Sandra Day O’Connor’s biographer Evan Thomas, whose book FIRST comes out in March 2019, revealed a long-held secret about the the Supreme Court Justice that eluded even her close friends and family — her fellow Justice, the late William Rehnquist, asked her to marry him when they were both in their twenties, NPR reports. The duo dated casually while attending Stanford Law School in the 1950s, but she eventually called it off, preferring him as a “study buddy” rather than a lover.

When Rehnquist graduated a semester early to become a Supreme Court clerk in Washington, D.C., Day wrote her parents that school “wasn’t the same without him [Rehnquist],” but she eventually met and fell in love with John O’Connor. Rehnquist, still holding a torch for Day, wrote her a letter asking for her hand: “Sandy, will you marry me this summer?” But Day rejected his proposal and married O’Connor in 1952.

Day and Rehnquist went on to work together when she became the first woman to sit on the Supreme Court in 1981 and maintained a close friendship. In fact, one of her sons, Jay O’Connor, told NPR: “Not only did they have a wonderful working relationship for over 25 years on the court, they had a wonderful friendship their entire life.”

The news about the two Justices’ romantic history prompts the question: Is it really possible to remain friends with someone you’re in love with? And if you do remain friends — can you still be happy and fulfilled even though the relationship didn’t turn out as you had hoped?

Helen Fisher, Ph.D., a noted anthropologist, senior research fellow at The Kinsey Institute, and author of Anatomy of Love: A Natural History of Mating, Marriage, and Why We Stray, and Jeanne Safer, Ph.D., a psychologist and author, break down how to stay friends with someone who can’t return your romantic affections — and still be true to yourself — along with when it’s best to stay apart for good.

Have a Reality Check With Yourself

“You have to be absolutely honest with yourself to make sure you’re not hoping the person will ultimately return your feelings,” Safer says. The author of The Golden Condom and Other Essays on Love Lost and Found stresses that even the quietest and slightest hint of romantic expectation signals it’s not possible for you to stay friends with your loved one. “If you have even a scintilla of a fantasy that that’s possible, run the other direction,” she emphasizes. She calls the phenomenon of continued longing for someone who doesn’t return your feelings “relentless hope, a notion from psychoanalysis, where a person pursues hope where there is no hope.” Holding onto that is not productive for your own well-being. Instead, use your time apart to prioritize yourself, and protect your heart.

Let Some Time Pass

Fisher says studies have demonstrated that the old saying “time heals all wounds” is true. “We’ve proven it in the brain,” she says, citing a study she and her colleagues conducted in which the participants, who’d been rejected by their partners, showed decreased activity in the ventral pallidum (the region of the brain linked to attachment), the more time that passed after their heartbreak. Safer agrees: “If some time has passed, and you’re not feeling so desperate or angry or empty about the rejection, then friendship is worth a try.”

Meet Someone New… and Do New Things

Another way to approach keeping the friendship of a loved one who can’t reciprocate your affection is to take space and revisit your relationship once you’ve found “someone else who can return your feelings,” Safer advises. Meeting them anew under the spell of another love might totally shatter your fantasy of them —in a healthy way. Safer can relate. “I reached out to a man who had treated me terribly decades ago, and had lunch with him,” she recalls. “It was a revelation. I saw what I had loved — and saw that I had so much more, in every way, with the man whom I married.”

Fisher adds: “Meet new people and go do new things. Novelty drives up dopamine — a neurotransmitter associated with the pleasure and reward systems in your brain — and it’ll make you feel better,” she says. And get some love and support from your friends, which will drive up your oxytocin levels, making you feel calmer and more relaxed.

Know the Limits of What’s Possible

“True intimate friendship is unlikely to be possible unless both people are otherwise engaged or one is no longer seriously longing for the other,” Safer says, stressing that while friendship might be possible in other instances, “it’s not for the faint of heart.”

As Virginia Woolf put it in her 1927 classic To the Lighthouse: “To want and not to have, sent all up her body a hardness, a hollowness, a strain. And then to want and not to have — to want and want — how that wrung the heart, and wrung it again and again!”

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  • Stephanie Fairyington

    Contributing Writer at Thrive

    Stephanie Fairyington is a contributing writer at Thrive. A New York-based journalist, her work has appeared in The New York Times, The Atlantic (online), The New Republic (online), The Boston Globe, and several other publications. She lives in Brooklyn, NY with her spouse Sabrina and daughter Marty.