his commute home.  And that’s when Jon asked Emily if she wanted to stay for another drink.

Jon is one of Emily’s favorite clients.  They work well together and even had started to become friends over the course of the year. Emily happily said yes to another drink (without a second thought). They were in the middle of a work related debate about the healthcare system and pharmaceutical companies – and Emily was about to make her big argument…

She made her point, and one more drink turned into another – plus small plates. Emily began to feel like there may be a little more going on than a friendly debate and celebration… Jon was definitely flirting. Was she flirting back?

Panicked, Emily instantly froze at the thought that she may be jeopardizing one of her company’s biggest clients. So when Jon reached for the bill, she immediately grabbed it and said her company would take care of it. And that’s when things quickly became more formal and maybe even a little awkward.  Nothing romantic had happened, but it seemed they both may have wanted it to…

Was Emily right to pick up the tab and make it clear that she won’t mix business and pleasure? Or should she have let Jon take the lead and see where the night may have taken them?

What should Emily do now? Anything? Tell us what you think!



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2 Responses to “Business or Pleasure?”

  1. Molly says:

    Emily was absolutely right to pick up the check. It was a business drinks. And if her boss asked her the next day to turn in her expense report, he would have gotten angry had she said, “Well, he picked it up”. Her boss would be furious and she’d have to explain that it turned into a date. What a mess!

    I think Emily should see how Jon reacts to her, and if she thinks there’s really something there, she can slightly flirt with him, and he can ask her out on a real date.

  2. Sue says:

    It was business and needed to remain business. Realistically the big issue here is what if she did or in the future decides to mix business with pleasure. It could cost her her job if things go south.

Any Thoughts?