DEAR DR. NERDLOVE: I’m not sure if I’m venting or looking for advice, but I need to share what I’m feeling. I’m really struggling and it’s hard to see a way forward.

On the surface, my life seems pretty good. I’m healthy and doing well professionally, but my living situation is a major source of stress. Renting is incredibly expensive and finding an affordable home feels nearly impossible. I feel stuck living in my family home, which adds to a sense of stigma.

What’s weighing on me the most is my dating and social life. I’m generally well-liked and respected, but I struggle to connect with people on a deeper level. I often get people asking me about how many hearts I’ve broken this week, but the truth is I’ve never been on a date. It’s heartbreaking, and I find myself sulking during my free time or crying into my pillow.

I’ve been trying to change this for a while. I’ve put myself out there and engaged in therapy, but nothing seems to work. I’ve met plenty of people, only to end up feeling alone again. I know relationships ebb and flow, but I can’t seem to hold onto anyone. I am making the effort to invite people out and grow these relationships further, but people my age already have their established social groups, are in relationships or have children, so this can be difficult, and I’m surrounded by it both at work and wherever I go socially.

When it comes to dating, I feel completely lost. I’ve been told that I have qualities that should attract others — kindness, empathy, intelligence — but it hasn’t led to any romantic connections. I don’t want to go down a negative path like RedPill, but it feels like I’m missing something fundamental when it comes to forming romantic relationships.

I can’t shake the feeling that something is off, and it’s leaving me feeling hopeless.

Change My Mind

DEAR CHANGE MY MIND: This is one of those times when I wish you had included more detail, CMM, because details matter. There are issues that comes up fairly often for people who are having struggles similar to yours that can be illuminating and give an idea of where the sticking points are hiding and how you can start addressing them.

One of the common issues – one you’ve almost certainly seen examples of in this very column – are when you’re dealing with problems that seem intractable but are, in fact, about what’s going on in your head, not out in the real world. Often these are problems that people have picked up via cultural osmosis rather than actual lived experiences; it’s something they expect, rather than something they’ve experienced. But the belief that it’s going to happen is so strong that they treat it like it has already happened.

Part of this is just a function of how our brains work; our brains respond to the things we imagine as though we actually experienced them. So when you, say, imagine going out and talking to someone, only to get brutally rejected, you honestly feel the pain of that rejection… even though it never actually happened. The problem is that you – and others – treat that as reality, rather than recognizing that it’s just your anxiety kicking in.

In fact, you drop a very common example right from the jump in your letter. You start with a very real, very relatable and very common problem: rent is absurdly high and home ownership is out of the reach of a significant number of Americans. That’s real and something that pretty much anyone you’re likely to date is going to understand. Hell, most people you’re ever likely to date will have experienced some form of this.

The part where it goes off the rails is when you assume that your living with your parents in a multi-generational household is going to count against you. In the span of one paragraph, you start by noting something that’s damn near universal, and then end it with assuming that nobody else could possibly understand, relate or empathize with it, never mind be (or have been) in the same boat as you.

This is one of those issues that everyone assumes is only happening to them when the truth is that it’s actually far more common than they realize. Nearly 16% of millennials (and upwards of 30% in some areas) lived with their parents in 2022 according to the latest census data. Gen Z is even more likely to live in a multi-generational home, with upwards of 31% living with their parents and 45% reporting being financially dependent on parental support.

(And all that is before we get into how the stigma about multi-generational households is a uniquely American phenomenon and built around the economy that the Boomers grew up with and that cratered as Gen X came of age.)

Now this doesn’t mean that living with parents can’t create logistical issues with dating – trying to get some alone time with your sweetie can be a challenge, for example – but it’s hardly the mark of shame you’re assuming it would be. Even if someone you would want to date hasn’t experienced it themselves, the odds are good that they’ll understand. Someone would have to be especially uncaring or ignorant to take that as a personal flaw, and that’s someone who just told you that you shouldn’t date them. If they lack the level of empathy or understanding for your circumstances, that’s a flaw in them.

The rest of the things you talk about are so vague that it’s difficult to advise you on what you might need to do. You don’t mention, for example, how you’re unable to grow these relationships or how you “can’t seem to hold onto anyone”. You comment about “established social circles” or having children or partners, but this doesn’t actually tell us anything useful. Is it that you’re running into scheduling conflicts? Is it that they just don’t respond?

Those details can be important, because of what they tell us and what they can show us. It could well be, for example, that you’ve got expectations that are out of step with reality. One of the reasons why I tell people to “date slow” is because they have a belief that the only connections that count are ones that lead to dates or relationships immediately. This is part of why so many people get hung up on doing approaches and getting numbers; they feel like it only “counts” if you get someone you just met to agree to go on a date… even though that’s not how most people start relationships. Dating apps have exacerbated this, in part because people don’t separate a specialized environment (where people have signed on specifically to meet people they might want to date) from how people have meet new people overall. We understand, for example, that someone we just met at work or talked to at the bookstore isn’t going to be our newest, bestest friend right away. But by the same token, a lot of folks seem to think that if talking to someone doesn’t lead to a date that weekend, then they failed.

But people rarely date someone they literally just met. It’s uncommon to vanishingly rare to start a relationship with a person we’ve only talked to for twenty minutes. The vast majority of relationships are born from connections that are built up over time as we get to know them as individuals. It’s one of the many, many reasons why propinquity – the tendency to start relationships with people we spend the most time with – is the most underrated aspect of attraction and meeting people.

This is why, for example, your problem may be one of expectations and the answer is that you need to just slow your roll. Sometimes it really is a case that you’re expecting an unreasonable result and wondering why nothing you do is working.

Another likely issue is your overall attitude and how you feel about yourself. As I’ve said many, many times, what you feel is happening and what is actually happening can be two very different things. Your attitude and outlook is the filter through which you see the world. Your brain is primed to show you the world as you believe it exists and to discard evidence to the contrary. If you believe that the deck is already stacked against you, you’re going to be prone to assuming the worst. You’re going see things in the most negative possible light because that’s what you expect to see. Take your belief that living with your parents is a mark against you. Because you believe this, you’re primed to see anything that isn’t 110% over-the-top excitement as rejection or a sign that you’ll be rejected. So, anything that could be seen as a rejection will be taken as one, even if it’s just “I can’t this week, but I’ve got more time next week.”

And yes, sometimes it really is the case that people can be busy as hell, and you have to book things out further than you would prefer. As we get older, our responsibilities and obligations stack up and our available free time shrinks as demands on that time grow. It’s frustrating, to be sure, but that’s part of life and you have to learn to work with it.

Similarly, the belief that there’s something “missing” and nobody could like you means that you’re going in to these interactions expecting things to go badly. As a result, you won’t put the same level of effort into it as you would otherwise; why bother, if you’re just going to get shot down? But it’s that half-assing and expectation of rejection that can cause the rejection. You don’t put your best self out there, you take mild inconveniences as insurmountable obstacles and read rejection into every micro-expression. And since this just serves to reinforce the idea that you’re unloveable, you have a harder time picking yourself up, dusting yourself off and trying again.

So I would recommend that part of what you need to do is start putting your efforts in shifting how you feel about yourself. Much of this is going to depend on acknowledging and accepting your good points, paying yourself compliments and being willing to hype yourself up without false modesty or weird disqualifiers. If you aren’t willing to believe that you may be wrong about there being something “wrong” with you or that maybe things aren’t as bad as you want to believe, then you’re never going to convince yourself, never mind show those good points to others.

(Put a pin in that, we’ll come back to it).

You have to be your own best friend and biggest fan before anyone else. If you don’t believe in your own worth first, you’re going to have a much harder time conveying it to others. “I understand why you wouldn’t like me, I wouldn’t like me either” is not exactly a winning marketing slogan after all. And you can’t rely on other people to tell you that you have value; very few people are going to be so motivated that they’re going to fight to change your mind for you.

So, start with learning to appreciate your value, to know your worth and to recognize that you have more going for you than you want to believe. Learn to love yourself, openly, loudly and proudly, and others will see it too.

The same goes for trying to connect with people. If you’re going into an interaction with the idea that you have to convince someone to first tolerate you and then like you – in other words, to gain their approval and justify your attraction to them – then you’ve already failed. You’re going to be so hyper-focused on trying to convince them to give you a chance that you won’t be authentic or present in the moment. You’ll be too busy looking for signs that she doesn’t like you and focused on not making a mistake rather than actually connecting with them or – importantly – finding out if they’re worth your time.

But there’s one more thing you’ve said that I want to drill in on. You say that you have the qualities that people say they want – that kindness, empathy, etc. It’s great that you have them, but how are you showing those qualities to others? One of the biggest mistakes I see people make is that they assume that simply having the qualities is all they need… but nobody knows you have them unless you actually demonstrate them. It’s one thing to say you’re kind. It’s another to actually go out and, say, help your elderly neighbor with their housework or volunteer at the pet shelter or do charity work.

People make jokes about how music is God’s gift to ugly people, but part of why the “broke, couch-surfing musician boyfriend” is a cliché is because musicians do something. Playing music makes people feel good and those good feelings mean that people will prioritize a relationship with them over the people that don’t make them feel good. If you have things to bring to the table, the first thing you have to do is actually bring them to the table, not just hope that others will divine their existence. The people who do the best with women are people who demonstrate the qualities that people want in a partner, not just insist that they have them.

This is why you have to be an active participant in your own life. You can’t hope that people might see your good qualities, you have to find ways to show those qualities. And they work best when you’re showing them because they’re just things that you do, not because you’re just trying to win people over. This is why trying to find “attractive” hobbies that women are intrigued by doesn’t help if you don’t actually like those things. It doesn’t do any good to learn how to dance if you don’t actually like dancing, any more than it makes sense to go to clubs to meet women if you neither like clubs nor the people who hang out in them.

Start looking within and find the things that you think that make you awesome and bring them forward. Be proud of them and be willing to show them off. Accepting and acknowledging you’re a sexy badass is the first critical step of being able to show that to others. Once you start to believe it, you’ll start seeing it – after all, if you’re going to see the things that confirm what you already believe, you may as well believe the things that help you. Change your attitude and you start changing your results. The rest flows from there.

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 was hanging out with some new friends of mine yesterday and we were having some drinks and joking around when one of them turned to me and said “You’ve never dated and it shows.” This kind of took me aback as I wasn’t expecting them to hit me with such a pointed and personal jab. It’s an accurate guess of course but then I got worried that I gave off “Virgin Energy” or something. I was just being my normal, goofy self so that got me worried that my default personality is unattractive or something. Am I overthinking this? Do I need to change how I act?

Big Maidenless Energy

DEAR BIG MAIDENLESS ENERGY: I swear (every f--kin’ day), half my job would up and vanish if folks just had better friends.

This is just some asshat doing the guy thing of “bonding by roasting each other” who’s giving you s--t and hit you in a sensitive spot.

I’m not necessarily against roasting or teasing among friends. Several of my friends and I will tease one another regularly when we hang out. But it’s not merciless teasing, it’s affectionate. Part of the unspoken agreement is that we avoid hitting the places we know would actually hurt and the overall vibe is that the joking is about an exaggerated and clearly not real version of the person. It’s never with the subtext that we believe it to be true; we joke because we know it’s not. Similarly, we’re just as quick to make similar jokes about ourselves because we all know we’re all ridiculous in all sorts of ways. It’s in-group joking and teasing, the sort that reaffirms that we’re all part of this together, and that we can do this because we know each other well and care about each other. And if it gets too real, we apologize and we stop.

This, on the other hand, sounds like someone trying to put you “in your place” as it were – mock you in such a way that it establishes you in the social hierarchy. That’s more the mark of an asshole, especially if they’re not someone who knows you well enough or is close enough to have the privileges that allow them to joke like that with you. If they’re doing it because they think it’s funny, but don’t intend to be mean, then they’re a bore. If they’re doing it knowing that you haven’t dated anyone and know it bothers you, then they’re an asshole. One is potentially correctable, the other is someone you probably shouldn’t waste more time on.

What I don’t think is that you need to change how you act, and I do think you’re overthinking things. Maybe you act around these guys in a way that seems stereotypically socially awkward, and the dude drew a conclusion. It’s certainly possible that you gave off “never dated before, ever” vibes like Steve Carrell trying to bluff his way through a conversation in The 40-Year Old Virgin and the guy picked up on it and weaponized it on you. But quite frankly, it’s much more likely that this was just variation #2302b of the standard “men who aren’t neck-deep in chicks are losers” insult and it just happened to be the truth. It’s akin to – again, referencing The 40-Year Old Virgin – someone riffing on “know how I know you’re gay?” except turns out the other person actually is closeted. Shotgun enough insults about someone’s lack of a sex-life out there and you’re more likely to score a hit eventually.

(Another possibility is that you told someone else in the group and word got around, and… well, a--holes are gonna ass.)

Do you need to act differently? Well, let me ask you: are you carrying a chip on your shoulder about having little dating experience? Are you making “oh woe is me, I am among The Great Untouched and it’s not fair?” noises all the time? Are you trying to hide or obfuscate your relationship history? Because if the answer to any of that is “no”, then no, I really don’t think you need to change anything. Even if you are somehow pinging on people’s “haven’t gotten any” radar, the issue really isn’t that you’re pinging it so much as “why are you treating it like a big deal?”

And that really should be your response to it: “so?” or “And your point is?” Because it’s really not a big deal, no matter how much some slapdick tries to make it one. Not ceding the ground that this is something to be ashamed of or a mark against you makes it a lot harder to use it against you; it makes the other person look like an asshat for trying. It also makes it that much easier to spot the folks you shouldn’t spend time with because they’re demonstrating themselves to be a s--thead and your time is too valuable to waste on s--theads.

Here’s the thing: being a virgin or having no relationship history is value neutral. As I’ve said many times before, being a virgin isn’t a measure of your worth or desirability as a person. It’s simply a marker of “have had this experience” or “haven’t had this experience” with no more meaning or significance than whether you’ve ever gone skydiving or seen the Grand Canyon. Any significance is arbitrary and what people make of it says more about them than it does about that data point. And if they’re going to treat it as a negative? Then that marks them as an asshole rather than saying anything about you.

I can tell you from experience: having sex isn’t going to change you as a person. Losing your virginity won’t make you wiser, more mature, more cultured or anything else. If you were to go out tonight, run into the woman of your dreams and just absolutely wreck a hotel room and leaving it looking like a blacklight Jackson Pollock painting, you would wake up the next morning as exactly the same person you were the day before.

Nor, for that matter, would folks be able to magically detect the “just had sex” on you. There wouldn’t be some glow surrounding you telling everyone that you got your ashes hauled. The only way people would know is if you told them. So unless you’re making your sex life – or lack thereof – a big deal in those conversations? Then nobody’s going to know, and it’s not really their business anyway.

TL;DR: a--holes are gonna ass and trying to avoid giving off “big virgin energy” is just going to come off like insecurity. Better to just treat it like the non-issue it is and be friends with a better class of people.

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 an older experienced dater (41 yr old lesbian) and have a higher body count than most people expect. These almost all happened between my mid 20s to 30s.

I’ve been regularly and rigorously tested for STIs and remain clear. I’m very fortunate. However, I’ve had my high body count thrown in my face by multiple partners recently. Despite showing them my multiple test results, and explain that’s long been in the past, they will insist that I must have something. Lately, I’ve stopped dating altogether. I’m tired of being shamed for a past that was to me, not something to be ashamed of, given it was consensual and enjoyable.

How could I approach this topic in the future should I try dating again?

What’s In A Number?

DEAR WHAT’S IN A NUMBER: This one’s easy. Date less s--tty people.

Ok, I realize this sounds like I’m being dismissive, but I’m serious. You’re framing this in such a way that it implies that this is an issue with you and you need to address it in some way that doesn’t trigger a s--tty response from folks who have retrograde ideas about STIs, sexual risk and “purity”.

And it’s not. The issue are people who have a problem with your sexual history. They’re the one who suck, here.  

Unless you’re dropping that info like a challenge, as a form of dominance or authority or some weird form of one-upmanship – and it certainly doesn’t sound like you are – then the question of “how to roll it out” really does make it sound like the issue is “how do I do this in a way that minimizes it” while tacitly accepting the frame that this is a bad thing – as though you should apologize for the sex you had or describe it in a way that makes it seem like having done it was a mistake.

Well… you shouldn’t. As you said: this was sex that you had that you consented to and that you enjoyed. That’s pretty much the end of the story as far as I’m concerned. You are 100% correct: this isn’t something to be ashamed of.

The number of people you’ve slept with isn’t really an indicator of anything than “the number of people you’ve slept with”. It’s value neutral, a data point in the sum totality of who you are as a person. It’s part of what made you the person you are today and, from the sound of it, you like that person. So the problem really isn’t how to roll it out to others, the problem is that the people you’ve been dating don’t like you. They like an idea of who you’re supposed to be in their heads. The person in front of them, not so much.

But here’s the thing: you’re not responsible for the person that folks think you should be, any more than you’re obligated to apologize for not being that person. You’re you. They can decide if they like you or not, number of sexual partners included, but that’s ultimately a them problem, not a you problem. The “you” problem in this case is letting s--tty people stick around after they make it clear that they’re s--tty.

And to be sure, folks can have opinions and preferences about the amount of sexual experience they want their theoretical partner to have. I’ve said many times: people are allowed to have whatever dealbreakers they want, regardless of what other people think. If someone wants to date a person who’s purer than the driven snow in Alaska, more power to ‘em. Other folks can have opinions about their dealbreakers, but they don’t get a vote.

But their having a dealbreaker doesn’t mean they get to be s--tty about it to you or accuse you of things that are more about their issues than about you. Doubly so when they’re so wed to the idea that they’re throwing it back in your face regardless of the evidence. Evidence, like, say, negative test results for STIs.

Now, there are other choices, of course. You could lie about your number of former partners. It’s not like someone’s going to demand references or to see the official punch card or visitor ticker over your bed-frame; you could tell them with a straight face that you’ve only been with $ACCEPTABLE_NUMBER of people and just go from there. But if I’m being honest, I think that’s unnecessary and a mistake. I can understand the feeling of “well, a little white lie that helps people get over their bulls--t at the start when they don’t know me”, but in my opinion if you feel like you have to conceal parts of yourself that don’t need to be concealed in order to date someone, then there’s a problem right from the jump. At best, I think this is just starting the clock on a time bomb that’s likely to go off.

On the other hand, you could just, y’know, not tell them. I don’t think the number of partners is important or even particularly revelatory. It can tell folks more about who you were at a particular time in your life, what your priorities were, what you valued and prioritized in relationships or connections with others… but I don’t think that’s something that needs to be shared, especially early on. Certainly not if someone is giving signs that they’re going to get weird about it.

Yes, having more partners means a greater risk of having been exposed to an STI. But that’s just life. Existence is a full-contact sport. Going skiing means accepting a greater risk of injury or death. Going out to eat means accepting a greater risk of food poisoning. Driving means risking life and limb. When we do these things, we do so with the tacit acknowledgement of the risks involved. It’s part of the whole deal and we don’t treat doing the acceptance of those risks as a sign of moral turpitude.

This is why, in my opinion, the only thing that someone’s really “entitled” to are the results of your STI screening, which is really the only part that’s any business of theirs. The rest can be filed under “none of your business”, or “I don’t kiss and tell”, “I don’t keep score”, “more than some, less than others”, or “enough to know what I like and who I want.” 

There’re folks who will clearly take this as a sign that you’re hiding something or get upset and demand actual numbers. But that says far more about them than it does about you and – again – it’s a them problem. You’re laying down a boundary that says “I don’t want to talk about it” with an unspoken “…yet”, “… if you’re going to act like this” or possibly even “…ever”. If they keep pushing and demanding to know, then they’re telling you valuable information about themselves. If you don’t want to share the number of people you’ve slept with and they get upset about it… well, that sounds like someone you probably shouldn’t be dating. If it’s that important, they’re free to go date someone who either has an acceptable number of former partners, or who wants to talk about it.

So my thought on how to handle it is: take it on a case by case basis, based on the person you date. You can lead off with a handwave that signals you’re not interested in talking actual numbers, or you can decide based on how they’ve acted so far. If she’s someone who’s shown that she’s not going to get weird and sex-shame-y about your romantic or sexual history, then hey, feel free to tell them if you want and feel secure in doing so. I’d say just be matter of fact about it, treating it like the data it is.

But if they’re getting judgey about it, or they throw it in your face? Then the only sensible thing to do is kick them to the curb and they can go find someone more to their liking. Because all that’s happened here is that they’ve demonstrated that they’re someone who is absolutely not right for you, and you’re better off without them. It’s certainly better than giving them any more of your valuable time, which they’ll just waste by being an asshole to you.

Your past is part of what makes you you. This includes your sexual history. This ain’t Build-A-Bear or a Baldur’s Gate character generator; they can’t customize your background to fit their idea of you. If they are going to object to your having a history like this, then they’re objecting to your whole self. It’s a package deal; you don’t get one without the other. You (and they) don’t need to dwell on it if nobody wants to, but it’s still just a fact of who you are.

If they have a problem with your number, they have a problem. But it’s not your problem. And if they can’t get over it and be a grown-up about it? Then they aren’t your problem either.

Good luck.

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