DEAR DR. NERDLOVE: I’m a 27-year-old man working as a Quantitative researcher at a high-frequency trading firm. On paper, my life checks all the boxes: I’ve got a high-status, high-income job, making well into the mid-high 6 figure range; I’m 6’1″, fit, and decently good-looking. I’m socially confident, well-spoken, and naturally charismatic. I have no trouble getting dates or casual relationships, and I move in impressive social and professional circles. Most people who meet me assume I have it all together.

But under the surface, I’m incredibly lonely.

Despite being surrounded by people and attention, I struggle to form emotional connections. My relationships — romantic or otherwise — often feel transactional. I frequently get the sense that people are more interested in what I can do for them than in who I actually am. Whether it’s networking access, career advice, or social status, it often feels like I’m just a means to an end.

It’s deeply unfulfilling.

I long for relationships with genuine emotional depth—ones where I’m valued not for what I represent or provide, but for who I am. But increasingly, I feel isolated. Vulnerability doesn’t come easily, and when I do try to open up, I often feel like I’m met with surface-level empathy or performative support rather than real understanding.

I am not even talking about romantic relationships in particular; even having a single friend with whom I connect would make me extremely grateful.

I don’t want to sound ungrateful. I know I’m lucky in many ways. But emotional intimacy feels like something I can’t buy, earn, or charm my way into — and it’s the one thing I want the most.

Successful but Starving

DEAR SUCCESSFUL BUT STARVING: You’re right, SBS: you can’t buy, charm or “earn” your way into emotional intimacy. That’s not how that works. Emotional intimacy is part of connecting with another person on a level that goes beyond what you can do for them or a value-for-value equitable exchange.

I think part of the problem is that you’re doing the same thing that a lot of guys do – in fact, something that I talked about very recently: you’re conflating what represents and grants social status with what people want in a relationship. I can’t help but notice that – again, like many folks in a similar position to yours – that you describe your appeal entirely in materialistic terms, right before you complain that all your relationships are surface level and transactional.

It’s great that you’ve got a high-paying job in finance, and I’m sure it does your ego good to move in such rarified circles. You’ve got the sizzle, sure, but where’s the steak? Where’s the substance to go with the flash? People don’t make friends with folks who “tick all the right boxes”, because people don’t make friends via math and spreadsheets. A six-figure income is great and all, but that’s not what actually makes you a desirable partner or friend… at least with folks who aren’t entirely focused on money or stock tips.

I’m asking this sincerely: what about you would make you a good friend to another person? Part of what makes people want to build relationships with us is what’s known as the “Reward Theory of Attraction” – we prioritize our relationships with people whose presence make us feel good and whose company we enjoy. This is part of why humor, for example, is a valued quality in a potential romantic partner. Not only does a good sense of humor imply emotional and social intelligence and empathy, but making people laugh spurs production of dopamine and oxytocin – hormones that hit the pleasure centers of the brain. People who make us laugh make us feel good, and we want to be with them more than with people who don’t make us feel good.

Hence, I’m asking you: what are the qualities – qualities that aren’t surface level charm, appearance or money – you have that would make someone want to spend time with you outside of a work context? Are you someone who’s fun to hang out with? Can you make people laugh or feel good when they’re around you?

After all, relationships – both platonic and romantic – are about connection. They’re about how we feel when we’re with people, about what they bring to our lives that goes beyond just commerce and transaction. They’re about shared values and interests, community and support. Without those at the foundation… well, you end up with the shallow connections you’ve already got.

So far, the qualities you’ve shared have been materialistic; it’s not really surprising that the connections you’ve made have been about what you can do for other people. So prioritizing less materialist qualities and characteristics and emphasizing soft skills will go a long way towards finding people who might be friends, rather than folks looking for favors or advantages.

Just as importantly, though is that I’m not sure you fully understand what you’re asking for and what you’re offering. One thing I notice is that you don’t seem as though you get what vulnerability actually is, how to actually be vulnerable, and when to do so. Being vulnerable with someone isn’t just about telling them your problems. It’s not just about “hey, I’m having a hard time” and asking for help or reassurance – especially if these are folks you don’t have much of a connection with. If they’re relative strangers or co-workers that you don’t get personal with on other levels, then I’m not surprised you’re getting a reaction of “that’s rough, buddy”.  

Being honest when you’re struggling or having a hard time with something is part of being vulnerable, sure… but it’s not the only thing. Vulnerability is about being open and honest with folks, even when doing so leaves you open to judgement or worse. It’s about not being afraid of being your authentic self or being sincere with people, even if it might make you look corny, foolish or cringe.��Are you able, for example, to talk about your hobbies without feeling like you have to apologize for them or explain why it’s ok to do things that aren’t “cool” or that have social cachet in the communities you spend time in? Do you feel like you have to justify aspects of yourself that other people might think are dorky or weird, or can you say �– to pull a random example – “Yeah, I adore the work of Andrew Lloyd Webber, especially his less successful stuff like Whistle Down the Wind or Bombay Dreams!” Do you feel like you have to maintain a constant façade to fit in with your co-workers and potential friends, or can you say “I love the things I love and I don’t care if you think they’re stupid?”

Another thing to consider is that vulnerability isn’t an all-or-nothing thing. It’s not a binary of “the floodgates are open” and “shut tighter than an agoraphobic clam”. We all have different levels of intimacy with people in our lives, and how much access people get to us is dependent on the strength and depth of our connection with them. Close family members and best friends get a greater level of access than, say, the guys hang out with watching the game at the bar, who get more access than co-workers that you’re on friendly terms with but aren’t actually your friends. We give people more access to us and our inner lives as those relationships grow and our connections become stronger and they show that they are folks we would want to give greater access to us.

But to get there, you have to start with the weaker ties and less-significant connections and build up from there. And that, I suspect is part of where you’re struggling.

What do you have going on in your life that would be a bonding point for you and a potential friend? Do you have anything in your life that isn’t about business, productivity or self-improvement? Do you have hobbies that you indulge in just because they make you happy? Or do you – like a lot of guys – see downtime as a waste if you’re not constantly on some upward trajectory? Are you out and about taking photos of interesting buildings in your city, just because they look neat, or are you focused on your rise-and-grind morning routine? Do you put together Legos for fun, or would that take away from reading Marcus Aurelius and maximizing your gains at the gym? Do you read anything that isn’t about work, business or otherwise related to getting an edge in life?

These are all a big part of actually having friends and a community: having interests and experiences in common that you can bond over. I can’t tell you how many friendships I’ve had over the years that started because we were geeking out over b-movies, rock producers, books and 80s cartoons. I have life-long friendships that started because we were all fans of the same authors and others that came about because we all were working in comics and loved to talk about the medium. Those initial moments of shared interests and mutual passions were what let us connect on deeper and more personal levels over time.

My advice for you is to do a little self-exploration and dig into what you have going for you that isn’t just about work, money or your appearance. What are your passions in life, what do you care about that gets you up in the morning and makes you glad to be alive? What sorts of things do you do to feed your soul? If you don’t have many that aren’t all about maximizing your productivity or being more competitive in business, then it’s time to cultivate those interests. Maybe it’s time to take some painting classes or learning how to play a musical instrument or finding some other outlet for creative expression. Maybe there’re some things you were into as a kid that fell by the wayside over the years; now’s as good a time as any to pick them back up again. Having things you care about and enjoy give you things to talk about and bond with over with people who also enjoy them.

Similarly, focus on what you can do for other people that would make them feel good. It may help to think in terms of love languages – acts of service or giving gifts, words of affirmation, quality time spent together could all give you a starting point to find the ways you would be a good friend to others.

Then start with embracing weak ties – finding people you are acquainted with and who you generally get along with, and spending time with them in social settings. It takes time to build the sorts of connections and emotional ties that bring us from strangers to acquaintances, and from acquaintances to friends; starting with folks you already kinda now helps speed things along. As you get to know them and as you get closer, you can give them greater access to you without worrying about over-sharing.

And as I said: open up and embrace vulnerability by being unashamed at loving the things you love or valuing the things you do. Worry less about being “cool” and more about being authentic to who you are at your core and find others who are equally as comfortable with being authentic. That sort of sincerity will win you more hearts than ticking all the boxes that say “this person is a winner at life”.

It takes time, it takes self-awareness, and it’s going to take practice. But if you can turn the same level of dedication that got you your high-status job and six figure salary towards your social life… you’ll be just fine.

Good luck.

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

DEAR DR. NERDLOVE: I found another one of your articles by chance and I thought your perspective was very insightful and nuanced so I was curious what your opinion on this would be:

Me and my ex broke up in December ’23 and I haven’t talked to him since August ’24. Yet through the entire process one thing has remained pretty consistent, my desire to never date anyone besides him.

I feel like I can live a perfectly happy life without a romantic partner, and so I don’t really see the point in trying to start a new relationship with someone besides my ex. I’m not even positive I’d want to date him again if for some absurd reason the stars aligned for us once again.

But I can’t lie and say I don’t hope we’ll cross paths again. I do want to see him again. I truly do love him so much; he was my best friend and changed my life in an INCREDIBLY positive way. I just don’t know if I’m crazy for still having hope. I don’t know if I’m crazy for wanting to stay single if we don’t get back together.

It’s not for fear of intimacy, I’ll tell you that. Ever since we broke up, I’ve known that I am capable of building another beautiful, loving connection with someone in a romantic sense. But it’s just not something that I want to experience with anyone besides him, is that okay?

I’m not sure if details about my relationship would be helpful or not, but it really wasn’t anything special. Not in an objective sense. We were just two teenagers who fell in love (and happened to live states away from each other), made silly promises of “forever”, and let our insecurities get the better of us. I’m sure you’ve heard stories like ours all the time, it really wasn’t anything special. But, it was very special to me. He was the perfectly average boy who saw right through me and I don’t care for anyone else.

I understand he probably wants nothing to do with me, and the chances of us ever meeting again are slim. And even if we did, the possibility of us actually making a relationship work is even more unlikely. That’s okay. I want the best for him, and if that’s a life without me so be it. I just don’t know if a life without a romantic partner is what’s best for me, everyone I talk to about this acts like I’m going to change my mind, and encourages me to find someone else. I don’t know.

Totally Single, Totally Fine?

DEAR TOTALLY SINGLE, TOTALLY FINE: I’ll be honest with you TSTF: I don’t think there’s really a problem here. There’s nothing saying that you have to be in a relationship, nor that going through life without a romantic partner is some sort of horrible experience. If you’re fine with being single and aren’t interested in going out and dating… well, ok. You do you.

It sounds to me like you’ve had your time to process the end of the relationship, you’ve given yourself closure, and you’ve got a fairly solid and matter-of-fact view about this. You’re aware that you could go out and find another partner – that you have the capacity to do so, should you choose to do so. You just don’t want to. You would like to have him back, but you also acknowledge that it’s over, and the odds of getting back together are slim and so you’re willing to just let things be how they are. And I really don’t have anything to say about that beyond “ok, cool.” Lots of people lead incredibly happy lives, full of meaning and joy, without being in a romantic relationship. If you’ve got purpose and friends and community and people who care for you, that’s all pretty damn good.

I think what may be tripping people up – it kinda made me take a second look – is when you talk about having hope for dating him again. While I get that you’re talking in the more abstract sense of “Yeah, I didn’t want that relationship to end and I still have mostly good memories and see it as an overall positive part of my life, so of course I’d want that back…” I can see how others would stumble over the word and be concerned.

I suspect that’s part of why you’re getting the reaction you do when you talk about this. I think that when you talk about how you feel, people see it from the lens that this is all a huge tragedy. I think folks are worried that you’re making a rash decision that you might regret. Maybe they’re worried that your heart is so broken that you think you could never love again and they’re trying to reassure you that there will be someone else. Or maybe they’re worried that you’re going to waste months or years of your life pining away like someone who’s waiting for her love to come back from the sea.

That’s not an entirely unreasonable worry, seeing as there’re a lot of folks who end up putting their lives on hold – for decades, in some cases – in hopes that they’ll finally make this relationship work. So it’s possible that they think you’re just going to cut yourself off from happiness and love in some misbegotten belief that he was your One True Love and you’ll live a life of quite misery until it curdles into resentment and you haunt your own house in the tattered remains of the dress you would’ve worn to your wedding like a post-modern Miss Havisham.

And I’m sure there’s also a certain amount of “couple’s privilege” going on, where folks think that a life without a romantic partner is inherently tragic or empty and that it can’t possibly be as fulfilling and meaningful.

That’s not true, but I could see why folks would be worried about it for you. Especially if this was your first love or serious relationship.

But like I said: if you’re taking a somewhat stoic “well, it sucks but it is what it is” approach and you’re not interested in trying to find love with someone else… yeah, go for it.

Now I will freely admit that I’m a little biased, seeing as I’m in the relationship-advice business, so I will say this: the only thing I would suggest is to not close the door for good on the possibility that you may decide to look for love again, with someone else. I don’t mean that you should go out there and actively date, or even that you should be putting yourself out there for love to find you. I just mean to not to make a declaration that you’re done with love and romance for good and forever, the end. There’re a lot of times when we all make grand declarations about things that may be true in the present, but change in the future. Sometimes it’s hard to acknowledge that our circumstances have changed and we don’t need to hold onto things we swore to when our circumstances were different. Foolish consistency and all of that.

But then again, that’s a day that may never come. Who knows.

As it is: it’s your life, and your decision. If you’re not interested in trying to date someone else and you’re perfectly content with your life otherwise? Sounds perfectly fine to me. If you’re ultimately content, that’s all that really matters.

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: A long standing and painful issue with a certain friend recently reared its head again. I want your perspective, because this causes me too much pain to process alone.

My friend and I are distant cousins, and we met as young children at a family reunion. We lived far apart growing up, so our in-person interactions were always family-facilitated. We are now 31.

When I moved away from home for college at age 20, I lived in an area close to Cousin, for the first time. It was amazing. He introduced me to his best friends, and I clicked with them immediately. The next 5 years were a dream. Not only did I hang out with Cousin often, I also found something I’d never had – a tight-knit friend group. 

(In middle & high school, I was bullied. I banded together with other bullied kids, but it was about survival, not genuine connection).

I met my husband through that friend group–he was Cousin’s high school buddy.

As for what happened… in early 2020, Cousin, me, my husband, and other roommates moved in together. Cousin wanted to keep the house very clean and neat, and we all agreed to duties on a chore chart. Thing is, I have ADHD, but I was undiagnosed and unaware at that time. I agreed eagerly to my share of chores…. and then executive dysfunction set in. I didn’t know that’s why, but my chores never got done. Cousin felt like I didn’t care, and I was incapable of articulating a reason otherwise. It was a source of frequent tension.

Then, Covid hit, along with a LOT more. For one, I graduated in May 2020 and my undiagnosed ADHD became hellish. I had developed coping mechanisms to manage school, but they didn’t transfer over to post-college adult life. I was falling apart and, again, couldn’t articulate why. Also, my mom died of cancer, and my husband developed a permanently disabling chronic illness.

Cousin was going through equal levels of hell; his mom unexpectedly became addicted to meth, tried to kidnap his sister, and then and abandoned their family; and his dad’s mental state declined so sharply Cousin–as the eldest child–had to manage the mess.

And on top of it all, yknow… Covid.

Cousin and another roommate responded to this by being controlling, implementing super stringent house rules related to Covid. I agreed to the rules but, I was so distressed and unstable I rarely followed through. This exploded into a huge fight in which Cousin and I both said extremely hurtful things, and he threatened to evict me. After, we both hid in our respective rooms, crying, for about a week; my husband and the other roommates were damage control.

Cousin and I made peace, sincerely apologized, and tried to move on but, it’s never been the same.

In 2021, husband and I moved out for unrelated reasons and I’ve almost never seen Cousin since, or even talked to him. We see each other at family events, we text on rare occasion. That’s it. I’ve tried reaching out, and his responses are friendly, but reserved.

I miss him terribly, but I don’t want to push him. The emotional side of me wants to send him a long, cringy text – the platonic version of, “I’m sorry, I’m sorry, please take me back, I’ll do anything, I love you”, but I know better. One of the things he yelled at me in our fight was that my mental problems were “too much”.

Mostly, I repress all this and pretend the wound isn’t there. It came up this week because a mutual friend was hospitalized, and I’ve contacted everybody including Cousin to plan a get together to support our mutual. Meanwhile, a second mutual friend told me I ought to reach out to Cousin, and implied that Cousin wanted me to, but Cousin’s responses are as reserved as ever.

So… help me?

Retry, Reboot, Ignore?

DEAR RETRY, REBOOT, IGNORE: If I’m being honest, RRI, I feel like 99% of anything that happened during 2020 should be quietly ignored like the entire final season of Enterprise. The entire year was cursed like someone had read from a cursed scroll while breaking all the seals around a giant obelisk marked “DO NOT TOUCH, DARK ONE IMPRISONED INSIDE” and we all went a little feral and came out with a greater appreciation for Edgar Allen Poe’s Masque of the Red Death.

But unfortunately, unlike mediocre installments in long-running sci-fi shows, we can’t simply retcon s--t into having never happened, much as we’d like to.

(While we’re wishing, if we could send everything in Buffy: The Vampire Slayer from s5 onward to the cornfield, with exceptions for “The Body” and “Once More With Feeling”, that’d be great.)

So, instead, we’ve gotta deal with things as it actually happened, even if there’s a certain amount of “look, we were all dealing with some s--t” in there.

Now, I’m going to be honest: some of what happened with your cousin is the sort of standard “living with roommates” s--t that is baked into sharing personal space with other people, undiagnosed ADHD or not. We’ve all got our various quirks, foibles and flaws and our own way of doing things and conducting our lives, and sometimes those just aren’t going to mesh cleanly with other people’s. Part of living with other people is trying to minimize those moments of friction and conflict, while also understanding that some of it is inevitable.

There’s also the fact that the more people you put into one living space, the more likely you’re going to end up with conflict. More people means more corners and edges that folks are going to bump into. Nobody goes into a home-share situation thinking “Cool, I’m gonna piss off everyone I live with by being the most obnoxious roommate possible!”  Most of the time, it’s a case of everyone having their own routines and habits that’re pretty deeply ingrained and it can take more than a couple months with a shared Google calendar and chore spreadsheet to get everyone working in harmony.

But acknowledging that this is something of an inevitability doesn’t make it easier to accept when it happens, just like having undiagnosed ADHD explains things but doesn’t necessarily make it better. I am incredibly sympathetic to how undiagnosed ADHD and its symptoms can f--k with you… but an explanation doesn’t necessarily change that things weren’t getting done when they were your responsibility.

And believe me, I get it; the main reason why I didn’t get evicted from various apartments when I was younger was that my bank implemented automated bill-pay systems. It was too late to save my credit score at the time, but it sure as hell meant I was having fewer days when the power would go out and I had to figure out if it was Florida Flicker and Flash doing its thing or if I forgot to pay the electric bill. Again.

However, while executive dysfunction and memory issues getting in the way of your chore rotation was annoying, I could see how seeming to ignore COVID safety protocols would really put people out of joint. At a time when we were all living with the very understandable terror of what COVID could do to us and when folks were turning trying to avoid getting sick into a political issue, someone seeming to be lax or outright ignoring safety protocols is going to stick in one’s craw. It’d be one thing if that only affected them – they chose to f--k around, they’re going to find out – but with how both virulent and dangerous COVID was, it can feel like they’re playing Russian Roulette with your health and the health of your loved ones too.

And again, I want to emphasize that I get it. ADHD f--ks with a whole bunch of different aspects of your life, and when you’re under the 24/7 stress that we were all living under at the time, it gets real goddamn bad. But knowing in retrospect that none of this was malicious or intentional and that you were struggling to get it under control can add context to how we see those events, it doesn’t retroactively change how we felt. We can try to be more understanding about it and acknowledge that maybe some of our reactions or responses to it were unfair or harsher than they needed to be… but the memory of how it felt at the time still exists.

Now I mention this, not to bag on you, but to say that forgiving is often easier than forgetting, and that can sometimes leave some residual friction. It’s not fair, necessarily, but it’s human. And I’m wondering, when you had your big peace-making apology session, whether you two ever talked about the emotional side of things and how you were both feeling at the time. Was it just apologizing and “I forgive you”, or did you two really dig in and air things out? If you didn’t, it could be that maybe while you’ve had your apologies and your forgiveness, there’s a lot that’s still lingering that went unsaid and continues to be unsaid. That sort of thing can sometimes hang around like Banquo’s ghost, even after two people’ve theoretically hashed things out.

But it’s also possible that, looking back on things and knowing what he knows now, your cousin could feel a little awkward about how he responded, too. Some things, once said, still echo in our heads, even when we know that we shouldn’t have said them, and that can be hard to get past.

For example, you mention that he told you how your mental problems were just “too much”, and how the pain of that has stuck with you. It’s very understandable how that affected you and I get why that’s made you very cautious about reaching out again. But I wonder if it’s also not the sort of thing that’s also bothering your cousin �– that he’s got the voice in his head saying “Jesus Christ, how could you say that, you f--king asshole?” 

Even if he offered a sincere apology for it – and it sounds like you two hashed at least some of this out – that’s the sort of thing where he might be wondering if you could forgive him for saying that s--t to you. Yeah, it may have been more in frustration and fear than honest feeling, but he may still be thinking “f--k, I actually said that… how would RRI ever forgive me for that?”��This is why I think it’s possible that some of what you see as his being reserved or distant could be embarrassment or shame, or not being sure whether you are comfortable and ready to pick back up from before things went ka-blooey, as much as it could be about him not wanting to be friends again. It could very well be that your cousin misses being friends too, but still feels weird about things, even after you’ve both talked things out, and isn’t sure how to handle it either.

Well, here’s the thing: s--t’s awkward right now. Part of the reason why everything feels awkward is that you aren’t sure how your cousin feels. I suspect your cousin doesn’t know for sure how you feel. And if it’s the case that both of you are walking around trying to act like everything’s normal and you’re both trying to pretend that you’re not missing each other and not saying anything… well, s--t’s just going to stay awkward. If you want to see if there’s a chance to fix this strained friendship, you’re going to have to stop pretending that everything’s cool and be willing to get a little vulnerable.  

So I think what you’re going to need to do is just put it out there: you miss him and hope to see him at the get-together for your mutual. That’s it. Acknowledge that truth, simply and directly: you miss him and having his friendship. Right now, you’re dancing around this without actually saying the words, and that’s a problem. Unless someone actually says it and just hopes that they’re implying it hard enough, nothing’s gonna change. It’s always way too easy to ignore or misread things when folks are trying to be indirect. And seeing as rejection-sensitive dysphoria tends to be part of the ADHD combo platter, there’s that part of your brain that’s going to actively look for anything that could be “nope, go away”.

So instead of dancing around the topic, someone’s gotta say the words first. Clearly. Simply. Unambiguously. And if someone’s gotta go first, it may as well be you.

You don’t need to beg for his forgiveness or plead for him to acknowledge you like a clingy ex who can’t accept the break-up. You don’t need to offer up an accounting of your sins as penance while asking to reconnect. Just keep it simple and direct. A straight-forward “I miss my friend and I’d like to be friends again if we could” is all you really need. Then the ball’s in his court.

Now, the big thing is, once you put it out there that you miss him and want to be friends again, you need to give it some time and to keep the anxiety weasels leashed. This means doing your best not to read anything into how long it takes for him to respond, the “tone” of his reply if it’s not a gushing “YES, ME TOO OH THANK GOD”. He may need a moment to sit with his feelings about things, he may need time to figure out how to say what he wants to say… or it could just be that s--t’s going to be a little strained or awkward for a bit because a lot of things went down, a lot of things were said and everyone may still be feeling shy and weird about it.

And that’s ok. Sometimes a person needs to take a beat to process. Not getting an immediate no is a positive sign. And if it is a no… well, at least now you’ve cleared away the ambiguity and you can actually mourn the loss of that friendship instead of being stuck in this limbo, where you get to relive the feeling of losing your friend over and over again, because you’re not sure where you stand.

But I suspect things will go a little more positively than that.

It may take some time to reacquaint yourselves and find your new relationship balance, especially if you’re both coming to this like a pair of well-meaning-but-shy cats. Or it may be that you two need to have a second talk and dig a little deeper into how you both behaved back then and why, so you can get to a better degree of understanding. But the more important part will be that you two can move forward with how this new chapter in your friendship will turn out.

Good luck.

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