Hear Me Out.
I like to tell my clients that dating is like applying for grad school.
We may not get accepted into our dream graduate school the first time we apply — but we (usually) don't give up on graduate school entirely. If we want our education badly enough, we figure out a way to make it happen.
Similarly, when we’re job-hunting, nobody expects the right work opportunity to materialise in front of us before we’ve submitted any applications. We expect that to find a job that meets all of our requirements and that we’re a good fit for, we’re going to need to conduct a thorough search, we’re going to need to apply to many jobs, and it might take us a while (and a good number of rejections!) before we find our perfect fit.
Dating is very similar to jobs and to graduate school. We get results the clearer we are on what we're looking for, the longer we’re consistent, the more resilient we are in dealing with rejection, and the better we get at recognising what we're NOT looking for.
But somehow, when we’re dating, everyone is quick to tell us that being effortful and strategic about dating is embarrassing, and that we should wait for "love to happen when we least expect it."
As a society, we don’t champion a lack of intentionality in any other major area of our lives quite like we do with love.
From the day our parents enrol us in kindergarten to the day we retire, we’re encouraged to focus on academic and career achievement.
In school, we’re encouraged to imagine what we want to be when we grow up.
Once we hit high school, the game is on in earnest. Our grades matter, our test scores matter, and the college we choose matters. As we near our 18th birthday, our parents take us to look at potential colleges, and we pour over course catalogues and decide on a major — both decisions that will shape our time in college and beyond.
During our time in college, we’re encouraged to think carefully about our career options and to apply for internships so that we can land a good job after graduation.
After graduation, we’re encouraged to apply for jobs or to graduate school. Whether we choose graduate school or a starter job, we know that the most important thing that we’ll take from the experience is what we’ll learn.
On our educational and our career journeys, we have books, classes, advisors, and consultants to support us, from high school guidance counsellors and SAT prep courses to graduate academic advisors and corporate coaches.
These resources create an environment that supports thoughtful decision making, and the emphasis on planning encourages us to take personal responsibility for our work lives and to make career choices that align with our values and our goals.
Education is important, and work is important, and the infrastructure of resources that we’ve built up around our professional development reminds us to take our education and work decisions seriously.
So, for that matter, is love.
In fact, the importance of love is one subject on which the research is clear: how satisfied we feel in our close relationships is one of the biggest factors in determining overall life satisfaction over the course of our lives: as important, in fact, as career or income satisfaction.
As writer Annie Dillard says in one of my favourite quotes, “How you spend your days is how you spend your life.”
Most of us, throughout the course of our lives, will spend as much time or more with our spouse or partner as at work. When we partner, if we partner for life, we not only choose a romantic or sexual partner, but we also choose a partner in finances, in work, in lifestyle, in family, in raising children, in health, in play, in retirement, and ultimately, even in death. As a couple, what affects one of us will also affect our partner, and the decisions we make are, in large part, joint decisions.
For that reason, who we choose as a partner is a CRITICALLY important area of our lives — one that will determine our overall life satisfaction at least as much, if not more, than our decisions around career or education.
And yet: Unlike career and education, this is the one area of our lives that we’re actively encouraged to leave up to fate.
In our romantic lives, we’re encouraged see love largely as a matter of “fate” or “luck,” and believe that, as the saying goes, “love will happen when we least expect it.”
Unlike biology or algebra, “How to Create Healthy, Lasting, Fulfilling Relationships” isn’t a class we were taught in school.
In college, there isn’t a centre on campus that teaches us how to figure out love, the way that there might be a career planning centre.
In graduate school, we aren’t assigned a “life partner picking advisor” the way we might be assigned an academic advisor.
We’re told that love is something that will happen “organically,” and that if it doesn’t, we’re “forcing” a connection — a situation akin to ramming a square peg into a round hole. We’re told that “what’s meant for us can never miss us,” as though it was somehow cosmically ordained that we (those of us for whom love HASN’T appeared on our doorsteps) are SUPPOSED to be forever matching with guys named Henry from Hinge who tell us that they “just aren’t ready for a relationship right now.”
The message is clear: love is beyond our control, and how it turns up and turns out is anybody’s guess, but career is something we can choose, influence, and plan for.
This underserves us in our love lives, and leaves us feeling uncertain and confused when it comes to relationships.
Most of my clients are women who are highly-educated, career-driven, and who have intentionally and thoughtfully planned out their lives — and yet, when it comes to their love lives, they feel unmoored and out of control in a way that they don’t feel in any other major life area.
They tell me that using dating apps feels like trying to fill a leaky bucket with a teaspoon: putting in a whole lot of work for not a lot of payoff.
They also tell me that they get a lot of matches — more than they can possibly keep up with — but that of those matches, only a tiny percentage seem to have their lives together. Of the few people that do, none of them want what they want: a committed, conscious, long-term partnership.
The reason that so many of the women I work with are feeling on top of the world in their careers, but baffled by love, is that they, like the rest of us, were taught that love requires a fundamentally different approach than their careers: one that relies on “fate” and “luck” rather than on effort or intentionality.
We’re told that love is a matter of fate, instead of a life goal that, like our education or career, we can take intentional, concrete steps toward.
But that’s not true.
The truth is that love, like so many other things in life — like our careers, and like our education — requires effort and intentionality to produce worthwhile results. And that effort and intentionality starts with dating.
There’s something that I firmly believe to be true. It’s counter-cultural, but in my experience of working with my smart, successful, on-top-of-their-game clients, this one shift sets them free from feeling disempowered by modern love.
That something is: Dating is NOT a matter of luck. Dating is a skill. And it’s one that can be learned and improved, just like we learn and improve any other skill.
Just like we set goals, make plans, and lean into our growth and development in our careers, we can apply the same intentionality to our love lives.
Those same qualities that make you wildly successful in your everyday life — intelligence, intentionality, direction, strategic thinking, tenacity, grit, and the ability to set goals and to achieve them — are the same qualities that will make you successful at love.
For that reason, I’m going to make a counter-cultural proposal: I propose that we treat dating like we treat our careers and our educations: with intention, with effort, and with a plan. I propose that we start expecting that love, like a career, won’t fall out of the sky when we’re not looking. And I propose that we start seeing rejection the way we might view rejection from a new employer or a grad school application: it stings, but it isn’t a sign that we should give up on our dreams of grad school. Instead, it’s an indication that we just haven’t found our match . . . yet.
In other words, I propose that we approach dating with the same mindset that we might have when embarking on any new venture that could seriously impact our futures — say, applying to graduate school or to a new job.
I know that my proposal may seem like a bizarre way to approach love.
Maybe to you, it sounds a little cold. Statistical. Even clinical.
But bear with me. I think that, once I explain it, you’ll find my proposition to be a freeing one.
(And, to be clear: What I’m proposing is that you learn to treat the process of DATING, particularly the early stages of dating, like you’d treat the process of applying to a new job or to graduate school. What I am not proposing is that you approach the RELATIONSHIP that you end up in like writing a dissertation or the PEOPLE you meet while dating like — heaven forbid — like your academic advisor. This is a metaphor meant to be confined to the process of looking for a partner only.)
With that in mind, let’s explore this analogy.
EXPECTATIONS:
A savvy job applicant expects that she might need to apply to a lot of jobs before she finds a good fit. She doesn’t expect every job she’s applied for to accept her application, and in fact, she knows that she may need to face a number of rejections before she gets accepted. If she doesn’t get the first few roles she applies for, or if her last role ended badly, she doesn’t give up on her search and swear off advancing her career forever.
Instead, she digs deep into her inner grit and cultivates the skill of rejection resilience to reassure herself that regardless of the outcome of any one interview, she is qualified for her dream role, and if she keeps looking and applying, she’ll find her perfect match.
When she’s interviewing, a savvy job applicant doesn’t go into every interview expecting the company she’s interviewing with to be The One, and, if they aren’t, she doesn’t take the mismatch personally. Instead, a savvy job applicant knows that job interviews are a two-way street, and that she’s interviewing her new company as much as they are interviewing her.
Similarly, a seasoned dater knows, as the saying goes, that she might need to “kiss a few frogs before she finds her prince” (or princess!). If any one date doesn’t go well, instead of despairing and swearing off dating forever, she draws a bubble bath, pours herself a glass of wine, and gives herself the night off before getting back to it in the morning.
Likewise, a seasoned dater, like a seasoned job applicant, knows that dating is as much about deciding whether she likes her matches as it is about her matches deciding whether they like her, and while she acknowledges that rejection stings, she knows not to take it personally. There are lots of people in the dating pool, and most of them won’t be a match for us.
AGENCY:
When she’s in the market for a new role, a successful job applicant doesn’t go around waiting for the right job to happen to her when she “least expects it.” That wouldn’t make sense. Instead, she knows that the fate of her career lies in her own two capable (and well-manicured!) hands, and she gets to work applying for jobs.
Likewise, a successful dater doesn’t expect love to come to her without her needing to put the legwork in to go and to seek it out. Instead, she understands that in order for her to meet her perfect match, she will need to first get clear on the kind of partner she’s looking for, and then find a way to meet more of those people.
LEARNING NEW SKILLS:
When she’s applying to graduate schools, a savvy grad student doesn’t think that she should already know everything that she’s about to learn in her masters or Ph.D. program. She doesn’t feel embarrassed that she doesn’t yet know how to write a dissertation or how to conduct a meta-analysis, and she certainly isn’t embarrassed that there are people who already know these things and who already have their master’s or PhD. She knows that it’s perfectly normal for a graduate student not to know these things yet, and that the people who know the things that she doesn’t have simply learned things that she hasn’t learned yet. She understands that everybody needs to start somewhere.
A savvy grad student also knows that, once she’s in school, she can ask for help if she needs it, and that doing so is normal and doesn’t mean anything negative about her. She knows that her career growth lies in learning new things and in developing new skill sets.
Similarly, a successful dater doesn’t expect herself to “just know” how to form healthy, satisfying relationships, and she doesn’t get down on herself for her past relationship mistakes or for her failed dates. She doesn’t look at her friends who are happily married and decide that she’s “behind” or “broken” for not having what they have (yet!) or that “love isn’t meant for her.”
Instead, a successful dater knows that the qualities that are involved in choosing happy relationships — including being able to spot green flags and to avoid red ones, picking healthy, emotionally available partners, and knowing how to build a healthy, secure relationship — are SKILLS, and that, just like any other skill set, these things can be learned and practiced. She knows that in her life, just like in her career, picking up new skill sets is how she will grow.
If she needs help in learning these skill sets, she isn’t embarrassed to ask for it. She knows that there’s nothing embarrassing about learning a new skill and that everybody has to start somewhere.
STRATEGY:
When we apply to graduate school, our goal is to figure out which schools are a match for our research interests, our likes, and our dislikes, and then to narrow down our options by evaluating each school’s good points against our criteria for what matters to us in a school. To this end, we need to get clear on what factors are the most important to us in a graduate school, and then to carefully evaluate each school against that criteria to decide whether or not they’re a fit for us. The schools also get to evaluate US, and to decide whether our test scores, our GPA, and our reference letters are a good fit for their program.
We also need a plan: what materials are we required to submit with our applications? Are our grades high enough to get in? Do we need any standardised tests to be submitted with our application? What about letters of recommendation? If we do need recommendation letters, who will write them? What should we include in our application essay, and do we need help writing it?
Throughout the application process, we’re narrowing down our options, submitting our applications, and sometimes hiring a career counsellor or admissions tutor to help us write our essays.
Similarly, when we’re dating, our goal is to get to know a potential romantic partner and to evaluate whether they’re a match for us. To this end, we should have an idea in mind of the kind of person we’re looking for, why that person is a good match for us, and why they would make a great long-term partner. We then need to take each new match or connection through a process that either allows us to qualify them as a compatible match, or to disqualify them as incompatible and not for us. The people we meet and match with also get to evaluate us, and to decide whether or not we’re a match for them.
We also should have some structure in place to guide our search: how do we plan to look for our partner? Do we plan to use dating apps, or to meet people in-person? How soon can we realistically expect to find our partner, and do we need to plan any major life milestones into our timeline, like being at a certain place in our career or having children? If we’re using dating apps, what pictures should we include to show that our profile is worth a second look?
Throughout the dating process, we would be well served by getting clear on what we’re looking for, putting ourselves out there in the places we’re most likely to find it. and maybe by hiring a dating coach to help us to write our dating profiles and teach us how to use the apps.
Whether we’re applying to a job, getting into graduate school, or scouring the apps for a potential romantic partner, we need a process for narrowing down what we’re looking for in the right candidate. Our process gives us a map for finding qualified prospects, whether that’s Oxford or Apple or Richard from the next town over. It then takes us through a qualification process that helps us to discern whether the prospective graduate program, the new job opportunity, or Richard is a good fit for us. It also helps us to showcase on our resumes, our application or our dating profiles why we would be a great match for Stanford, or Google, or Richard.
To sum up: Nobody expects us to get a job without applying. Why are we expected to find the love of our lives without dating?
Very little that’s important in life was ever achieved through just going with the flow and waiting for the thing that we REALLY want to happen when we least expect it.
For most of us, this isn’t how we approach our career. This isn’t how we approach our education.
Why have we accepted that “going with the flow” is how we’re supposed to approach dating? And might it be time to rethink that approach?
In reality, love, like so many other things in life, requires effort and intentionality to be worthwhile. And that effort and intentionally starts in the beginning of our love story: with how and whom we date.
Those of us who have been thoughtful and deliberate in our educations and in our careers already have the core of what we need to succeed at this new venture. We just need to apply what we’ve already mastered to master a new, but no less important, area of our lives: love.
In the same way that our intentionality, our sense of direction, our strategic thinking, our tenacity, our grit, our ability to set (and to achieve!) our goals, our creativity, our willingness to learn new skills, and our intelligence have helped us to succeed in our careers, we can apply these same qualities to succeed at love.
THIS is how we’ve been successful at work and in life, and this is how we’ll be successful at love:
Not by waiting for love to happen when we least expect it, but by applying the same blend of intentionality, creativity, and proficiency that we apply in our broader lives to our love lives.
PS. If you're drained from drowning in a sea of dreadful dating dossiers and want nothing more than to just find someone attractive and normal for once — I see you, I was you, and I'm here for you!
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