DEAR DR. NERDLOVE: As a man who’s still figuring out dating and has been played before, what are the signs someone is just using you for free stuff? Not only that but when is someone being dishonest about their intentions or dating in bad faith? (for lack of a better term)� �Any advice is appreciated!��Sincerely,

Watching Out

DEAR WATCHING OUT: Amusingly, I received this letter shortly after having read an article about a supposed trend of “foodie calls” – that is, Gen-Zers going on dates specifically for free meals. To be frank, I think this, like a lot of other supposed ‘trends’ is more the creation of a credulous media looking for content and falling for blatant engagement bait rather than an actual trend, but it’s the sort of thing that tends to find fertile ground in dudes’ imaginations.

I’ll be real with you, WO: I think the likelihood that someone would be looking at you – or literally any other guy who isn’t Daddy Warbucks – as a literal meal ticket is so low that you’d have better odds winning the Powerball. You might have reason to be concerned if we were talking about a pig butchering scheme by someone you never actually met or if you have been bragging about how much crypto you have. You might even have reason to worry if you were a mid-tier government employee or working for an NGO that’s currently drawing the ire of conservative wackadoos. Maybe, maybe you find someone who’s dating for “content” rather than to actually date, but again, the odds are such that you’re more likely to be attacked by a shark. In fresh water. In Missouri.

But someone who is actually sitting across from you at dinner or walking next to you in the park? I seriously doubt you’re at risk of a gold digger trying to get your stuff. Especially if you’re not trying to impress women by at least giving the impression that you’re rich as hell.

(Frankly, if someone is trying to win people’s affection with ostentatious displays – or implications – of wealth, they shouldn’t be shocked that it attracts people who just want their money. If you’re gonna chum the water you swim in, you really can’t complain when a shark takes a bite.)

Now, how do you tell if someone’s playing games or dating in bad faith? Well, the answer is simple: pay attention to their behavior. The vast majority of head games people play tend to be incredibly obvious, regardless of gender. Most of the time, people who play games or aren’t being honest about their intentions follow the same playbook, whether it’s red pill/PUA bulls--t or The Rules or whatever the current TikTok dating “advice” trend is popular, and they really aren’t subtle. If they’re someone who blows hot and cold seemingly at random, only seems to give you attention when you’re pulling away or seems to be trying to push you towards particular behaviors or dates, it rarely takes Lt. Columbo to figure it out.

If I’m being honest, the fear of someone playing games or trying to con you – especially if you’re a man who dates women – tends to be far more prevalent than people who are trying to f--k with you. A lot of guys tend to think that they’re important or significant enough that people would want to invest the rather considerable time and energy it takes to date in bad faith, and quite frankly, they aren’t. The vast majority of people on the dating scene aren’t interested in playing games, and the ones who are tend to be trying to avoid vulnerability or risk rather than trying to get one over on you.

But the truth is that most of the time when someone says that a person was playing games or dating with false intent, the real answer is that the person supposedly being messed with got over his skis and thought there was more to the date than there actually was. It’s far more likely that someone “playing games” is actually someone who doesn’t know what they want, is bad at communicating or simply just isn’t that interested in you in the first place. The idea that someone’s going to invest time and effort into messing with you because f--k you, that’s why is usually more about your own anxieties than it is about malfeasance.

If you’re really worried, then pay attention to your Spidey-sense when you feel it start tingling. But in those moments, you need to ask yourself which is more likely: that someone is trying to pull one over on you, or that you’re reacting to your own pre-existing fears and expectations? And if you’re still not sure, try laying it all out to a friend – one who isn’t excessively online – and see what they think. Often, just the act of trying to explain it to someone else will help you realize what the most likely reason is.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: I could use your help figuring out if I’m the a--hole or if my friend is overreacting and I don’t know if I trust Reddit to give me a good answer. 

Here’s the setup: I’ve been seeing “Tiffany” (not her real name, obviously) casually for about a little over two months now. We’re both in our mid-to-late 20s. We met on a dating app and I was clear up front that while I’m open to exclusivity at some point, I wanted to keep things casual for a while at first. I also made it clear that “casual” in this case meant no long-term expectations and that while I wasn’t seeing other people at the time, I didn’t see this as being exclusive and I didn’t expect her to be exclusive either. If she were going to date other people, that’s fine, I just would like to know, and I would offer her the same courtesy if that changed for me too, and that we would talk about things if we decided our feelings were changing or we wanted to change the nature of the relationship. She agreed that this was what she wanted too, and so we started seeing each other.

Here’re the details: Tiffany and I have gotten together/gone on dates about 10 times in that time; about a date a week on average. The number is important for reasons I will explain in a moment. Sometimes they were proper dates, sometimes they were just one of us coming over to the other’s apartment, hanging out and eventually having sex. We’ve slept over twice in that time, once at my place and once at hers. 

Now for the problem: last weekend was what would be our 11th date; I went with her to her friend/sorority sister’s birthday party at her friend’s house. When she introduced me to her friend, she introduced me as her boyfriend. Apparently, I stiffened up or did something that Tiffany noticed, because she said “Whats’ wrong?” and I told her that I didn’t think it was appropriate to introduce me as her boyfriend. She got tense and asked what I meant in that I-don’t-want-to-cause-a-scene tone of voice and I told her that we had never talked about this and while we were dating, we were still casual. She pointed out that we had been on 11 dates at this point and it was silly to think that we weren’t a couple. I replied that the number of dates didn’t matter because you don’t automatically become a couple after you see each other a set number of times. She pointed out that I wasn’t seeing anyone else and she wasn’t seeing anyone else. I said that this was true, but that doesn’t mean we’re in a relationship either. Then she pointed out that she had closed her dating app account once we started going out. I said that this was fine but that didn’t obligate me to call myself her boyfriend.

At this point, it was clear that things were getting awkward, so we decided to just drop it and try to enjoy the party. We didn’t stay long before she insisted on leaving because the mood was ruined, at which point we argued on the steps in front of her apartment about what we were. I explained that I see applying a label like “boyfriend/girlfriend” or being a “couple” as something we both talk about and agree to. She said that this was stupid, we had been on so many dates and weren’t seeing each other and liked each other so obviously we were exclusive and even if we weren’t, I should have just gone along with it and not embarrassed her in front of her friends, especially after she said that she was bringing her boyfriend to the party when she RSVPd. I disagreed and said that you can’t just spring that on someone and that we had agreed in the beginning as to what this was.

Now we’re on a break while we both calm down before we say something we would regret and I am honestly confused about what’s wrong here. Am I being an a--hole for not going along with this, or was I right to be bothered that she just told everyone without talking to me first? Was she overreacting because I didn’t go along with it? Was it ok for her to just decide this and I’m the one who doesn’t know how dating works? 

I will be honest, I’m not sure if there’s a point to asking this because I don’t think whatever we have is going to continue one way or another. I don’t think I’m wrong on this, but if I am, I would rather make sure I don’t make this mistake again in the future. 

Who’s The A--hole Here?

DEAR WHO’S THE A--HOLE HERE: Well, this dragged up an awkward memory, WTAH, because I’ve been in the same position as you before… just on the other side of things. Back in the Before Times, the Long Long Ago, I was seeing a woman who told me, straight up, that she wasn’t open to having anything more than a casual relationship. Seeing as this was when I was at my peak of both insecurity AND not knowing what the hell I was doing, I said “you got it” … and then immediately decided that I could change her mind. And, in fact, at a friend’s party, introduced her as my girlfriend, without telling her that I was going to do that.

Things didn’t go as dramatically as yours did, but that did serve as part of the reason why we broke up not long afterwards and served as a lesson learned: if someone tells you that they aren’t open to a particular label or type of relationship, you listen to them, instead of taking that as a challenge.

Now, I will admit to being An Old, and I think some of the discourse around modern dating is more than a little silly. Every time I read about “soft launching” or “hard launching” a relationship, my eyes roll back in my head far enough to see my own brain, and I think describing a relationship like an IPO or a restaurant opening invites way the f--k too much capitalism into dating. Honestly, I thought s--t like “Facebook official” was stupid too. But at the same time, while mores change and trends change, there’re some things that I believe don’t change… and that includes that relationships require everyone to agree that they’re in one.

I’m firmly of the belief that there are no relationship status changes that happen automatically or without prior discussion. It doesn’t matter if it’s one date or ten dates; there is no milestone or point in time where things kick in without everyone discussing it. All relationships and relationship changes are double opt-in; you both have to affirmatively agree that you’re exclusive or that you’re $INSERT_LABEL_HERE. The only exception to this rule, the only thing that can be decided unilaterally is that you’re no longer in one. Nobody can put you into a relationship without your agreement, and nobody can keep you in one without it either.  

In fact, I believe that until and unless you have an explicit Defining The Relationship talk, you should both work under the assumption that what you have is casual and not committed. I also believe that, while a DTR talk doesn’t need to be some elaborate, formal thing, you should, at the very least, define terms and make sure you’re on the same page about what you both expect. Assuming that everyone is working from the exact same playbook is how you end up with unnecessary arguments about what being part of a couple “means”.

So, in principle, I agree with you that Tiffany was wrong here. Telling other people that you were her boyfriend without running it by you and then springing it on you out of the blue like she did is not cool, the same way it wasn’t cool when I did it lo those many years ago. I also don’t think you were entirely wrong to say “hold up”, at the party. Yes, it made things awkward as hell, especially if this was the first time you were meeting her friends, but she was the one who made it awkward first. Much like how I feel about elaborate public proposals, I think pulling things like this only serve to pressure the other person to agree simply to avoid making a scene and that is some ol’ bulls--t.

I do think that the party wasn’t the time to start hashing things out. As a general rule, making someone else’s celebration about you (the general “you”) or your relationship is a massive party foul. It’s rude and incredibly self-centered. Now, in fairness, I can’t think of a particularly graceful way to un-ring that particular bell, but I do think that you would’ve been better off saying “we’ll discuss this later”, or at the very least, pulled her aside and not had the discussion in front of her friends. So, while I think Tiffany was in the wrong and put you in an untenable situation, I don’t think you covered yourself in glory here.

Now I will give Tiffany this much: I don’t think this was malicious on her part, and I don’t think she did this in order to try to box you in. I will admit that my own past version is coloring my opinion here but I suspect that Tiffany just wasn’t thinking about it at all. I suspect that in her case, she was working under the assumption that This Is How Things Are Done and believed that this was the universal rule for everyone. And it may well be how things worked with her and her social circle. That doesn’t make it right, but as I said: I don’t think this was her trying to push you into something you didn’t want or agree to.

So, I would say that Tiffany here is The A--hole, with caveats. I think what she did wasn’t cool, but I think it was more born out of not thinking and making assumptions, rather than intent. I think the way you responded could’ve been better, but again with the caveat that I’m not sure there’s a way anybody could thread that particular needle perfectly. And while it’s possible this relationship could survive this fracas… I’m not entirely sure it should. I think the best thing you could do here is consider this break your break up and move on.

Just be sure to tell Tiffany when you do decide this, so that there isn’t yet another awkward public disagreement about your relationship.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: So navigating the swamp pit that is modern is because all the chaos and contradictions especially as autistic virgin in his late 20s. From being told to women are the happiest when single, to married men to actually being the happiest but then being told to date for a relationship is weird and out of date that hooking and being slutty is now trendy and sexy, that slut shaming is wrong but shaming someone who’s got little experience or god forbid being a virgin (especially if he’s a man) is an acceptable target because that’s an incel after all. 

That there is a loneliness epidemic for men that we deserve because the actions of the terrible ones and to be told not to mansplain despite that I’m autistic and I love explaining and info dumping (there is literally no difference between the two) and of course this contradiction that lives rent free in my head for classic “Don’t compare yourself to others” to then when I step into the dating the women I’m interested absolutely have lots of experience (because i seriously doubt any woman is a virgin in her late 20s unless she’s like Amish or some other deeply conservative religious community or is by choice) and I get hit with the “weak men don’t fear comparison” when I start to get insecure about her previous partner and how I will measure up especially well from I’ve heard/seen virgins are not very good in bed. Even when insecurities like how where previous lovers like? Where they taller than me? More ripped than me? Had a bigger member? Better body? More sex drive? More suave? It doesn’t help that a piece of advice I was given by a woman about being suave and sexy goes “if you gotta ask then you don’t deserve to know” once again women’s words.

I know this is written chaotically and secreted brained but that’s what it basically feels like, even planning a simple coffee date feels like a red flag to a lot of women (and women have told me this) because it’s a sign he’s a basic boring bum ass loser. So like there is no winning for me man.

What do it do doc? How can I counter these conundrums and contradictions? How do I unscramble all this chaos? Just relax and be chill? To be a Micheal B Jordan and not a Shameik Moore.

Countering Chaotic Contradictions

DEAR COUNTERING CHAOTIC CONTRADICTIONS: This one’s easy: these aren’t contradictions. You’ve taken a bunch of various comments, complaints and hot takes without actually understanding them, dumped them into a food processor and hit “frappe”.

Let’s start with an obvious one: mansplaining and infodumping aren’t the same thing. Mansplaining is when someone – generally a man, but not always – is trying to “educate” a woman about a subject that not only does she already know, but often knows better than the person trying to explain it to her. It also tends to come with a heaping helping of condescension and an attitude of superiority and unearned certainty.

My trying to explain the new Critical Role campaign setting in detail to my wife is infodumping. My deigning to tell her about the conflict between the Tudors and the Plantagenets while she sits directly below her diploma for her Masters in medieval British history would be mansplaining.

(It’s also notable that there’s a time and place for infodumping, and the importance of crafting your explanation to the audience so that they’re both receptive and able to follow along, but that’s another topic entirely.)

Then there’s things like “women are happier when single and men are happiest when married”. This isn’t about dating, it’s about how (cis, straight) men generally reap benefits from being married, while women do the lion’s share of the work in not just the home but in the relationship while also having a job and their own lives to manage. In other words, it’s about the way gender roles and social expectations affect men and women differently and why.

Meanwhile, the Male Loneliness Epidemic isn’t “about the actions of the terrible ones”, it’s about how the toxic and restrictive ideas about masculinity and expected male behavior makes it harder to find new friendships or maintain the friendships they have. This also relates to that aforementioned “men are happiest when married” because part of the problem is how men tend to rely on their female partners not just for all their emotional needs but also to act as social secretary and manage most of their social lives for them.

You’re also taking random posts on social media (“a coffee date is a red flag”) and treating it as though it’s a universally held opinion instead of being both niche as hell and also blatant engagement bait. Are there people who think a coffee date is boring or dull? Sure. Do women think it’s a “red flag”? I’m sure if you look hard enough, you’ll find someone who actually thinks this, but they’re not just an exception but likely not someone whose opinion you ever need to worry about in the first place. And if you’re seriously worried about that, then all you need to do is plan a different date – you have almost infinite options in almost infinite combinations. Go on a walk downtown and look at street art. Get ice cream and hang out in the park. Go play skee-ball or shoot pool or race go-karts. A little creative thinking and even just a little research works wonders here.

Then there’s the things that you’re just assuming, basing on other people’s random posts on social media or making up out of whole cloth based on nothing but your own imagination. Being told “dating for a relationship is out of date”? What? “Hooking and being slutty is trendy”? Even if I assume you mean “hooking up” rather than “sex work”, that still sounds like a Charlie Kirk manque demanding a return to “family values”, not an actual social trend.

But once we get to “…dating the women I’m interested absolutely have lots of experience (because i seriously doubt any woman is a virgin in her late 20s unless she’s like Amish or some other deeply conservative religious community or is by choice)” and we are well into “now you’re just making s--t up to be upset about” territory because this is just recycled bulls--t from people who have never actually talked to a woman or have even the slightest idea of women’s dating experiences. Remember what I said before about mansplaining? Guess how this fits into the concept. You’ve taken your assumption based on literally nothing but your guess of what women’s social lives are like and are treating it like a fact, despite having no evidence, data or even basic conversations with other women. You hold onto it because it justifies and validates your anxieties and makes you feel worse about yourself – classic masochistic epistemology in action.

This is precisely where the rest of the letter comes from. It has nothing to do with facts, reasoned opinions or even sensible conclusions based on research and experience and everything to do with how you feel about yourself. You’re starting from a base of “I’m not good enough”, imagining a situation where this gets confirmed and then treating this imagined scenario not only as something that has happened, but is also an inevitability and then projecting it outward onto others. That’s not a contradiction, that’s just you.

Can a virgin be good in bed? Absolutely. Lots of people – including people in the comments section on this column – have talked about having had amazing sex with virgins. By the same token, having had lots of sex is by no means an indicator of skill. Once again, talk to women and you’ll find how many “players” are horrible in bed – whether they’re generally only interested in their own pleasure, won’t listen to or check with their partner about what they might like or just thinks that foreplay is something that happens to other people. There’s a reason why the best way to be an amazing lover is to work on your communication skills, not trying to master the Swirly-Go-Round or the Texas Tornado.

But what about her exes? Well… what about them? They’re her exes, not her partner, and they’re her exes for a reason. Again, this is your insecurity talking, not reality. If someone wants to date you, they want to date you. They’re not looking for a replacement goldfish, they’re trying to build a relationship with you, specifically. If she wanted a Mortal Kombat palette swap for her last partner, that’s who she would be with already. As it is, the more you’re comparing yourself to their ex and trying to figure out if you have more or less points on a spreadsheet that doesn’t actually exist, the less you’re actually, y’know, paying attention to what your partner wants. 

And that’s ultimately where all of this is tripping you up. You’re not actually paying attention; you are, at best, reading a headline and imagining the rest. I’d say you’re looking LLM summaries except even Grok manages to be right by accident on occasion. If you want to stop getting bewildered by all these seeming contradictions, it would behoove you to actually research some of these topics – and I mean beyond Reddit, Discord and TikTok.  

Similarly, you’re treating other men as a primary source for what women want when their source are still other men who think listening to women is gay. And as long as whatever they say lines up with your low opinion about yourself, that becomes the unvarnished truth.

If you want to start getting untwisted, start with working on learning to love yourself instead of trying to live up to what slapdick grievance peddlers say you “should” be. That way, you might start understanding some of these supposed contradictions instead of just using them punch yourself in the junk over and over again.  

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com