The Birthday Boy

...h this woman: $600! My first concern is for his safety. Maybe I listen to too many true crime podcasts, but I’m worried that something bad will happen to him and I’ll never see him again. I know that many people visit sex workers and live to tell the tale. And now, as I sit here writing this, I realize that it’s sex workers who are the more vulnerable ones. So, maybe his safety is a non-issue. Still, I’m his mom and I worry. My other concern is that engaging with this woman may mess him up sexually. He hasn’t had any prior sexual experiences and I’m worried that if this woman is his first experience, it will make ordinary, real-life pedestrian sex uninteresting for him in the future. I have no one to talk with about this which is why I’m reaching out to you. I’ve always maintained an open and non-judgmental relationship with my son, but I’m really struggling with this. He already has an appointment and I’m super ambivalent about this and need your reassurance. They Grow Up So Fast “I’ve always been kinky,” journalist and author Jillian Keenan wrote in her 2016 memoir Sex With Shakespeare. “My fetish appeared early, long before I knew anything about kink or the diversity of sexual lifestyles. As a child, I pored over any book that mentioned spanking, paddling, or thrashing. Tom Sawyer and The Whipping Boy went through many early reads, as did, believe it or not, key entries in the Oxford English Dictionary…. I looked up the definitions for spank, paddle, thrash, and whip so often that, after a few years, my dictionary automatically fell open to those pages.” Keenan’s memoir tracks her two lifelong obsessions: the plays of William Shakespeare (way kinkier than your high school English teacher ever let on) and her love of spanking, obsessions that have intersected and informed each other in surprising ways throughout her life. Reading Sex With Shakespeare might give you some comfort, TGUSF. Because Keenan, who like your son was raised by a single mom, found a community of like-minded kinksters as an adult, found love and lost love and found love again, and along the way made a name for herself as a fearless foreign correspondent. And like Keenan, TGUSF, your son is kinky and always has been. Now, not every pre-pubescent child’s obsession becomes a full-blown kink in adulthood; if that was the way it worked, there would be a lot more dinosaur fetishists out there. (And there are some!) But your kid’s kinks, like Keenan’s kinks, were hard-wired early and a first sexual experience that’s strictly vanilla won’t erase them. He is who he is, TGUSF, and while dating is going to be a little bit more of a challenge for him, TGUSF, you son is gonna have a much easier time finding like-minded perverts out there—friends, play partners, and potential romantic partners—than kinksters did before the Internet came along. All that said, I don’t think you should get your son a sex worker for his birthday (or go halfsies on one), TGUSF, and I don’t think your son should’ve asked you to. Being close is fine—being close is wonderful—but you can be close and have or establish healthy and appropriate boundaries. “There are things a mother has a right not to know,” my mom liked to say. She knew her kids, once we were adults, were out in the world taking risks and exploring our sexualities and making mistakes and sometimes getting into trouble. Mom was there for us when the shit hit the fan, but she didn’t want to know where we were, who we were with, or what we were getting up to at all times. Because she didn’t wanna worry more than she, as a mom, was going to anyway. So, when I called my mom once from a sex dungeon in Berlin (on her birthday!), and she asked where I was, who I was with, and what I was doing, I lied to her. If your son is old enough to book a session with a sex worker, TGUSF, he’s old enough to pay for it himself. And if he needs to talk about it with someone and he doesn’t have a friend he can confide in about his kinks, well, that’s what Reddit and Twitter and sex-advice columnists are for. His sex life isn’t your business, and he shouldn’t make it your business. Also not your business: how your son chooses to spend his birthday money. If he spends his birthday money on a PS5, that’s something he could share with his mom. If he spends his birthday money on a sex worker, that’s something he should lie to his mom about. If your son doesn’t know he should lie to his mom about that kind of stuff yet—if he doesn’t know there are things a mom has a right not to know—then you’ll have to tell him. P.S. My first sexual experiences were exactly what my mom wanted them to be—very straight and very vanilla—and they didn’t make me any less gay or any less kinky. That’s just not the way it works. I’m feeling a little lost about something. I’m a 42-year-old gay man and I’ve been married for nine years. My marriage has been very rocky, and I should’ve had the courage to end it much sooner. I have now made the decision to do so and will be filing right after the holidays. When we took a break last year and separated, I briefly met an incredible guy. More recently, I’ve come to know him better and I think he is really special. I’m not divorcing because of him, but sometimes it takes meeting a special person to realize what you’re lacking in your own relationship. I’ve talked with him about the situation, and we will remain friends whatever happens, but he doesn’t want to be a “rebound.” I don’t want him to be that either. I’ve only come to know him better in the last couple of weeks, and I’m scared of asking him if he’d be open to dating me when the divorce is final. I’m afraid that if I do that, I will scare him off and I don’t want to lose him as a friend. Dreaded Rebound Relationship Here’s the funny thing about rebound relationships… when they work out, no one remembers they were rebound relationships. They’re just relationships. But when two people get together shortly after one or both got out of a prior relationship and it doesn’t work out, everyone stands around saying, “Oh, yeah, those rebound relationships, they never work out.” I say this as someone who has been in a rebound relationship for almost three decades. I met my husband the first night I went out after getting my heart broken. I almost didn’t give the guy who would eventually become my husband a chance, DRR, because I’d heard—again and again and again—that rebound relationships never work out. “If it weren’t for rebound relationships, I wouldn’t have been with the incredible man I’ve been with for 19 years and counting,” said my friend Dr. Daniel Summers. “When we first met, I was still mired in sadness after having been unceremoniously dumped shortly before. Not only did I still have feelings for the other guy, but the man also who would eventually become my husband watched me cry over him. And then, it clicked. The guy who was right in front of me was the one I had been looking for all along. Nobody would ever call him my ‘rebound husband.’ They simply know him as the guy I was lucky enough to meet at the right time.” Maybe rebound relationships would have a better reputation if people like me and Dr. Summers occasionally referred to the men we married as “rebound husbands,” if only to remind people that, yes, rebound relationships sometimes work out. And since very few of us wind up married to the first person we dated seriously, most of us are in rebound relationships that somehow worked out. All that said, DRR, it’s Mr. Incredible who has qualms, not you. He’s the one who’s worried about getting into a potential “rebound relationship” with someone who just got divorced. Maybe he believes what everyone assumes to be true, i.e., rebound relationships never work out, and getting into one that does work out might be the only way to convince him otherwise. Getting into one that doesn’t work out, on the other hand, could wind up confirming his priors. It’s also possible he isn’t interested in dating you—bound or rebound—and his stated wariness about being your “rebound” is a white lie meant to spare your feelings. But there’s only one way to find out how he really feels: initiate that divorce, follow through, get it finalized, and then ask Mr. Incredible—assuming he’s still single—how much more time has to pass for your relationship to be out of “rebound” territory. Follow Dr. Daniel Summers on Twitter @WFKARS. Send your question to [email protected]