Estimated reading time: 19 minutes
Dear Dr. NerdLove:
I’m writing to you because of a problem I’m having with my fiancé’s parents that I’m worried is only going to get worse.
I’ve been with “Janet”, now my fiancé, for three and a half years. Our personalities clicked from the moment we met at a creative-professionals-under-30 Meetup and we both realized very quickly that we had found our better half. I can’t believe how lucky I am that someone as talented, creative and ambitious as Janet, and she feels the same about me. We’re looking forward to being married and raising a family together.
In that time, I’ve gotten to know her family and while her cousins, aunt and uncle all like me, my relationship with her parents has been polite at best. They’ve never been rude or openly inhospitable to me, even in a well-mannered way, but it’s impossible to miss that they’re tolerating me at best. I am not the only person who’s noticed this; Janet has mentioned it several times as well, to me and to her parents.
The central conflict is that her parents are very small-c conservative – they are very firm on holding to long-running family traditions and ideas of what is or isn’t “appropriate” for people. They are big believers in conservative dress and careers and maintaining a very top down, Father-Knows-Best style patriarchal family dynamic. I, on the other hand, come from a family of aged out punks, former hippies and I-Remember-When-Burning-Man-Hadn’t-Sold-Out bohemians. While I can clean up nicely and I’ve got a degree and a steady job in a creative industry with a health salary, I’ve still got more Joe Strummer in my DNA than Joe Kennedy. Janet was a private Catholic school and church girl, I was a high-school troublemaker, insert joke about opposites attracting/skater boy lyrics here.
When their precious little girl brought home a guy with tattoos and piercings, who is most comfortable in a t-shirt and jeans and Docs instead of Brooks Brothers shirts, pleated slacks and loafers, there were some gritted teeth and forced smiles. They clearly thought their daughter was having a rebellious phase and hoped that they could wait things out.
(I feel like I should point out that Janet was 26 and considering a graduate degree when we met.)
Obviously, that didn’t happen. Now it seems as though they’re hoping to actively interfere in our relationship with a goal towards changing her mind. This is where it gets strange.
When it was becoming very clear that we were serious, and I was getting ready to propose, her father pulled me aside towards the end of a family visit. He told me that while his daughter could make her own decisions, he would not give me neither his permission nor his blessing to ask for her hand in marriage. Yes, he actually used the word “permission”. According to him, I was not a good match for his daughter, and he didn’t want to see her “wasting her potential”. I told him that this was fine, I hadn’t been intending to ask his permission, seeing as it was 2025 and not the 1950s and Janet was her own woman who could make up her own mind.
Since then, both her father and her mother have been making comments to her about not “rushing into things”, “thinking about her future” and about whether certain careers (such as, say, mine) could actually support a family. Janet, now officially my fiancé, pointed out that between her salary and mine, we have a very comfortable income that easily supports our chosen lifestyle, and we’ve even saved quite a nice nest egg in our savings account for our future house and family. This doesn’t seem to have made a difference.
They have also apparently been making a point to bring up “Brad”, a guy that Janet knew in high-school and college and how well he’s been doing lately. Brad is the son of one of her father’s friends, and according to Janet, her father had always hoped that she and Brad were going to get together some day. In fact, he had never really stopped trying to set them up, even after we started dating. Brad, in contrast to me, regularly wears suits and ties, quarter zips and khakis when he’s feeling casual and spicy. Unlike my “not serious, not ‘real’” job, Brad is in finance, on the glide path to joining the c-suite at his company and, also according to Janet, about as interesting as an empty beige wall and half as exciting.
Where things are getting weird and frankly uncomfortable is the fact we’re going to be spending the holidays with her family as per one of their unbreakable traditions, only we have just been informed that, in a stunning coincidence, Brad will be joining us. His family is out of the country while he had to stay behind for work and according to Janet’s father, it would be a shame for him to be alone for the holidays.
I don’t think I’m being excessively unreasonable to see this as a setup. I don’t have any worry about this actually working like he hopes, but I DO worry about the precedent this is setting for our future relationship. This feels like an escalation, and I can’t help but think that if this doesn’t get nipped in the bud, it’s only going to get worse. It’s very genteel boundary pushing now, but I don’t think I’m wrong to expect that there will be more, and possibly less genteel pushes and interference down the line. They’re already making noises about not being at the wedding, pointed questions about who’s going to pay for it all, and about limits on Janet’s ‘future when he’s gone’.
(We both feel that these are series of veiled financial threats. This is not out of character for her father. He long used money as a means of control, such as leveraging his paying for school and first apartment as getting a say over her education, university attendance and choice of majors.)
Neither of us are worried about the money. As I said, we’ve got a comfortable living and good savings. However, the behavior is bothersome and I don’t know how to handle this without an actual confrontation with her father, which Janet also wants to avoid. Janet strongly wants me to have a good relationship with her family, and that means it’s important to me. How do I deal with future in-laws who not only don’t like me, but seem to be set on actively bent on sabotaging our engagement?
Planet Schmanet, Janet
There are times when I get letters that seem implausible enough that I feel like possibly investing some time into trying to track down which Hallmark Christmas movie or mid-tier shoujo romance manga they come from, just for the challenge. And then I remember that I’ve got deadlines and my hyperfocus would just lead to reading far too many Wikipedia and TVTropes pages, so better to just roll with it as though it were real.
(In fact, I’m somewhat tempted to throw open the doors and make a challenge for 2026: send the best letter to an advice column based on fiction and let’s see what happens.)
As per usual, I want to give my standard disclaimer about fake letters: I’m not terribly bothered by someone slipping a creative writing exercise past my filters and bullshit detector as long as there’s actually something useful to be learned. After all, all letters to an advice column are functionally fictional to everyone but the LW. And in this case, I think there is a useful lesson to be had from this.
In this case, PSJ, the lesson is this: this isn’t your fight to pick, and doing so is going to cause more problems than it’s worth. If you want to respect Janet’s wishes to have a healthy relationship with your in-laws, that is.
Now, that doesn’t mean that they’re not doing anything wrong here. I would agree that your future in-laws’ behavior is weirdly retrograde, boundary-pushing, and frankly, head-scratchingly passive-aggressive. It sounds to me like your future father-in-law has never fully accepted that a) he has a grown-ass adult for a daughter with her own life and free will, and b) that he doesn’t live in some weird John Hughes or Joel Schumacher movie. Which is especially sad because at least the rich asshole bullies and villains are interesting.
(Plus it would lead to wacky Wedding-Crashers/Meet-The-Parents-esque shenanigans that would make for a memorable holiday visit instead of trying to quietly drink away the second-hand embarrassment at watching all this sub-par manipulation go down. Hope the wine’s good enough to make up for it. Although if he invites you to try his special vintage of Amontillado, I recommend you decline. Politely.)
He also, apparently, managed to raise a child to adulthood without ever learning the lesson that obvious parental disapproval has a tendency to make the forbidden fruit all the more tempting. I mean, shit, even The Fantasticks knew how to lead with that one.
You are correct: you don’t need his blessing or his approval. It’s nice to have, and it makes the future relationship a little less contentious. However, seeing as how women’ve had the right to vote, own property and manage their own finances for the last 3/4s of a century, it’s hardly necessary.
I’m also somewhat surprised by the implied-if-apparently-impotent threats of financial coercion. Sure, writing them out of the will is a tried-and-true way of keeping failsons and daughters in line, but seeing as Janet has her own career and bank account entirely separate from them, I’m not sure what the point would be. Maybe the estate she would inherit would mean wealth beyond dreams of avarice, but it hardly sounds like meaningful leverage to threaten it when she’s handling her own bills. Maybe it’s because he thinks you’re a filthy gold digger trying to woo his daughter in order to abscond with her money?
Dunno, I’m running out of hackneyed plots at this point.
The point is though: he may be your future father-in-law, but he’s not your father and getting in his face about this isn’t going to have the effect you might hope. About the only thing it will do is confirm that you’re some greaser thug from the wrong side of the tracks and cause him to dig in his heels even further. To be less colorful but still perfectly blunt about it: you have no leverage here to work with. You don’t have the sort of relationship where your disapproval would make a meaningful difference, nor do you have any sort of moral authority or influence to back up or enforce the consequences in a way that would be meaningful.
You know who does, however? Janet. Your fiancé. His daughter. You know: the one he seems to be ignoring and treating like furniture while having these man-to-man discussions with you (and, I guess, Brad). Frankly, I’m a little surprised Janet isn’t the one getting in his face over this, seeing as she’s being disrespected even more than you are. Now, maybe it’s the case that she feels like this is just the family dynamic and expects it to blow over. Families have their quirks, and a lifetime of enduring passive-aggressive manipulative bullshit shows up in all sorts of ways. But the fact of the matter is that you are correct: habitual line-steppers tend to keep line-stepping until someone makes them stop.
I don’t know if your future family is seriously (or fictionally) trying to sabotage things or not, but this sort of interference isn’t going to stop. While they may not try to honey-pot you into a divorce or persuade your fiancé to dump you for a Man In Finance, the odds of them being intrusive grandparents who undermine your authority with your future children or interfere with their upbringing is pretty damn high. Father may not actually know best, but Grandpa seems like the kind of person who’s going to try to assert his will through the grandkids as proxies in his weird-ass dominance and control games.
You and Janet need to have a talk about her family’s behavior, and then she needs to have a very pointed talk with daddy dearest. He doesn’t need to approve or bless the marriage, but he sure as hell needs to accept it and to stop trying to interfere – now and in the future. And while he may think that he has a financial lever to hold over Janet’s future, she has a far more potent one: her presence in their lives. Her disapproval weighs a hell of a lot more than yours does and has much more impact than throwing threats of disinheritance around.
If she’s as uncomfortable with her folks’ behavior as you are, then she needs to take point on this and make it clear that the bullshit has to stop. She may have grown up with it, but the key word here is “grown up”. As in: she is one, and they need to act like it. It’s one thing to tolerate it when one’s folks have actual control and authority over you. It’s another entirely to continue tolerating it when you’re a full-ass adult and their levers of power have been disconnected by her having her own life and finances.
If they’re going to play stupid games like this, they get to win stupid prizes, and those prizes include “spending the holidays with her husband’s family”, “breaking family traditions” and “not having a relationship with their grandchildren.”
Not to mention, there’ll be no wacky sequels where they have to adjust to meeting your punk/boho family and your mother-in-law drinks magic mushroom tea by accident and trips balls while your father-in-law tries to wrap his head around the concept of tofurkey or doing a Three Wise Men with your punk uncle.
Good luck.
Dear Dr. NerdLove,
Over the years, I’ve cultivated a physique, lifestyle, and sense of charisma that have opened many doors for me. I used to focus heavily on getting matches or likes on dating apps, believing those numbers defined my value. But as time went on, I realized that simply being myself — showing up with my presence, energy, and confidence — brought me far more success with women than any swipe ever did. I’ve connected with fascinating, beautiful women in real life, and those experiences have been meaningful and validating in ways dating apps never were.
This brings me to my question: why was I so fixated on Tinder matches in the first place? Looking back, it didn’t set any real limits for me; instead, it made me feel terrible about myself. And I wonder why so many younger men put themselves through this cycle of comparison and rejection. It feels like there must be an epidemic of low self-esteem fueled by these platforms — not caused by women, but by the design of the apps themselves. Yet many men end up directing their frustration and anger toward the easiest target rather than the system that’s actually harming them.
I’d love to hear your thoughts on this dynamic. Why do so many young men fall into this trap, and what can be done to break free from it?
Thank you for your time and for the work you do.
Sincerely,
Me myself and I
Oh this one’s easy, MMI: it’s a numbers game.
No, seriously. It’s numbers all the way down.
In the Before Times, the Long Long Ago, when dating apps were branching out beyond Spring Street Personals and online dating was something you were vaguely ashamed to admit to be doing, the numbers were about how many sexy singles you (the generic “you”) could potentially meet in your pajamas, compared to how many you could meet out at bars or at the park or the company mixer.
What they were doing in your pajamas I’ll never know.
The vague shame of “having” to use the apps tended to be outweighed by the fact that it was possible to message more people and set up more dates in the span of an hour than you could in an entire weekend. It had the benefit of ensuring that you knew everyone you encountered were single and ready to Christian Mingle, and if you were a little shy or anxious about talking to someone in person, you had the benefit of text. You didn’t have to have to be a silver-tongued graduate of the Lando Calrissian School For Players, you could let your fingers do the talking and have enough time to think of what you would say next instead of blue-screening in front of someone.
That all changed when the Tinder Nation invaded. Tinder’s jab-jab-hook combo of showing matches by proximity, swiping mechanic and open “we’re all just here to fuck, right?” attitude swept over the public like smallpox and changed the game. It was the first time you would click a button on your phone and see people you would swear would never be on a dating app, never mind one that had the self-consciously edgy safe-sleeze like Tinder, which gave it the sort of underground cachet that immediately precedes mainstream acceptance as all the normies rush in and ruin the vibe. It quickly became the most popular app… and the one that cemented the idea of swipes-as-validation.
See, Match was kind of for squares, eHarmony was for marriage minded people who didn’t want to admit they were using a dating app, but OKCupid had the nerds and the geeks and freaks who where loving the idea that for once they could use their words instead of relying solely on their looks. Fun little quizzes and answering the right questions could give you percentages that suggest just how compatible you were with people you saw – and to a degree, it worked. If you and some anonymous hottie had a 95% match rating, you had good reason to expect that you would at least get a reply to your initial message.
Tinder, however, was openly marketing itself as The Hot People Fuck Store, and that set a certain tone. With its focus on pictures, minimal profile text, no messaging unless you had a mutual swipe right, on the other hand, meant that you might never know who saw or didn’t see your profile. You had to hope that your hometown honeys were swiping on you, otherwise you had no way of wowing them with your wit and wisdom. You were sending swipes into the void and hoping to get something back… and that made it clear who was Hot and who was Not.
It also didn’t help that OKCupid was doing “social experiments” on its users and blogging about the data. I’ll spare you my usual rant about sample size errors, a lack of control groups and blatant P-hacking, but their supposed ‘studies’ that were no such thing set a lot of the groundwork for the incel shitstorm we see today.
The most infamous of these data-driven discoveries was the infamous “who messages who” post on their blog, that helped give rise to the idea that women were only messaging men who were their “equal” in looks.
(They weren’t; in fact, one of things that gets missed is that while women rated men as less attractive than men were rating women, women were messaging a much wider array of men, while men were all messaging women of around the same ‘hotness rating. In as much as hotness can be meaningfully measured in a 5 star standard with no real delineation for looks, personality or skill at making a profile.
I was THERE, Gandalf…)
This helped kick off the wildly misunderstood Pareto Principle into meme legend by trying to apply it to dating: first positing that 80% of the women were first messaging, and then as the original idea continued to be corrupted, dating the top 20% of the men.
And once Tinder monetized things further with benefits like being able to see who swiped on you… well, suddenly you had actual “evidence” as to whether you were one of the Blessed 20 or not. Lots of dudes, taking it as gospel that women were uniquely blessed with attention, while men were struggling for crumbs, would prioritize trying to match with as many people as possible, often by trying to shotgun love into existence. They would swipe right on every profile and then try to decide who they actually wanted to date after the matches rolled in.
Tinder, for its part, started playing silly games too, setting up its internal algorithm that tried to pair the pretty people who wanted to party. The internal ranking system would assign you a score and show you to people who had similar scores – scores based on, paradoxically, how many people had already swiped right on you vs. left and what their score was – assertive mating done by data nerds. If you had lots of hot women swiping right, your score went up and you were shown to numerically hotter people. In theory, this was supposed to make for better matches. In practice, fives were feeling like they were being told to clam up because a 10 was swiping.
Getting more matches – not dates mind you, matches – became as much of the goal as anything else because it was like a digital data dick measuring contest for dating. Get lots of matches and clearly you were hot stuff. But the problem was – and still is: matches mean precisely two things: jack and shit, and jack left town. Matches don’t mean a thing if you don’t actually turn them into dates, and that’s where a lot of folks were falling down. Even the supposed digital dimes weren’t getting the dates they thought they deserved.
Since then, the Trouble With Numbers has continued as Match Group has continued to play games with hotness. Everyone on Hinge, for example, has complained about Rose Jail, where they try to convince you to convert by saying “sure, we’ve shown you people we think you’re a good match with but let’s be real: the folks you wanna see are behind this here paywall and you only get one shot per week with them if you don’t pay up.”
Ironically, being put in Rose Jail meant you were often less likely to get messages because people get really squirrely about paying to message people and even squirrelier about getting a SuperLike or Rose or someone paying to talk to you.
So now, the numbers are already dismaying, but you’re also being told that the real hotties, the stars of the show, are waiting as long as you kick in an extra ten bucks per. So you’re not just getting no-dates from the mid-tier, but the S-tier weren’t even seeing you. And this, on a service that you’re paying for, and being told that it is the way to meet people in the 21st and a half century.
It certainly didn’t help that as the popularity and ubiquity of dating apps grew, the number of people meeting in person wasn’t growing in parallel. Worse, 2020 rolls around and now none of us are out and about, so dating apps are the only safe-ish method of meeting and mating. And since social skills follow the pattern of ‘ashes to ashes, dust to dust, if you don’t take it out and use it, it’s going to rust’, fewer people put in the practice to put themselves into the path of love.
All of which only serves to confirm the confirmation biases of the loneliest, angriest and frequently most entitled awful people who have a hard time understanding that “what, women are things!” doesn’t get you a lot of dates.
And it’s the entitlement aspect that’s part of what’s leading men to blame women – the same entitlement that keeps framing the male loneliness epidemic as something women need to deal with and solve. Even wags like Scott Galloway who supposedly decry the Red Pill Mythos still validate it when they play into the idea that it’s women’s standards that are causing problems. Certainly not a problem of dudes not raising their game or recognizing that toxic tropes about what makes a man desirable get doubly dangerous when social mobility is a distant myth and the seemingly sole path to prosperity is lined with grift and graft. So start that drop-ship side-hustle, invest in crypto and hope that NFT line go up because that’s the only way you’ll reach the supposed low-end of the “your bank account must be THIS high in order to ride”.
As for what’s to be done: well, honestly, it really is a matter of “go outside and touch grass”. I’ll wave my hands at the overall archive where I’ve written extensively about what guys need to do to get better with women, but much of it can be distilled down to “you gotta live your life in meat space and actually talk to people like a person.” The vast majority of road blocks tend to be self-imposed and helplessness that people don’t’ want to unlearn – to the point that a thirft-store decorated apartment and a small group of friends seems like an unimaginably impossible goal to a truly shocking number of people.
But like I said: it’s numbers all the way down – a 1 to 10 scale in 1s and 0s that started with good intentions and turned toxic the more people focused on the numbers and not the people.
