!! OMG, good advice: Your Friend Dorothy answers the last questions of 2020 !!

Your Friend, Dorothy

Illustration by Eric Kostiuk Williams

Many questions and few answers bubbled up during this most unusual year. Our advice columnist Your Friend, Dorothy is here to help you make sense of a few relational conundrums that you can carry forward for a fruitful 2021.

Should you party with your parents? When is a prospective lovers’ musical taste a dealbreaker? What to say to the oblivious and inappropriate coworker?

Read Dorothy’s good advice after the jump, and scroll to the bottom to submit your own question!

Dear Dorothy,

I need your advice. I just met this super hot guy online. We’ve chatted a few times and have a really great, super flirty rapport. I was going to suggest meeting for a socially distant walk and seeing where things go when he mentioned that his favorite song “CHRISTMAS SHOES” was on the radio.

I’m so devastated, I can’t even. Do you think there’s hope for us? Or should I just move on?


Dear Unimpressed,

Wow, that’s a big one. I mean usually, I tell people that you don’t have to have *everything* in common, in fact it’s often better if you don’t. I’ve also encouraged many a baby gay to look beyond mere style and really consider substance. No joke, you will go through the looking glass when it comes to defining what’s hot as you age.

But such an egregious violation of style… and let’s just face it, decency cannot be overlooked! When I first heard that song, I was actually kind of surprised that the tale of a (literally) dirty, poor kid with a loving and terminally ill mother didn’t radicalize people, or at least inspire them to lionize something more than buying a goddamn pair of shoes for the woman. It’s sort of like seeing baby formula locked behind a cage at the drugstore. *shudder*

So can this hook-up be saved? Well, that depends. Maybe dig a little deeper. Was he being ironic? (Still in poor taste.) Does he have a story-of-self that relates to the song? Maybe you can both talk about the need of popular culture to do better.

If his feelings are sincere and the vibe is undeniable, well then, Unimpressed, the “no talking” rule is always an option.

Dorothy signature

Dear Dorothy,

Like a lot of recent college grads, the COVID situation has got me living back at home with my parents. They’re pretty chill and even though we’re probably more in each other’s way than would be ideal, it’s actually pretty livable.

They’re both in their sixties, case counts are high in my area, and I’m an only child so our bubble is pretty tight. I normally look forward to cutting loose with some serious partying for New Year’s Eve, but this year, going out with my friends is a no-go for obvious reasons.

So, I’m wondering… Would it be cool to party with my parents?

Finally Unable to Bear Another Round


I applaud your concern for your parents and your willingness to keep the party closer to home this year. This kind of responsible behaviour will hopefully ensure many more years of celebrating for you all. But you raise a good question: is it cool to party with your parents? Based on your description, it sounds like you have a warm and loving relationship that could handle a notch or two more on the intimacy meter.

Over time and across cultures, people have often used drugs and alcohol to enhance experiences and deepen bonds. It’s that endless search of transcendent experiences that remind us of what it is to be alive. My most basic advice would be to start small. Do you enjoy wine together over dinner? Great, then maybe take it farther with a nightcap or three together around the Kwanzaa lights or something to enhance that Rummoli game on New Year’s Eve. I’ve often thought it’s a great alternative to rye and ginger for all of those old gals with type two diabetes.

The key here is to stretch and not shatter the bond. Tread carefully and keep your wits about you. Who knows, maybe this will start a new holiday tradition?

Dorothy signature

Dear Dorothy,

The office Christmas party (or any other party) obviously didn’t happen this year, and all the quiet has me thinking about the Ghosts of Christmas Parties Past. A couple of years ago, my spouse and I hosted the office after-party at our place.

It got super awkward when a young, straight, cis-woman colleague of mine asked my spouse if he was the top or bottom. He brushed it off quick enough but it still annoys me. Should I confront her?

Versatile, Duh

Dear Versatile, Duh,

Wow, I’m sorry that you and your partner had to host such an abrasive colleague. Please, pat each other on the back for staying gracious. While her age or inexperience is no excuse for asking such a personal question, maybe you could chalk this up to utter cluelessness.

If I’m being charitable, I’d guess that she was trying to exhibit her knowledge of gay culture, and as we’re seeing here, a little knowledge can be a dangerous thing. It’s also a good reminder that people lose track of their boundaries very quickly when drinking, even at a work event.

Unless, your friendship with her has deepened since, confronting her now probably won’t do much good. If anything like this happens in the future, I’ll tell you my favorite response to deeply personal or inappropriately probing questions. Give a sly smile and ask, “Why do you want to know?” Either you’ll make a new friend or expose a false one.

Dorothy signature

Got a burning question, or just something burning down there? Get answers from Your Friend, Dorothy, the OMG.BLOG in-house advice columnist.

Receive thoughtful, compassionate advice from your friendly neighborhood den mother who’s been there, done that, fucked it, smoked it and lost her T-shirt on the dance floor. She’s po-mo, poly, pan and a social compass to help you land safely as you soar.

Email your questions to [email protected] or DM them to @omgblog.

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