DEAR DR. NERDLOVE: This keeps happening and I genuinely don’t understand what I’m doing wrong.
I tend to click with women who are sweet but haven’t had a lot of attention. They’re usually a little insecure, maybe on the heavier side, maybe not used to someone actually showing up for them. I make them feel good about themselves — I notice things about them that most people overlook. I put in effort, I give them compliments, I listen, I make them feel wanted.
They always respond so strongly to that. They light up. They open up. They tell me I make them feel seen. And I like that connection at first. It’s intense, but in a good way. We’ll spend time together, hook up, talk late into the night. But after a while, it shifts. They start needing more from me—texts all day, constant reassurance, deeper conversations I’m not always in the mood for. I start feeling boxed in.
By that point, I’m usually losing interest anyway. Sometimes I meet someone new, someone fresh, more exciting. And yeah, I’ll act on that. I usually break things off with full transparency.
What I don’t get is why it always becomes this huge betrayal. I never told them we were exclusive. I didn’t make promises. I just treated them well and connected with them, and now I’m being accused of leading them on or using them. They’ll say I made them feel special “just to take it away,” or that I “knew what I was doing,” like I had some evil plan. All I did was lose interest and move on.
When I try to explain, I get accused of being manipulative. I am always honest about what I want and let them know that they’re projecting things on to me that I have never agreed to. But they always twist that into me “messing with their heads” or “blaming them for being hurt.” One even said I made her feel crazy for having feelings, which — how is that my fault?
I don’t yell. I don’t lie. I just try to be calm and remind them what we actually said to each other. But somehow I end up being the villain because I didn’t feel the same intensity forever.
At this point I’m wondering—is there something about the kind of women I’m drawn to that makes this a pattern? Or is this just how dating works now? It feels like if you give someone a little kindness, suddenly you owe them everything.
Would appreciate your take.
— Always the Bad Guy
DEAR ALWAYS THE BAD GUY: Normally with a letter like this, I’d be more inclined to say “if you’re looking to be slapped around, hire a dominatrix” but hey, these deadlines won’t meet themselves.
And then I got to that last sentence. So, I guess it’s time to acquaint you to my good friend, The Chair Leg of Truth.
This isn’t a problem of you being an innocent bystander catching strays or women taking out their issues and excessively high expectations on you, super chief. This is entirely you’re doing.
The actual problem is glaringly obvious, ATBG. This isn’t one thing so much as a cascading series of choices that keep leading to the same place. And despite how you try to frame it, it’s one that is entirely your doing. This ain’t a case of “man, these chicks are so unreasonable”, it’s you pulling s--t over and over again and then wondering why people think you’re being an asshat.
As the saying goes: if one person calls you a horse, you’ve met a crazy person. If ten people call you a horse, you better check yourself for a saddle and bridle. And hey guess what…
None of this is accidental, and it’s very clear that it’s not. We’ll start with the fact that you know that this is a pattern you repeat over and over again – same behaviors, same people, same outcome. It’s the old – if inaccurate – saw about the definition of “insanity” being “doing the same thing and expecting a different result”.
Well, you keep indulging in the behavior and acting perplexed why it happens every time. Hmm who knows, maybe it keeps happening because you keep doing the same things to very similar people. How bizarre. How strange. How utterly unexpected.
If you know enough to know that if this is an actual problem, then maybe you should stop doing these things, especially if it leads to people being hurt and upset at you. Except that would require actually having some empathy instead of being irritated that they’re mad at you for doing the thing that keeps getting people mad at you.
Now, were this a series of innocent mistakes and misunderstandings, then much of this could be avoided if you took steps at the start. There’s nothing inherently wrong with a relationship style where you prioritize a series of short-term connections. Some folks are simply wired to need a lot of novelty, whose relationships tend to be frequent and intense but brief and whose interest fades fairly quickly over time. But it becomes a problem when you know this about yourself and yet you don’t make it clear to the people you meet that this is how you work and what you have to offer. Telling them up front that “hey, I can only do short-term” or “this is only going to be a fling” allows them to make the informed decision as to whether that’s something they are down for or not.
Of course, there will always be people who hear that and either ignore it or think that they can change your mind. You can’t control for that, unfortunately; they’re setting themselves up for heartbreak because they don’t want to acknowledge that they chose to ignore the warnings.
(Ask me how I know. Go on, ask me.)
Not telling them and/or allowing them to think there could be more, on the other hand, is s--tty, and no amount of “well I didn’t say…” isn’t going to excuse it. Yeah, I talk about “don’t assume you’re exclusive if you haven’t had the exclusivity talk”, but this isn’t a universally observed rule. Things would be a lot easier if it were, but we ain’t there yet, and playing it off as though it were is disingenuous. And more to the point, if you know or have reason to suspect that someone is starting to think you’re exclusive, or is acting like you are, then relying on “well I didn’t say we were an item,” doesn’t serve as a “get out of blame free” card.
Seeing as you can recognize this pattern, you understand precisely what’s happening and why. Shockingly, people don’t appreciate being told they haven’t been led on simply because they didn’t double check the fine print of a contract they didn’t know they were signing.
Next is the fact that you recognize that this keeps happening with the same “type” of people – people who are particularly vulnerable to someone being caring and attentive and acting like they want a relationship. It’s not an accident that it’s always this particular combination of traits, and the fact that you acknowledge it means that you know damn good and well what you’re doing. It’s not a wacky coincidence that keeps happening, you’re targeting them. This isn’t – as your passive-voice indicates – something that just happens. It’s not “you tend to click”, it’s that you’re doing this to people who will respond to this particular behavior, and reward you with the attention and sexy times you want.��Or did you think folks were going to see “chubby chicks with self-esteem issues” and just assume that they were getting too hung up on a guy they should think of as out of their league?
This is then followed by “I treat them in ways men don’t normally treat them – like I’m actually interested in them as people and potential romantic partners.” Well congratulations for acting like someone who’s actually attracted to them and wants to date them instead of using them for sex and a self-esteem boost, humanitarian of the year, you are. It’s so unreasonable that they think you’re leading them on.
Oh, except for this part: “We’ll spend time together, hook up, talk late into the night. But after a while, it shifts. They start needing more from me—texts all day, constant reassurance, deeper conversations I’m not always in the mood for. I start feeling boxed in.”
OK, so you’re feeling boxed in because they’re expecting you to continue behaving in the manner that you started behaving? How f--king unreasonable of them. I mean, how dare these women think you might actually like them and want to date them when you have been acting like you like them and want to date them.
One of the things I talk about when I talk about how to maintain a casual relationship is to avoid treating it like a romantic relationship, especially if it’s primarily about casual sex. This means not sending signs that you’re interested in more by not acting like you’re interested in more. You don’t need to get up and wipe your dick on the curtains and bounce as soon as you get off, but having those long talks into the night and all that time spent together? Yeah, you’re giving every indication that you’re interested in something less casual and more connected and then slapping them down when they respond to that.
Now could all this be avoided? Well of course. This keeps happening after all and you clearly have enough pattern recognition to complain about it. You could start by not giving them the full court press at the start, which sets up the situation. You also know that you could be having conversations much earlier, checking in to say “hey, I get the feeling that maybe you and I are seeing this differently, and I just want to make sure we’re on the same page about what this relationship is.” Except you don’t. Not until you, as you put it, are getting bored and are ready to find someone new, not before.
Why is that, I wonder? Because if you didn’t play it this way, allowing them to think that there’s more than there actually is, they wouldn’t sleep with you? They’d pass on casual sex in favor of finding a committed relationship with someone else?
It’s at this point where you’re playing the game of “letter of the law, but not the spirit”. Breaking things off “with full transparency” isn’t you being honorable or kind, nor honest. Full transparency involves being transparent from the start, not waiting until you’re done and saying “Look, I’m bored here, this was never serious for me and I’m just gonna go f--k someone else now, toodles!” And while yes, you didn’t make promises, you just behaved in ways that strongly imply that you feel a certain way and allow them to work under the assumption that this is how you feel.
It’s one thing if you realize that you made a mistake by acting in such a way that another person made a reasonable inference and you didn’t catch it until it was too late. It’s a s--tty thing to do, but it’s a mistake made out of ignorance and misunderstanding, and one that a lot of folks make. But it’s a mistake that most folks – people who genuinely feel bad about having hurt someone like this – make once.
It’s another when this keeps mysteriously happening, involving the same behavior with similar people, all of whom seem to respond with the same degree of hurt and betrayal. That’s when it starts looking deliberate and targeted.
To not recognize that this isn’t just a bunch of stage-4 clingers that you keep accidentally seducing requires a level of profound and deliberate ignorance. And quite frankly that’s what makes it very hard for me to buy that you have enough awareness to see all the other aspects of this but somehow this is your sole blind spot.
They’re acting hurt and betrayed because you were acting like someone who was genuinely interested in them. You were giving them care, attention and validation, spending time on dates and having those long, deep, involved conversations and then getting upset that they took that as a sign that you were dating. You allowed them to believe this, never correcting them or – if need be – ending the relationship sooner because they were getting too invested, and you rely on the fig leaf of “well, technically,” as if that made it better.
It’s weird how getting all legalistic and pedantic doesn’t make someone feel better, huh?
And again, don’t think I don’t note the “subtle” hints of “I am being calm and rational, unlike these clingy, unreasonable, emotional dames, so clearly it’s not me.”
The problem isn’t that you lost interest. That happens, faster to some than others. The people who know this about themselves, who don’t want to hurt others, lead with this, so that folks know what they’re getting into.
Nor is the problem that you didn’t maintain the “same level of intensity, forever”. Nobody’s expecting that. The problem is that you used them. You act in a way that leads people to believe one way, to people who you say are vulnerable to this behavior, and then try to disregard your own responsibility in the matter by trying to hide behind technicalities and hoping that people are going to buy into the idea that women are just overly emotional and chubby chicks get too clingy.
You want to break this pattern? Start by being honest from the jump. You haven’t been with them and you haven’t been with me.
Because yeah, you’re the one being the asshole here. That’s entirely on you.
Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com