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, et cetera). 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 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, it came up while my mom and I were at dinner. She had 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 love each other and have been happily married for more than 40 years. Your take would be appreciated.
—Son Of A Cross-Dresser
Unless your father is in some sort of emotional distress or your mother is in some sort of danger, I really don't see the point of this conversation, SOACD. It doesn't sound like your dad is struggling with shame. If your dad had to abuse alcohol in order to give himself permission to cross-dress alone in a hotel room, you surely would have mentioned that fact.
It sounds like your dad has successfully integrated cross-dressing into his life without harming himself or neglecting and endangering your mom, SOACD. You could say it's possible your parents' marriage is an ongoing success not despite the cross-dressing but because of it. If dressing up in women's clothes and occasionally escaping the confines of masculine performance helped your dad feel centred and emotionally whole, having this escape and having some people he could be open with about it—some straight male cross-dressing peers—could have made him a better husband and father.
I don't see what this convo—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. Even a married person has a right to some small degree of privacy, and each of us has a right to a small zone of erotic autonomy. 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.
Q My 19-year-old younger brother is doing financial domination online. He maintains a Twitter account that's mostly photos of him giving the finger and looking smug. He also posts pics of his feet, videos of him urinating (no penis visible, just the stream), and lots and lots of "bitch shots," i.e. crotch-height photos looking up at him from below. He uses a lot of homophobic slurs in the tweets that accompany these images. I would have exactly zero fucks to give about this if my brother wasn't still a teenager and wasn't posting photos of his face. I warned him the internet is forever, and facial-recognition software is a thing and people who don't understand the role-play aspect of his hate speech will think he's a bigot. This could come back to haunt him socially or professionally. Complicating matters somewhat, my little brother is a straight boy and I'm gay. He's not making a ton of money doing this, but he's making enough that my parents are wondering how he's buying all those super-expensive shoes. What do I tell him? What do I tell them?
—Falling Into Nefarious Doings Of Male Sibling
A You've already told your brother the internet is forever and the low-key, low-stakes pseudo sex work he's doing could come back to haunt him, FINDOMS. Beyond that... well, there's really not much more you can do. Your brother is an adult, as are the men paying "tribute" to him, as they say in FinDom/FinSub Twitter, and he's free to make his own choices. As for your parents, if your brother is old enough to set up his own Twitter and Venmo accounts, he's old enough to come up with a plausible lie about those shoes.
Q I'm 25 years old and polyamorous. I'm in a relationship with a 28-year-old man since August 2018. It was just him and me when we first started dating, and then his old flame came into the picture. This whole time he said he was not interested in having kids and a home and a primary partner. Since he got surgery in June and is now unemployed, he's had a lot of time to think, he says, and now he's decided he wants kids and a home and a primary partner. He knows I do not want any of these things, so he says his old flame is the person he's going to do this with. He has made jokes about being an "alcoholic" since I first met him, and I thought it was just a joke. But now he's spending money he simply does not have on alcohol. It worries me. Do I hang in there? Do I throw in the towel? I love this man very much, but I'm so confused.
—Previously The Primary
A I'm so sorry, PTP, but it would appear you've lost the unemployed guy with the drinking problem to another. But take heart: You're young enough to meet someone who wants what you want and doesn't want what you don't. I'm certain that after meeting this person—or even long before you meet them—you'll be able to recognize that your ex did you a favour. Sometimes we dodge the bullet, PTP, but on rare occasions the bullet dodges us.
Have a question about sex, sexuality or relationships? Email it to Dan Savage, it could get answered in the column some week soon.