DEAR DR. NERDLOVE: I need dating advice help for a boy in my kid’s friends’ group. He’s in 9th grade, a little neurodivergent, and has trouble reading social signs. He keeps crushing on 10th graders way out of his league and who already have boyfriends. He’s convinced that if he pesters them enough, they will go out with him (they’ve been polite, but the most recent one blocked him on literally every comms device she has, and he STILL didn’t get it). 

There have been 3 girls he’s done this to this year. How do we have a come to Jesus with him to get him to slow his roll and basically stop assuming that every teenage crush can be converted into a girlfriend? 

The constant drama can’t be fun for the objects of his crushes, and it definitely isn’t fun for all his friends. 

Other Person’s (Concerned) Parent

DEAR OTHER PERSON’S (CONCERNED) PARENT: Every time people talk about high school being the best time of their lives, I have to wonder what the hell they’re talking about. While it’s been a damned long time since I was a high-schooler, I remember with shocking clarity just how little I understood was going on with… well, pretty much everything… and how much of my day-to-day existence was functionally holding on to anything that made the slightest bit of sense by my fingernails.

And this was never so true as being a ninth grader with a crush and absolutely no goddamn idea what to do about any of it.

It can be goddamn hard to reach kids at that age, particularly if you’re trying to give them real, helpful advice. It especially doesn’t help that there’s a host of bad actors and influencers who look at kids like him as prime targets for their grift. The constant waves of hormonal changes, trying to establish an identity separate from one’s parents, social status maintenance and maneuvering that bordered on Machiavellian and the desire for relationships that one barely even understands at the time are a perfect formula for chaos and drama that would make soap opera writers say that it’s a bit much. This is a time when kids can be vulnerable to manipulative bobble-throated slapdicks with an agenda to push; it’s a lot easier to sell a solution when it feels like you don’t have the first fucking clue about how to get someone to like you.

The tricky thing especially is that kids don’t like admitting not knowing what they’re doing and telling them to knock it the fuck off doesn’t always work. The good thing is that kids aren’t dumb, and a combo of appealing to their brains and invoking empathy can help open the door enough to encourage them to take new suggestions on board. It just may be a little difficult for you to be the one to crack that door if you’re not someone he’d come to for advice or if you have the sort of relationship with him that would allow you to offer it in the first place.

It sounds to me like this kid could use a couple of strategic suggestions more than anything else, and some pointed questions would be the start.

The first thing I’d suggest is just pointedly noting what they’ve been doing and asking “…so, how’s that working out for you, so far?” Simply noting that they’re 0 for 3 is the start for planting the seed that their current technique isn’t getting them the results that they would hope for. Doubly so considering that it would require him to acknowledge that at least one of his crushes has shut him out entirely and why she did it.

I’d recommend following that up with asking “how, exactly do you see this working? What about this is supposed to get them interested in you?” At every step, ask: “ok, but how does this work? What about this is supposed to make you more appealing to them?”

The point is less to say, “this isn’t working, kid” and more to get them to think things through. As a general rule, it’s more persuasive if you can get someone to come to a conclusion on their own, rather than giving them the solution. Since God knows teenagers can be prone to Underwear Gnome thinking (“Step 1: annoy girls. Step 2: ??? Step 3: girlfriend!”), asking them to walk you through how it “works” can often go a long way towards making them realize that maybe they need to try something else.

This is also where you ask what happens after she says “yes”; a lot of the time, kids like him are so focused on the immediate goal that haven’t actually thought about what to do if they succeed. Realizing he doesn’t have next steps can help him understand he needs to put some more thought into this and change things up. Otherwise, you end up with the awkward moment at the end of The Graduate: ok, great, you two are running off together after she ditched her fiancé… now what?  

(Were I more of a horrible person, I’d also point out that trying to hit on these girls while they still have boyfriends is a losing game, but that relationships in high school are often measured in weeks and months rather than years. He’d have better luck playing a waiting game than trying to swoop in while his crush is still in the middle of high school “THIS IS A LOVE TO LAST FOREVER” drama.)

I would also suggest flipping things around and asking him how well he would respond to someone pestering him constantly to hang out or to go out with them. The odds are good that he has at least one person in mind who he finds annoying; prompting him to realize that he is being that person to the girls he has a crush on might be enough to trigger some empathy and recognize that this is a losing game for him.

While he’s considering this, I’d point out to him that hectoring someone into giving you a chance is far less effective than actually being a more desirable option. Not in the “girls want high-status boys” sense but in the “hey, he dresses well, takes care of himself, has some confidence and is fun to be with” sense. Getting someone to go on a date with you doesn’t matter if you don’t have substance to make them want to go on a second date. Or a third or fourth, for that matter. Working on that personal development and being a person that women are more likely to want to date is going to get him better results – now and in the long term – than just focusing on the short-term goal of “get Sarah to talk to me”.  

And while this part isn’t necessarily going to be persuasive to a kid – even smart teenagers have a pronounced tendency to assume they’re the exception to, well, everything – there’s always the fact that if it did work on someone, that’s a warning sign. I can speak to this from experience: the one time I managed to Nice GuyTM my way not just into getting a girl to break up with her boyfriend but to date me instead, I ended up in a toxic relationship for years and it took even longer to undo some of the damage that did to me. If he somehow manages to annoy a girl into giving him a shot, the odds are very good that he’s going to have an object lesson in why sometimes single is better.  

(It helps if you read that in a strong Maine accent.)

The last thing I would note – and to be fair, this is something the kid is probably not going to want to hear – is that part of the goal is going to be less trying to help him get with his latest crush and more about squashing bad habits early and getting a better setup for future success. There’re reasons I tell folks not to stress dating in high-school; for all that it gets romanticized in pop culture and among folks who think they missed their window, high-school romance isn’t all it’s cracked up to be. It tends to be far more chaotic and dramatic because, well, teenagers, and it’s very rare for a high-school couple to last past graduation and even rarer to last past the first year of college. So while your kid’s friend may not end up with the head cheerleader, getting him to change his ways now will pay huge dividends for him a little later on.

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: Your stuff on leaving an incel mindset has been extremely helpful for me! I just need to get out there…

Anyway, I do have one hang up at the moment and it’s with regard to traditional gender roles in dating. I don’t if it’s where I am or what, I frequently come across notions (both online and in person) of a man taking charge being attractive (not mention apparently men doing manly things or like calloused hands). 

Not being one who needs or wants everything my way (I’m pretty chill and flexible), it rubs me the wrong way like there is yet some other roadblock. Do these women really mean it or am I in the wrong place?

Any advice or things to look out for?

Following The Leader

DEAR FOLLOWING THE LEADER: Ok first and foremost: I understand why this would rub you the wrong way, but if you’re taking it like a personal affront – that they’re doing this at you – then you’re going to spend a lot of time being annoyed for no reason. This isn’t a roadblock, so much as it’s a compatibility check. Taking it as a universal “every woman feels this way” is a very good way to spend most of your time being upset by people who don’t exist over opinions they don’t have.

It’s always good to remember that confirmation bias is a thing; if you expect to see it all over the place, you will. And seeing as how this is something that hits you in a sensitive spot, you’re more likely to be looking for it and expecting to see it.

But the bigger issue is that what you think they’re saying and what they’re actually saying aren’t necessarily the same thing, nor do they necessarily apply to you or the people you might want to date.

The thing is, “taking charge” is a very vague and nebulous idea and what people mean when they say that is going to vary from person to person. Functionally speaking, there’re two primary ways to interpret this that’re going to be relevant to your question.

The first is exactly as it sounds: there are definitely women who like traditional gender roles, who like the idea of the man taking the dominant or more assertive role in the relationship. That’s just how they roll and that’s great for them, just as it’s great when women prefer to be the more dominant one and like a more submissive or less aggressive partner. As the famous tweet goes: some guys like dating more outspoken and assertive women because someone’s gotta tell the server he didn’t order the mashed potatoes and it’s not going to be him.

The same applies to women who like men doing manly things or like dudes with calloused hands. Some women absolutely will. Some women like men who are softer or whose skills and interest lie elsewhere – there’s a reason why there’s a long and glorious history of poets, musicians, artists and intellectuals getting laid like bandits. It’s down to personal preference.

None of this is universal. It’s not something every woman wants or expects, nor is it something every man is expected to do except by people who are very invested in seeing men being in charge at all times.

If you’re not someone who’s necessarily a Type-A, My Way or The Highway personality that’s fine. It just means that you’re not going to be compatible with someone who wants a guy to be the Dominant Leader. Which is also fine. You don’t want to date someone you can’t rock with or who can’t rock with you.

The second interpretation has less to do with traditional gender roles and more to do with the amount of work that women do in relationships with men. One of the most common issues in straight relationships is how women often find themselves in the role of cruise director; they end up being the person in charge of maintaining social connections, planning dates, meals and outings, keeping the calendar and managing schedules and appointments, etc. This is one of the reasons why a lot of men deal with social isolation, especially after relationships end or their partners die; they’ve come to rely on their partner to basically manage their lives, including their social lives.

This tends to be exhausting, especially for people who are already up to their eyeballs in trying to maintain their own lives. So, it’s not entirely surprising that a lot of people saying that they want to see men actually show up for their lives and take their turn at the tiller instead of just outsourcing it to someone else.

It can also be frustrating when someone never has a preference or opinion about something, because it means that they’re always passing the buck for making decisions off to someone else. Even folks who like being The Planner or The Organizer like having times when someone else does the planning and organizing for once. I like planning outings and dates, but I have to admit, I love it when someone I’m dating plans and proposes a date for me, too.

So, in this interpretation – and one that I think is more relevant for you – what this would mean is that women want to see you step up and be present for your own life. They would like you to take charge of your end of things and to be an active participant, instead of someone so chill and flexible that they seem to have no opinions or wants of their own… or who expect the other person to divine their wants and preferences and have a snit when their partner doesn’t turn out to be Jean Grey or Betsy Braddock.

Just remember: this isn’t a roadblock. Depending on circumstances, it’s either an issue of compatibility or a request to shoulder your share of the labor in a relationship. Both of which are eminently reasonable and both of which will help ensure a stronger, happier relationship overall.

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’m in my early 20s, single, male, had less than a handful of dates in my life and I have a question: just where is a man supposed to meet women? 

You can’t hit on women at work, you’ll get fired for harassment, possibly sued and put on a list somewhere and if you break up you’ll probably get in front of HR anyway for creating a hostile work environment or something.

Can’t approach women on Instagram or TikTok or Snap, they’ll screenshot you sliding into their DMs and post it so their followers can laugh at you.

Can’t talk to women when you’re out during the day, they’ll call you creepy or say you’re harassing them. 

Try to talk to women at a bar? That’s not what they’re there for, go away please, you’re being creepy. Clubs? Same thing, try to flirt after someone’s been grinding up on your dick and rubbing her ass in your face, get told that’s not what she’s there for or she just lets her friends get in your way while she goes to dance with someone else. 

Obviously dating apps don’t work if you’re not one of the top men on the app. 

So where’s a guy supposed to meet someone? I clearly missed my window in high-school and the dates I had were with girls in college who were in my class and I never got a second date with any of them. So what do I do now, just stand outside like a homeless puppy and hope someone gives me a forever home? Because it seems like we’re not supposed to talk to women ever. 

No Talkie No Touchie

DEAR NO TALKIE NO TOUCHIE: If that’s going to be your attitude then… yes, there’s no talking to women, ever.

Ok, more seriously, NT2: I get that you’re frustrated, and not entirely without reason. But based on your letter I get the feeling that your bigger issues with not being able to talk to women is this surly attitude more than any “rules” about where you are or aren’t “allowed” to talk to women.

While I’m allowing for hyperbole, you’re coming in with a lot of assumptions and facts not in evidence. The way you frame these scenarios implies that these consequences are universal, unfair, arbitrary and happen because F--K YOU PENIS, THAT’S WHY. You’re coming into this with the presumption of not just hostility on the part of women but malicious intent, and that’s going to screw you far more than tripping over your dick while trying to do a cold approach. 

Some of these speak more to your ideas on how women think or move through the world while also exaggerating the risks to men, rather than the reality on the ground. This sort of antagonistic “I can’t do anything because Jenny Killjoy will complain to HR” attitude is going to salt your game far more than social norms. It tends to speak to how you think of women and how this is somehow abrogating your privileges, and most women are going to pick up on that before you even open your mouth.

So that’s the first thing you want to work on if you want to be more successful at meeting women.

Now I’m going to put the dating app issue aside; that’s an entirely separate beast and something I’ve talked about multiple times before. It’s also yet another misunderstanding of how the Pareto Principle works, and that’s before we get to the gender imbalance on most dating apps.

Instead, we’re going to focus on the idea that you can’t approach or talk to women in public anymore.

This is a complaint that I hear pretty frequently and to be perfectly fair to you and to them: everything you’ve said is true… to a limited extent. But before you run off and crow about how unfair it all is, the issue here isn’t about how women have locked men out of dating or whatever, it’s about expectations, attitude and not understanding… well, a whole lot of things, but mostly not understanding women’s experiences and the social contract in general. 

Now seeing as I conceded that this is true to a limited extent, for my next trick I shall astound the audience and acknowledge the validity of The Brad Pitt* Rule: it’s allowed if you’re hot.  

(*In reality, Brad’s star’s waned rather considerably, seeing as he’s been credibly accused of spousal abuse, and he famously smells like unwashed feet and pit-stank, but he’s still the person folks reference soooo…)

Here’s the thing: this rule is correct… in as much as “people enjoy talking to people they want to talk to”. I am willing to bet, for example, that you’re not necessarily interested in having a conversation with someone who looks like someone crossbred skin cancer with syphilitic blindness and stank so bad they had cartoon lines radiating off them. Nor, I imagine, would you be interested in talking to someone who kept trying to turn the conversation to why you should invest in his Bitcoin scheme or who kept insisting that joining NXVM would solve all your problems, even after you clearly said “not interested”.

You might also not be in the mood to talk to someone after you’ve had a s--tty day at work, a fight with your friend or parents or had to say goodbye to a beloved pet, no matter how friendly or attractive they might be.

In all of these cases, you have reasons why you wouldn’t be receptive to someone wanting to chat, and you would be understandably annoyed if that person kept insisting on talking to you, regardless of your opinion on the matter. And if this happened to you, repeatedly, whenever you were just out minding your own business and going about your life, you might not want anyone to so much as look in your general direction, never mind come over to say “hey”.

You might also start having strong opinions about autonomy and boundaries when those same people started complaining about how it wasn’t fair that you weren’t giving them a chance or how you should be open to talking to anyone who came over to you.

So it is with approaching women; it’s not that you’re not “allowed” to talk to them or approach them, it’s that you’re missing (or ignoring) that women don’t necessarily want to talk at that moment – either in general or to you specifically, for whatever reason. Doubly so if you don’t take the hint the first time around. Triply so if you think that they’re not being interested or open to talking is unfair because reasons.

While folks think the rule is “rules don’t exist for hot people” – hence “the Brad Pitt rule” – the rule is really about “people get to decide who they want to talk to, and when, and about what.” If you think it’s unfair that women “only” want to talk to someone if they’re hot enough (they don’t, hotness is idiosyncratic, etc.) then I would point out that fairness doesn’t actually enter the picture. Not when your definition of “fair” really comes down to “won’t give me what I want”. Nobody is obligated to give you an opportunity any more than you are obligated to give others the chance to talk to you if you don’t want. Welcome to having boundaries and bodily autonomy, hope you survive the experience.

Someone who isn’t interested in talking to anyone at that moment – because they’re busy, because they’re not in the mood, whatever – might, and I stress might, make an exception for someone they find attractive. They might also be willing to talk to someone who makes them laugh or is able to distract them from what’s bothering them. But all of this continues to fall under “talk to someone they want to talk to”; their reasons may seem shallow but it’s their reason. You may have opinions, but you don’t get a vote. But I stress might make an exception, because you can still be hot and still annoy someone, be rude or offensive or otherwise be unwelcome.

The real issue isn’t whether someone is “hot” enough to “get away with it”. It’s that most of the time, the guys who are complaining about this are guys who don’t bother to read the room. They aren’t bothering to try to see if the person they’re hoping to talk to is open or interested in talking and, more often than not, they’re not interested in a conversation, they’re just trying to get a date or into her pants… without knowing the first thing about her. This is one of the reasons why I tell people that if you don’t have a lot of experience or you’re not socially well-calibrated and you want to hit on women, you should focus on places where talking to strangers is not just permitted but expected – places that are explicitly for people to meet and mingle. In these venues and events, it’s understood that chatting up strangers is the norm and it’s a primary reason why folks go there. It won’t make up for a lack of charisma or poor social skills, but it’s a place where you can at least know that talking to strangers is the norm.

Compounding this is that – as I said – most of the time, guys aren’t interested in talking, they’re interested in approaching. That is: they’re trying to get a date from a stranger, not just make pleasant small talk. This changes the dynamic of the entire interaction. It’s no longer about meeting and connecting with someone, specifically it’s about coming in with an agenda and not caring about the person. It’s saying “I know nothing about you except that you have something I want,” and a lot of folks are put off by that. Even people who are down to clown with a stranger prefer someone who’s interested in them as an individual, not just an ambulatory Fleshlight.

There’s also the fact that this behavior works against the people who are doing the approaching. Moving in on a stranger in an attempt to get a date tends to be counterproductive. Leaving aside questions of whether the attention is wanted, or the person is single and open to dating, the vast majority of people don’t date someone they met only 20 minutes ago. Even on dating apps, there tend to be multiple conversations before a date happens.

Taking slower approach by taking dating off the table and instead just focusing on being social, getting to know someone and being fun to talk to isn’t as sexy to brag about to your friends (or strangers on the Internet) but it’s more effective and efficient in the long run. Giving someone the opportunity to get to know you and for you to know them is a much better method to building the sorts of connections that lead to dates and from dates to relationships.

Now putting this in practical terms: you’re totally within your bounds to talk to women when and wherever you meet them. But if you want them to actually be interested in talking to you and possibly get a date down the line, you need to take a different tack.

First: read the room. If you’re not in a social venue like a bar or a specific event like a singles mixer, pay attention to who’s actually interested in talking and who’s giving clear “do not disturb” signs and respect those. If you’re not sure, err on the side of “probably not”.

Second: don’t do approaches. Don’t just hit on women. Just strike up a conversation like a normal person. This could mean making chit-chat in line to get coffee, sitting next to each other at the counter at a restaurant or food court, even someone waiting for the bus or the train… but again, only if they’re actually interested and open to talking.

There are more opportunities for this than you’d think. People can and do enjoy small talk, even with strangers, if the other person isn’t a jackass. Focus on getting to know someone, learning more about them and seeing what makes them tick. You know you find them attractive, but that’s all you know about them. You want to know them as a person: the classic “what do they have going for them besides their looks”.

Speaking of…

Third: focus on your social skills, especially being fun to talk to. Leaving aside that this is a very valuable skill to have overall, if people enjoy talking with you, they’re going to want to keep talking with you. Nobody says “well I enjoy that person’s company and so I will never speak to them again,” after all. They say “man, I want to keep this conversation going!” They will prioritize talking with you because you’re fun to talk to.

I can’t emphasize how most of the sex-gettingest men I know aren’t the hottest, richest, fittest or most famous. They’re dudes who simply know how to make people feel good when they chat and are fun to be with.

Similarly, I can’t tell you how many women I know whose relationships always start with “I just had the most amazing conversation…”

Yes, you can and should work on your presentation – your style, your hygiene, your grooming and so on. It’ll make you look better and feel better, which will help your confidence and thus improve your physical attractiveness. But it’s your social skills and ability to actually connect with people that are what lead to relationships.

You want to be the sort of person who can talk to anyone at any time, in any place? Start working on being interested in talking to everyone and being someone people like to talk to.

Do that and you’ll never have to worry about being “allowed” to meet or talk to women again.

Good luck.

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