How to Do It

My Boyfriend Recently Introduced Me to His Family. Turns Out I Already, Uh, “Knew” His Brother.

Not sure how to handle this one!

A man looks upset next to a grimace emoji.
Photo illustration by Slate. Photos by Getty Images Plus.

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, 

I’m a 30-year-old gay guy. After years of lots of really hot flings but no long-term relationships, I think my current boyfriend could be the one. He’s much more wholesome and innocent than the guys I’ve been with in the past, which I actually really like. Plus, the sex is great! We’ve been together for six months, and he recently took me on a trip to his home state to meet his family (parents and two siblings, plus some extended family). Everything was going great until his brother showed up.

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I didn’t realize this beforehand, but the thing is, I hooked up with his brother once a few years ago. We connected on Grindr, the sex was really hot from what I remember, and then we never saw each other again. Turns out that the brother is in the closet. No one knows he’s gay, and throughout the whole trip, other than a bit of awkwardness at first, he didn’t acknowledge our previous encounter. It was as if we had never met (and trust me, we did).

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Things are getting serious with my boyfriend and I love him. So my question is: Should I tell him about the hookup? It’s not that I want to be like “hey babe, I had sex with your brother,” but I’m worried that if it somehow gets out one day, then my boyfriend will feel hurt and betrayed that I kept this from him. Or should I just keep my mouth shut and hope for the best? I don’t want to ruin the best relationship I’ve ever had over something that happened before we even met …

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— Sibling Rivalry

Dear Sibling Rivalry,

Your anxiety is understandable, but the priority here should be to protect the privacy of your boyfriend’s brother. Your boyfriend could have any number of reactions to the revelation that you hooked up with his brother—that outcome is uncertain. The impact the release of this information could have on the brother’s life, though, will more than likely be profound. That’s the most delicate component of this situation. Coming out is a process, and it’s his to go through. You shouldn’t risk complicating that for your own reasons, which exist in the realm of love but are nonetheless ultimately selfish.

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Keep in mind that if you reveal this information, your boyfriend could get offended on the principle that you released sensitive information about a loved one of his. Some people are really against outing, though “outing” may not be the right word here (are you actually certain the brother identifies as gay or otherwise queer, for that matter?). Your unit with your boyfriend is important, but this is family stuff and beyond you—as far as the brother was concerned, you were just a trick. You mean too little to him to wield such a power, and the responsible thing to do is stay out of it and let things happen as they do. If the brother does end up coming out, and brings along with him the truth of your tryst, just hope that your boyfriend understands that you did your best in a tough situation and that you were trying to be respectful by withholding information. If he’s truly compassionate, which is to say a partner worth holding onto, he’ll get it. If he doesn’t, he’ll be telling you a lot about who he is.

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Dear How to Do It, 

Writing in with open relationship trouble. My partner and I each did something off-limits: I got drunk and kissed someone in front of mutual friends, outing us to them as open, which my partner had asked me not to. Meanwhile, my partner repeatedly told me about their hookups after the fact when Id always asked to know in advance and have veto power. Is one of these things worse than the other? And/or do we both just suck at open relationships?

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— Are We Bad at This?

Dear Are We Bad at This,

From the outside, neither of these things strikes me as worse than the other, and I’m not even sure how one makes that call objectively. If one thing caused more pain than the other, that’s “worse” according to my rule of deferring to the most sensitive person in the relationship.
However, more important than the transgressions is the recovery from them: Did these acts create lasting damage in the form of trust issues? Have they altered you or your partner’s understanding of the relationship? If not, then they’re actually no big deal. It’s important to set and honor boundaries, yes, but it’s also important to be forgiving and understand that no one’s perfect. People slip up. Sometimes those slip-ups are detrimental, but when slip-ups actually turn out to have little lasting impact on the relationship, they can show you that you’re stronger than you think and that your rules actually can withstand some loosening. I’m inferring that you’ve actually talked about these off-limits breaches after the fact, and that’s important—checking in, communicating, showing your partner where you are falling short are all part of the process. But having the ability to write your own relationship rules means retaining the ability to rewrite them.

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You shouldn’t be asking me if you suck at this; you should be asking yourself. Your partner denied you the veto power you thought you had, and did not follow proper protocol. Can you live with them? If this were to happen again, would you accept it and forgive? Could you see, even, allowing post-hook-up heads-ups moving forward? Totally fair to say no to any or all of these questions and to make a push to following your rules as they were initially drafted. But if you can deal with the situation as it’s playing out, and not how you envisioned it initially, you’re probably going to have a lot less tension there, and your shared life will be undoubtedly easier. Sometimes our partners need to be allowed to be themselves, even if we think better of it.

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Dear How to Do It, 

I want to give it a go. And by it, I mean blowing another guy. I am, up to this point, a straight guy, 45 years old, who missed out on college experiments and teen exploration. So I want to try blowing another guy, but have no idea how to find someone. For various reasons, I am not interested in downloading an app … I dont want to get my picture out there. I just want to give it a go. I am also not interested in a park or an adult bookstore. How can I find a guy who will let me suck his penis to see if I like it and want to do it again?

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— Its Going to Blow

Dear It’s Going to Blow,

Given your stated parameters, your options include: Going to a gay club/bar, using a more text-based online platform like Doublelist, cruising the gym sauna/steam room (careful: getting caught having public sex there could, at minimum, revoke your membership), setting up a gloryhole in your own house and advertising on apps (given the gloryhole setup, you wouldn’t be obligated to show your face and in fact the idea that you don’t see each other is part of the point of a gloryhole), or using your sparkling personality to woo potential head receivers in your day-to-day. Most of these things will require more effort than just loading up Grindr or sitting at the receiving end of a prefab gloryhole, but them’s the breaks. If you want to circumvent modern conveniences, prepare to be inconvenienced.

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Did you write this or another letter we answered? Tell us what happened at howtodoit@slate.com.

Dear How to Do It, 

How do I bring up sex toys with my spouse? I was injured several years ago, and I’ve had urogenital issues ever since. She is aware of this and has always been supportive. After failing two different erection tests, my urologist brought up sex toys. I am interested in using a hollow strap-on, but I don’t know how to express my interest in using one as an alternative to penetrative sex. I like the idea of being able to act out traditional sex while also hopefully pleasing her, but I really don’t know how to bring it up. Tips would be appreciated.

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— Back in the Saddle

Dear Back in the Saddle,

One very easy thing you could do right now is just show your spouse the letter that you wrote. You state your predicament and interests quite clearly. If you’d rather do this out loud, stick with the facts: “My urologist recently brought up involving toys in our sex. What do you think about that?” Or, “I have an idea I want to run by you: Would you be interested in trying out a hollow strap-on? I like the idea of being able to act out traditional sex while also hopefully pleasing you.” Something that bodes well for you here is that she’s already understanding and supportive of your erectile issues, so what you’re saying isn’t likely to come as a shock. You’re also centering her pleasure in such a way that maximizes the potential appeal of such experimentation. If she’s as compassionate as you think she is, at the very least this won’t be a hard conversation to endure, even if it doesn’t turn out the way that you want it to. I think your task here isn’t so much to find the right words—you have them all in front of you—it’s to find the confidence to say them. Take a leap, it’s worth the risk.

— Rich

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