I’ve been on your site for quite a while, and found it super useful and relatable, with plenty of great advice. For reference, I’m a 24 year old male with zero relationship experience. Never had sex, never been in a relationship, never kissed anyone, never even held hands. The most I can say I’ve done is been on one casual date that didn’t really end up going anywhere.
I’ve struggled with clinical depression all my life, something I only was cognizant of a couple years ago (I’ve started taking meds to help me with this). In the past, I used to be incredibly socially awkward and had trouble making friends (much less girlfriends). As I grew older, I found that I had a passion for film and filmmaking and allowed it to take me to film school. Once I started my undergrad, I told myself “OK, new leaf, new people, new community. Now’s the time to jump into the dating pool”. Well, as you can guess, nothing really happened these four years. Not so much as a woman being even remotely attracted to me.
I graduated my undergrad and, afterwards, went to go attend a postgrad in Film Studies at Cambridge. Again, I told myself “OK, new leaf, new people, new community, hell new country. Now’s your chance”. So, this time, I made a really concerted effort to put myself out there. In some ways, it was successful. I made a lot of really good friends at Cambridge and was, in general, considered pretty popular on campus. My love life was a totally different story. The first girl I asked out (also the first girl I’ve ever asked out in my life) rejected me. Felt pretty down about it, but picked myself up and asked another girl out. She also rejected me (turned out to be gay-we still became good friends afterwards though). Felt really down about that but, later in the year, I asked another girl out. She rejected me too (she had a boyfriend). And, uh, yeah, that was about the extent of my dating experience.
This slew of rejections, plus just a complete lack of experience in general, had forced me to do a lot of thinking and self reflection. Was I just a boring, uninteresting person? I don’t think I am, honestly. I’ve been told by many people that I’m a really cool guy. I have a passion that I’m pursuing, and have even started to pick up some hobbies (for instance, I’ve been teaching myself guitar and really enjoying it). Is it because I come across as a dick and I don’t realize it? Again, I truly don’t think that’s the case, as I’ve been told by my friends that they consider my a genuinely nice person. Is it my looks? Jury’s out on that, honestly. I feel like I’m generally pretty average looking, though. I’m no Ryan Gosling, but I’m not exactly a troll either (although, what I do have going against me is that I’m of South Asian descent [thanks, colonialist beauty standards!]).
So, I’m not horrible looking, and I do believe I have some interesting qualities. So, what explains my lack of experience? Well, recently I’ve had a realization.
I may have good qualities, but I lack attractive qualities.
Now, you may think, what’s the difference between the two? To which I’d respond: isn’t there a difference between a friendship and a relationship? Whilst one set of social skills is great at forming one bond, it doesn’t necessarily transfer over into a different type of bond. So begins my search of how to develop attractive qualities. However, much of the advice I found online seems to be a bit too generic and vague to really be actionable. Communicate. Be considerate. Be funny. Have open body language. Etc. Which is great stuff to have, but I feel like I can do that already. However, despite doing these things, while I’m great at making friends, I’m not so great at finding a partner.
This has led me to believe that maybe this dating thing isn’t really for me.
I guess this long-winded buildup, then, is leading to one big question that has been haunting me. If I know that I am not attractive, is it morally justifiable for me to ask women out?
I know this may sound like a strange question, but hear me out. I know for a fact that I’m not an attractive person (my complete lack of experience speaks to that). So, as a result, any instance of me asking a girl out, or even flirting with her, will result in an uncomfortable, unenjoyable experience for her. If I’m not able to be smooth or charming in this context, I know for a fact that I’m going to subject her to an experience that is (to put it mildly) less than pleasant.
However, let’s say, by some miracle (maybe she had low standards that day or something) she’s receptive. Alright, great, now maybe we’d go on a date. But guess what? I’d still, unfortunately, be my unattractive self. And soon, she’d realize that and realize she’d be wasting her time with me. But, let’s say, by an even further miracle, she decides to go out with me some more and it eventually it turns into a relationship. Well, by that point, I’d be so wracked with insecurity and guilt because the entire time I would be thinking how she would be better off with a more attractive guy. Hell, even a one night stand would be unfair to her. My lack of sexual experience would mean that I wouldn’t be able to perform in bed, which, again, would result in an unpleasant experience for her.
All this is to say that, given who I am, I think that trying to date women is a selfish task on my part. I wouldn’t really be bringing anything to the table and, as a result, would not be giving her a good experience, whether sexually or relationship-wise. And, as such, I feel like it is morally unjustifiable for me to be entering the dating scene. I should have gotten the awkwardness out of the way about six years ago and, because I didn’t, women my age would be (to quote Danny Glover) “to old for this shit”.
Anyway, sorry for the long message. I guess I’m just writing to you because I do find you very insightful in your responses. So, what do you think? Am I just not dating material? Would others be better off if I were single? Or is there some aspect about myself I can fix in order to become attractive? Would love to hear your thoughts!
Cool but Not Hot
There’s a genre of question I get on occasion where the letter writer isn’t asking for advice so much as asking for permission. Sometimes it’s permission to do the thing they already know they need to do. Other times it’s permission to give up. And honestly… more often than not, folks who are asking for my permission to give up are barking up the wrong tree. I mean, let’s be real: you don’t need my sign-off on this. I’m not The Relationship Council, where you have to get my blessing in order to quit trying. If you want to quit, then hey, you do you chief; just don’t expect me to validate your choice or belief that you’re hopeless and helpless. You may have noticed that’s not exactly what we do here at NerdLove Industries.
Case in point CBNH: if you just want permission to quit trying, then that’s all on you. But I’m not going to put my stamp on “yup, you’re fucked, may as well give up.” Especially when you seem to have put a lot of thought and effort into reaching conclusions that are, honestly, kinda batshit. I mean, you’re not the first person to write in with the idea that their just being interested in someone is an insult to them, but I think you may be the first who tried to frame it as being a moral issue. So congratulations, that’s a new twist on an old rationalization.
It also makes absolutely no sense. I mean, for this to be somehow immoral, unethical or selfish you would have to remove free will from the equation entirely. Your position — that your being unattractive makes it immoral for you to ask women out on dates — would require that women were, for whatever reason, unable to turn you down or that you were somehow coercing them, tricking them or otherwise preventing them from making a free and informed decision. And unless you’re Kilgrave or holding their goldfish hostage, I’m not entirely sure how you would accomplish that.
Congratulations; you’re a prime example of someone who’s pre-rejecting himself — something I literally just wrote 5000 words about.
The problem with your logic here — such as it is — is that you’re assuming that women are stupid, blind or both. First, in that trying to talk to somebody is inherently an immoral act which… I mean, ok there Chidi, gonna have to see your math on this one.
First, you’re assuming that things are going to be SO unpleasant that just talking to them would be be harmful and… dude. Look, I have seen some folks say and do some truly heinous shit while trying to flirt. Not being smooth or trying to flirt while not looking like a supermodel doesn’t even crack the top 100 of “awful experiences”, no matter what your jerk brain (or shitheads on incel boards) tell you. It also requires that women be unable to end the interaction if and when they so choose. Now, if you’re following them around the bar and refusing to leave them alone or clinging to them like a lovesick barnacle then yes, that wouldn’t be a great time. But “I don’t know how to flirt” is not only not in the same league, it’s not even the same sport. This isn’t apples and oranges, this is apples and fish.
Then there’s the idea that her going on a date with you or getting into a relationship with you would be equally immoral because… reasons. Once again, you’re deciding things for other people, assuming that either they have no agency or that you know their tastes and wishes better than they do. The latter is presumptive and the former is just insulting. Unless you are a master of disguise or you’ve managed to somehow convince these women that you’re someone you’re not — and I don’t mean “they think I’m cool but I’m not”, I mean “They think I’m a producer at Warner Brothers who’s going to get them a role in the next Justice League movie” — women are perfectly capable of deciding whether they are or aren’t interested in going on a date with you. They can decide for themselves whether they want to hang out and see where things go. And honestly, unless your date goes horrifically badly — and again, not “said something awkward” but “dude is trying to sue for a shitty date” bad — a mediocre date isn’t an ethical violation.
The same with if she decided she wants to date you. People don’t decide this after one date. They tend to decide this after they’ve gotten to know you, been on dates with you and spent enough time that they can make an informed decision. So by the time someone decides that yes, they want this to be official? Then you can safely assume that she’s seen enough that she wants to pursue something serious with you. So unless you’re living an actual lie, you’re creating an absurd scenario to justify a decision you want to make. And if that’s how you want to roll, then more power to you… but at least be honest that this is what you’re doing and what you’re angling for.
But also, dude. King. Your dating “experience”, such as it is, consists of asking three people out on a date. Ever. THREE. And of them, one was gay and the other was already seeing someone. Not to put too fine a point on it, but you’ve got a sample size of one rejection that could be considered indicative of anything. At least, unless you’re going to try to insist that your attempt at asking the second woman out was so bad she spontaneously turned into a lesbian and the third developed a boyfriend out of the clear blue sky.
In which case, I’ve got some friends who might want to speak to you.
So you asked out two people who were never going to say yes even if you were Ryan Gosling crossed with Harry Styles and one who turned you down because… well, you don’t know why. All you know is that she turned you down. That’s it. And as I’m often saying around these parts, the reason why women will reject you often have absolutely nothing to do with you, personally. You’re not just assuming facts that aren’t in evidence, you’re making shit up out of whole cloth based on one actual rejection, one woman who doesn’t date men and another who was already in a relationship. That’s not a reasonable sample size to draw conclusions from. That’s not even a rounding error.
And the logic on which you’re basing this is, to use the technical term, coocoo bugfuck bananas. Isn’t there a difference between friendship and a relationship? Um… no. Friendships are relationships, just like friends-with-benefits relationships are relationships. Is there a difference between friendships and romantic relationships? Yes, but also no. I mean, I could imagine a romantic relationship between two people who couldn’t be friends but would anyone actually do that in real life? Not for very goddamn long, no. If you’re trying to start relationships with people you couldn’t be friends with, well there’s your problem.
But the thing is, the skills that you use to make friends are the exact same skills you use to find romantic partners. Can you joke around with your friends? Can you tell them that you like them and enjoy their company? Can you share intimacies with them, be vulnerable with them, support them when they need it and get support from them in return? Congratulations: you’ve got the skills you need to date. Because here’s the thing: flirting is the art of telling someone you like them and having fun with them. Emotional chemistry comes from having things in common, bonding over shared values and interests, engaging in exciting experiences together. If you can make friends, you can find relationships.
But — I hear you cry — what about sex? What about chemistry? Well… what about it? Thus far, your biggest issue there is a lack of experience. But I hate to tell you this: everyone starts out with exactly zero experience in trying to build excitement or sexual interest. The only way anyone gets that experience is by going out and trying to learn. Some people may have a natural talent or more inherent charisma than others, sure, but that doesn’t mean any more than how some folks have natural athleticism or a gift for music or mathematics. The fact that there’re folks who may have an advantage doesn’t mean that everybody else is screwed. People learn how to date the same way they learn how to play guitar, play soccer or write code: practice, practice and more practice.
You haven’t practiced. You have barely even tried. You did the thing a lot of folks do: “tried it once, wasn’t instantly good at it, gave it up as a hopeless cause.” In this case, you had a couple mild disappointments — and I’m sorry, being turned down for a date is a mild disappointment — and decided that you got fucked by the fickle finger of fate. It seems like you’ve been waiting for other folks to do the work for you, rather than actually putting yourself out there, taking your lumps and grinding out your experience points like the rest of the world. But that’s not how this works, any more than someone is just going to show up one day and decide that you’re their new feature director. Just as someone trying to get work in film needs to be getting jobs at studios and production companies, making films, entering festivals and trying to make a name for themselves, if you want to date, then you need to go out and try to date.
Are there best practices that would probably help? Yes, absolutely; I have an entire series of articles, books, podcasts, youtube videos and courses that cover this. But you can’t just study theory and become an expert; you have to actually have boots-on-the-ground experience. And you don’t.
Now the key to all of this comes early on in your letter: you say you’re dealing with depression. And the problem here is that, I don’t think you’ve quite realized how much depression lies to you or how much it fucks with your head. Depression lies to you. It drips poison in your ear, convincing you that all of your worst fears are true. And part of what’s so insidious about depression is that it lies to you in your own voice. You believe it because it sounds like it’s just your own thoughts, coming to natural and understandable conclusions. It’s not; it’s your depression, fucking with you.
You say you’ve started taking medication to treat your depression. That’s great! I’m a huge proponent of better living through chemistry; if you can’t make your own serotonin, then store bought is perfectly fine. But not only do you need to make sure you’re taking the right antidepressants, but you need to learn how to handle your depression. You need to learn how to recognize it, how to manage it and how to push through so that you aren’t just believing the worst about yourself. If you’re not complementing your medication with counseling… well, honestly, you’re not getting the full benefit. Even a self-directed series of cognitive behavioral exercises like Mood Gym could go a long way towards helping you recognize the difference between your thoughts and when depression is just fucking with you.
So if you’re not already talking to someone… well, that’s where I’d suggest you start. I would also suggest talking with your psychiatrist to make sure that the antidepressants you’re on are actually working for you; it can take a while before you find the right dosage and the right medication.
But more than anything else: if you want to get better at dating, then you have to put in the work. You have to be willing to go out and get rejected. You have to talk to folks, flirt with folks and shoot your shot. I’ve joked about the banality of the quote, but Gretzky isn’t wrong: you miss 100% of the shots you don’t take. There’s no learning without experience, and no improvement without making mistakes. If you aren’t making mistakes, you’re not trying, nor are you learning. All you’re doing is staying in your comfort zone and, well… how’s that working out for ya?
You’re drawing conclusions based on faulty evidence and an insufficient sample size. You’re letting your depression fuck with you and tell you lies, and treating them like they’re true. You don’t know that you’re “just too unattractive”, you don’t know that no woman could be into you, you just know that you’ve asked out one stranger, one queer woman and a woman with a boyfriend. That’s it.
If you want to give up, then you can go ahead and give up. But if you actually want to get good at this dating thing? Then you have to be willing to get up, dust yourself off and get back out there. Like a wise man once said:
Let me tell you something you already know. The world ain’t all sunshine and rainbows. It’s a very mean and nasty place, and I don’t care how tough you are, it will beat you to your knees and keep you there permanently if you let it. You, me, or nobody is gonna hit as hard as life. But it ain’t about how hard you hit. It’s about how hard you can get hit and keep moving forward; how much you can take and keep moving forward. That’s how winning is done! Now, if you know what you’re worth, then go out and get what you’re worth. But you gotta be willing to take the hits, and not pointing fingers saying you ain’t where you wanna be because of him, or her, or anybody. Cowards do that and that ain’t you. You’re better than that!
You need to learn what you’re worth, so you can go out and get what you’re worth.
You’re better than that, CBNH.
Dear Dr. NerdLove,
Dude, I just don’t know what to do. I’ve never been married, and I’ve only had a few long-term relationships in my 52 years. For a long time I didn’t even try to date at all, because I had just given up. But a few years ago, something convinced me to give it another shot, so I looked at all the online dating sites and created accounts on a few of them. I’ve met a few nice guys, I’ve met a few assholes, you know how it goes. I did date one guy for about a year and a half, he really loved me, but I just couldn’t fall in love with him, no matter how hard I tried. So that ended, and a few months later, the world went to shit with COVID.
By that time, I was actually feeling like getting back to trying to date, so I looked here and there, even though I was going to be very cautious about who I met and where. So there I was on Tinder, and I met Kermit (not his real name, obvs). Our texting on the site was fine, he asked for my number so he could call me, and then he actually did call me. We talked for an hour and a half, and right from that first phone call, there were all kinds of bells ringing. We decided to meet a week later, a picnic at a park. It was A-MAAAAA-ZING. We clicked like nothing I had ever experienced before. I didn’t even think I COULD feel that connected to a man! My head was spinning.
And the connection wasn’t a one-time fluke. We kept seeing each other, not as often as I would like, but his schedule was wonky because of COVID and because he has primary custody of his 12-year-old daughter. After seeing each other a few times, he kinda threw me for a loop when he told me he was seeing other people, but I appreciated that he was honest and direct with me about that. The next time we saw each other, I initiated the dreaded “Define the Relationship” talk. He was again very honest with me, said he was still getting over his marriage, and he wasn’t ready to be in a committed relationship, but he really liked spending time with me, and wanted to keep seeing me. I have never felt a connection with anyone like I do with him, so I told him that I could be patient until he was ready.
We have so much fun when we’re together. We laugh a lot, we like a lot of the same things, we have similar outlooks on life and similar values, the sex is fantastic, and I genuinely like him. But the texts became less frequent, and the times we got together started getting farther apart. Now it’s been a year since we first met, so I brought up the “Where are we going” talk again. He said he liked spending time with me, he always had fun with me, but he still wasn’t ready to be in a committed relationship. Then he told me a little more about his marriage, and it turns out it was a lot more toxic than I had realized.
Basically, she was nuts, treated him like shit, and now he’s pretty fucked up about relationships. Even though it’s going on two years since they split, he’s just not able to be in a committed relationship, and he doesn’t know when he will be ready. He was actually great through this whole conversation, he gave me time to process, time to talk without interrupting, and when I got a little quiet, he asked if I wanted to talk about it some more. I asked him what I was to him, a potential long-term partner, a friend with benefits, or what. He took about 10 second to think about it, and said that I might be a long-term partner at some time in the future, but right now I’m a friend with benefits, and he knew that wasn’t what I wanted to hear. Through this whole conversation, he was so kind and gentle, but still direct and honest, even when his truth was painful to me. I really like the way he communicates.
So after we had talked about all of this, I told him that his ex had massively fucked him up, and he would really benefit from talking with a therapist. I see one myself, I know the value of getting professional help. He didn’t get all macho and defensive about that, he said I was probably right, and he’d think about it. So this brings me to my question. How long do I keep waiting?
I read your column, so I know you’re going to tell me that he’s not The One because there is no One. But dude, I’ve never connected like this, never felt like this about anyone else in my entire life. Over 50 years of thinking that there was just no one I would ever have the kind of best-friend-and-lover relationship I’ve always wanted, then Kermit blew all that up. I know he’s fucked up from his toxic ex, and I know I can’t fix him, but he seems open to getting therapy, so he may fix himself. So how long do I keep waiting? The thought of giving up on him and moving on makes my heart hurt. I have a great, full life, so it’s not like I’m just sitting around waiting for him to text or call me, and I can certainly keep doing that if he’s on the road to getting his head back together right. So, your thoughts?
Here’s my thought PH: what’s more important, the man or the label?
This isn’t an idle question. I want you to ask yourself whether you could be happy having this guy in your life, if the price of entry was that you and he are “friends with benefits” for now?
It sounds to me that, up until you had the first Defining The Relationship talk, things were going swimmingly. It was only after, when he realized that you and he seemed to be on different pages that he pulled back. And, in fairness to you and to him… that was probably the right call, at least at first. If you wanted something from him that he couldn’t provide — or wasn’t in a place where he could provide it yet — then it would be cruel of him to keep things as they were. After all, this meant that he was keeping you from finding the kind of relationship you wanted.
But the relationship you wanted… is with him. You want the experiences you were having with him, the fun you were having, the feelings of being heard, appreciated and also amazing goddamn sex. Which, hey, legit. But there is a part that he can’t give you right now and that’s exclusivity. He’s still dealing with the fallout from his ex-wife and all the way that’s fucked him up. It’s not really a surprise that he’s not ready for something serious or long-term right now.
At the same time: he clearly likes you, loves spending time with you, loves talking to you and you two have great chemistry. You and he have a relationship; as I’ve said before, a friends-with-benefits relationship is a relationship. It’s right there in the name. It doesn’t just mean “fucking without expectations of commitment”; the friends part is as crucial as the “benefits”. And from the sounds of it, he seems to be taking the “friends” aspect seriously and giving it the consideration and weight that it’s due. The relationship may be casual, but he’s not treating you casually. He obviously would like to be in a place where maybe this could work… but he’s not there yet.
But what you have now — a functioning relationship, if not an exclusive one — is something you and he both get a lot of value from.
Which brings me back to your question: is the man or the label the most important part here? Are you able to meet him where he’s at right now, enjoy what you have right now and be in the moment while he’s working on his issues? Are you able to appreciate what you have with him now, even if it means that for now you can’t expect exclusivity or long-term commitment? Is this relationship able to meet enough of your needs that you’re satisfied and happy, knowing that there’s a part that you can’t have yet… if ever? Or is this an all-or-nothing situation?
I’m not asking you this in this way because I lean one way or the other. I’m asking you like this because I don’t know if you’ve asked yourself whether you can accept what he has to offer for now, even if it’s not everything that you want. Sometimes we can let our hopes or expectations obscure what we have. Sometimes our idea of what we want — or what something like a particular label would mean — keeps us from fully appreciating what we’ve got.
What you have is a relationship with a man who clearly likes you and cares about you. It’s not the relationship that you would prefer to have with him… but is he, specifically, worth the difference? Are you able to accept what he can give now, knowing he’d like to be able to give more but can’t? Knowing that it may take him time to get there… and knowing that he might not get there?
I’m not gonna lie: that’s a really difficult question. And that answer could very well be “no”, you can’t be friends with benefits. Not having exclusivity or expectations of commitment would mean that things are too painful, or that you might feel he can’t or won’t give as much as you need or as much as you give him. That’s legitimate. That’s a real, understandable concern, and you would be well within your rights to say “I’m crazy about you, but I can’t do this.” That doesn’t mean that you don’t care for him enough, nor does it mean that your feelings weren’t real or strong enough or that you weren’t strong enough. It just means that, as much as you are over the moon for each other, he isn’t right for you. There’s no good guy, no bad guy (well, besides his ex), just shitty luck and worse timing.
As the song goes, sometimes love (or something approaching it) just ain’t enough.
Speaking strictly for myself: my belief is that sometimes it’s worth it to take what someone can give right now. If they’re that awesome and you can see things working out down the road — if it is a possibility, not something that has definitely been cut off — then being willing to be in the now and appreciate what you have can work. But the operative word is “can”, not “will” and not “should”. It’s acknowledging the possibility of it working, not the guarantee. It’s resolving to be in the moment and savoring what you have, knowing that it could still end. But, to my mind, it’s the old hoary cliche of “better to have loved and lost”; sometimes our lives are enhanced by our lovers, even if the relationship didn’t go the way we hoped. Even if it does end, it’s possible to look back and say “well, at least we had that for a little while”.
But that’s not every relationship, nor every person or situation. I’ve tried it before and it didn’t work out, and that hurt. A lot. I’ve tried other times and while things didn’t go the way I’d hoped, it brought a lot of good to my life. And it’s not going to be the right approach for every person. It may not be for you. I don’t know. The only person who can answer that question is you.
If you are willing to give that a try — and that’s a mighty big “if” — then I recommend your saying so to Kermit. Tell him that obviously you want more than he can give right now, but you also appreciate what you two have and you don’t want to lose that yet. Have a different Defining The Relationship conversation this time, more of a “ok, how will this work?” convo and see if you can make an arrangement that works for you both. But if you do — and again, I stress if — then you have to accept that this comes with the agreement that he’s going to work on things at his own pace. That means you can’t push him, even if it seems like he’s not doing anything; that’s a great way to cause the whole thing to fall apart. If he’s not ready to work on himself or talk to a therapist, no amount of outside pressure is going to change his mind. But the reward of having you in his life can be the motivating factor that encourages him to work on his shit.
But if you can’t do this, or it seems like he’s not working on his issues and you’re out of patience, out of energy or it just hurts too much to stay… then let him go. It’s going to hurt. It’s going to hurt a lot. But the clean break heals the fastest, and ending it now, while you still care, means that there’s a better chance of having something together in the future, even if it’s a platonic friendship. Staying in something that hurts too much will just curdle affection to anger and respect to resentment and taint the happiness you’ve had already.
You’re the only one who knows what choice is right for you.