Valentine’s Day may very well be the most libertarian holiday. 

As Scott Alexander put it in his landmark piece:
“The way people think about love is the last relic of the way that libertarians think about everything.
Love operates on the non-aggression principle. To a first approximation, the only rule is that you may not seize it by force. Otherwise, anything goes.
(except prostitution – the significance of which could be an entire post of its own)
Love is unfair. Some people go on dozens of dates with supermodels, then have happy marriages with their perfect partner. Other people die alone, through no fault of their own. They were born ugly, or with fewer social skills, or with less money, or disconnected from the social networks that would allow them to meet good partners. Usually when something is this unfair, we demand it be made fairer, maybe through redistribution. In love, nobody demands this – except incels, who are universally loathed for it.
Love is unsafe. A mistake in love will ruin your life. Usually when something is this dangerous, we regulate it. Here are some common-sense regulations on love that could be part of your chosen party’s platform at the next election:

• Nobody is allowed to date without a license. These work like drivers’ licenses; you have to take a short class, and pass a short test demonstrating that you understand consent and basic relationship skills.
• Dating licenses can be revoked for sufficiently serious crimes – eg cheating, domestic abuse, or persistent alcoholism/drug use.
• Three month waiting period for marriage.
• Centralized government database of who is in a relationship with whom at any given time. You can check the database to make sure your partner isn’t leading a double life.
• After three messy breakups, you have to take a remedial relationship skills class before you can date again.”

Love is undoubtedly the last bastion of libertarian thinking. Who better then to turn to for dating advice than libertarians? Here are some valuable lessons inspired by the works of some of the greatest libertarian intellectuals.

Ayn Rand

“To say ‘I love you,’ one must first be able to say the ‘I.'”
Love, in its truest form, is a celebration of values. It is not the abdication of self but the glorification of one’s highest ideals reflected in another. To love another person is to recognize in them the virtues that you hold sacred and to affirm your own worth through their existence. A relationship must never be a sacrifice—neither of your happiness nor of your soul. Instead, it must be a trade of equal value, a partnership of those who stand as individuals yet choose to walk the same path. The person you love must inspire not mere affection, but admiration—love them as you would love your own ambition, your own purpose, your own life.

Friedrich Hayek

“The curious task of economics is to demonstrate to men how little they really know about what they imagine they can design.”
A relationship is not a construct that can be engineered, nor is it a system that yields predictable outcomes through deliberate design. Like the market, it thrives on the spontaneous interactions of two individuals adapting to one another in ever-changing circumstances. Attempts to impose control or design upon love often disrupt its natural flow, much like central planning distorts the economy. Trust in the processes of mutual discovery, let the relationship evolve organically, and resist the temptation to micromanage its course. In love, as in life, freedom to adapt and grow will yield far richer results than rigid planning.

Milton Friedman

“The great danger to the consumer is the monopoly—whether private or governmental.”
Love, like the market, must operate under the principle of mutual benefit. Beware of monopolistic tendencies in relationships—where one partner exerts undue control or dependency arises. The healthiest partnerships are those that preserve competition of ideas, equality of contributions, and voluntary participation. Provide value to your partner, as they should to you, and foster a dynamic where freedom reigns and incentives align. A relationship is most prosperous when it is a free exchange of affection, trust, and respect.

Ludwig von Mises

“Man is not, like the animals, a being that is determined by instinct. He chooses between alternatives.”
In matters of love, as in economics, man acts purposefully. His decisions are guided not by base instincts but by deliberate choice. When selecting a partner, one must weigh alternatives with care, considering both the immediate and the long-term. Do not be swayed by fleeting emotions or superficial charm; instead, choose a person whose values align with your own, whose presence enriches your life. A partnership is an enterprise of mutual benefit, built on reason, trust, and the conscious decision to pursue happiness together.

Murray Rothbard

“Liberty is the condition for growth and creativity in all relationships.”
A relationship, like society itself, thrives when grounded in the principles of liberty. Coercion has no place in love; the bonds between two individuals must always be voluntary. A healthy partnership respects the sovereignty of each person, allowing for growth, creativity, and the flourishing of both. Never impose your will on another, nor accept the imposition of theirs upon you. Love, when freely chosen and unburdened by control, is the most profound expression of mutual respect and shared joy.

Thomas Sowell

“There are no solutions; there are only trade-offs.”
In the realm of relationships, perfection is a fallacy. Every partnership comes with trade-offs, and the key to success lies in recognizing and accepting them. Do not waste your time seeking a perfect partner—they do not exist. Instead, focus on the compatibility of values and goals, the alignment of interests, and the mutual willingness to navigate the trade-offs together. The strength of a relationship is not in avoiding conflict or sacrifice but in managing these challenges with honesty and pragmatism.

Bryan Caplan

“Humans are good at hedonically adapting to most material conditions. You get used to your house, your car, your clothes, your granite countertop, and your money. What humans are bad at hedonically adapting to is… other people. If you spend a lot of time around humans whose company you enjoy, you will probably be happy. If you spend a lot of time around human whose company you detest, you will probably be unhappy.* Over your lifetime, you will probably spend more time around your spouse than any other human. So while finding good friends and good co-workers is crucial for happiness, finding a good spouse is even more so. “

And for the most detailed instruction one can look no further than Bryan Caplan’s He is the One and She is the One blog posts, where the grand economist draws on some relevant academic social science and psychology, blended with cumulative life wisdom to tell the reader what to look for in a person he or she is going to marry.

Love is like war: easy to begin but very hard to stop.

– H. L. Mencken