At 36, she realized something that knocked the wind out of her. Three years had passed since her last date. A decade since her last serious relationship. The realization hit hard enough to make her cry for two days straight.
She is not alone in this experience, though the loneliness itself is real. What she calls being "chronically single" comes with a particular kind of pain that people in relationships often dismiss or fail to understand. When coupled friends tell her "love will find you when you least expect it," they mean well. But the words only deepen the sting of feeling rejected and unheard.
Growing up in New Orleans, she watched sitcoms like Living Single and Girlfriends where characters navigated romantic entanglements with the ease of a laugh track. They went on dates. They had meet-cutes. They had what looked like effortless romantic lives. She assumed hers would follow the same script.
It did not. There were no meet-cutes in the grocery store. No friends watching from behind a newspaper to make sure things were going well. Hardly any dates at all.
The Weight of What Never Happened
The grief she feels is not about lacking a romantic partner in the abstract sense. It is about the small moments that come with romantic love. Cuddling. Affection. The butterflies when someone likes you back. Holding hands while spending aimless time together. The ups and downs of meeting new people and seeing where it goes. These are not trivial things. They are fundamental human experiences that shape how we feel about ourselves and our place in the world.
"I deserve to be loved, desired, and seen," she says. "Everyone does." The absence of romantic intimacy can make a person question their own worth, even when they know intellectually that they are worthy. The spiral of confusion and sadness becomes a familiar companion.
Friends who have navigated chronic singlehood understand this in a way that others cannot. One of her fellow single friends described the experience as harder than people assume, which is exactly why dismissals hurt so much. The grief is real. The mourning is for a life that never materialized, for experiences that never happened, for love that was never received.
She is not without love in her life. She has deep friendships and family bonds. She has already made plans to live in a nursing home with two of her oldest best friends. She considers her close circle her "forever life mates." What she lacks is romantic love, and that absence carries its own weight.
The current dating landscape does not help. Los Angeles, where she now lives, ranks among the worst cities for dating in America. A 2025 survey found that only 26% of L.A. locals think dating is great. She has joked that she would love to meet that 26%.
Dating apps were supposed to solve this problem. She tried them. It took a year of swiping to get one date with a man who insulted her appearance and insisted that men should always make decisions in relationships. She quit after that. The experience only reinforced that the apps were not going to be her answer.
What she wanted was what the sitcom characters had: third spaces. Coffee shops where people naturally gathered. Bowling alleys. Bars where regulars became friends. Places where meeting someone felt organic rather than transactional. Those spaces have largely disappeared from modern life.
When she has attended in-person dating events, the pattern is always the same. The room fills with women. The organizers beg men to sign up. Sometimes there are so few men that women are turned away. When she asked a man why he avoided these events, he said men found them intimidating. But is not dating intimidating for everyone? Is not vulnerability required on all sides?
She still hopes for the moment when a friend says, "I have a guy I think you should meet." She checks in regularly with coupled friends, single friends, and even coworkers about this. The response is always some version of: they do not know any available men, or they do not know anyone "good enough" for her. She suspects the real reason is that they do not want to disappoint her or get caught in the middle if things do not work out. But unless someone is a walking red flag, should she not be the judge of compatibility herself?
At this point, vulnerability feels risky. She has been single for so long that walls have gone up. She braces for rejection whenever flirtation happens in the wild. The lack of dating experience has taught her to expect the worst.
After her birthday crisis, she gave herself permission to sit with the sadness. At 36, she is still grieving the experiences she did not have, the love she did not receive, the small joyful moments that came for others but not for her. She did not have to be over it yet. No one gets to tell her when the mourning should end.
She finds comfort where she can. In the sitcoms she loved as a kid. In knowing that her character arc is still being written. In the friendship that matters most to her, summed up in the theme song of her favorite show: "I'm glad I got my girls."
Author Jessica Williams: "The dating crisis is real, and the people experiencing it are not wrong for grieving what they have been denied."
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