Estimated reading time: 12 minutes
Dear Dr. NerdLove,
I’m a 29-year-old heme/onc fellow at a major academic medical center, and I’m in the last stretch of a decade-plus of training that’s about to make me an attending oncologist. On paper, I’ve done everything right. I’m the kid of immigrant parents who sacrificed a lot for me, and I paid them back by doing exactly what was asked: all AP classes, a merit scholarship to a good undergrad, a strong MCAT, a T20 med school, a competitive residency, and now a fellowship where I spend my days telling people whether their cancer is treatable. I’m good at my job. I’ve been good at every job, every test, every hoop, since I was a teenager.
What I wasn’t doing during any of that was learning how to date, or even really how to make friends outside of school and work. There was never room for it. Every year there was a bigger test on the horizon, and the unspoken rule in my house was that anything that wasn’t directly building my CV was a distraction I couldn’t afford. So I didn’t date in high school. Didn’t really date in college, either, beyond a couple of false starts I didn’t know how to follow up on. Medical school and residency are not exactly fertile ground for building social skills from scratch when you’re already behind, and I told myself there’d be time later.
Now I’m watching “later” arrive. Friends and co-fellows who came up alongside me are getting married, having kids, building lives outside of the hospital. I’m happy for them, genuinely, but underneath that I’m aware of something that feels like grief. I gave up over a decade of the period when most people figure this stuff out, and I don’t know how to start figuring it out now, at 29, with no real practice and a job that’s about to demand even more of me as an attending.
I don’t think I want sympathy so much as I want to know where to actually start. Is it too late to build these skills from the ground up? How do I go from “person who has never really dated” to someone who can do this without it feeling like another exam I’m bad at? And is there a way to grieve what I didn’t get to do without it curdling into resentment toward my parents, who I know loved me and wanted the best for me, even if “the best” left this part of me undeveloped?
Signed,
Behind the Curve, Ahead on Paper
It seems like we’re on a streak of “I’m in a high-stress, time-intensive job” letters lately…
So here’s the short answer, BtCAoP: no, it’s not too late. It’s never too late to learn a new skill. People pick up new skills all the time, at every stage of their lives. And that’s all dating and making friends really is, when you boil it all down: a skill. That’s why we call them social skills. I realize I emphasize this point a lot – like, a lot a lot – but that’s in no small part because people seem to get it into their heads that there is just One Time In Your Life to learn how to socialize, make friends and date.
The way that folks seem to segregate social skills as being unique to all other skillsets that is part of the problem. People keep positioning these skills as something you can only learn in this incredibly small window of time and lamenting that they’ve missed that opportunity and trying to develop them now will forever show that they’re a loser, like a social Mark of Cain.
But that’s not how it works. That’s not how any of this works, in part because nobody notices or cares. I have been on more dates with women than you’ve had hot meals; never once – never – has anyone ever asked me about my dating history or gave a damn about when I had my first serious girlfriend, lost my virginity, any of it. Because it doesn’t matter.
Here’s the thing, BtCAoP: the only thing you truly missed out on was the time in your life when meeting new people was convenient. High-school and college are times when making friends and socializing is at its least difficult because you’re spending most of your waking hours with people around your age in approximately the same stage of life, at a time when you have relatively few demands on your time. It’s easy to hit the cumulative 200 hours to make a close friend because you’re seeing the same people every day for hours at a time. But the fact that it’s the most convenient time doesn’t mean that it’s the onlytime in your life when this can happen.
There is literally nothing stopping you from making friends, developing your social skills and finding people you might want to date. You have to work around your schedule, sure… but that’s true for literally everyone. And while I get that it feels like you’re at a disadvantage because you need to learn while everyone else supposedly already knows what they’re doing (they don’t, but that’s another issue), here’s the thing that you’re missing:
The way you learn those skills is by using them. That’s it. Everyone learned their social skills by going out and being social. You’re not an exception to this rule. You weren’t out sick the day they taught the “how to make friends” seminar. You didn’t have a scheduling conflict that kept you out of the “here’s how you date” classes. You just had other priorities and spent time doing other things. That’s it. You are just as capable of learning as everyone else. You just have to go out and do it.
And to be frank, you already have the skillset. You said it yourself: you made friends in your program; it’s making connections outside of work or your degree program that is intimidating you. This is not so different from the struggle people have meeting folks after college; you were in a place full of people who had similar ambitions, goals and values, and spending all your time with them. Now you’re trying to expand outside of the sphere of convenience, and that’s stressing you out.
That stress is ultimately self-inflicted, because it’s based on unfamiliarity and imagination, not reality. You already know what to do. The way you made friends with fellow med students and coworkers is the same way that you make friends outside of that sphere… and it’s also how you find people to date. It’s not a different proficiency that you need to pick up. The skills are the same; the only difference is when and where you’re applying them and the kind of relationship you’re trying to build.
Now I understand that you’re worried that your lack of experience is going to mark you out or make people not want you around. You’re worried that your supposed lack of skill is going to be so noticeable that it’s going to hang around you like cartoon stink clouds around a skunk and drive folks off. But as it turns out… that’s not how people look at making friends. Having a social life isn’t level-gated; you don’t need to have reached level 5, have a Charisma of 15 and meet these pre-requisites to socialize. Nor are people going to brush you off because they’ve got a higher proficiency bonus than you or because they’ve been making friends for decades and you just started. All of that is just anxiety trying to “protect” you from the possibility of embarrassment – a fate that is not only vanishingly unlikely but a wild exaggeration of what you might actually experience.
Here is the truth: we’re a social species. We like having other people around. We like meeting new people, we like the feeling of growing attracted to someone and we like new relationships. All of that means that we tend to be pretty damn forgiving when it comes to peoples quirks and idiosyncrasies and occasional rough edges; most of the time we don’t notice or care, and when we do, they’re just part of what makes that person unique. Unless somebody’s behavior or mannerisms are causing actual problems, people tend to just accept them.
Is there some way of approaching this without feeling like you’re going to do badly on a test? Sure… stop thinking about it like it’s a test. You’re just going out and meeting people. Some people are going to like you, some people aren’t. Like any skill, you’re going to have to get through the pain period, that moment of conscious incompetence where you’re aware of how much you have to work at this and think about what you’re doing. But – again, as with any skill – you get better at it by the doing, and before long, it becomes muscle memory. It’s much easier to get to that stage if you stop seeing everything as pass/fail and just focus on vibing with folks. The biggest difference between someone who’s socially skilled and someone who’s less experienced but still learning is that the more skilled person is going to recognize certain situations more readily and have more experience navigating them. That doesn’t mean the last person can’t; it just means that one person has been down that road before.
I understand that you, like many other folks in situations similar to yours, worry that people will look at your inexperience as a problem. There’s a wide-spread belief that potential partners are going to turn inexperienced men down because they don’t want to have to “teach” someone how to date or how to relationship. But while this can be technically true, that doesn’t mean that they’re correct. The complaint that women have isn’t about having to teach inexperienced men how to date, it’s about having to coach men through how to be grown-ass men. It’s not about dating inexperience, it’s about men who never get around to learning how to communicate or engage with their emotions and treat the women in their lives as a combination of secretary, live-in maid and courtesan. If you’re capable of running your life and don’t need someone to be your cruise director or emotional translator, you’re going to be ahead of the game.
There’s only one issue that women may have legitimate concerns about regarding your lack of experience: the worry that you’re not going to know what you want or that you’re going to feel like you aren’t going to be willing to commit because you’ve “missed out” on dating around. This, however, is easily avoided; you do some introspection and figure out what it is that you want before you start dating and then be up front about it. If you’re not ready for or interested in long-term commitment, then don’t offer it or imply that you’re open to it. There’s literally nothing wrong with your saying that you’re only looking for something short term or not expecting more than casual dating. If you’re worried about what might happen if you commit to the first person you date even semi-seriously, then be clear early on that this is not on the table. You don’t need to say that it’s because you’ve never dated before, simply that it’s not your goal or what you want at this point in your life.
Will people judge you for that? Quite possibly… but that’s almost always them reacting to their history and experiences with other people. Other times, that’s a matter of their expectations and ideas about How Life Should Work. But in either case, that’s not your fault, nor your problem. That’s their issue, and it’s a mark that they’re not someone who’s right for you. People will choose not to date you if you’re only open to short term or low-commitment, but that’s a good thing; that’s your filter at work, removing incompatible matches from your dating pool. Being clear about what you want, what you’re open to and what you’re not open to will help you avoid the majority of mismatches on the dating scene.
And here’s the last thing that I think you need to hear: the path to social success isn’t linear, nor does it mean that folks who have lots of social experience are always going to be smoother than a jar of Skippy. As plenty of folks can tell you: skills get rusty and that includes social skills like dating. People who’ve gotten divorced or left long-term relationships or who had to step away from the dating scene often struggle to get their feet back under them again. The fact that you’re starting to date isn’t going to mark you out as a weirdo or loser. It just means that you may have areas where you don’t have as easy a grasp on some dynamics that others do.
However, all of this is theoretical until you actually put yourself out there. Because that’s the only way that you’re going to get experience at dating: going out and putting yourself out on the market. You can study all you want, you can read all the books I’ve written, watch every video on dating and browse the archives all you want, but none of it is going to be a substitute for just dating. There’s no amount of theory that makes up or replaces experience on the ground. Theory gives you ideas and a rough structure to work from; experience teaches you that sometimes theory isn’t going to work for your circumstances and what actually works for you instead. Don’t worry that you aren’t necessarily sure how this relationship will progress. Every date you have and every relationship you have is going to be different, because every person you date is going to be different. You’re not going to be able to avoid mistakes, because everyone makes mistakes. That’s life, and that’s part of how you learn.
In fact, part of why making mistakes is important is because sometimes you’ll learn that a “mistake” is actually the right move. What is right with one person and one relationship won’t be with another; this is always true, regardless of whether you’re brand new to dating or you’ve racked up so many notches on your bedpost that Casanova thinks you may have a problem.
So, if you want to get better at dating, the best thing you can do is just get out there and start meeting people. Socialize, talk to folks, see who you vibe with and who you don’t. If you feel like you’re catching the right kind of vibe from them, ask them on a date. You’ll have times when you trip and fall on your face. You’ll have times when you think you’ve met The One, only to learn that maybe you got a little over your skis. And then there will be the times, those magic times, when you meet someone that who will click into place and you’ll wonder where they’ve been your whole life.
Learning to date, even if it’s later than you would prefer, isn’t a sign of weakness or failure. It’s the start of an adventure, a journey of discovery and exploration and finding the wonderous in other people… and yourself. Nobody really cares when you start; they’re just glad you made it.
You’ll be fine. I promise.
Good luck.




