My Boyfriend Used to Date My Son and I Don’t Know What To Do


Dear Dr. NerdLove:

I recently met a man on a dating site. He’s younger but I think I’m over that part. When we first started talking, when I asked his last name it sounded familiar and I asked if he had relatives near where my son lives. I mentioned my son’s name, and he said he knew him and his wife. And one of his grandkids went to school with my grands.

Fast forward to more intimate talks. Namely, a three way. After his divorce he had one. Not a problem for me, anything before me is none of my business. It’s who he had it with that is my problem. It was with my son and my daughter-in-law. So I’m having a BIG problem with that. Shocked isn’t the word for it. I would have thought they were the most vanilla sex people I could think of. According to the new guy they are on several hook-up sites, etc.

I haven’t seen them since I found out, that is going to be hard. I’m not bringing it up but just knowing is going to be strange.

Now back to the guy. I’m beginning to really like him. But how do I have a relationship with someone that slept with my family? We have agreed that the subject never comes up again. I’ve been a widow for 3 years, I’ve had a few dates in the last year but this is the only one that seems like it might go beyond dating.

Stuck In The Middle With Ew

Alright, let’s address a couple issues right off the bat.

First, if this situation seems familiar it’s not just because “banging my son/daughter’s partner” is a popular theme in porn but also because recently Dan Savage fielded a question regarding a man discovering that his boyfriend had a threesome with his parents and wasn’t sure how to deal with it. So apparently this is a thing…

Second, my standard position for potential fake letters and scenarios is simple: I’m not terribly worried about them. While yes, there are folks who use advice columns or subreddits for creative writing exercises (or to get their jollies), most fake letters are pretty self-obvious. Of ones that “get through”, my feeling is that if there is potential utility for my readers that can be taken from reading a letter that may or may not have actually happened, then there is value there, regardless of whether the author is sitting back going “gotcha!” And, just by virtue of the nature of advice columns, most letters sent in are theoretical exercises for the rest of the readership anyway, regardless of the objective reality of the events depicted.

Now with those out of the way, there seem to be two issues at play here.

The first is dealing with the shock of finding out things about family members that you may well have preferred not knowing. I’m of the opinion that one of the most important gifts you can give family members is the gift of Not Knowing Shit You Don’t Need To Know. There are a lot of things that people in general don’t need to know about the lives of their parents or of their children, especially when it doesn’t directly involve folks not involved. Now for a lot of people, this is an area with a lot of nuance. Knowing that your family member is polyamorous or involved in a poly triad, for example, is one where it may be useful knowledge. It makes it easier to understand family dynamics, realizing your baby isn’t cheating on their partner (or being cheated on) and could well involve issues like notifications, next of kin or powers-of-attorney in the event of emergencies. On the other hand, it can also be an issue if one’s family is hostile to anything other than strict orthodox monogamy and heterosexuality.

However, “your child and their partner are kinksters or practice consensual non-monogamy” is almost always a “Shit You Don’t Need To Know” and often will be “Shit You’re Happier Not Knowing”. These are things that don’t involve or require that parents (or children, for that matter) to be aware of and, in most cases, involve things that parents or children would prefer not to have in their heads. Even sex-positive folks don’t necessarily need to or what to know what their kith and kin get up to behind closed doors; being cool with their choosing to do so isn’t the same as knowing about it.

Unfortunately in this case — and for once, through no fault of the letter-writer’s own — you’ve found out things about your son and daughter-in-law that you’d rather not know. Unfortunately, as far as their sexual proclivities go, this isn’t something you can unknow, without sci-fi technology, experimental brain surgery or deep sips if Unsee Juice. However, the good news is that this fundamentally changes nothing for you or for them; it’s not something that affects your relationship with them, nor is it something that’s inherently harmful or negative in their lives. If anything, it’s apparently a net-positive for them; having sexual adventures in their lives is actually good for the strength and longevity of their relationship. So while you have been burdened with extremely cursed knowledge, you can, at least, recontextualize it into “this is something that enhances their lives and makes their relationship better and so good for them.”

And then stuff that particular awareness as far down the memory hole as you possibly can.

Now, as for your new beau… well, if I’m being honest, this all comes down to lines and what lines can and can’t be crossed for you. This is going to have to be a very personal matter and one that can be difficult to untangle for folks. It’s an area where it’s kind of difficult, if not impossible, to have a universally applicable stance. To give an example: I am firmly on the record as saying that “you don’t get to call dibs on other people”, which includes dictating who can and can’t date your ex, your friends’ exes, your siblings, etc. However, I, personally, would find dating someone who also banged immediate blood relatives of mine to be a step too far. Having a sex-partner in common with folks you may know socially is one thing; having one in common with family reaches a level of “um… yeah, not for me” that I have a very difficult time imagining being cool with. Especially if said family members were my parents or (theoretical, non-existent) children. That’s a moment when crossing the streams seems like a great way to induce full-protonic reversal.

So, unfortunately, I don’t really have an answer for you in this case. The potential for things going Real Goddamn Bad when — not if, but when — your son and daughter-in-law learn about your new prospective boyfriend seems higher than what I would consider an acceptable level of risk, especially if you, your son and daughter-in-law don’t have the kind of relationship where you can talk frankly and openly about sexual experiences. It would also involve being able to compartmentalize the shit out of things so that everyone involved (with, apparently, the exception of your match) can deal with the “I Don’t Want This Image In My Head” factor which is, likewise, pretty goddamn high.

If you and they are able to sit down and actually talk things through and get to a place where this won’t be a barrel of squick for everyone involved… well, blessings on you all. My personal feeling on the matter is that there’re thousands upon thousands of other eligible singles out there, and most of them won’t be looking to “complete the set”, as it were. As lovely as I’m sure this guy is, there’re others out there who are equally as awesome and haven’t had threeways with your immediate family. I’d recommend finding one of them.

Good luck.


Hello Dr. NerdLove! I’d love some advice on a little bit of an embarrassing situation. I feel in crush with a Twitch streamer over quarantine. I realize that the relationship (not really a relationship) is completely one-sided and parasocial, though he knows my Twitch identity and the details about that identity that I’ve divulged in Twitch chat and Discord. He’s not too big of a streamer (recently about 20-50 views a stream at a time) but he is professional.

I’m actually on the older side (I’m 26 y/o and he’s 25) and am used to going for things that I want without fear of rejection. I want to confess my crush at some point because I feel like not doing so would always give me a small sense of remorse. There will also be a “what if” in the back of my mind. I know I will get rejected because he is a professional streamer, and he literally just doesn’t even know me. Not to mention that I can’t even envision a future in the possibility that he would be remotely curious (we live in different states and are still navigating our careers). But still, I want to confess my crush at some point.

If I should do it, I’m not sure what my best ask would be? A request for an online date conducted on Zoom? A request for a date if he is ever in my state? Or should I be waiting for an opportunity to meet him in person? Or should I use DM’s to see if he might be receptive to more casual chatting not in the context of a public Twitch chat?

Would love to know what you think!

Hopeless Online Admirer

I see it’s that time of year again.

Every so often, I get letters from folks who have developed a one-sided crush on a celebrity — whether it’s a podcaster, Twitch streamer, YouTuber, porn star or someone from TV, movies and so-on. The problem is… well, like I said, they’re all one sided. This is what’s known as a parasocial relationship — that is, a one-sided relationship born out of feeling like you’re connected to someone because you’ve consumed so much of their content that you feel like you know them personally. This is an issue that is practically older than steam; as long as there’ve been celebrities, there’ve been folks who’ve developed one-sided, even borderline obsessive crushes on them. Silent film stars like Rudolph Valentino had people proposing marriage to him in letters. Hell, the term “Liztomania” was coined in 1841, when composer and conductor Franz Lizt’s fans would mob him in hopes of getting hair, bits of clothing and even his backwash from his coffee.

And this was in a time when mass communication was next to non-existent. With the advent of the Internet and social media, we all are mere clicks away from talking to and interacting with our favorite celebrities and content creators; hell, these days, you can have some of your favorite lower-tier celebrities send you a personalized message through services like Cameo or enter charity auctions to hang out with them.

But while Facebook, Twitter, Instagram et. al may allow you to have contact with some of your faves, there’s still a certain level of remove between you and them; after all, who knows if that’s actually Mark Hammil posting to his Twitter account or his social media person?

(Yes, I know Mark’s pretty hands on with his social media accounts; I was pulling a name at random.)

The modern forms of celebrity — and the way that content creators are encouraged and incentivized to interact with their audience — however, blurs the lines considerably. There are powerful financial reasons for creators, actors, musicians and the like to foster a sense of community and connection with their fans. This not only helps solidify the connection the fan feels to the creator’s work — helping encourage them to be a long-term fan — but also to create a sense of familiarity, even investment in that person and their works. It’s one thing to ask someone to buy your content; it’s another to encourage them to subscribe to your Patreon or OnlyFans or what-have-you because it offers them greater access to you and fellow fans.

(…I say while very pointedly not looking at my Patreon or Ko-Fi accounts and coughing awkwardly.)

Livestreaming, likewise, blurs the lines between fan and creator. These are times when you often are interacting directly with your favorites — you may even get direct shoutouts from them or replies to your comments in the chat. And, again, this helps create a sense of connection between you and your favorite streamers… one that often helps spur on that sense of “we have a connection”.

Except… honestly, you don’t. Part of what makes something a parasocial relationship is that it’s inherently one-sided and — critically — a fantasy. You don’t actually know that person; you have only seen so much of what is a carefully curated part of their lives that you feel like you know them and have a connection with them. It’s a feeling that — deliberately or not, calculated or not — is encouraged by the nature of the medium and how creators support themselves in this day and age.

And unfortunately, this leads to a lot of inadvertent heartbreak when folks realize that their inconvenient and unrealized crush is exactly that: unrealized. And likely to stay that way.

Now in your case, HOA, there’s a level of self-awareness here. You’re aware that yes, it’s one-sided. Yes, it’s completely parasocial. Yes, he’s aware that you exist in as much as you are a regular in his streams and he recognizes your username. You’re also aware that he’s gonna say “um… thanks” at best.

That doesn’t actually change the math on this.  In fact, in some ways, it makes things worse.

Here’s the thing: being aware that what you’re doing is a bad idea and doing it anyway doesn’t magically make it a good idea. It’s just a bad idea compounded by your choosing to ignore the warning signs and barreling headlong into the “find out” half of the equation. And, speaking as someone who has friends and acquaintances who have various levels of celebrity and who’ve dealt with fans having crushes on them… it’s almost always uncomfortable as shit. In fact a number of folks have talked about how uncomfortable and awkward it was to find out that people they  matched with on dating apps turned out to be fans. There really isn’t a good way to say “thanks but no thanks”, especially publicly, to a fan that isn’t going to make things feel painfully weird.

Rather than asking “what’s the best way to tell them,” I think it’s better to ask yourself what the point of telling them is, especially with the knowledge that it’s not gonna go anywhere. This feels a lot less like “shoot your shot and see what happens”  so much as “well, this will guarantee that senpai will notice me,” and getting that extra bit of validation of knowing that your fave now knows exactly who you are. And if that’s the case… well,  honestly, that’s not a great look on anyone.

But even if that’s not the case and it really is the “look, it’s a one in a million shot but people DO win the lottery,” well… considering how uncomfortable this tends to make people, I’m still pretty firmly on the side of “nope”. Going through with it with the full understanding of just how this tends to make folks on the receiving end feel is kinda selfish at best.

And honestly? That feeling that “well, if I don’t, I’m always gonna wonder?” I am here from the future to tell you that in this case, throwing away your shot won’t be one of the great regrets of your life. Odds are that the feeling of “but what if…” is going to fade into the background faster than you can imagine, especially after the inconvenient crush on your fav fades and becomes vaguely remembered cringe.

Do yourself a favor: put your energy towards meeting someone else. Someone who actually lives close by, who’s looking for a relationship and — importantly — who actually knows you and wants to date you.

Good luck.

This post was previously published on


Join The Good Men Project as a Premium Member today.

All Premium Members get to view The Good Men Project with NO ADS.

A $50 annual membership gives you an all access pass. You can be a part of every call, group, class and community.
A $25 annual membership gives you access to one class, one Social Interest group and our online communities.
A $12 annual membership gives you access to our Friday calls with the publisher, our online community.

Register New Account

Log in if you wish to renew an existing subscription.

Choose your subscription level

By completing this registration form, you are also agreeing to our Terms of Service which can be found here.



Need more info? A complete list of benefits is here.

Photo credit: iStock


The post My Boyfriend Used to Date My Son and I Don’t Know What To Do appeared first on The Good Men Project.

Older Post Newer Post