I have been flirting with a woman in her 30s and we have been planning some kinky play. I also have a thing for her mother (who is in her 50s) and have done some light kinky play with her. Both are cool with me playing with each separately, but I’m still feeling a bit uneasy. Is this just social conditioning coming at me?

Here I am trying to roll gently back into columnist mode after a two month hiatus, but nooooo, you all wouldn’t want to give me an EASY question, would you? THAT WOULD JUST BE WAY TOO KIND. Well strap yourself in folks, because I never back down from a challenge!

Your situation is more like “traditional” polyamory and kink than you’d immediately think. On a base level, you’re walking into a pre-existing dynamic. Look at it as though you were interested in a woman who had other established play partners active in her life, and you’re the shiny new toy (or the woman is the shiny new toy, or you’re BOTH shiny new toys...whatever, you get it). You’d want to do your due diligence in respecting how these people are connected, observing how they communicate and interact with one another, and just generally taking the overall temperature of the dynamics involved before making the decision to integrate yourself.

I never thought I’d use any of my mother’s advice in my column, but it seems an appropriate time to do so, so here it goes: Trust your gut. You have my permission to decline this particular arrangement without passing judgment on these women’s boundaries (or therefore lack of); you can also put your decision to play with the daughter on hold until you get to know both of these women better. I’m telling you, a false sense of immediacy has been the death of many a dynamic with great potential!

If you want to continue to push past your uneasiness and I can’t convince you otherwise, I would advise you to schedule a meal with both women, with the explicit caveat that the evening NOT devolve into anything physical, or even flirtatious. In fact, establish a set time that you “must” leave by, and go easy on the wine at dinner. Look, I don’t know that these women aren’t going to entice you into some incestual shit, and frankly, neither do you.

Then, be up front with them. Unpack your uneasiness, including how you’re wavering between the “appropriateness” of it all vs accepting your unease as a construct of social and sexual conditioning. Ask them questions about their relationship with one another. What was their relationship like prior to them coming out to each other as kinky? What motivated them to do so? Have they ever shared a play partner before, or are you the first one? Have they discussed what their boundaries would be between one another?

Examples of good questions could be:

• Are they comfortable sharing public space with you together?
   

• What level of conversational disclosure would they observe in terms of discussing you with each other?
   

• How do they imagine scheduling individual time with you would work?

Examples of red flags could be:

• If they're living together
   

• If they aren't financially independent from one another
   

• If you sense any kind of competitive vibe between them

Have a list of your own personal boundaries on hand to run by them (and remember, those boundaries are allowed to fluctuate and be edited over time!). Talk about how private or public you all feel comfortable being with your connections to one another, and how to handle scrutiny from the outside. Finally, if applicable, talk about safe(r) sex practices.

If it seems like a hell of a lot of labor, that’s because it is. And if you’re already thinking, “This is WAY too much work!”, well, then you have your answer.

This is the first - and potentially last - time in the history of this column that I’ll make this request, but to satiate the curiosity of everyone reading this: PLEASE write back and tell us how it all worked out! I’m already on the edge of my seat...