DEAR DR. NERDLOVE: I’m in a situation that has me genuinely confused. My girlfriend complains that we don’t have enough sex. From my perspective, I always thought she, as a woman, would feel relieved that I don’t push for it as much.

For years I worked on reducing my sexual desire through meditation, discipline, and channeling my energy into other aspects of life. My reasoning was that male sexual desire is naturally stronger, and that by lowering mine I would actually make things easier for her.

Here’s what confuses me: if heterosexual female desire were as strong as male desire, wouldn’t we see more evidence of it in everyday life? Women openly seeking sex, a whole market built around it, etc.? Since I don’t observe that, I assumed my girlfriend would appreciate my lower libido rather than feel frustrated by it.

Now I find myself surprised that she wants more, and I don’t understand. Am I misinterpreting the difference between male and female desire? How can I reconcile the discipline I’ve built in managing my impulses with my girlfriend’s needs?

Thank you,

Namast3

DEAR NAMAST3: Alright, I’m going to be honest – when I got this letter, I nearly tossed it aside as an obvious s--tpost. But as I’ve said many times before: I’m not overly concerned about folks trying to slip fake or bulls--t letters past me if there’s something for other readers to take away from it.

And considering how often “women say they want this but men say they don’t, who should I believe” comes up… well, this is at least more plausible than some letters I’ve answered.

So: yes, you’re misinterpreting the difference between male and female desire. The idea that men are the lustier gender is actually very recent; for a very long time, it was assumed that women were, in fact, the more sexual gender. Ovid wrote about how Tiresias was force-femmed by the gods in order to settle a bet over who likes sex more, declaring definitively that women did. Medieval folklore, likewise, was full of female witches and demons who tricked or coerced men into fulfilling their insatiable needs.

I’d also point out that there are a number of women in history who were rather famous for being hornt up. One of my favorites is Julie d’Aubigny, a French opera singer and flagrant disaster bisexual, who would repeatedly beat men in duels after having been caught flirting with their wives and who burned down a convent as part of a plan to rescue one of her lovers.

It wasn’t until the late 19th and early 20th century when the view started to shift – a process that was promoted, in part, by the proto-feminist movement of the time. The idea was that men were the more bestial and baser of the genders, and it was on women – who were more spiritual and “pure” to help them reign in their animal lusts and impulses – a belief that has continued well into the modern era.

But to assume that women were uninterested in sex or that there isn’t a series of industries supporting that interest requires a certain amount of nearly deliberate ignorance. Magazine racks and book shelves have been littered with guides and advice for women on attracting men and having better sex. Shows like Sex in the City and Fleabag put female desire front and center and movies like Fatal Attraction portray that desire as powerful and terrible. The Twilight books were not shy about how much Bella wanted to bone Edward and I have no idea how you could’ve missed the entire 50 Shades of Grey phenomenon that brought BDSM to middle-America. And that’s not counting the literal terabytes of woman-written smut, from romance novels to fanfic on An Archive of Our Own that’s spicier than hardware store hot sauce.

S--t, you can find vibrators for sale on the racks at CVS and Walgreens, while you still have to go to the counter and show ID to get allergy pills.  

So, I can’t help you with why you haven’t seen this, because it hasn’t exactly been hidden.

The reason why women aren’t as openly seeking sex or wanting sex in their personal lives is because society still punishes them for it, especially if they’re seeking then “wrong” kind of sex or in the “wrong” way. Witness the hue and cry over every female singer, from Madonna to Sabrina Carpenter, from Sade to 20 Fingers, to Khia, to Lizzo and Cardi B. for singing or rapping about wanting to get d--ked down like a champion. Every time, there’s been a clutching of pearl necklaces and fluttering hands about how awful it all is and what sort of example they’re spreading. Even basic sexual and reproductive health care for women, from hormonal birth control to HPV vaccines are treated as though they encourage “innocent young maidens” to become rapacious Jezebels.

And of course, guys have a tendency to lose their s--t when women are more open about their sexual interest; part of the reason for all the ‘tradwife’ fetish material that showed up everywhere was catering to dudes who get uncomfortable around the flouting of “traditional” gender roles in the dating scene.

So yes, Namast3, women do, in fact get horny. In fact, women’s capacity for sexual desire is as varied as men’s; just as men can be asexual or have low libidos, women can be absolute f--k-monsters. The difference is a combination of social opprobrium and the fact that sex – from pregnancy to the spread of STIs to physical assault – is riskier for women than it is for men.

But even if this wasn’t the case, there’s still the matter of you talking to your girlfriend about what she wants instead of just making assumptions. It would be one thing if this were a case of mismatched libidos, where she would like to be having sex more often than you; that happens quite frequently, especially among couples who don’t prioritize sexual compatibility when they’re looking for a relationship. But instead, this was you unilaterally assuming that you knew your girlfriend better than she did and apparently not bothering to check in with her.

Here’s a handy rule of thumb: if “common sense” says one thing about what women want and your girlfriend says another, side with your girlfriend. I promise you: she knows what she wants far better than a bunch of angry single guys and slapdick grievance peddlers on Reddit whose chief source is “Dude, Trust Me”.

How do you “resolve” the difference between your discipline and your girlfriend’s desires? Well, I guess you decide which is more important for you: continuing to repress yourself until you’re single again and you can find someone who’s not as horny, or a lot more banging with your girlfriend.

Your call.

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’ve been reading your blog for a few years now. I remember when I first got exposed to the ideas of personal responsibility and living with intent. Naturally, I hated it. Over the years I internalized these ideas to get where I am now. I’m no longer in student debt and I’m moving out of my unhappy family home very soon. I have an in-depth dating question but first I’d like to get some context out of the way as well as some very substantial progress I’ve made mentally.

I’ve done a lot of crazy things over the past 2 years. From jumping out of a plane to completely changing careers. My idea of who I am got broken, built up, broken again, and it has happened yet again. Only this time, who I am feels comfortably familiar. I was abused growing up. It didn’t come from my family, who were more neglectful due to circumstance, but rather my teachers and school staff. I was told over and over again how worthless I was and how I would never amount to anything. That I should have been more like my classmates. Never achieving, always behind. Always measured by a yardstick when I needed a meter stick. I am autistic, so my path has always been different from everyone else’s’. Of course, my abusers didn’t understand or care to understand this.

I was a happy-go-lucky kid. I had a childlike wonder and enthusiasm for life like no other. I laughed quickly as well as cried. I could endlessly talk about my passions like they were physically a part of me. I was goofy, kind and most of all: deeply intelligent (though I was taught to doubt this). I didn’t believe my abusers at first. I was just a confused kid wondering why these adults were being so mean to me. Eventually though, tragically, the dark words and manipulation began to stick. By 10 years old I was convinced I was worthless and wanted to die. I was 10. The loving kid who liked Animal Planet and Discovery Channel and could talk endlessly about Lord of the Rings and Star Wars, was dead.

And he stayed dead for almost two decades.

Until now.

I often grappled with the question “when will I be lovable.” And I’ve sent enough letters about it. Always convinced I needed to find some mythical “good enough” standard to be considered dateable but more importantly: worthy of existing. I tried so desperately to be cool. To learn cool skills, develop charisma, become that sexy somebody who could f--k any woman I wanted. I took the Grimes Test but took the absolute worst lesson from it ever.

Unless you are constantly improving, you are nothing.

Your worth is what you provide, not who you are.

“What do you bring to the table?” Didn’t become a question of what kind of person I was, but what my “sexual market value” was. Self-worth coming from the absolute most shallow, inconsequential places imaginable.

I obsessively compared myself to everyone who was doing “better” than me. I needed to be more, all the time. More this, more that. More, more, more. I never felt enough simply being who I was.

Until I realized something: I wasn’t comparing to other people, I was comparing to a magical, non-existent version of myself. A Shadow. One that was everything I wanted but would always be out of reach because I made it so.

So I stopped trying to be cool. And it has been the absolute best decision I have ever made. I looked the Shadow in the eye and told it “You Don’t Get to Speak for Me.” Ever since, the person I lost to abuse, has come back to life.

I’m myself again. After nearly 20 years, I’m myself again. I finally shed the mask that was forced onto me. I’m sure you’ve heard of the term “autistic masking.” That’s essentially what was done to me, only it was bolted to my face like an Uruk-Hai Berserker at Helm’s Deep. Any uniqueness, any edge or humanity, was scrubbed from my personality to be more palatable to neurotypicals.

I am making the executive choice to say “f--k that” and bring back my weird, goofy, wonderfully passionate self. I know it’s not “optimal.” I know it’s not the ripped, master chef, effortlessly charismatic cartoon character the Shadow whispered in my ear for decades.

But I don’t care. I don’t want to be perfect. I don’t want to be cool. I don’t want to be optimal. I want to be ME.

I was at a drive through and saw a dog-shaped cloud and laughed at it for like 10 min because it made me happy. I like to make weird jokes that people probably won’t get but I don’t care because I find them funny. I want to gush about the things I love because I love them. I want to be kind to people because it’s important and everyone should be kind.

Now don’t get me wrong, I will continue to grow as a person until the day I die. But now it’s gonna be on my own terms. Not in accordance with someone else’s.

This finally brings me to my question: what would flirting look like for me? I know that at its core it’s just showing interest in a fun way and communicating it to someone with vulnerability and sincerity. But I’m still trying to figure that out as I’ve tried some flirting styles in accordance with the mask I wore but now that the mask dropped, I’m kind of back to square one. A pretty good comparison to me personality wise is Jacksepticeye. He is also autistic and we’re very similar people. Bubbly, happy, and have endless joy we want to share with the world. Probably not the most stereotypically “masculine” but I don’t care to be what’s en vogue.

So I guess that’s it. What might it look like for me, given all I’ve provided. Thank you so much for everything you’ve done for me, and helped me do for myself.

Sincerely,

The Unmasked

DEAR THE UNMASKED: I’m glad to hear about all the progress you’ve made, TU, and how you’re returning to your most authentic and honest self. That’s incredibly important, not just for dating and relationships but for having a good and satisfying life. I’ve talked before about having been in the PUA scene and watching a LOT of the folks I hung out with hit serious downward spirals that, in a couple of cases, ended with them in the hospital or worse. Almost every time, it was because they were trying to be someone that they thought they were “supposed” to be, instead of who they were.

That’s damaging under the best of circumstances. It’s even more so when you’re dealing with being neurodivergent or you have issues with depression or emotional dysregulation. So finding (or returning to) your true self, embracing it and honoring it is a huge, huge step in the right direction.

It’s also a reminder of an important point: fun beats “cool”, hands down, every time. Which, conveniently enough, is also how we’re gonna segue into the answer to your question.

The thing about flirting is that the way you flirt can be as varied and unique as the person doing the flirting. This is because there’s no one way to flirt. There’s an underlying principle to flirting correctly, but the method – and the people those methods work for – are going to look differently depending on who’s doing the flirting.

The issue at hand is that a lot of people think flirting is how you generate attraction – that if you know how to do it right, you’ll be irresistible. But that’s not the case. Flirting isn’t generating attraction; flirting is the expression of attraction. The core of flirting is very simple: you’re telling someone you like them, in a way that’s enticing and fun, and ideally, you’re encouraging them to have fun with you. That’s where the reciprocal attraction comes from – the fact that someone is enjoying and appreciating the time they’re spending with you.

Flirting is also a subtle way of screening for people who are right for you. Flirting, after all, doesn’t work if it’s not fun for everyone involved. While there is a skill aspect to it, if someone’s idea of fun or enjoyment doesn’t line up with yours, you’re probably not going to be a good match. One person’s banter is another person’s tedious ‘why can’t you ever be serious’ or, worse, feels like negging. That implies a mismatch; if they’re not enjoying it, then that may well be a sign that your personalities won’t mesh the way you would need for a strong or serious relationship.

If folks aren’t responding well to your flirting, it’s good to both ask if your flirting style needs a little polish… but it also is worth asking if you’re flirting with the right people.  Yeah, you want to flirt in a way that other people will respond to… but if it’s something that’s not in alignment with who you are as a person, then you aren’t going to be enjoying it. And if you’re not enjoying the flirting that the other person responds to, the odds are good that you’re not going to enjoy a long-term relationship with them. After all, if you feel like you have to act in ways that aren’t authentic to who you are in order to express interest and find reciprocal interest, it stands to reason that this is going to be a trend in the rest of the relationship.

The trick to finding your flirting style is knowing yourself and expressing yourself in an authentic manner. If you’re someone who, for example, likes banter and word play, then a more teasing and playfully antagonistic form of flirting might work for you. If you’re someone who’s more sincere and direct, then banter may not work for you, but appreciation and enthusiasm might work better, instead. Something along the lines of “hey, I would love for you to introduce your favorite thing to me”, for example, will hit some folks like an atomic bomb – the idea that someone wants to hear all their thoughts about KPop Demon Hunters will be like their birthday, Christmas and Hogswatch all at the same time.

Recognizing and embracing your personality into your flirting is also helpful for building and maintaining emotional momentum. One form of flirting – that folks often don’t recognize as flirting – is “pebbling”. The name stems from the way that male gentoo penguins will seek out a great pebble to present to potential mates; it’s an offer of the first stone to building a nest. In a flirting context, pebbling is finding and sharing something that’s either relevant to the other person’s interests, or that they might find interesting, funny or sweet. It’s a way of saying “I’ve been paying attention to the things you like and I wanted to bring you more of it.” You’re showing that you care, not just by bringing something you think they’d enjoy, but showing that you understand and respect their interests and passions.

The fact that you’ve been returning to your authentic self is an opportunity to think about the ways you’d like to express interest and the ways you like to have fun with people, as well as the ways that the people you’d most like to date would have fun. Since you’re prioritizing fun and joy, perhaps that’s where you should start: both sharing the things that bring you joy and being curious and interested in what brings other people joy. As an exercise, you might want to think of how to “pitch” your interests to folks – what about it do you find fascinating or fun and why? What got you into it, what about it speaks to you and how would you describe this to someone who may be encountering it for the first time? People make jokes about the whole “It’s X Meets Y” formula for books, TV, movies or video games, but this comparison to something familiar makes for an easy entrance into a topic; it gives the other person a familiar starting place that can make it feel less strange, esoteric or intimidating.

The benefit of this exercise is that you can then turn it around; if you can explain your interests and how they hit you just right, you then have a structure about how to ask about someone else’s interests. So what is it about this genre of music or that sport or that hobby that speaks to them? How’d they get into it? You can even get playful with it by inviting them to be a little self-aggrandizing; if they had to impress $CELEBRITY_JUDGE, how would they go about doing it? What would they pick as an example, how would they make it their own and so on.

And that part’s important; flirting is reciprocal. It’s not showing off, it’s sharing. Guys who use humor in their flirting, for example, have to be careful that they’re not just performing. There’s a difference between being silly and jokey and testing your tight five, after all. You want the person you’re flirting with to flirt back, whether that means volleying teases right back or having the opportunity to gush over their favorite things, to playfully invite you to “chase” them or what have you. When they do, you want to respond positively; if someone says “oh, I love watching vocal coaches reacting to $SONGS” and you go into a rant about how they just interrupt a song and drag a 3 minute ditty into a 20 minute YouTube video, then all you’re doing is shutting them down. Instead, it’s better to say “I’ve never really gotten into that; what do you like about it?” and let them explain it. Even if you still don’t like it, the fact that you can appreciate that they do and want to understand why it has meaning for them is appealing.

The last thing I will tell you is that flirting is a skill, and the only way to improve it is to do it. You can theorize all you want, but none of that will help without actually putting it into practice out in the field. While it may be awkward at first, any mistakes will help you fine tune your approach. If things seem to be falling flat, change it up a little and see if taking a different angle works better. That trial and error will help you find the way that works best for you and with the people you like.

So take that introspection and unearthing you’ve been doing and play around with it. Think about what you would like to share with others and how, and then use that as a basis for encouraging them to share with you. It may take a little practice, but before long, you’ll be flirting like a champ.

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: Apologies ahead of time, but you tend to ask for more details from people so this may be a long one.

This isn’t a letter for a problem I’m having, but instead looking for advice on how to help someone else.

I’ve been trying to help one of my best friends all the way from childhood, “M”, score a date for years now, but it’s never really worked out and recent events have me feeling a little guilty.

M and I are part of a fairly tight-knit and supportive friend group we’ve had since grade school. We’re all in our mid to late 20s now, and most of us haven’t had extraordinary issues with getting dates or entering relationships. Except M.

M has never been in a relationship, nor been on a single date. Thing is, he’s tried for a really long time. He’s asked people out all the way since high school, but he’s never had the slightest luck. He’s asked a lot of people out in person, tried the apps, and has even both asked us to and had others offer to try and set him up on a date.

Somewhat complicating things is that within our friend group, M is actually the most engaged in our local community and willing to go out and do things in town. He’s involved in a lot of local organizations and hobby groups, and despite being more introverted he has the widest social net and number of connections he’s cultivated compared to most of us. So, when he did ask us to set him up, none of were really able to come up with anything.

I’ll try to list what I think he has going for him and what’s going against him. Some of these are my observations, some come from things you recommend in your articles, and others are things I’ve gathered from speaking with women we’re mutual friends with. None of these are judgements, just bouncing off points – I do genuinely think he’s a catch.

+ Earnest, genuinely kind and thoughtful. I can’t count the number of times he’s been there for others in the friend group or I’ve seen him help others around the town.

+ Great listener, good at asking questions and using that to show interest in a person. He knows how to make people feel good about themselves and always tries to bring out the best in others.

+ Really smart, takes interest in a lot of things, has a wide range of hobbies, and can usually give really thoughtful input on different topics.

+ Loves to cook for others

+ Bare minimum here, but he’s avoided a lot of the usual toxic masculinity stereotypes. He couldn’t give less of a s--t about body count and the like. Not a single whiff of any incel-adjacent tendencies.

+ Incredibly well-liked and socially well-adjusted in a non-romantic context. It feels like every time I’m out in town with him, I’m meeting a new person he’s on really good terms with. Friends with lots and lots of women too, so I don’t think he has any issue with seeing them as regular people like lots of guys do.

– He’s fairly short, at least within our circles, around 5’4 or so. He’s always seemed to be genuinely okay with this though.

– He’s struggled with his weight for as long as I’ve known him. It’s something that’s always bothered him.

– He’s struggled with depression and anxiety for a lot of his adult life, and has his periods of getting really down. Used to be very prone to spiraling and withdrawing if something bad happened. He does regularly go to therapy and has been working on it. He’s good though at asking for reassurance while still putting in work and not offloading all the emotional labor onto others.

– Bad self-esteem. It’s not constant and when he is feeling that way, I don’t think it’s super obvious, but I know it’s something he’s struggled with internally.

– Can be a bit shy if he’s surrounded by strangers with no one familiar with him.

– A refrain I came across is that others think he’s too “innocent”. I’ve noticed he can clam up or get a little uncomfortable if dating or sex comes up outside our closer group. It may be relevant that several mutual friends have thought he was gay or asexual at some point.

– He identifies as a sub, at least in the bedroom. We’re in a redder area of the U.S so I’m not sure how many people nearby would be compatible in that regard. I recommended fetlife to him, but he said the only community nearby looked incredibly sketchy.

– He never quite figured out how to flirt. He’s still pretty awkward at it and when I’ve seen him try it or he’s recounted examples, it can feel like him and the other person are speaking different languages. I think the previous two points also feed into this – he’s said he usually tries to “play coy” and subtly invite the other person to take the more forward role in flirting, but it’s never quite worked for him. It seems he feels this is the way he’d like to be able to flirt; I don’t know if it doesn’t fit him or if he just needs better examples of how to do it.

– He used to take a long time to actually ask someone out. It’s gotten better (used to be months when we were younger, now it’s more like weeks), but he can still hesitate for a bit long when he catches feelings for someone.

He used to be good about putting in the effort to ask people out. He was never the type to cold approach or ask someone out he didn’t know very well – he always preferred to get to know someone as a friend through hobby groups and social events before making that jump. (Though, he did say he doesn’t think he’s demisexual or anything to the extent of that)

I asked him to ballpark at some point how many people he would ask out a year, discounting dating apps, and he said anywhere from 5 to 13 depending on how many new people he met. He’s also said he’s much pickier on personality than appearance, and isn’t wanting to date anyone conservative or into traditional gender roles. From what me and others have observed, he definitely has a few “types”, mainly being artsy types and more assertive or dominant personalities.

A while after we graduated college, though, he suddenly stopped asking people out and I noticed him seeming down a lot more often. I talked with him about it, and he said he got tired of feeling bad after the years and years of rejection and was “giving up” at least for a good while. He told me he felt like shooting his shot with people was only hurting him time after time and that if he was “meant” to have any success at all, surely it would have happened by now.

To be fair, I sympathized with him – he’d already spent a lot of time working on himself, and asked out way more people than any of us ever had to find our first relationships. I didn’t feel like I had the right words back then to help him, as I was also at a loss as to why he was doing so drastically worse with dating.

Reading your articles, I definitely think he gets RSD, and maybe it just got too much for him after all those years. I tried to encourage him, but as far as I know he did stop asking anyone out for around a year.

This brings us to the past few months- enter “C”. She came into the friend group through a mutual friend, and her and M hit it off pretty well.

C got a really good first impression from M when she first hung out with the group and even had noted how “sweet” he was to our mutual friend after. They ended up talking a bunch together and when her dance group was looking for a cameraman to shoot videos, he stepped in and started helping them.

As the weeks go on and the two get closer, C starts to get increasingly flirty with M to the point where all of us notice it. She gets very handsy, giving him hello and goodbye hugs, playing with his hair, holding his hand when she’s leading him places, and cuddling him when we had a movie night. To clarify, she does this sometimes with other women, but M is the only guy she’s like this with.

M lightens back up a bunch, finally feeling like he’s making a romantic connection after years of waiting, and asks me and a few others in the group one day if we thought she was into him. I of course tell him I think she’s really into him and encourage him to ask her out.

Unfortunately, when he did ask her out a few days later, she turned him down, saying she only saw him as a friend. This did crush him for a few days and since I’ve noticed him seeming a bit down again – particularly when the group’s talked about our dating lives. He hasn’t talked much about how he’s felt about what happened, but he did say he feels insane for feeling so certain, having heard for years that “he’d know it when someone likes him” and “the right person will make it easy.”

I do feel a little bit guilty and wonder if I should have gone to C and asked her if she liked M before encouraging him to ask her out. Going forward, is there any advice you’d recommend to give to him, or more conductive ways to help?

I want to encourage him, but I don’t want it to feel hollow after all my previous feedback and efforts to help him out weren’t able to get him anywhere.

Looking at all I’ve written, I know it may look like I’m overly involved in my friend’s dating efforts but keep in mind this is over the course of years and years. It’s not like he was constantly coming to me for help and not putting in his own efforts.

Bro In Need

DEAR BRO IN NEED: Before we get to anything else, I want to point out something that M said – something he clearly believes, which means he needs to scrape it out of his brain and not think it again: “if he was “meant” to have any success at all, surely it would have happened by now.”

I run into variations of this mindset all the time. It’s almost always a “nobody else struggles with this like I do” or “other people don’t have this problem” or “it shouldn’t be this hard”. It’s all a remix of the same basic thought: “everyone else has it easy, so the fact that I struggle with meeting someone means that there’s something wrong with me”. And I can tell you for a fact that this isn’t the case. I’ve been doing this gig for over a decade and I can tell you, with absolute certainty, that people struggle to find dates and relationships all the time. There are literal scrolls written by Roman philosophers about how people struggle with relationships. This is a problem that is, quite literally older than steam. As long as people have been pairing up, people have had problems doing so and seeking out help for it. It’s one of the most common experiences imaginable.

It’s entirely possible, for example, to have dry spells that stretch for years or longer. That doesn’t mean that there’s anything wrong with the person who’s struggling; it just means that they’re having a long string of bad luck. It’s a thing that does happen; it may be long odds, but that isn’t the same as being impossible. There’re also always factors that can influence one’s luck. It’s entirely possible, for example, that where a person lives is a major contributor to their dating woes. A queer person who lives in a small town in a conservative state is going to have a much harder time finding potential partners than if they lived in a larger, more cosmopolitan city with a more welcoming and accepting attitude. A liberal atheist in a right-wing, Christian community is going to struggle to find people to date too; that’s not a flaw in them, just an issue of who’s populating the dating pool.

It’s also important to remember that you can do everything right and still lose; that’s just life. It doesn’t mean that you’re uniquely f--ked or that you have some flaw that people can’t see and you should just give up and accept it.

I would also point out that, in the grand scheme of things, asking out 5 – 13 people a year isn’t that many. Considering how long you say M takes to ask someone out, as well as some of his other qualities, I’m kind of surprised it’s that high at all, which makes me wonder if maybe he rounded the number up a bit – either for his own ego or so you would think he was doing more.

Now, without following him around like I’m filming a nature documentary, it’s hard to say what he might be doing wrong. His taking a long time to ask folks out can definitely be an issue. While I believe in dating slow, there’s dating slow and then there’s going so slow that if his dating strategy were a snail, he’d be getting lapped by other, faster snails. However, the bigger issue, I suspect is how he’s flirting – which is to say, not at all. I don’t think he’s actually playing coy, so much as just really hoping that someone else will pick up on the psychic emanations radiating out of him and be willing to do all the hard work for him. Which is a lovely idea but even the most assertive and outgoing woman out there is going to need at least some indications that he actually likes her.

I suspect that one big issue is that he’s afraid of rejection. And I get it, rejection sucks, especially when that’s all you’re experiencing. But I think that he’s stuck in a state of suspended animation, where he’s fundamentally the same person he was in college and hasn’t made any substantive changes in his behavior, outlook or lifestyle. It seems like he plays things so safe that he basically takes no chances until well after the window of opportunity has closed.

It’s clear that he’s a sweet – and safe – guy and that’s what women like about him. While that’s a good thing in general, if you combine that with being very passive, you end up creating the image of a person that’s more of a stuffed animal and not a potential partner. I strongly suspect that a big part of why C felt so comfortable getting handsy and playful with him was precisely because he’s such a teddy bear that she could flirt for fun without worrying… but the problem is that he wasn’t flirting for fun. He thought it was serious, but when combined with both his tendency to wait an interminably long time and to not really make any substantive moves on his own, this all but ensured that she didn’t know he was interested and was likely surprised when he asked her out.

Now, a thing you mention that pinged pretty hard to me is how “innocent” he seems to be and how he clams up and gets uncomfortable when the topic of sex or dating comes up in your circle. I wonder whether this is a matter of genuine discomfort with sex – for example, the possibility that he may be asexual – or if he feels uncomfortable because he has so little experience. I remember back in college, before I met my first serious girlfriend, I felt pretty left out and weird listening to my more experienced friends talk about their love-lives. It felt like a conversation I was excluded from because, well, I had no experience to speak of. I do wonder if he’s feeling the same way – he feels like an outsider looking in, a guy out in the cold, nose pressed up against the glass while watching everyone else whose inside, warm and happy and having a good time and wishing he could be part of it.

As someone who’s been that guy… that’s a hard feeling to shake, especially if it’s been going on for, well, his entire life. And the longer it goes on, the harder it can be to feel like you can change it. At the same time, I can also say, definitively that the change is possible… but it takes a willingness to make changes and to do things differently. And for it to really work, he has to feel like he’s the driving force behind it, rather than other folks are working behind the scenes to make it happen like a bad episode of a sitcom.

So here’s an important question for you: have you talked to him about his love life and asked if he wants your help? That part’s going to be important. You mention feeling bad that you hadn’t talked to C before he made his move, but I think that if you had done that, your friend would’ve lost his s--t. There’s being a guy’s wingman and cheerleader, and then there’s getting a little too involved. If you made that sort of move unilaterally, I think M would’ve not only felt like it was out of line, but I think he would’ve tried to dig a very deep hole and pull it in after himself. To him, I suspect it would’ve felt like his mom trying to arrange a date for him – it would’ve reinforced his feeling like a loser. Look, he’s so bad at this that his friends tried to get involved on his behalf, like you all were in junior high again and asking Cindy if she liked him or like-liked him.

So I think it’s going to be important to say “hey, I know you’re still struggling and I’d like to help if you want it. What kind of help would you like? I can be a friendly ear and just listen when you want to vent. I can offer suggestions, I can point you in the direction of resources, I can be the head of your cheer squad, or I can even be your wingman, but I want to know what would work best for you.” And then let him tell you what would be most useful for him. It may well be that he isn’t ready to hear anything from you or his other friends; there is likely a part of him that thinks “well, they have to say that there’s hope, don’t they?” It’s hard hearing that you’re a catch when everyone seems to skip straight to the ‘release’ part of the program, and at a certain point, it’s understandable that he might think you’re just lying to him or not telling him what you really think.

In terms of what he could do… a lot is going to be about his developing and sustaining his self-esteem. I’m sure the combination of his height and weight bothers him, and makes him feel like he’s already out of the running. I suspect that’s part of why he doesn’t really flirt; it’s not just that he doesn’t know how, but he doesn’t feel like he can. It’s hard to flirt and be playful with someone you’re into when you don’t think that they could actually like you in the way you like them. Finding ways for him to start feeling better about himself and more like he has the capacity to be desired rather than a cuddly toy is going to be important. So if you two do talk about what he can do and how he can get better, part of the conversation should be “ok, so what can we do that will make you feel like you’re hot?”? He can’t do much about his height, but height isn’t the defining quality of hotness either. So what else would help him feel sexy?

He also needs to be willing to move a little faster and take risks. One of the problems he’s facing is that the skills he needs to develop are ones that can only be developed through actual use. You can’t learn how to flirt from reading or watching videos. You can see how other people do it, pick up ideas and things to try, but otherwise, it’s like trying to learn how to play basketball by watching Slam Dunk or how to make knives by watching Forged in Fire. Theory is great and all, but if you want to get better, you have to actually do the things you’re trying to get better at. That means being willing to flirt and to fail at flirting and to make mistakes. Confidence, after all, isn’t about feeling assured about success, it’s about knowing that mistakes aren’t fatal. Part of the point of making mistakes is to learn how to not make them, but another part is to learn from those mistakes – how to not let them throw you, how to roll with them, how to recover from them and how to stop being afraid of them.

He also needs to be willing to accept that he’s allowed to want what he wants – whether it’s just to be seen as a sexual being, to be a sub and find someone to top him and to feel frustrated. I strongly suspect that he feels like a loser and that he should feel bad for feeling that way. That, I think, is part of why he’s become fatalistic; he doesn’t feel like he has the right to feel frustrated or upset or even angry about it. I can appreciate his not wanting to seem like an incel, but pretending to be resigned to it and trying to repress his feelings isn’t the answer. Like I’ve said many times: the answer to feeling helpless and frustrated is to take action, not to try to stop feeling.

Speaking of which: you mention he’s going to therapy. If he hasn’t already, he should also see about the possibility of getting medication to help with his anxiety and depression. He should also consider the possibility that any anxiety and depression he has is a symptom and not the root issue. I was treated for depression before I got my ADHD diagnosis and it was only afterwards that I realized I’d been trying to treat the wrong condition. So that’s another avenue he may want to explore.

I know I’m talking a lot about internal work rather than developing his skills, but – again, speaking from experience – focusing on the skills doesn’t help without that foundation of inner work first. Part of the reason why I got into the PUA scene was because I was trying to feel like I had a way to get around my lack of inner self-worth – that if I had the instruction manual, everything would fall into place. But that was, at best, putting a bandage on a sucking chest wound; none of the techniques were going to change the way I felt inside. The skills honestly matter far less than changing how he sees himself; once he starts seeing himself as a piece of meat as well as a person, the rest comes far more easily.

You’ve got a good heart and you’re a good friend to M. Just make sure that he’s ready to accept that help and then talk with him how best to help him. That’ll go a long, long way to helping him make the changes he needs to have the sort of dating life he wants.

Good luck.

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