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Posted inDear Gabby

Good friends don’t always make good bosses

by Dear Gabby February 20th, 2022February 21st, 2022

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Dear Gabby,

Some years ago, I accepted a job knowing that a good friend would be my boss. Turns out, good friend didn’t make for good boss. It was an incredibly stressful situation, and I ended up retiring earlier than I planned to, just to be done.

The pandemic hit soon after, and at the beginning, my good friend and I made a few Zoom and social distanced dates, which were fun. Neither of us has reached out in months though, and I’m starting to wonder if this is a friendship worth maintaining, or is it dying a natural death? What do you think?

Not Lacking for Friends, But Kinda Miss Her

Dear Lacking,

Only you can know whether this is a friendship worth maintaining, but I do believe that friendships can go through lots of ebbs and flows over time. Perhaps you are in a temporary ebb. Since you were friends before she became your boss, and you “kinda miss her,” why not reach out and test the waters? She could be very busy or preoccupied or dealing with something that requires an ear from an empathetic friend. I have worked for two very good friends and I agree it can be dicey! But it sounds like this one may be worth at least one more roll of the dice. 


Dear Gabby,

My husband has three degrees and yet, when he opens the refrigerator, it’s as though he enters an altered state, not unlike a standing coma. Negotiating the contents of the fridge seems completely beyond him, like he is suddenly being asked to calculate the gravitational pull of the moon. If it isn’t right in front of him, he doesn’t see it. If it isn’t in a clear container, he won’t open it. And if it’s not something he already knows is in there, he won’t explore. If I save him something that I know he likes – even though I want to eat it – it will spoil if it doesn’t have a neon sign that says “Here I am!” and then neither of us is happy. Is it so much to ask for a grown man to use his eyes? Didn’t cavemen forage? I do not understand.

So Smart, Yet So Challenged

Dear Smart,

I believe I’ve been married to your husband for decades! While there are, indeed, many kinds of intelligences and I want to give your husband the benefit of the doubt (not really, I just feel obligated to say that), I don’t believe that refrigerator logistics is one of them, so really, he has no excuse. I can only advise you to do what I do. Put everything that you really love in the back of the frig where you know he will never see it and put all the just-about-to-spoil things in the front. Call me competitive and cranky but hey, finders keepers! 


Dear Gabby,

We’re thinking about redoing our front yard. We absolutely love how a neighbor did hers, but we don’t want to be total copycats. How much imitation is flattery, and how much is just being obnoxious? Is there a right way to proceed?

Good Fences Make Good Neighbors, But What About the Yards Themselves?

Dear Good Fences,

How considerate you are! Why not invite your neighbor over for a lemonade, or perhaps a Long Island iced tea, and talk to her about how much you love her yard. Then you can pick her brain for her thoughts, ideas and contractors, as well as problems she ran into while building this Garden of Eden. 

While buttering her up, you can feel out whether she would be offended or flattered if you did something similar. My guess is that she will be flattered and happy to share. In my experience, gardeners are absolutely evangelistic about gardening, approach it with the zeal of a convert and are only too happy to convert you into the fold. Go with sod.


Dear Gabby appears in the RoundTable every Monday. Yes, Gabby is an advice columnist – but not just any advice columnist. Because that would be boring! Gabby combines wisdom with wit. And a pinch of snark. She is not a trained therapist by any means, but has seen and loved many in her day. Her aim is to make you think while she makes you laugh. Gabby welcomes all questions and queries and is only too happy to hear your opinion, no matter how much it may diverge from hers. Write to Gabby at news@evanstonroundtable.com.

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Dear Gabby

Dear Gabby appears in the RoundTable every Monday. No question is too serious, too silly or too snarly for Gabby, who combines wisdom with wit and a pinch of snark. Her aim is to make you think while she... More by Dear Gabby

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