Hi readers! Shayla Love here, science journalist and longtime fan of Your Mileage May Vary. I’m honored to be subbing for Sigal Samuel while she’s out on parental leave. I’m diving into your questions as a way to help understand human nature and our choices through multiple lenses: philosophical, psychological, and beyond. Please send in any emotional, body/brain, sociological, perceptual, or other kind of life quandaries you might have.

My best friend confessed his love for me one year ago and I rejected him because I was unhappily in love with another man, and I was never really physically attracted to my best friend. He was devastated. I am happy our friendship survived.

Over a year later, I find myself thinking about how it would be like to be in a relationship with my best friend. He is the only man who ever showed me genuine love and support, and I wonder what if I try…maybe I will fall in love with him. However, I am concerned about hurting his feelings again. Is it selfish of me wanting to try this love out because it promises security and appreciation?

Dear Fanning the Flame,

I can’t blame you for being curious about the common “friends to lovers” storyline. It’s often portrayed as the best kind of pairing: Two people have the foundation of their friendship plus a newfound love; the romantic relationship is like a soaring addition to an existing sturdy house. 

But real life is not always like the movies, and it sounds to me like you haven’t actually had an awakening of desire for your friend. In fact, it’s the opposite: He once expressed feelings for you, and you confronted a lack of physical attraction for this person. Now you’re wondering if it would be possible for you to fall in love if you tried. I think you’d agree that your timing is suspect. After a breakup, it’s common and understandable to seek out comfort and intimacy. Still, I detect a philosophical streak in your question beyond the issue of whether or not this would simply be a rebound. 

If your friend has always appreciated you, made you feel safe, and loves you — could that be a form of love that’s better than what you had in your last relationship? Maybe that is what love is.

Is it? Over a long night of drinking some 2,400 years ago, one group of thinkers allegedly debated the true nature of love, as Greek philosopher Plato describes in The Symposium. 

Aristophanes, a playwright, tells a story that most closely aligns with the love we see in the rom-coms of today. He said that humans used to be larger creatures with four arms and four legs. After annoying the gods, Zeus cuts all the humans in half, creating the two-limbed bodies we have today. The result is that people wander the world looking for the one person who used to literally complete them. If you followed Aristophanes’s fable, you shouldn’t try to be with your friend unless you felt that deep longing that one has when meeting their other half. 

The rest of the dinner party companions have more circumspect ideas. Phaedrus, a Greek aristocrat, thought that true love inspired people to become the best possible version of themselves. Pausanias, a military man, thought that love driven only by attraction to someone’s body was “vulgar love”, and that “noble love” was the love of someone’s values. Eryximachus, a doctor, asserts that love is also about moderation, and it needs order, much in the way the natural world does. Finally, Socrates says that even if you start out with physical infatuation, you can eventually transcend that and end up loving wisdom itself, the highest form of love. As I read it, the men are grappling with how to make love make sense, while acknowledging that it can make us lustful and impulsive. Shouldn’t its best manifestations instead be practical and virtuous?   

You could easily justify trying to date your friend with these theories that try to wrangle and tame love. For example, if your friend inspires you to be the best version of yourself, you could decide that’s enough to go for it. You could also decide that because you admire your friend’s character, and not his body, that’s a noble love, and better than the vulgar love of attraction. 

German philosopher Arthur Schopenhauer wrote in his 19th-century essay “The Metaphysics of Sexual Love” that he distrusted the feeling of being desperately in love. He considered romantic love to be a biological drive disguised as a real emotion — one whose goal is to trick us into procreating. You could even see your lack of attraction as an indication that you’re able to act more rationally, and not be deceived by that cunning trickster, passion. 

I know you’ve recently gone through a breakup, but I hope you can feel how bleak these views can become: to see love only as the window dressing for the propagation of a species, or as just a bridge to the love of wisdom. 

This cynicism has other consequences. Wondering if you could redefine love in a relationship with your friend isn’t like a wine-fueled dinner party bouncing around thought experiments. It involves your best friend and his own feelings too, and could risk not only hurting him, but also robbing him of a better romantic partner. 

For Simone de Beauvoir, the 20th-century existential philosopher, the most important aspect of life was freedom: We are technically free to do whatever we want, and it’s the choices we make with that freedom that determine our authenticity, or lack of it. De Beauvoir worried about forms of love that stole freedom from other people. In narcissistic love, she wrote in The Second Sex, a partner doesn’t love the other person, but loves the fact that the other loves them. It’s a relationship built on the self-interest of one of its members. 

I want to gently point out that it sounds like there may be aspects of the narcissistic relationship in your dilemma. While it may be intriguing to consider what it’s like to date a friend, you don’t seem to be as romantically interested so much as you are interested in his interest in and support of you. Actually involving yourself in such a dynamic could take his freedom, as well as your own capacity to learn from your break-up, then find a partner you’re genuinely drawn to for their own merits.  

I’m not saying friendship isn’t an important ingredient in love. Many of the most successful, very long-term partners I know have developed a deep friendship with one another. This friendship helps them stay kind to each other and have fun over many years when work, health, or stress can interrupt more passionate times of connection. But those same couples also had the undeniable spark of attraction at the start of their relationships too. They didn’t have to try. Sometimes they tried not to feel as strongly as they did, and still weren’t able to stop. 

Even in cases when a relationship first launches platonically, if something more is there, the undeniable, reciprocal pull tends to emerge soon thereafter. In H.G. Wells’ 1911 novel, The New Machiavelli, which was largely based on a real-life affair Wells had, he writes about a college graduate called Richard who meets a young woman, Isabel. The two become friends and are entranced with each other’s minds. But they quickly start to notice more between them, despite trying to push such thoughts away.

They fail at this attempt. Richard has a moment of realization, when he turns to look at Isabel’s face one day. “And something — an infinite tenderness, stabbed me,” Wells wrote. “It was a keen physical feeling, like nothing I had ever felt before. …From that time forth I knew I loved Isabel beyond measure.” I think you owe it to yourself, and your friend, to pursue connections that have this quality, especially at the start. 

You should also make room for and appreciate your friendship. If it never becomes romantic, that doesn’t make it a lesser relationship. The couples therapist, Esther Perel, calls friendships their own kind of love story. She once described a simple exercise to help appreciate that bond. Take a few minutes and think about a friend who isn’t a family member or romantic partner. “Recall a time when that friend reflected you back to yourself, created space for joy, or helped you remember who you are,” Perel suggests. Then, send a message to that friend about that moment, and thank them. 

Having a good friend by your side in the aftermath of a breakup is a gift. Work on maintaining and nurturing that friendship, and make sure you spend some time helping him with his life too. Don’t fixate on whether you should attempt to fall in love. The truth is, for better or for worse, if you love him, you won’t have to try.

Bonus: What I’m reading

• I’ve always been interested in the history of love, by which I mean the differences over time in how love has been expressed and discussed. William Reddy, a historian of emotion, has an excellent book called The Making of Romantic Love; you can also check out a syllabus for a class at Duke University he taught on the subject. 
• For a deeper dive (and refresher!) on Plato’s Symposium, I found that there was no better person to turn to than Melvyn Bragg and his guests on the BBC In Our Time episode on the philosophy of love. 
• Arranged marriages are an interesting window into understanding the growth of love. Mansi Choksi’s nonfiction book, The Newlyweds, follows three couples in India who attempt to marry for love; here’s an excerpt that was published in Harper’s Magazine. 

This story was originally published in The Highlight. To get access to member-exclusive stories like this every month, become a Vox Member today.

Editor’s note, September 20, 8 am ET: We’re bringing you some of our best-loved Your Mileage May Vary columns while Sigal Samuel is on parental leave. The one below was originally published last September.

This unconventional advice column offers you a unique framework for thinking through moral dilemmas. It’s based on value pluralism: the idea that each of us has multiple values that are equally valid but that often conflict with each other. Submit your own question here.

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The Jewish High Holidays are coming up, and that includes Yom Kippur. It’s a holiday that encourages people to reflect on their behavior and make amends. That’s all well and good, but I’m someone who struggles with scrupulosity — constantly worrying about my morality and if I’m doing The Most Possible Good™.

In practice this is far more paralyzing than motivating. Fixating on the ethical implications of all possible decisions makes it harder to take any action, and I’ve lost hours scouring my memories of my past behavior for immorality like a football player watching footage of their games to analyze what they could do differently. Guilt simply isn’t serving me, but I worry that saying to hell with all that means I’ll stop striving to be a better person and become morally complacent.

I’ve observed Yom Kippur for decades, and don’t want to simply avoid the day. But the holiday is a moral scrupulosity trigger. How do you think I should approach this? I want to stop feeling guilty for letting guilt get in my own way.

Dear Scrupulous, 

Have you ever heard the story about what happened when God decided to give the Bible to flesh-and-blood human beings? According to the ancient rabbis, the angels hated the idea. They argued that humans were deeply flawed mortals who didn’t deserve such a holy scripture; only angels could be worthy of it, so it should stay up in heaven. 

It fell to Moses to rebut the angels’ argument. He asked them: What do you angels need the Bible for? The Bible says not to murder, not to commit adultery, not to steal — do you have jealousy or other emotions that could lead you to do those things? The Bible says to honor your father and mother — but you don’t have parents, so how could you ever do that? And the Bible says to sanctify the Sabbath — but you never do any work, so how could you even honor the Sabbath by resting? 

The angels saw that Moses was right. Angels are really great at one thing: being perfect. But perfect creatures are static. They don’t experience painful challenges, they don’t grow, and they don’t make choices that add beauty to the world. We humans do those things. God gives the Bible to humans not to make them into angels — but to make them better at being the unique thing they are: human animals, with feelings, flaws, and all, that can learn to use their capabilities in more beautiful ways.

I think there’s a lot of wisdom in this story. And I want you to notice how far it is from demanding that humans do “The Most Possible Good™.” That language suggests a maximizing ethical theory like utilitarianism, which says that we have to do the action that produces the greatest good for the greatest number. In other words, we have to optimize. 

Moral optimization may be possible for angels, but not for humans. We each hold multiple values, and sometimes those values are in tension with each other, forcing us to strike a balance as best we can. We’re not omniscient beings who can know with certainty how best to strike the balance. 

What’s more, sometimes different kinds of moral good straight-up conflict with each other. Think of a woman who faces a trade-off: She wants to become a nun but also wants to become a mother. She can’t balance between those options — she has to choose. And what’s the better choice? We can’t say because the options are incommensurable. There’s no single yardstick by which to measure them so we can’t compare them to find out which is greater.

Given that this complexity is baked into the human condition, it’s impossible to be a perfect optimizing machine. And the more you try to force yourself to be that, the harder it’ll be for you to actually help others, because you’ll just be so burned out. As you’ve already discovered, the optimizing mindset is exhausting — you end up expending a lot of precious mental resources that you could be spending on something else. It can even lead to paralysis. And a lot of the time, there’s no knowably best decision.

So instead of trying to optimize everything, you can adopt a goal that’s humbler but more realistic: to live in line with your values as best you can. 

I know that can feel scary. Optimizing makes being human feel less risky. It provides a sense of control, and therefore a sense of safety. The unspoken premise is that if you optimize, you’ll never have to ask yourself: How could I screw up that badly? 

But there’s another way to feel safe. It’s about leaning into the fact that we are imperfect and vulnerable creatures and that even when we’re trying our hardest there will be some things that we do not do optimally.

Of course, we should still try to live in line with our values. But in those moments when we fall short, we shouldn’t berate ourselves, thinking, “I sinned!” In Hebrew, the word we typically translate as “to sin” (lachto) actually means “to miss the mark.” It’s the same word we’d use to describe someone with a bow and arrow who’s targeting the bullseye but misses it slightly. This is a useful image, because it reminds us just how normal it is to miss the mark. Just as the archer’s arrow is buffeted around by the wind, we’re buffeted around by all the physical and psychological conditions acting upon us — naturally we won’t always hit the bullseye! And when we do miss the mark, we deserve compassion.

I know what you’re thinking: What if adopting this mindset means you’ll become morally complacent and let yourself off the hook too easily? This is one of the most common objections to practicing self-compassion. But research shows it’s not well-founded. In fact, psychologists have found that more self-compassionate people are better able to acknowledge when they’ve made a mistake. They’re more likely to want to apologize and make amends to others when they mess up. And they try to do better the next time around. Why? Because, to them, mistakes don’t feel so psychologically damning. That allows them to take more — not less — responsibility for their actions.

Yom Kippur can feel terrifying when any mistake you’ve made over the past year seems damning. But according to the ancient rabbis, Yom Kippur is not meant to be a somber day — it’s one of the happiest days of the year! After all, it was on Yom Kippur that Moses descended from Mount Sinai carrying the second set of tablets inscribed with the Ten Commandments, ready to gift them to the people. 

You probably know what happened to the first set of tablets: Moses shattered them after seeing the Israelites engaged in idol worship. What’s less known is that, according to one rabbinic story, God’s response to the shattering of those tablets was to actually congratulate Moses. Why did God think breaking them was the right move? And what was different about the second set? 

While the first tablets had been fashioned by God and God alone, the second tablets were a human-divine collaboration: Moses carved the stone and God inscribed the words. And while the first tablets contained only the words of the Ten Commandments — a black-and-white, rule-based morality — the rabbis tell us that the second tablets contained within them all the stories and interpretations that Jewish sages would later develop.

In other words, God recognized that you can’t just give humans a list of moral rules and call it a day. Maybe that would work for angels, who live in a simplified, disembodied world, but our ethical life is just too messy and multifaceted to be captured by any single set of universally binding moral principles. Yet God chose people over angels anyway, inviting us into the collaboration and embracing our humanness rather than rejecting it.

So, to the rabbis, Yom Kippur was a happy day because they fully expected that God would accept and embrace messy humans. 

Please, don’t try to be more zealous than God.

When you’re taking action, by all means, aim your arrows as true as you can — try to hit the bullseye, the place that captures as much of what you value as possible. But once you’ve released the arrow from your bow, let it be. 

If it turns out that you missed the mark, that you acted suboptimally, I put it to you that that is okay. You are not an angel. You are not a perfect optimizing machine. You do not have access to a magical mathematical formula that can consider countless incommensurable variables and spit out the very best move with certainty. You are human and you do the best you can with what you’ve got. 

The wisdom of these millennia-old stories is that that’s good enough for God. Let it be good enough for you, too. 

Bonus: What I’m reading

• Writing this column reminded me of The Mindful Self-Compassion Workbook, written by the psychologists Kristin Neff and Chris Germer. It really helped me develop a self-compassion practice, which has in turn helped me get a grip on my own scrupulosity. I also strongly recommend the eight-week self-compassion course run out of Neff and Germer’s nonprofit, the Center for Mindful Self-Compassion.

• I’ve always associated the philosopher Thomas Nagel with questions about consciousness, but I recently learned that he’s also super interested in questions about religion. In a great essay called “Secular Philosophy and the Religious Temperament,” Nagel asks: What, if anything, does secular philosophy have to put in the place of religion? More specifically, can it answer the question: What is the underlying nature of the universe, and how can the human individual live in harmony with it? 

• In this Aeon essay, philosopher Elad Uzan argues that AI will not be able to solve ethics for us, despite what some people hope. Drawing on the mathematician Kurt Gödel’s famous incompleteness theorems, Uzan writes, “just as mathematics will always contain truths that lie beyond formal proof, morality will always contain complexities that defy algorithmic resolution.” 

Hi readers! Shayla Love here, science journalist and longtime fan of Your Mileage May Vary. I’m honored to be subbing for Sigal Samuel while she’s out on parental leave. I’m diving into your questions as a way to help understand human nature and our choices through multiple lenses: philosophical, psychological, and beyond. Please send in any emotional, body/brain, sociological, perceptual, or other kind of life quandaries you might have.

My wife says I’m a people pleaser. I want to turn over a new leaf (maybe to please her?!) so I’m making a resolution to be less of a weathervane and stand up for myself more. But it’s hard — I love to fit in. I’m a joiner and a collaborator. It’s not that I’m passive, it’s more that I find other people’s “ways of being” contagious. Sometimes I catch myself slipping into imitation of the friends or colleagues I’m talking to.

What’s a chameleon to do? Or, more scarily, who am I when I’m alone? How do I find out who I really am?

Dear Identity Crisis,

At first glance, it’s a bit funny to be accused of being a people pleaser as if it’s entirely a bad thing. It sounds like you have others’ interests genuinely in mind, and that seems like a nice way to build connection.

But I find the term people pleaser to also be a sneaky euphemism. Do you want to know how this sort of behavior is often discussed in the psychological literature? In studies, it’s not always called people pleasing; it’s called lying. 

In fact, wanting to please other people is an incredibly prevalent motivation for lying; it’s more common than lying for personal gain or pleasure. When psychologists evaluated the top reasons that people lied in their everyday life, many wanted to seem more agreeable. Their lies support seemingly magnanimous goals, like complimenting a friend or making sure a social interaction went well. But they were lies all the same, defined by the researchers as a “message that one gives to another in which they are deliberately deceiving them.” 

I find this shift in perspective helpful, if a little harsh, if you’re looking to break a people-pleasing habit. It’s one thing to think about yourself as dedicated to keeping other people pleased. But when you consider that actually, all of your interactions are suffused with lies, the approach becomes a bit more unsavory. 

Imagine the situation in reverse: What if you found out that all the time you had spent with a close friend, they were keeping their real thoughts and feelings from you? You might feel differently about the time you’d spent together. I can bet it certainly wouldn’t feel as authentic. 

I used to be a bartender, and I would be nice and mildly obsequious to frequent customers. Several of them I genuinely liked. But I’ll never forget the uncomfortable moments of running into a regular elsewhere — and their figuring out that we weren’t actually friends. There’s a distance between two people when one’s main role is to please the other. You are creating that distance, even if you may not realize it, and not even getting tipped for it. 

So for starters, try trusting that the people around you are able to handle your real thoughts and feelings. But what are your real thoughts or feelings? This points to the bigger conundrum you face: Who is your true self? 

You’re in good company worrying about this. Religious figures, philosophers, and scientists alike have been trying to figure out if there even is a continuous self, and if there is, what is it made up of? 

Scientifically speaking, there’s not a part of your brain that’s “truer” than others, or where the true self resides. But your ideas about your true self matter, according to research by Rebecca Schlegel, a social scientist at Texas A&M University. She has found that people have greater well-being and find their lives to be more meaningful if they think that they’ve made choices that align with who they “really” are. 

When people make a decision that they think aligns with their own true self, it regularly leads to feeling more satisfaction with that decision — more so than choices steered by considering what other people want, by religious belief, or by advice from others. 

Doing this yourself can be remarkably simple. In one experiment, Schlegel asked participants to make an arbitrary decision and told some to “use your true self” to make up their minds, and others to “use rational thinking.” Those who framed their choices as being guided by their true self were much happier with their selection. For you, it could be that just introducing the question — what would my true self do? — can start making your life feel more like it belongs to you. 

If it feels odd to ask your true self what to do, defining your truest self as what’s moral about you isn’t a bad place to start. Researchers have found again and again that when they ask people which of their traits feel the “truest,” it’s usually the parts that are morally good. When I call my mother on her birthday, that’s my true self. When I say something hurtful to my friend, that’s a deviation from my true self, who knows better. I wasn’t myself this morning, I might say as an apology. So you could make a list of your best qualities, like your generosity or your creativity. Then, when you ask what your core self would do, you’ll have even more specific guideposts to follow. 

Of course, if having a true self still doesn’t feel relatable, you can turn to an approach I’ve found helpful in my own life from Eastern traditions, like Buddhism and Taoism. They endorse the idea that there is no rigid self at all. In Buddhism, this is called anatman, which translates roughly to “no self.” This teaching emerged in response to an earlier Hindu belief: a concept called “atman,” which asserted that all people had an eternal and unchanging core, similar to a soul. Anatman was a rebuttal to that idea.

I’ve found that anatman relieves some of the pressure around all of this. We feel as if there should be an essence to us, some permanent quality that persists over time that you can point to. But anatman reminds us that there’s no aspect of the self that doesn’t change.  

Life is long, and we transform throughout it. As we grow, we learn new physical skills like playing soccer and the piano, and eventually acquire back problems and wrinkles. Our minds evolve too. We read novels, maybe we can do calculus, and we develop political convictions. Hopefully, we gain the skills of being kind and patient. In all of these developments, change is the only constant. This is why the Buddha thought that you couldn’t find the singular, stable self in any of these places — not the mind, the physical form, our habits, or our perceptions. “What is impermanent, subject to change…cannot be taken to be ‘me,’ ‘mine,’ or a ‘self,’” the Buddha taught. 

You asked what you, as a chameleon, should do? You could frame everything you do as being in service to your deeper self. Or you could try halting the search for a strictly defined, enduring version of you, and start making decisions based on who you want that person to become.   

Bonus: What I’m reading

• My book club just read Love, Always, a novel by Ann Beattie, about a group of people who start a magazine in rural Vermont. It’s a summery tale, though somewhat frustrating, about what happens when people don’t change themselves, and only follow their worst instincts. 
• This is a fascinating story of multiple selves in Popular Mechanics by Michael Natale. It documented what happened when seven men confessed to being the culprit of a plane hijacking in 1973 in the Pacific Northwest.
• Over the course of several nights recently, I watched the 1926 silent movie, Faust, directed by F.W. Murnau. It’s a haunting tragedy about the consequences of wanting to hold onto a quality of yourself indefinitely — in this case, staying young forever. I was amazed by the special effects they pulled off for that era! An evergreen reminder that if someone promises you something that’s too good to be true (especially if he looks like the devil), it probably is. 

This story was originally published in The Highlight. To get access to member-exclusive stories like this every month, become a Vox Member today.