I mentioned on Monday that I’ve got something cooking about romance and hinted that I’d throw that up sometime this week. That’s not what this is, that idea is still cooking. I’m trying to work out how to be honest without being too presumptuous, too specific, or too vague. It’s possible, but needs editing. But I’ve had a lot on my mind, and those conflicting wants to both write more but also be cautious with my time. I’m half-watching a long lecture and stewing on some things, so I’m gunna split focus and slap some keys.
I’ve recently had a few incredibly unsettling experiences from data apps. A quick note, this isn’t an academic paper and I’m likely to get some facts wrong, also I’m not going to be a stickler on language. Off the break, I’m going to use the term “app” for all internet dating options, many of which somehow don’t have actual apps in 2025. There are reasons for them lacking apps, but that’s not the point of this. I’m also using “dating” pretty liberally. Some of these apps are meant for what I’ll distinguish as traditional dating, with room for anything from somewhat casual to the most serious. But we all know that some apps aren’t meant for a shred of romance, just the hookup, and many apps that are advertised for classical dating don’t get used that way.
For my part, I keep coming to the same thought that the apps aren’t what they used to be, that what they used to be may not have been good to begin with, and it’s probably not what I’m looking for now even if it was. I need to just quit them, but I don’t. Most of the last year or so not deleting them has been more about laziness and convenience. I would not go on them most of the time and then pop in when bored, not really having expectations and just having an alternative to doom scrolling. But I’m not much of a doom-scroller otherwise, and I have plenty of idling alternatives. So it’s really just a part of me that holds out hope there are real people still on these app and that one of them might just be interested in me. It is, frankly, not a sound theory.
It stems from an era that I think has long since past. At the risk of making it sound like this is all the apps were ever used for or blowing up someone’s spot, there was a time when you would just get on one and you’d have a “date”. That “date” was usually just a pretense to a hookup, and sometimes you wouldn’t even bother with the pretense. You’d just hook up. Actual dating did exist, and I have met a surprising number of couples that started from online dating. Go ahead and add that to my growing list of regrets, because I don’t think I used it for that even once during that era, and now I wish I had. I worry that might have been my best chance at something real, but we’ve gotten off track.
Then or now, there is a sort of dance, somewhat a simulacrum of the real world version of an opening. There are many versions, one goes a bit like as follows. You match in the middle of the work day and spend the next few hours excitedly pinging each other with questions you hope will help you learn more about each other and get you closer to finding out if you like them. If you do, you start working on closing that deal. But while the questions seem good and useful, they don’t really help, and sometimes get you to resent the other person for some small thing that, if you really knew them, you probably wouldn’t care about. With every message, you risk either side of the dance, endearing yourself to or alienating yourself from them. You need to make a move to get out of that app quickly or the momentum you had at the beginning starts to accumulate drag. As the days drag on and the rapid back and forth draws down to a trickle, if something hasn’t happened, one of you just stops contacting the other, and you both stay in each other’s match list forever as ghosts of what never was. But you do that dance because if you make a move too early or improperly, you risk ending the entire interaction without satisfaction.
This is not true for everyone, but since everyone has their own pace and their personal set of dating rules, often specific to just that app, it can be hard to intuit just when it’s appropriate to ask for more, and what that more should be. For a while there, I would throw out an option to meet at a local bar within the first few messages. I don’t drink anymore, so that option doesn’t really work for me, but similar options exist like cafes, movies, or other tried and true dating staples. But people are very cautious these days, and rightfully so. As frustrating as that dance could be, these days you’re lucky if you even get to it. Sometimes people will make their decision based on your very first message, and while it’s not uncommon to see the phrase, “‘Hi’ gets blocked” in a profile, it’s even more common for people to have this attitude without the warning. Fair enough, we can all do better, but the alternatives that this attitude generates can often be far worse. With the shift in attitude in genuine daters, it means that most friendly interactions on these apps are now suspect, and you should also be cautious. The new game is also to get off of the apps, but that has become an incredibly dangerous gamble, whether you’re being asked to move to another app or meet in person.
Crucially, it’s not to meet in person. It’s never to meet in person, which makes some real world sense, given the various dangers. There is a whole set of meeting etiquette that I’ve yet to decipher and seem to be getting worse at, because the game of jumping from app to app is both tiresome and worrying. Moving from a dating app to a chatting app always strikes me as a little crazy. I know there are dating apps that made staying on them difficult. The business models often mean that users need to pay for a subscription to be able to have conversations and some require it to contact anyone at all, which like, how exactly is this thing supposed to work at all? So it makes sense that people got used to the idea that they might be able to spit out a few short messages to get to a free chatting app, but most of the dating apps today don’t have that model. So ignoring how unnecessary this jump is, it still happens almost always.
Some chatting apps are probably safer than the dating apps, but that bar is extremely low. More often, most chatting apps aren’t really safer, they just give the impression of being safe. Some should be obviously unsafe, as they tie directly to your cell phone, so moving to that app means you just gave a stranger your actual real phone number. Sometimes your matches will just bypass the safety theater entirely and just ask for your phone number. In an earlier era, this would be great – it meant you were about to meet up very soon. But over the past decade or so, the technological bad actors have become incredibly sophisticated and giving them any bit of personal information, no matter how disconnected you think it is from your important stuff, can give them a foothold on scamming you, especially your phone number. I need to recount some of this, but I can already see this post being far too long, so let me borrow some lessons from that English Comp. class and try to tighten up. I’m going to tell you about three levels of current, unexpected dating app problems.
Sex workers
This is the first level, and while I do find it disappointing, I’m not terribly bothered.
A week or so ago, I got into a fun conversation with a woman on one of the apps. It was playful, a little sexy, and it seemed like we were both interested and having fun. She even took my many faux pas as charming, which is nice. Then I did an image search on her profile picture, and it turns out that she’s an Instagram model. That’s not immediately damning, but it usually means one of two things. For the first, if she isn’t using the same name or a similar handle, that isn’t the same person. It’s someone who stole her pictures and is using them to scam you, more on that in the next section. The second version used to be less likely, but seems very much on the rise, and it’s exactly what my experience was – this was advertising. She is a real woman and that real woman is the one with that Insta account, but she is never going to date me. She was trying to get me interested so I would follow her to an Onlyfans account, and become a subscriber.
My view on sex work is that it is extremely common, perfectly normal, and frankly and good service that should exist. What bothers me about this, I think, only exists because many forms of sex work aren’t legal, and those that are legal are also heavily stigmatized. As such, the market that undeniably exists for people to pay for sex, companionship, or sexually related materials as was this case gets pushed into hidden, creepy, and dangerous corners. Since there aren’t legal and fair places for providers to advertise and manage their work, they are naturally going to make space for themselves in the closest versions of existing infrastructure. Sex workers are selling sex, dating app customers are often looking for sex. So they are, of course, going to join dating apps to look for patrons. Many legal versions of sex work suffer from the same stigmas and can’t really practice their profession anywhere but places already considered porn. Yes, you can have an Onlyfans account, but you can’t advertise it on Facebook. Because of the legal and social mess, sex workers can’t even be fully honest on the dating apps and find themselves having to pose as potential love interests, later springing the sex transactions on their confused and likely upset matches. That has the potential to ruin the matches’ day, and the impression I get from sex workers is that they don’t much like it either. While it’s fair to be upset for being tricked, when that’s how you put food on the table, I frankly can’t blame the sex worker, either.
From what I can gather, sex workers would much rather have things as I described earlier and there is a ton of evidence from places with legalized sex work that it benefits basically everyone. Perhaps surprisingly, that everyone includes people who don’t want anything to do with sex work, and even those that actively dislike it, as it gives the activities places to go that aren’t the back alleys of literally everywhere else.
Classic scammers and bots
If you’ve not been on a dating app before or in some years, count yourself lucky, because the scam game is out of fucking control. The story I related above is not uncommon, and frankly the best version of what could happen. I had a pleasant conversation and declined to become a patron, not a big deal. Most of the time, when you get a match on almost any dating site these days, that is not someone there to date. That is someone, or some thing, there to take your money. Not a provider looking to exchange materials or services for money, but rather someone looking to get a hold of your personal information so they can hack, social engineer, or otherwise scam their way into your bank account.
I don’t have a story for this one, instead I have what feels like a million instances where I’d have a somewhat off but otherwise OK seeming conversation that always ends up with them trying to get increasingly private and unnecessary information out of me. Phone numbers, email address, locations, names, all the stuff that you should not be sharing with strangers. It’s kind of amazing how many of these scams are going, and how few apps seem to even try to stop them. They certainly take no responsibility for them.
The new AI scammers
The scammers and bots have been a problem for a good while now, and usually, it’s not very hard to catch them. There will be something obviously wrong with their account, or a picture that’s way too professional or clearly something from the late-90s or early-2000s that the scammer scraped off of a different app, facebook, or a porn site. But sex always finds its way around every new technology and social movement, and with the improvements to AI chatbots, it was just a matter of time. And it seems like the time for dating app AI scams is now.
I was on another dating app, I don’t recall which. I was in good spirits and feeling charming, so when I was contacted by an account with the pictures of a very good looking woman, I was suspicious, but completely game to give it a go. We shot a few messages back and forth, and before long, she wanted me to go to a different app. She didn’t opt for the normal shady apps already known to be scammer friendly and she didn’t ask for my phone number. She suggested going to google chat, which is both practical and, as I don’t have any important information attached to my account, safe enough for my estimates. But things did seem off, and this extremely good looking woman was a little too into my extremely not good looking self. I can be quite charming, it’s true, and every woman I’ve ever dated has been entirely out of my league, but this woman has never met me in real life and she’s acting like I’m the most attractive and most interesting person to ever live. She sent me some pictures, tasteful and not nude, and asked me to share one as well. In retrospect, I perhaps should have been more cautious, but I agreed. And then I was absolutely sure she was not a real person.
In the background of my picture were posters from a podcast that I listen to. Now, I love this podcast, and it’s probably my favorite, but it’s not well known. When my match casually mentioned how I’m interested in “some good old tabletop games”, it became obvious that my Spidy-senses were right from the beginning. Below is a screenshot of that conversation, if we can call it that. I’d normally redact the name, but being that this isn’t a real person and googling it only produces various celebrities that look nothing like the person in the photos, I don’t think there’s anything to worry about. Though I won’t share the photos, because I have a strong feeling that they are of a real person, probably not going by this name, and they don’t deserve to get their spot blown up because some shithead scraped their pictures to support their weird scam. Or maybe the pictures are also AI. They didn’t include hands or spaghetti, so it’s hard to say.
This response is off the charts unsettling. People do not talk like this. What the fuck are we even doing, some pretty lady with the boots with the fur isn’t going to casually be all “that’s a great TTRPG podcast.” and then recite almost verbatim the ways the podcast is often referred to on streaming and review sites.
I almost gave up the game too early, though, asking if she’s an AI chatbot. Rookie move on my part, really, but I was caught off guard and I didn’t know how to proceed. But her claiming to not understand what I meant and trying to pass it off as her being super fluent (whatever that means) gave me room of my own to pass off my comment, claiming that I was just being silly. So I asked if she listened to any other podcasts, and she gave me a pretty strange response. If you read through it quickly, it seems passable, but pay attention even a little and it’s pretty obviously the results of LLM processing. Can you imagine a person writing like this into a google chat? I figured that I’d string her along with some simple questions and eventually trap the AI, but I accidentally stumbled into confirming my suspicions immediately. I asked her for recommendations, and boy did she ever deliver.
Four popular and acclaimed podcasts in a perfectly formatted, numbered list with standardized blurbs that must have come right out of an AI generated slop article, complete with technically correct but socially weird punctuation like semicolons and, as always, the em-dashes. Absolute madness. I’ve been too disturbed to look into it, but I am quite curious just what the point of this is.
I’m going to now speculate wildly, please don’t take any of this as confirmation of anything, I’m just guessing and trying to make some sense of things. The time between responses was very long, which suggests that there was a person in there somewhere. Perhaps someone at a desk in a scam farm hilariously copy/pasting between the chat window and an AI chatbot window. But is this just an improved version of the existing scams, or is this a (slightly) more sophisticated operation? Could this be part of the legit AI companies trying to gather more data to make more natural sounding bots? Make no mistake, the existing AI companies are extremely unethical, so I don’t think any of them would have qualms trying to train up a “digital real girl” by seeding feelers into existing dating apps. Given that both the dating apps and the AI chatbots are rapidly approaching an oncoming bubble burst, I could see them doing this as part of an agreement to try and find the money from each other’s products. I should really look into this, but I don’t want to, and I’m hoping someone who knows what they’re doing like some Jamie Loftus or Ed Zitron sort could take this on. Because this is absolutely bananas.
The Takeaway?
I don’t know what to take away from this. I’m going to open up the comments on this post, at least for a little while. I don’t think I’m getting any traffic, but on the off chance that someone drops by and has something to add on the subject, I’m extremely interested.
Honestly, I can’t see a way forward for the apps. That’s not true, in fact, I can see many ways forward, but few that actually make any of them sustainable and useful. It’s entirely possible that the current owners of these apps might make them financially sustainable, albeit on a foundation of stacked bubbles. They could convert their business model to advertising and fill their slop app with slop ads being viewed by endless slop AI bots. The advertisers won’t be advertising to any real people, but whatever, a significant portion of the advertising game is bullshit anyway. It’s just rich pricks passing the same bullshit money back and forth between each other, so who cares? But the apps are already a mess, and this sort of thing isn’t going to make them any more useful. No, I think for the actual humans, the dating app world may very well be dead. I guess we’re all going to just have to learn actual interpersonal skills, and man, that’s a real drag.
That’s it for now and probably until Monday. Have a good weekend and watch out for overly friendly matches.