!! OMG, good advice: Your Friend Dorothy talks MILFs, thirds, and COVID pounds !!

Your Friend, Dorothy

Illustration by Eric Kostiuk Williams

As our second pandemic summer winds down, it’s hard not to reflect on where we’ve been vs. where we are now. Taking a look in the mirror literally and figuratively might surface some things, but worry not: Your Friend, Dorothy offers perspective that puts your sleep paralysis demons back to bed.

This month, one reader is feeling a way about his mom’s new dating habits, another is navigating the delicate waters of adding a third to their relationship, and one more is looking for help feeling comfortable with changes in their body.

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

Dear Dorothy,

I’m a young gay guy and I’m worried that my mom is being a MILF. Not just by dressing sexy, which she always does, but by starting to date young guys she finds online. I am so embarrassed I could die.

Mrs.Robinson’s Son

Dear Mrs.Robinsons’s Son,

I think it’s fascinating that you’re ready to die of embarrassment over your mom inhabiting one of the most powerful female archetypes in western culture. Ever consider that maybe you’re the one with Mommy issues?

As a self-identified MILF, I can tell you that there are few things more satisfying than putting on a pair of tight jeans and some leopard print and driving to Costco in my minivan with the tunes blasting. And it’s even more exciting now that MILF-dom seems to be having a moment.

Have you seen the 2018 French comedy MILF? It’s an empowering and relatable story of three best friends in their forties meeting younger men while on vacation. (Why are The French so good at sex? I guess that’s another collumn.) The MILF theme song at the end (by Ben Molinaro) is also mos def worth a listen. “MIIIIILFFF, so bewitching…”

There’s also an extraordinary MILF in Maine making the news these days for driving around in her “MILF-mobile” sporting vanity plates that say, “TITSOUT” — an OBVIOUS reference to breastfeeding and something she celebrates by driving around topless, which is totally legal in Maine, by the way.

Mrs.Robinson’s Son, as a gay man, I know you must know, that shame is for beginners. So, let’s consider how you can get over this and help your mom own her MILFness.

Ever consider how your perception of the MILF concept is informed by the fetishization of youth in our culture? This is something that may serve you now, but believe me, it won’t always.

Or, maybe you find things MILFy and MILF-adjecent icky because they catter to cisgender, heterosexual, patriarchal notions of sexuality? Maybe you can help your mom push the MILF stereotype further by queering the space!

Traditionally, we think of MILFs going after young men. Maybe talk to your mom and ask her, “What if they didn’t just?”

Climb on board that minivan, son! MILFs need you.

With motherly love,

Dorothy signature

Hi Dorothy,

We’re a bi-cis mf couple that are looking to add a bit of excitement to our lives now that vaccinations have made hooking up feel safer. We were thinking of looking for a third person (m or f or enby) to join us but aren’t sure how to go about this. Any tips?

Good Things Come in Threes

Dear Good Things Come in Threes,

How exciting indeed! Nothing adds new relationship energy to a duo like the addition of a third and no drug can top the giddy, fuckstruck feeling that hits when this goes well.

So how do you make it happen and happen well? First, to the Internet! It may surprise you to know that just as sure as you and your partner are looking for a special guest, there are special guests out there dreaming of finding you. The myth of scarcity around sex is part of the scourge I call prude-itis. It serves only to try to hamstring our desires and make us forget that sex is fun and relatively easy to find. (Gay men, I know, you know this but it needs to be said for all of us queers with veistiges of hetero-normative culture embeded deep in our pyschies). So free your mind and your booty will follow.

Put an honest, relatable and authentic profile up on a dating site, with recent flattering (or as pos!) photos that highlight who you are and what you are looking for. Swipe right early and often because who knows what magic and beauty you’ll find when you scratch below the surface. Do your best to have both you and your partner be in on the chatting and always identify who is talking (it can be confusing for the third party not to know).

As well, make sure you and your partner have a serious conversations before around the general plan and your boundaries. No third wants to sit at the edge of your bed while you two work out your shit. On this same note, it’s a buzzkill if everyone is not an enthusiastic participant. So don’t do this if it is only to please one of you .

Above all, be kind, considerate and respectful. It takes a big leap of faith to jump into someone else’s relationship and when you’re part of the couple it’s easy to forget that the power dynamic will always be two against one. You hold a lot of privilege in this position so use every opportunity to center the experience on your special guest.

If the idea of wading into the dating world is overwhelming but you still want to make this happen, consider hiring a sex worker. Why settle for an amateur when you can have the expertise of a professional sex-sommelier? And sex workers know they get paid to go away after the experience (they’re counting on it). This has the added benefit of simplifying any relationship energy you and your partner might have around the experience.

Normalize paying professionals for sex. Sex work is not just work, but important frontline work. Can we bring some of the same energy we have for health care providers to sex workers? It ain’t so different.


Dorothy signature

Dear Dorothy,

One of the things I got up to during the pandemic was gaining a few pounds. I’m not normally that body-conscious, and I didn’t think it bothered me that much. I’m feeling good, and my partner and I have been enjoying some good sex.

Recently, though, my partner asked me about having a third person joining us in bed. This is nothing new to us, however — COVID-conscious as we are — it’s something we haven’t done since before this all went down.

I’ve always been pretty enthusiastic about group play, but this time I felt hesitant. My partner and I are both double-vaxxed, we are now comfortable with finding a hook-up, so it wasn’t COVID. I realized to my chagrin, that I was nervous about someone else seeing my belly.

Carrying The Covid 19

Dear CTC19,

It’s true that many people are feeling the after effects of all of that homemade bread we baked to get us through the March of 2020. And continually looking at our own faces during the interminable Zoom calls of 2021 hasn’t done much for our self esteem.

What can I say? We took the stay-at-home orders to heart and did our best to keep everyone safe. Falling out of shape and adding a few extra pounds isn’t anything to beat ourselves up about. The past 19 months have been hard and we still have some bumps ahead.

So yeah, I could offer you some advice about how to get active and reshape that shapely figure of yours, but I’d rather we think more about the meat of the issue, if you will. Why is being fat so frowned upon in our society? I remember back in uni we were asked to list all the attributes society uses to label fat people — lazy, unmotivated, lacking in self-discipline. And then all the attributes society uses to label fit people — driven, efficient, capable.

Notice anything about these groups? Who do you think has more money? Which group do you think works in better paying jobs? Which group would you want to hire? The fit people! Because they’re better capitalists. So CTC19, fatphobia is a capitalist affliction. Don’t let it colonize your mind.

Hide your self view on those Zoom calls and move on with your life, baby.


Dorothy signatureGot 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 @omgblog Instagram.

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