How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!

Dear How to Do It,

My 13-year-old trans son recently told me that a friend’s mom gave him, the friend (also trans), a vibrator. I know my kid thinks his friend’s mom is generally wacky and that she does not support her son being transgender and is generally ultra-religious, so I said something like, “Wow, that surprises me, and it seems kind of intrusive to get that from your mom.” (I was actually wondering if this was some kind of don’t-be-trans thing from the mom—like, clitorises are great! Here, have a vibrator! Look! Fun! I had no idea where this conversation was going.)

My son replied, “Yeah.” Then he went on, “Well, I guess it’s not illegal or anything. I guess it wouldn’t be hard to get one, even for a kid. They could probably figure it out … ” I wasn’t sure where all this was going, so I said again, “It seems like a weird thing for a mom to give a kid out of nowhere. I guess if a kid asked me for one, I’d get it for them.” At which point my kid made that pleading I-want-a-puppy face, and I said, “You want a vibrator?” And he said, “Yeah,” and I said, “OK, I’ll get you one.” So my questions are, is there any reason a 13-year-old shouldn’t have a vibrator? I can’t think of any special health hazard or anything—is there one? I guess I’m actually kind of happy he’s feeling that accepting of his body since I know with dysphoria, for a long time, he just felt like everything “down there” on him was gross and wrong. Am I crazy to think this whole thing is good, maybe? Am I crazy to get my kid a vibrator if he wants one?

—Vibin’

Dear Vibin’,

Philosophically, I see nothing wrong with you buying your 13-year-old son a sex toy, as he will be masturbating anyway. Just as you wouldn’t try to stop a fish from swimming or a bird from flying, so should you not attempt to impede a teenager from masturbating. By providing a vibrator, you are not merely being sex-positive; you’re fostering efficiency. That is good parenting, if you ask me.

But I’m guessing that part of why you’re asking this question is because facilitating a teen’s sexual expression is taboo and may feel like a weird thing to do, given teens’ vulnerability to exploitation. I thought it might be useful to get a legal expert on the record here, so I talked to Larry Walters, a First Amendment lawyer who serves as general counsel to the Woodhull Freedom Foundation, a nonprofit that advocates for sexual expression as a human right. I asked Walters if you could get in legal trouble for giving your son a vibrator, and the answer is probably not. “If a law enforcement agency wanted to prohibit the gifting of a toy to one’s child, I think there are significant constitutional issues that could be implicated in terms of family privacy rights,” he told me.

Regarding your health concerns: I haven’t come across any compelling arguments against a teen using a vibrator, but I’ve heard quite a few anecdotes in favor of it (such as this one). The notion that vibrators will desensitize genitals is sex-negative fear-mongering. A vibrator is preferable to whatever makeshift aid not manufactured for the purpose of masturbation your kid would forage (and teens, they will a-forage). Advise him to pay special attention to instructions, cleaning, and care, and don’t start with something that seems too advanced or complicated. This seems to me like a healthy situation from a sexual and communicative perspective, but maybe talk to your kid’s doctor, just to be safe, about any potential dysphoria-related issues that may come up here.

Dear How to Do It,

I have had an attraction to men most of my life. Because of my lifestyle, I have never acted on my urges, and my life has been me just pleasing women. However, for me to finish, I have to think of being with men. My current wife and I do love each other, and over the years, she has asked me if I’m gay. My wife has had problems getting me off for years, and this has caused multiple issues within our marriage. At this point, we both understand we love each other, but the love is gone. We don’t sleep in the same room, and we are pretty much together for the kids.

I have asked her in the past to try and use toys on me during sex, but she was disgusted with the idea. Over the last couple of months, I have looked on gay or bi dating sites. But I don’t know what’s real, or they ask for money to initiate conversations. I am not exactly a club kinda guy; I fantasize about “bull” type men, I just don’t know where to start. This is my first time ever attempting to act on the urges I have had since I was young, and these sites are basically turning me away from trying this and finally finding the real me. My question would be: Before I start adding money to join sites, is there a way or place to just talk to someone and find that comfortable place? I don’t know what all the abbreviations mean or how to classify myself. I just know this is something I have thought about for a long time, and I am nervous. I just want to find a place that I can talk without worries it’s a paid model, or someone fake, or a scam. Any advice?

—Looking

Dear Looking,

I sure hope you aren’t asking me how to cheat on your wife. Since I made a New Year’s resolution to give people the benefit of the doubt more often and it isn’t yet February, I will operate under the assumption that you’re behaving ethically. If you have already told your wife that you’re going to pursue your nearly lifelong hankering for men and she has given you her blessing, keep reading. If not, go directly to jail, do not pass go, do not collect $200. (And by that I mean: Go have a conversation with her, figure out your agreement, or consider a divorce, as needed.)

I’m not sure who is asking you for money to initiate conversations—the dating sites or the men you’re trying to talk to. But either way, you can do this kind of chatting for free on hookup apps like Grindr or Scruff. I can’t imagine anything grimmer than having to pay for the uncivil treatment common in virtual spaces where men cruise for sex, so don’t do that. As you feel comfortable, put up a decent picture, fill out the fields you understand (you can Google the ones you don’t), and maybe focus on guys who approach you with sentences instead of acronyms. You can even write “new to this” in your bio.

But honestly, it sounds like you may need a more neutral forum before you start shopping for dick. I think you should check out more discussion-oriented spaces, such as the r/comingout or r/GayMen subreddits. You could also look into your local LGBTQ+ center (find it here), since it may offer support/discussion groups and/or social events that will create low-pressure environments to meet and speak with other likeminded men. In terms of finding “bull” type men, whatever that means precisely, it sounds like you’d have the best luck in spaces for bears—when you’re ready, you can try a leather bar. While speaking with strangers online, you always run the risk that they could be lying to you even about something as major as their identity (what the kids call “catfishing”). A good thing to remember, though, is that they can’t steal money from you if you don’t give it to them. So don’t.

Dear How to Do It,

I am a college student, and this question concerns a friend of mine, who we’ll call Jaime.

Jaime is one of my closest friends, the subject of my unfortunate affections, and also my manager at our shared workplace (we both turned 21 during fall semester). We met at the beginning of the year when I began volunteering for the campus department we now both work in. Jaime, as manager, was tasked with training me. I very quickly realized there was chemistry between us. While I tried to just ask him out when we’d first met and save us all the heartache, my mouth found itself incapable of coughing up those words and I accidentally fell into a great friendship with him instead, eventually going to parties with his friends and drinking with them. Our friendship grew very close, and every time we drank together the physical closeness increased.

Jaime is asexual, and though he’s certainly got a dirty sense of humor, both of us are typically very touch-averse people. But when we drank together, the touch boundary disintegrated, and this too slowly escalated, from holding hands and hair petting to eventual cuddling. Our college is not an especially big drinking school, but typically when parties happen people drink a lot, and Jaime is no exception. All of this would not be my problem, except Jaime started making unwanted sexual advances while drunk. Not unwanted by me—unwanted by his sober self. While nothing too serious happened, just cuddling and the discussion of sex, it was still alarming to him. We discussed this later, sober, and decided we wouldn’t drink together because of this and only be friends—though I told him about my “crush.”

In the weeks following, we became closer friends, and I was hired to work in the department with a paid position, meaning now he was officially my “boss.” Jaime continued to act too close for someone who doesn’t reciprocate a friend’s feelings. His usual sex jokes, often targeted at himself or me specifically, continued, as did jokes about our relationship dynamic (“Guess we’re just electric together, huh?” when we shocked each other with static, etc.), and about dating and relationships. I thought that he might have misconstrued our earlier conversation, and we had a conversation about this. It ended up fairly one-sided—the only thing he had to say was that he’d never been interested and wouldn’t ever be, and he was sorry for the mixed signals.

The whole thing left me feeling shitty, and our friendship is currently in a rocky place. While I have talked to people (and my therapist) about how to rebuild a friendship if Jaime still wants one, and how to keep things from being awkward at work, I can’t stop thinking about the discrepancy between his behavior drunk and sober. He’s got no memory of most of these nights, and his justification sober is that he’s a “try everything once” type of person (as am I), and while drunk he might have wanted to have sex to see what it was like, and it was not personal. He maintains there isn’t any attraction on his end. Obviously. nothing is going to happen here, and the “no” is the half of the mixed signal you have to listen to, but I can’t get over the disjunct. The whole thing has me shaken and frustrated with every piece of the equation, but mostly myself, and asking the age-old question, “Why isn’t he into me?”

—Just Not That Into You

Dear JNTIY,

Jaime’s issues, which seem numerous, are beyond you. It’s trite to say that this is about him, not you, and even if you understand this on some level, it may not entirely satisfy you as an answer. But I can say with fair certainty that it’s true here, and I think committing to that belief will make the situation more tolerable.

Alcohol reduces inhibitions, and for some reason Jaime feels the need to maintain them otherwise. There’s probably some shame and personal mismanagement happening there. It sounds to me like he’s still got a journey ahead of him regarding his sexuality, but even if not, and his asexual identity is fixed and immutable, it’s not like you had a real shot anyway. Mixed signals are irresponsible means of communication, at best, and that he continued such transmissions after you discussed them (not to mention your crush on him) is borderline cruel. From your description—and it was rather thorough, no shade—you have been a good friend, and he has not. He doesn’t deserve you. You’re young enough to have the energy to search for the good in everyone, and to believe that friends are worth keeping. That is sweet, but there are advantages to growing old and jaded. You’re less likely to waste time on people who don’t deserve it, for one thing. Do yourself a favor and get a head start on that now. Forget Jaime and move on.

Dear How to Do It,

I’d like some input on hookup site etiquette. I’m a reasonably attractive sixtysomething single gay man, and I’ve had some success in meeting men on one of the sites that does not focus on a specific type of guy—apparently a fair number of younger men are into daddies, which can be discerned in their profiles . Lately, right after hooking up with a few men in their 30s and 40s, they’ve blocked me from their profiles, and their phones if we exchanged numbers. In every case, the sex was great, I’ve been careful about consent, and there was some lovely and affectionate after play.

There was no discussion or expectation of getting together again—I’m not looking for a relationship. I’m not social media savvy—no Facebook, Instagram, etc.—so is what I’ve described a common practice? Perhaps ghosting is a way to avoid having to say “no” if I were to propose meeting again? Or maybe I misread how they experienced our time together? Is etiquette and social media an oxymoron? Generation gap? Your thoughts would be appreciated.

—West Coast Daddy

Dear West Coast Daddy,

Shame strikes again, I reckon. One can be of many minds about the same hookup: At the very least, there’s the pre-hookup mind and the post-hookup one. The former is one of openness and excitement; the latter can be clouded by regret. I have no way to say what it is about you exactly that these guys are responding to, but take solace in the possibility that it may be nothing.

Residual shame from unresolved issues related to their queer sexuality (or their “daddy” preference) may cause these guys to immediately attempt to erase from their memories and lives any trace of the sex that just took place. They may have boyfriends (or girlfriends) and be paranoid about them finding out what happened. Or yes, perhaps they enjoyed the encounter less than you did and were putting on a show to get through it. You just don’t know what’s happening in people’s heads.

Blocking in general—no matter how needless or confusing it is to the person being blocked—is, for whatever reason, indeed fairly common on these apps. Etiquette does exist in the abstract, but the problem is that its interpretation and application varies widely. The problem with unwritten social rules is they float freely in the ether. One guy may think it’s more polite to block someone instead of bluntly explaining why he isn’t interested in hooking up again, and another may believe the opposite. This disparity and its attendant tensions are consequences of quick, imprecise hook-up app matches. Very much like Curb Your Enthusiasm, these apps frequently expose the futility of civility in a space where subjective interpretations of that very notion clash so readily. However, hook-up apps are nowhere nearly as humorous or brilliant as Curb, and actually kind of tragic at times, even. There’s the rub. Good luck?

—Rich

More Advice From Slate

Recently, I was hooking up with a guy from Grindr who was behaving a bit oddly. He invited me to his apartment building but said we had to meet in the building’s pool showers and not his apartment because he was being “discreet.” After we finished, we were getting dressed in the locker area, and he said, “Sorry if I seemed jumpy, but I’m married, and I live with my wife here.” Wife. In an apartment down the hall. I just gave him a look and left, but I felt a little guilty after. What do you think is my level of responsibility here?