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My Boss Just Asked Me Out to Dinner. What Do I Say? 

Eliot Kaplan  |  July 5, 2019

Tricky, tricky. Ever found yourself in this situation? Your answer may depend on what your boss says next. 

HerMoney’s JobScripts tells you in detailed, measured fashion exactly what to say in every office situation and how to respond no matter how the conversation turns. It takes you all the way through the interaction, leaving you feeling confident that YOU are the one steering the conversation. And confidence is at least half the battle. This week, we’re tackling the tricky topic of what happens when a supervisor asks to spend time with you outside of work. 

Q: I like my boss a lot. He has been nothing but good to me for my first three months on the job, and expresses his confidence in my abilities often. With that said, I’m still relatively new here, and I’m hoping to impress in every way possible. My boss just asked me if we could have dinner one night next week to sketch out first steps for a big project we’re working on, where I’m being positioned as the leader of my small group. My boss is married, and he knows that I have a boyfriend. While I have no reason to suspect that he has bad intentions, my gut is telling me to be wary. With that said, I don’t want to flat out decline his invitation, because it’s important to me that we maintain a good relationship. What should I say? 


A:  Sigh. I understand your concern. Thankfully, in my experience, most male bosses (and men period) are honorable, reliable and trustworthy. While there’s no reason you should immediately suspect the worst of your boss, you absolutely need a script in case things don’t go the way you’re hoping. 

You say: “That sounds great but I have evening plans all this week. Is there any way we could have a meeting during office hours? “

The response you’re hoping to hear: “Yes, that makes perfect sense.  Sometimes it’s easier to focus out of the office and away from the co-workers we’re going to be discussing.  Do plan for a good two-hour lunch. I’ll book that big sushi place around the corner.”

You say: “Thanks a lot. I think we can get it done during that time and if not, we can do another lunch or breakfast next week.”

Case closed. Enjoy your lunch — and know that your boss is one of the good guys! 

But what if he says something else instead? 

The response you’re dreading:  “We need to get away from prying eyes. This is important to me, and you know how much I enjoy spending time with you. My secretary already booked Le Cou Cou for 8 p.m.  What kind of wine do you drink?”

You say: “You’ve been fantastic to me since I got here, Mr. Smith.  I just don’t feel comfortable in that situation. I understand that we may be talking about team members and the upcoming project, so why don’t we just grab lunch around the corner?  Or, I’ll come in early and we can have coffee or breakfast together at the office.”

Then there’s always the chance of a real curveball. 

The response you didn’t see coming: “You’re being ridiculous. I’m asking you to do evenings because I’m booked up with corporate meetings all day every day from 8 to 6.” 

You say: “Okay, I understand. I tend to be a pretty picky eater though,  so how about if we go to that (fill in the blank with the brightly lit, non-intimate, local haunt where the bartender knows you like a sister). I’ll make the reservation.”

About Eliot:

Eliot Kaplan spent 18 years interviewing over 5,000 people as Vice President of Talent Acquisition at Hearst Magazines. He now does career coaching at coacheliotkaplan.com. He knows there’s a WorkScript for every office dilemma, so send your problems to jobscripts@hermoney.com for Eliot’s expertise.

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