DEAR DR. NERDLOVE: I have a bit of an odd question; I want to share a situation and get a third party perspective on it too see if there were red flags or if I was just being a little too jaded. 

Bit of background I was in a (for me) very serious relationship with someone I loved deeply, and they dumped me last November, I took a lot of time to get myself healthy and good and joined the dating pool again this summer looking for something casual and low key. After some chatting and first dates that didn’t go anywhere, I start talking with Jon. He’s flirty and fun over text, a little intense with asking a lot of questions about what I like and don’t like, but English isn’t his first language, so I give him a little grace. 

Side note, trying to sext with someone who learned English a bit later in life can get wild and not in a good way lol. 

After a week of texting and him bringing up meeting in person I let him know I’m interested, and let’s find a coffee shop or park or something to meet at first. He suggests his house. I let him know that I need to meet in public first, and add in a bit of humor with “so you know I’m not a serial killer before we head back to your place”. He changes the subject, and we keep chatting. Couple days later he wants to talk on the phone, and again brings up me coming over, this time asking, “do you REALLY want to meet in public first?” And I say yes, then get off the phone because I hate talking on the phone. 

I also start to notice that while I’m sending him pictures, he never sends any back and makes excuses when I ask for them, so I let him know that I want to TRADE photos not just give them, and try to turn it into a sexy game. When he sends me a pic of him in a state of undress I’ll match it. Sounds hot to me. I don’t get any photos, so I stop sending them, I give him another 2 weeks but all I get is some casual “how are you?” And “it’s been a long time since I’ve had sex, I’m horny” so finally I wash my hands of the whole mess and end things (even though they never really started). 

I’m 37 and don’t have time for the sort of nonsense I think he was doing. Sorry this got so long. So after reading that whole mess, were there actual red flags or is my calibration off? 

Thanks for your help!

Red Flags Look Like A Parade When You’re Color Blind

DEAR RED FLAGS LOOK LIKE A PARADE WHEN YOU’RE COLOR BLIND: I’m going to start off by saying that these sound less like red flags and more like pink one. What you describe here doesn’t sound like you were picking up on signs that something was off or wrong or that you would otherwise be in danger. But that doesn’t mean that you weren’t getting a vibe from him that made you feel less than comfortable and feeling less secure about meeting up with him.

Part of what makes me hesitant to say yes or no is the language gap; he wasn’t a native speaker and English as a language is notorious for not making a lick of goddamn sense to anyone who comes from a country and culture with a language that isn’t as kleptomaniacal as English. English isn’t a language so much as the grammar of three different languages in a trench coat, but they keep shuffling around and punching each other in the junk as they all fight to be the head instead of the legs while running around and grabbing up all the dropped idioms they find in the street.

It’s certainly possible that his grasp of English – which, as you said, made sexting a challenge and not even a sexy one – was getting in the way of things. Consider, for example, that while the words are basically the same thing, there’s a very significant difference between horsing around and pony play. Or a butt dial and a booty call. Or “I’m sorry Daddy I’ve been naughty” and “Forgive me, Father, for I have sinned”.

It’s also possible that there were cultural misunderstandings. It may well be that he assumed that what with pictures being traded and all, that this was a done deal. Asking to meet up in person may have seemed like an extra and unnecessary step, especially to someone who may never have grasped the difference in the risks that men and women face when it comes to meeting a stranger, especially for sex.

But mostly it seems that what he wanted was low-effort sex and getting pictures and wasn’t that interested in anything that slowed those down or giving much back.

So, as I said: I would call these pink flags more than red ones. There’re a few places where maybe wires were crossed and misunderstandings slipped in, or he could just be a garden-variety jackass.

Now to be clear: that doesn’t mean that this was all fine and dandy and you missed out on some quality sex because you need to recalibrate your Spidey-sense. Far from it. Regardless of my thoughts on these particular flags, I think there was enough there that you made the right call to say “yeah, I’m not doing this.” The fact that he seemed to not take your request to meet up in a neutral public place first seriously was more than enough to disqualify him for whatever sexy times you had in mind. The fact that he didn’t seem to grasp that this was just a vibe check before you went back to bang out rather than a “you’re not getting laid the first time we meet” suggests that either he didn’t understand – but didn’t think to ask to clarify things – or that he just wanted the sure thing to also deliver itself to him like he was ordering Uber Eats.

It’s also possible he’s just one of those time-wasters folks run into on dating apps and hook-up sites, who wants to collect pics (and maybe swap a couple) but not meet up. He may have been cool with your showing up on his doorstep wearing nothing but a coat, heels and a smile, but he didn’t have any interest in being proactive about it. Which is, unfortunately, frequently par for the course.

Regardless, even under the most generous interpretation, it sounds like you missed out on what would’ve been lousy sex. Under the worst… maybe there was something rotten in the state of arousal. But while I don’t think you necessarily dodged a bullet, I think you definitely dodged some unsatisfying d--k.

But a thing I want to emphasize here is that just because I think these were pink flags rather than red ones, that doesn’t mean that they weren’t red flags to you. And more to the point, even if there were no red flags, that doesn’t mean that you made the wrong call. Just because someone isn’t tripping your Spidey-sense doesn’t mean that their behavior still can’t be disqualifying. You wanted to meet up in person for a vibe check before you decided to get d--ked down and he clearly didn’t want to. That’s all you really need to say “yeah, nah, we’re not doing this”.

You’re allowed to set standards – for your safety, for your comfort, for your pleasure, even for s--ts and giggles if you feel like it – that your potential partners need to meet. If they don’t meet them, for whatever reason, you’re allowed to decide that this is a deal breaker. You can decide to call it off because you had a bad dream about him that you couldn’t shake. You are allowed, at any point, to decide that you don’t want to see him or his junk, for any reason, no matter how arbitrary. Other people may think it’s excessive or stupid or unnecessary but that’s their lookout, not yours. It’s your body, your call, nobody else’s. Other people can have opinions about it, but they don’t get a vote.

So to TL;DR it: I think these were more pink flags than red ones. But even if they were green flags, you’re still allowed to say you’re not feeling it because reasons. And flags or no flags, I think you made the right call for you.

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: After being single for some time and dealing with some traumas that happened in that time, I’m getting ready to get back out there to find someone with the hopes of getting married and having a family. The catch you ask. Well, the issue is dating itself or my lack thereof. As a 39-year-old male I have never had a serious long-term relationship in my life. My two longest relationships were roughly two months before they ended. I’ve always struggled with dating ever since I was a teenager and finding anyone interested in me was aways like pulling teeth. I often went years without dating anyone because I couldn’t find anyone potentially interested in me.

On top of that I had some health issues in my early 20’s to early 30’s that because of my health issues I voluntarily took myself out of the dating scene because of what I was going through limited what I could have done and to be honest I was never going to be successful then when I was having my problems. My last attempt at an actual relationship was 6.5 years ago. Trying to get back in, I feel that my lack of experience is the albatross across my neck that is going to be setting off all sorts of red flags with potential partners.

My lack of experience and lack of long-term success in dating has always been something that I have a lot of shame for along with my other problems. My lack of experience has basically killed any confidence I have with dating. Part of me knows I will be successful, and I will find someone, however part of me knows that I am going to be a failure and stuck being alone and miserable the rest of my life. I certainly don’t believe in karma, but it sometimes feels like this is the karma I get for my past behaviors.

So, what can I do to get some of my confidence or lack thereof back?

Thanks

Bad At Dating

DEAR BAD AT DATING: Ok, dropping the “karma for past behaviors” makes me wonder precisely what those behaviors were that this would be karma for. If this wasn’t due to egregious behavior or having done something heinous, then I’m not sure how they would condemn you to permanent singledom. I would also assume these are in the past and things that you have either grown past, sought forgiveness for, made amends for or all of the above. If not… well, I’d start there.

But that aside, I have a quick question, BAD: if you encountered a woman your age who had never been married, hadn’t had a relationship for longer than a few months and had, for a time, deliberately taken herself off the dating market because of other issues in her life… what would you think of her? Would you see that as a red flag? Would you think that this meant that there was something seriously wrong with her?

And if so… why? Why, specifically, would you see this as being a warning sign? Especially if she had the qualities you were looking for in a partner? Are those real worries, or are they ones that you think you should have, all evidence to the contrary?

But maybe you wouldn’t automatically assume that she’s somehow damaged, flawed or otherwise an unsuitable partner. Maybe you could empathize, understand that dating can be difficult and sometimes life will throw sand in the gears. Perhaps you could understand, even without personal experience, that sometimes s--t happens that’s outside your control and means that dating and romance has to be put on hold while they deal with these other issues.

So why would you give that grace to someone else, but be unworthy of it yourself? Why would you assume, with no evidence, that your inexperience would be seen as a negative or a warning sign, especially when you could understand why it wasn’t a red flag in others? I mean, you’re not so uniquely benevolent that you have wellsprings of charity that other people don’t have, no Buddha-like beneficence that makes you stand out from the rest of the world. You’re an average guy, same as everyone else. So why are you capable of giving grace while also being uniquely incapable of receiving it?

Or is it just that you’ve heard other people say this with no actual evidence and taken it on as gospel? And before you say it: social media doesn’t count as actual evidence, any more than one person’s TikTok video is indicative of a political or social trend.

Another question for you: what is this lack of relationship history going to say about you that’s inherently bad – so bad that no context or knowledge of you as a person could make up for it? What is it going to say that’s missing? That other women didn’t like you? And? It’s not as though women can’t understand other people not finding them attractive or struggling to find a partner. Nor is it that having lots of former partners automatically says anything good about a person. A guy who has fifty exes isn’t automatically more desirable than someone who only has one, and in many cases might be less desirable.

Now the next question for you, BAD: how are people going to learn about this lack of dating experience? Because I have been on more first dates than you’ve had hot dinners and I’ve never had anyone ask me for my relationship resume, nor even the number of people I’ve slept with. I can count on the fingers of one hand the people I’ve had relationships with where the extent of my dating or sexual history has come up, and none of them asked about it up front; it was something that came up organically and only after we’d been dating for a bit. Even fewer asked or cared about numbers; the only times any of it mattered was because a particular past relationship was directly relevant.

So unless you’re having a deluge of people who are asking you to list out references with up-to-date contact information like you’re applying for a job, the odds that this is ever going to come up is low. Or if you have some compulsion to spit it out before your appetizers have even arrived, that might be a red flag… not because you have no dating history, but because you’re demonstrating lower social intelligence than most people would want in a partner.

But if we assume, quite reasonably, that you’re like anyone else, if/when it does come up, the odds are that it will be in context of a relationship with someone who actually knows and presumably understands you and why you might have struggled with relationships. If they have so little empathy, compassion or understanding that this would suddenly change how they feel… well, that’s a flaw in them, not a flaw in you.

And related to that: why would you want to date someone who is going to immediately judge you based on… well, literally nothing? Are you exclusively attracted to judgmental women? Are you only into women who have a very stringent checklist and who reject anyone who doesn’t tick every single box? Are you really going to find yourself wanting to be in a relationship with someone who has no compassion, no understanding, no ability to say “oh, that must have been rough, I’m sorry you went through that”? Would you really regret not being in a relationship with someone who would say “you are a great guy, and you have all these wonderful qualities, but you didn’t get the stamp of approval from at least 5 other women first and so with regret I have to end this?”

Writing it all out like this makes this whole thing seem pretty absurd, doesn’t it? Well, that’s because it is. Your dating history isn’t an objective mark of anything other than the number of people you’ve dated. It doesn’t negate all your other qualities, nor does it override the reasons why someone would be attracted to you. It’s not definitional, any more than being left-handed or having hazel eyes is definitional. It doesn’t tell people who you are. It doesn’t mean you’re more or less desirable; it just means you haven’t dated. It’s a data point, not the sum totality, and not even the most significant data point.

It means exactly as much or as little as you make it mean. People are far more likely to assume it means something negative because you act like it does; you’re the expert on you, after all, so clearly you know something they don’t. But if you just treat it as no big deal, they are more likely to treat it as no big deal. And the ones who do are people who have self-selected out of your dating pool as being utterly wrong for you.

Improving your self-confidence is going to be contingent on no longer treating this as anything than a neutral fact. It may have informed part of who you are today, but if you like who you are, that’s not a bad thing. So the key is to realize that it’s only as big of a deal as you make it. If you can go around your daily life without the Scarlet S (for “single”) turning you into the town pariah, you can date without it being the dealbreaker you think it is.

This is as big of a deal as you make it out to be, BAD. So choose how much you are going to let it define you. You’re the only person who can.

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 reaching out because I’m feeling incredibly confused and frustrated about my relationship, and I really need your perspective. I’m currently dating this stunningly beautiful girl, and I can’t help but wonder why on earth she’s with someone like me. When I look in the mirror, all I see is someone who isn’t physically attractive. I don’t have a gym body, I don’t have money, and honestly, my face isn’t anything special

I’ve tried using Tinder, which everyone seems to treat as the ultimate solution for finding attractive partners. People rave about how it opens doors to incredible connections and allows you to meet people who genuinely appeal to you. But for me, it’s been a complete disaster. I’ve never had any luck on that platform. Every time I swipe, I’m painfully aware that I’m not the type of person that most girls are looking for.

So here I am, with this girl who could have any guy she wants, and I can’t help but think: what does she see in me? Does she have a vision problem? Is she just looking for a charity case? Or is there something about me that I’m completely missing? I feel like a misfit in a world where physical attractiveness seems to be the only thing that matters, and it’s eating away at my self-esteem.

To be honest, I’ve even started to consider whether I should just end things with her. I mean, she’s so beautiful that I can’t shake the feeling that I’m somehow holding her back from being with someone who truly deserves her. It feels like I’m living in a fairy tale where I don’t belong, and I worry that I’m just a placeholder until she finds someone better. The thought of her being with someone else who matches her beauty and charm only adds to my anxiety.

I’m genuinely wrestling with all of this, and I’d love to hear your thoughts on how attraction works beyond physical appearance. Is there something deeper that I’m missing, or is this just a situation that’s doomed from the start? What really matters in the end when it comes to relationships?

Thanks in advance for your help. I really appreciate it.

Stand In Boyfriend

DEAR STAND IN BOYFRIEND: There’re three separate issues embedded in your letter, SIB, but they’re all twisted and tied around each other like horny snakes, creating a Gordian knot of insecurity. And while it’s probably better to cut the damn thing in half, I wouldn’t be me if I didn’t pick them apart a bit first.

So, let’s start with the face you see in the mirror. There’re a couple of things here. The first is actually fairly simple: you’re basing your judgment on your attractiveness on what other men have told you that women want, not what women necessarily are interested in. The qualities you mention – the gym body and money, in particular, are qualities that men tend to admire in other men. These are symbols of status and power to other men, things that other men want to have or to emulate… but not necessarily what women want.

In fact, if you ask women – and I mean literally ask the women in your life – I think you’d find very quickly that your bank account or take-home pay isn’t even in the top 10 of qualities that they’re looking for. The idea of “a man must have money” is a consideration in as much as that women want someone who isn’t going to be a drag on them than wanting Daddy Morebucks. Yes, there’re women out there who (supposedly) want men to be a walking ATM that spoils them and takes care of everything… but this is far more a product of social media than reality. You’ll see a lot of “want a rich man who’ll take care of me” videos on TikTok or whatnot, but those are selling a fantasy to men, not an actual significant population of the dating public. ��(This, incidentally, includes tradwife types; it’s rather telling that they tend to already come from money and are, in fact, running a business of their own, rather than just keeping house for their husband. It’s a fantasy at best, a con at worst.)

While there are genuine gold-diggers out there, they’re few, far between and very, very obvious about it, and you, specifically, are not likely to encounter them in the first place. There are far more women who really just want someone who is going to pull their weight and not be frivolous with money in ways that will make things harder. This is far less about “I want a partner who’s a provider” and more “I want someone who’s a responsible adult and isn’t going to sacrifice the rent check because he wanted a bigger TV”.

The same goes with “gym bods”. This is another area that’s a trivially simple belief to debunk. It just requires going outside and actually paying attention to the couples you see. Go to the park, the zoo or Costco, Target or WalMart on any given weekend and you will see couples all over the place… and significantly, many if not most of them aren’t going to look like they spend all their time pumping iron. Men are far more into the athlete look and what it says than women are. While yes, women have body types that they love – aesthetically or otherwise – what they’re attracted to can be as wide and varied as it is for men. If you can be attracted to someone who doesn’t look like Sydney Sweeney or an Instagram fitness influencer, it should be obvious that women can be too.

I would also point out that not thinking you’re attractive doesn’t mean that you objectively aren’t. A thing that guys rarely consider is that, quite simply, they’re not their own type. Not having facial features that you think are attractive doesn’t mean that you look like the Toxic Avenger; it just means that those aren’t necessarily features that you would think are hot. That’s very different from being objectively ugly. And as I’ve said over and over again: if I had a nickel for every guy who insists that he fell out of the Ugly Tree and hit every branch on the way down but in reality, mostly needed a better haircut and skin care routine, I’d be swimming through my money bin like Scrooge McDuck.

Seriously, go watch some Queer Eye and notice how a simple haircut and better fitting clothes can be transformative.

The next issue that you bring up is Tinder specifically and dating apps in general. I don’t know who told you that Tinder was this amazing place to make incredible connections, but they either were misled or delusional. Tinder’s never fully gotten away from its hook-up app origins and has always focused on a far shallower, split-second judgment rather than forming real connections. It’s always been a place where your ability to look good in photos (which is not the same thing as being physically attractive) is the primary concern. But it – and most dating apps in general – are designed to be frustrating. They are set up to encourage mindless and continual swiping, and your choices (and the choices of others) are constrained both by an algorithm and a user experience that’s intended to annoy you until you’re ready to pay money to be less annoyed. Think of dating apps as being akin to Candy Crush; you can play for free, but they’ve designed it in such a way that you are pushed to convert and buy their boosts to alleviate the frustration.

It’s also important to note that not only are there massive gender imbalances in the user base (approximately a 70/30 male/female split, depending on your source), but it also takes a VERY large number of swipes on average per match and a number of matches to get a date. So, part of the frustration is that there is a limited pool of potential partners overall and the expectation that it will be a quick turnaround from “sign up” to “get date” has always been more marketing hype than reality.  

This is part of why I’ve been telling people to deprioritize the apps and focus on meeting people in person. If you’re going to use the apps, you want to do so deliberately, mindfully and with serious restrictions on how you use them.

Now all of this is to lay the groundwork about your real issue – the mistaken impressions and outright deceptions that are part of the insecurity you’re feeling. You’re experiencing these things, not because they’re objectively true, but because of things that play to your anxieties, deliberately and otherwise.

Now, let’s talk about your girlfriend. And rather than focus on the concerns that your insecurity is throwing your way, let’s focus on things that are concrete. Instead of absurd “what if’s” that only make sense if you are begging the question, let’s pay attention to what is most likely, most reasonable and actually comports with the real world.

Let’s start with an obvious one: yes, sometimes people will date someone they’re not attracted to simply because they are trying to have A Relationship. But this tends to be more male behavior rather than female behavior; guys who are picking someone because they are looking for the chance to have sex. Women who behave like this tend not to seek out placeholder relationships; they are more likely to stay in relationships that no longer work rather than to seek out someone they’re not into. Even the whole “cuffing season” schtick (which, quite frankly, I think is more media hype and memes than reality) is more about “find someone who’s good for the short term”, not “I will take what I can get”.  

But then the question would be: why you? Why would someone pick you if you had no desirable qualities, even if you were a short-term partner by design? What, realistically, would be her motivation? And I do mean realistically; the idea that she’s so myopic that you look like an Impressionist painting rather than a person is absurd on its face. So too is the idea that she’s just pranking you or that she’s taken pity on you. I hate to tell you this but people – not women, people – don’t date people out of pity or for charity. If she chose you, she chose you for a reason, so what reason would that be if she didn’t actually like you and want to date you specifically? Again: is there something that a reasonable outside observer would agree is the case? Or is it more reasonable to say that this is your insecurity talking?

Here’s another thing to consider: what, if anything, about your girlfriend’s behavior would lead a reasonable outside observer to think that she doesn’t actually like you or motivate her to lie to you about wanting to date you? Leave aside your feelings about your attractiveness; that’s not evidence, that’s speculation. I am talking about her behavior, her actions, things that she has said and done. What reason would she have to date you besides wanting to date you, specifically?

Has she acted bored or disappointed when she’s been with you? Has she made comments about wanting better or more or things you don’t offer? Has she talked you down, compared you unfavorably to other men or said that she wished you were more like X person or Y person? With everything you know about her, has she ever done or said anything that would lead a reasonable person to think that she’s the sort of person who would engage in that sort of behavior in the first place, never mind with you specifically? ��And here’s the single, most important question: why don’t you trust your girlfriend? Has she said or done anything that a reasonable outside observer would think is deceptive or indicative that she’s using you? Or is this entirely down to your insecurity and your unwillingness to accept that this is exactly as it appears?

Here’s the thing: I think you’re so invested in your belief that you’re unattractive that you’re afraid to be wrong. You want to believe this is a trick because then you aren’t responsible for this relationship; if it ends, it was always going to end, not because you did something to hasten that ending. People are frequently afraid of success, because now they have something that they have to work at and maintain. They’re responsible for the outcome of their own choices and the dildo of consequences rarely arrives pre-lubricated. It’s much easier when failure is assured, especially if you can blame it on The Universe instead of having to acknowledge your own agency. Hope, after all, is a very scary thing when you’re not used to having it.

So at the end of the day, this comes down to whether you actually trust your girlfriend or not and whether you respect both her choices and her agency. The idea that you should break up with her “because you’re holding her back” is actually kind of insulting; it implies that you know better than she does and that her actual desires and choices mean less than what you think she should want. If you don’t trust her, then yes, you should break up with her. Not because she’s lying to you, but because that lack of trust is corrosive, and it’ll destroy the relationship anyway. It’s incredibly harmful when someone you love calls you a liar every time you say that you love them, and in time you quit fighting them over it because the pain just becomes too much.

But if you do that, then you also have to admit that you didn’t break up with her for the greater good, you did it because you couldn’t let yourself trust her or be happy with her. You snatched defeat from the jaws of victory because you wouldn’t accept that maybe this was exactly what it seemed and she actually cared for you because you’re you.

So maybe the relationship you need to focus on more is your relationship with yourself. This letter is precisely the reason why I bring up the Ru Paul quote over and over again: you don’t love yourself, and so you can’t accept that others love you. So perhaps what you need more than anything else is to learn to love yourself, so you can recognize and accept love when it’s freely given and not a trick.

So, were I you? I would stop questioning why your girlfriend is with you and start questioning why you can’t accept it. And that’s the sort of thing that’s best sorted on the therapist’s couch, not by pushing away people whose only crime is liking your company and finding their time with you to be enriching and pleasurable.

You’ve got a good thing here, and one that goes directly against your own bulls--t beliefs. Maybe you should lean into that instead of fighting against it. Sometimes stories really do have a happy ending. So hie thyself to the therapist’s office and do some couple’s counseling with yourself. It’ll make you much, much happier overall.

Good luck.

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