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