Tough Love: Do I Like Being Single Too Much to Fall in Love?

This column exists because of the way Abigail writes about love. I asked (okay, begged) her to be our advice columnist after reading a few sentences, from her piece about “When Harry Met Sally,” which are addressed to the kids these days who’ve given up on romance. “By all means, study hard, travel, find a good job, have mimosas with friends,” she wrote. “But don’t mistake subplot for storyline. When love arrives, drop whatever you were doing, grab an Uber, take the first flight out.”

For Valentine’s week, she returned to this idea. In her latest advice column, she responded to a 30-year-old single woman who is extremely happy with her life, and is wondering why she’d bother with dating, and if she has to settle for some unsatisfying guy. A fair question! But if you ever find yourself unsure whether love is worth it, scroll down and read what Abigail has to say on the matter. Oh, and remember: Love’s not supposed to be easy. Often, it’s pretty tough.

Abigail’s column is usually for paying subscribers only, but we’re making it free for everyone, just for Valentine’s Day weekend. If you want to read Tough Love every week, become a subscriber here and sign up to get the column here. And if you want Abigail’s advice on a quandary of your own, you can write to her by clicking here. —Freya Sanders

Dear Abigail,

I am a 30-year-old single woman. I am happily single—I have a successful career, make good money, live in a desirable neighborhood with my cute and companionable dog, and have best friends who are also single. I travel, enjoy sporting events, go to exercise classes, drink cosmos, run marathons, and spend lots of time out in the city with friends.

After ending a four-year relationship last year, I see my singledom as a complete gift. To be free, happy, and independent after years of being unsure or unhappy is a blessing. I eat exactly what I want for dinner, play Joni Mitchell at full volume in the car, FaceTime my mom for hours in the evenings. I never have to explain my choices in home decor or get annoyed at how someone cleans the bathroom.

Yet I know that I dream of a partnership and being a parent. When I venture into the dating scene, I struggle with the ups and downs: the instant hit I get from male validation, the blow to my self-esteem when I’m ghosted, the anticipation before a date, the fixation on wondering what I did wrong, disappointment with lack of connection, and guilt when they pursue me but I’m not interested.

I don’t think I was in love with my last boyfriend, and I’m starting to worry I will never feel that transcendent feeling that so many people talk about. Am I just too cold? Too practical or realistic? Too critical? Too protective of my own world?

My mom tells me it will find me when I am not looking. I feel so fulfilled by my other relationships, but I want to experience real, all-consuming, romantic love. Do most people settle to beat a biological clock, or do you think we all get a chance to feel it?

Trying to remain optimistic,

Jenny

Jenny,

Your life is so full already. You’re not actually missing anything.

Being with some guy is totally not worth upending your life over.

You don’t need a man to “complete” you.

If the right partner comes along to join you in this journey, great. If not, who cares?

You’re so awesome—don’t even think about settling!

Now that we’ve regurgitated the prevailing pablum, maybe we can clear the decks for some truth.

Here is what you’ve brought me: a successful career, a good income, a little dog, weekend marathons. Uber Eats when you need it, SoulCycle when you want it. Cosmos with friends just because. Spotify cued to your bespoke playlist, set to the volume that feels right to you. Nightly hours-long FaceTime sessions with Mom.

A whole life, furnished with extensions of yourself. Nothing messy or unpleasant or personally demanding. You peer into the world on your screen like Narcissus into the pond, and think: I’m obsessed.

And I get it. You spent four years dating a guy you never loved. Now you’re experiencing a kind of singlehood euphoria. But singlehood euphoria has no natural end date in our world of engineered distractions. You could easily go on this way for another decade or more, by which time your desire to have children may have been subverted by biological fiat.

You ask me whether you should remain optimistic about getting the chance to feel in love, but lack of optimism isn’t your problem. You’re not tempted by the male offerings around you because you’re brimming with delight at your table for one.

And so, you haven’t asked the most relevant question: Why would a man want to enter your world? You’ve made no room for him in your life. You don’t seem to have one patch of bare wall on which he might hang a poster.

You enjoy your life, as you should. It’s admirable that you’re successful and self-sufficient—you can buy yourself flowers, as Miley Cyrus would have it. The deal you offer a man is essentially this: I’m awesome and totally self-sufficient, looking for a man who’s awesome and totally self-sufficient so that we can be awesome and independently self-sufficient, together. That’s the prevailing ideal today, and there’s nothing sinister about it, per se.

Except that it isn’t the stuff of love.

It is, instead, an ideal designed to eliminate dependence and inconvenience. But love, dear Jenny, is built of exactly those things.

You say you want to “experience real, all-consuming, romantic love”—but it’s the experience you say you’re after—something you hope to feel, not a man you might come to need. In your description, romantic love becomes just another bucket-list item, like Machu Picchu. You don’t mention the sort of man you’re seeking, perhaps because any man is just a vehicle for emotional rush. In so many ways, you’ve told me not only that you don’t need a man, but that you don’t particularly want one.

When Aristophanes—over 2,000 years ago—described one soul in two bodies, each half yearning for wholeness, he had it right. Love is two people who want each other very much and come to need each other—for comfort and counsel and joy and even to share pain.

Not a roommate to clean the bathroom to your satisfaction or earn half the income or even yank luggage off the baggage carousel, but someone who makes your life whole, someone you ultimately can’t bear to be without. A life of love isn’t one that minimizes dependence, but one that risks it.

You wrote to me, so I have to believe you haven’t entirely sealed yourself off from the possibility of finding love.

But love requires humility. It requires the realization that you’re not always so awesome and complete—something your friends and mom and nearly every voice in self-help culture will expend their last breath denying.

Your mother assures you that love will find you when you’re not looking. That’s disastrous advice for a daughter who’s just exited her 20s. And Jenny, forgive me, it strikes me as self-serving, too—given that she’s installed herself as your standing date most evenings.

Nightly FaceTime with even a caring and generous mom won’t bring you any closer to finding someone. Neither will dating apps, which mostly leave you demoralized and unmoved. But accepting setups and meeting young men out in the world—even those who aren’t a perfect match—can, with each date, bring you closer to finding love. They each have the ability to expand your social world, help you refine what you’re looking for, even just shake you loose from a routine of self-focus.

You ask if most of the women in my generation “settled” to beat a biological clock. No, we didn’t. We didn’t go around thinking that any man we met would be unaccountably lucky to have us.

We found a guy we thought was cute who made us laugh. We gave him a shot and let him surprise us. We fell in love and let our hearts get pummeled and stretched. We had all kinds of great sex with him and got married (in either order), had a bunch of kids, and built a home.

And it never once occurred to us that we were “settling.” Half the time, we look over at our boyfriends-turned-husbands, with their graying hair and gorgeous eyes, the reassuring heft of them, which deters intruders and quiets our fears and calms the kids, and wonder what they’re still doing with us.

Any time you give blood, you offer up a vein and suffer the pinch. Only then can you attempt something truly extraordinary: saving someone else’s life. Love entails this sort of reckless surrender.

You’ve been chasing a feeling. But needing and being needed—the bottomless empathy and vulnerability they require—are exquisite not because the feeling of love is so special but because the person you love is, to you.

And suddenly, you find yourself changed. You learn to cook, even though you hate cooking, even though it bores you to tears, because the thought of his expression when he realizes you did this for him is just too great to pass up. The sight when he first enters a room evokes such a wave of tenderness, you can’t help but reach out to touch him. You save up all your best thoughts and worst fears just to share them with him and are only able to sleep after you’ve heard his voice, which resounds in your whole being as security.

Real love is attainable, Jenny. And you’re young and talented and no doubt lovely, which means you still have a VIP ticket. But you won’t find love in your apartment, and Instacart won’t deliver it. True, if you found the right guy and gave him a shot, he would disrupt your perfectly set table and usher in moments of self-doubt and heartache—but also all kinds of ecstasy. It’s worth the risk.

Think I’m just blowing smoke?

One year ago, I set up a friend’s brother with a friend of a friend—a man and woman I knew only slightly. Both were settled into careers, pushing 40, living in different states when I gave the brother her number. Both were fairly certain they would never find love.

Within six months of meeting, he had packed up his things and moved to be closer to her. Within a year—this past Thanksgiving—they were married.

They sent me photos—the fancy shots from the wedding I wasn’t able to attend and a million casual ones of them clutching each other, smiles filling the screen. Jenny, you’ve never in your life seen two happier faces, shiny with disbelief at their own good fortune.

They look back on years of educational attainment and career achievement with mute astonishment. They can’t believe they found each other.

They can’t believe they wasted so much time.

Onward,

Abigail