At 38, I Figure I’m Destined To Be Single Forever. Now What?

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Hi Meredith,

I’m 38, have built a solid career, have wonderful close friends (in this city, they’re all married with no single guys in their orbit I could meet), spend my free time volunteering with an organization that matters to me, regularly play music with others, and increasingly focus on the hobbies that bring me joy – most of which are solo and/or in female-dominant spaces.

As the world has opened up over the past few years, I’ve been making the extra effort to try new things that push me outside my introverted comfort zone. All of these activities build my community and fulfill me. In short, life is about as good as it gets for a single woman in this world. But I lack and still crave the physical and emotional intimacy of a long-term relationship. Heading toward middle age, I recognize that the cultural dream (mythic promise?) of a loving partner to build a life with is statistically unlikely to be my future reality. Friends and my therapist regularly tell me to not give up hope of the serendipitous encounter (since at this point I’ve swiped through all possible people on the dating apps with minimal success). But living with unfulfilled “maybe around the next corner” hope leaves me demoralized instead of optimistic.

When do I give up on the promise of a partner as the plan, how do I transition my life’s expectation from “find someone to share my life with” to “build a life where I’ll be able to care for myself, by myself, in my old age, without regrets”? How can I live this life that meets 85 percent of my emotional and physical needs, plan to be a spinster forever, while also not shutting myself off to the unexpected corner should it appear? And how can I convince my well-meaning people that not every great person finds someone great to love them back? Love is as much luck as something deserved or earned through jumping through the right hoops. Sometimes that particular luck may never visit a person’s life.

– Great yet luckless


It’s been a while since I saw the S-word in a letter. For a record, I say “bachelor” when I’m taking about my unmarried state. People understand what I mean.

You can tell your well-meaning friends/family that hearing “there’s a lid for every pot” is infuriating when you’re the pot. If they know some lids, great. If not, they should keep silent. Be clear that when they talk about this, it seems like they’re shocked you haven’t managed to buy a winning lottery ticket. Like you’re not trying hard enough to get that ticket! Hopefully the empathetic people will understand. If not, you can always say, “Let me know when you have someone I might like!” Giving people responsibilities tends to shut them up.

You ask when to give up on romantic love. I don’t think that’s the right question. At my age, I’ve had to accept the lack of permanence of any of this. Some people in my orbit who were very in love 10 years ago are divorcing. A few people who said they’d never use an app are now on five. Some people didn’t want kids but had one. Everything got weirdly messy and unpredictable in my early 40s, and there was some relief in that. It meant that all of life’s questions hadn’t been answered. My own life started to change a ton (in good ways, but also uncomfortable). It wasn’t that a bunch of single people found partners out of nowhere – although some did – but it felt like there was an aggressive musical chairs situation, where a bunch of people tossed their chair across the room and took another.

To be clear, some people in my life got married in their 20s and 30s, stayed married, and are very happy. But they’ve also dealt with unanticipated changes with moves, family caregiving, wild job situations, etc. Very few people stayed on a path they thought they understood and could control.

I know you want to control your narrative so you can prepare for whatever sadness, loneliness, and other feelings pop up over the years to come. I won’t tell you you’re going to meet someone, but I will say … you don’t know what will happen. You have no idea who will be caring for you when you’re old. If I was asked to bet on your relationship status at 45, I would decline. It would not be a safe gambling situation.

You know enough to call marriage (or anything like it) a “mythic promise.” Another mythic promise? Control and consistency. Please stay in reality, do what you love, take breaks from dating when you need them, and admit that the whole thing is a moving target. You might stay single and move to Paris like a TV character. You could meet someone and only date that person for two years before you break up.

You don’t know what will happen. I don’t either. There is no inevitable future. Scary, but true.

Please keep me posted.

– Meredith

Readers? Is the path set at 38? How do you adjust your expectations as you date into your late 30s and early 40s? How do you tell loved ones that their optimism about your dating life can feel awful?

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