Q: I’m a 35-year-old bisexual man in a LTR with a man. My question, however, has to do with my parents. As an adolescent/teen, I was a snoop (as I think most of us are, looking for dad’s porn stash, etc). I was probably 12 or so when I found evidence of my dad being a cross-dresser. There were pictures of him in makeup and women’s clothing, and correspondence (under an alias and to a separate PO box) with other men interested in cross-dressing. As far as I could tell, he did this alone in hotel rooms while on work trips. Two years ago while on vacation, it came up while my mom and I were at dinner. She had recently found evidence, and she needed to take a short break to visit a friend out of state to process. She suggested I bring it up with him (I guess) because I’m queer and she knows I used to help host pansexual play parties. My dad is a devout Republican and comes off as very masculine. I see them only a couple times a year. Should I try to bring this up with my dad and let him know that I’ve known about his cross-dressing for more than 20 years and offer my knowledge about kink and alternative sexuality? Or just let him do his thing and we all retain the illusion of ignorance? My parents are still happily married—and whether it is more companionate than lusty, they love each other and have been married for more than 40 years. Your take would be appreciated. —Son of a Cross-Dresser

I don’t see what this convo—coming 20 years after you discovered his cross-dressing and two years after your mother discovered it—will achieve other than embarrassing and humiliating your father. Your parents’ long, loving, successful marriage coexisted with your father’s cross-dressing for four decades, and I don’t see why it can’t continue to coexist with it now. And if your mother is sad that your dad never shared this with her and wants to reassure him that he didn’t need to hide this part of himself from her and that she loves him just the same, she doesn’t need to deputize her bisexual son to initiate that conversation. If she thinks it would be a relief and not a torment for her husband to know she knows and that knowing hasn’t changed how she feels about him, she should tell him.

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