Poor little single girl :(

Why does society pity women for being selective? A rant, of sorts.

“I’m 32 and dating in New York City. And you know who else was 32 and dating in New York City? Carrie Bradshaw, Season One.”

That was the opening line of every TikTok video I made about dating in New York. The videos oscillated from optimistic (I’m going to do everything NYC has to offer!) to ominous (I found out this guy was a serial cheater and a liar!)... but they all started the same way: comparing my experience to Carrie Bradshaw’s.

Something was validating about that intro. It was my way of saying, “See!!! Carrie was 32 in season ONE! She didn’t get married until the MOVIE!” It rebranded my singleness to chic and city girl-approved… something I had been extrinsically searching for in this era of mine.

The dilemma of the eldest-born daughter.

As the token eldest daughter meets first-born grandchild, there’s a natural pressure I put on myself to be my best. To set a good example. To be a winner at life! But with my relationship status, “success” seems out of my control.

I can’t study for hours at the University of How to Get A Husband and graduate with honors (what I assume would be a tall, coiffed-haired neurosurgeon a la McDreamy). I just have to… be. I just have to wait for the stroke of luck that happens to every happy couple and be ready to embrace it when it does. That’s the hardest part.

Now I know what you might be thinking… “There are things you can do, Caylee!” Let’s review some popular questions and phrases that sneak their way into almost every catch-up conversation I have these days:

• Have you tried the dating apps?

• You just need to put yourself out there!

• What about joining some kind of club?

• Don’t your friends have anyone they could set you up with?

• It will happen when you least expect it!

• What about [insert nameofman here], I always liked him!

And we can’t forget the most cutting of them all…

• Have you thought about what are you going to do with your eggs?

• Don’t you want to be a mom?

• Why don’t you just get a sperm donor?

That’s like, way harsh Tai.

While I know most people are well-intentioned and curious and just want me to be happy… it doesn’t always feel that way. The line between interrogative and inquisitive is fine. And it gets smaller and smaller with every lap around the sun.

The plight of the modern woman

I’m now three years into my thirties and feel content with myself, my life, and my relationship status, but…

“I couldn’t help but wonder…” why is a woman’s relationship status such a defining metric of her success? And why is it the only seemingly interesting thing about her? Do women actually think that settling is bad? Or is it better to settle than stay single for too long?

When you think about it, selectiveness is a modern ideal. In the US, white women were not allowed to vote until 1920. Black women? Not until 1960. We couldn’t initiate divorce until 1969, and we couldn’t get credit cards until 10 years after that. We haven’t been able to fully think for ourselves until recently… and given the current state of the country, it’s back up for debate.

This perspective empowers me. A reminder that this IS in my control. I might not be able to order a McDreamy at the drive-thru, but the choice is mine. I could have married my ex-boyfriend (and the one before him, too). I chose not to. Having a ring and a wedding is the easy part – the part where you can dance, celebrate, and drink the second thoughts away. It’s after the after-party that counts. That’s when your second thoughts have long-term, painful consequences. There aren’t enough karats in the world that could make me rationalize that choice.

I’m looking for the real fucking deal. The can’t eat, can’t sleep, reach-for-the-stars, over-the-fence, World Series kind of stuff. I want someone to hold a boombox outside my window. A 90s rom-com set in New York City where they actually do live happily ever after. And the best part about this dream? It’s 100% possible. I see it in my friendships, my parents, my grandparents, in books, in songs, in paintings that are hung in the Met. It’s literally everywhere!

Women didn’t fight this hard, for so long, for some girl in 2025 to settle for mediocre when she had her independence. The reason my singleness is the most interesting thing about me is because it goes against the entire history of a woman’s place in the world and still feels like an act of rebellion.

So yes—I am on the apps, and putting myself out there, and I’ve joined a club or two, and I’ve been set up before, and I think I want to be a Mom if I find a really great person to go on that journey with me. But unless it’s a soulmate-level shit, I don’t want it.

Stop pitying the single girl. Tbh—she deserves some praise.