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Dear Gabby,

My co-worker is one of those people who talks incessantly about himself and never asks anything about you. A simple “Hi, how are you,” on the way to the restroom can turn into an earful about the book he just published, the talk he just gave, or if you’re really unlucky, his recent divorce. In the meantime, you could have just won the Nobel Peace Prize and he wouldn’t say boo. It is so annoying! How can I subtly say to him, knock it off!

Signed,
Can I smash his face in?

Dear Can I,

Yes you may, but only in your very vivid fantasies. I am sorry to say that I am very familiar with this personality type as I also have worked with some of them, dated some of them, and honestly, am related to some of them. And in my experience, avoidance is the best strategy here. That may mean retraining yourself to say just “hi,” instead of “hi, how are you?” Seems ridiculous but it will do the trick. Another ploy in these situations is to have a pre-planned out, like, “Sorry to cut you off but I have to run to a meeting…” These may seem like very juvenile schemes, but only because they are. What your co-worker does is very junior high-like and so, you may need to be junior high-like in return. The alternative is to boldly call this person out and say to them, “In all our conversations, you have never once asked me about myself: my family, my job, my health, nothing. Why is that?” But once you open that door, you never know what you will get…perhaps an apology with a genuine vow to do better, a fake mea culpa or worst case, a long launch into more of his own baggage about why he is so self-centered. Oh, the irony. Who needs that? With the time you save from these one-sided soliloquies, you could write a book, and then make sure you tell him all about it.

Dear Gabby,

My daughter is a sex worker and is making really good money from it. She used to be a barista and was always suicidal and broke. She lives somewhere where sex work is legal and regulated, she gets excellent healthcare and I’m very proud of her for being good at what she does. I’m also comforted by the fact that she has enough money to live. The problem (for me) comes when people ask me what my daughter does for work. Should I risk their judgement and tell them? Or is that a breach of my daughter’s privacy?

Signed,
Sexy MF

Dear Sexy,

What your daughter does for a living is her business and hers alone. What other people know should also be solely up to her. I applaud you for being so supportive of her chosen career! As many parents fail to grasp but you seem to know well, our children have their own lives, journeys, opinions, directions, and values. Our job is to support them in what they choose. Bravo to you both. When people ask you what your daughter does, just say, “she’s in hospitality,” which she is, and if they ask for specifics, just say, “if I tell you, I’ll have to kill you.” That should stop the conversation. If pressed further, I would just say, “she’s a concierge,” which is sort of true, or “she works with a very discreet clientele and I really can’t really talk about it.” They will fill in the blanks and assume she’s called on to find organic marmite for Archie when Harry and Meghan visit or tap a sugar maple at 3 a.m. for fresh syrup when Trudeau comes to town. And I say, let them!  

Dear Gabby,

I moved to the area about five years ago from a smaller town, and I’ve always had a car while living here. When it snowed last month, I noticed furniture strewn about the streets as people rushed to call dibs on their dug-out parking spots. In the summer, furniture on the street means: Free Stuff! Am I a bad person if I see an item being used for dibs and decide it would be the perfect complement to my back porch furniture? 

Signed, 
Winter Dumpster Diver

Dear Winter,

Five years in Chicago is enough to know that we take our dibs very seriously, so you may not be a bad person, but you could be a dead one. Don’t do it. At least not in broad daylight. 

Dear Gabby appears in the RoundTable every Friday. 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.