Olivia has been with her boyfriend for eight years. They’ve lived together for the last six, share a dog, and even have the same health insurance plan. But no ring. No spontaneous trips to romantic destinations where she could secretly get a light pink manicure. No suspiciously shaped bulge in his pants on an otherwise normal date night.
At dinner recently, I asked her, impulsively and nosily: “Do you think he’s going to propose soon?” I didn’t mean to corner her; I just care. And also I am a menace.
She looked down at her plate, cheeks flushing. “He better,” she said, “or it’s over.”
Our friends have started getting engaged in slow, smug succession, one proposal announcement after another. And there we are, clapping and smiling, while privately calculating how long they’ve been dating and whether it’s less time than Olivia’s eight-year slow burn. Usually, it is, which feels unfair in the universally annoying way that aging and comparison always are.
Later that night I trudged back to my apartment and flopped into bed, sliding under my pink sheets. I mentally compared my own situation to Olivia’s: Sure, she isn’t engaged yet, but she’s still going home to someone. Then I picked up my laptop from the other side of the bed and clicked it on, ready to engage in my blue-light-and-Reddit routine. I ended up on a subreddit called Waiting_To_Wed that bills itself as a forum “for anyone waiting on a proposal or a wedding for any reason” (diplomatic and tragic).
Scroll on for five minutes, though, and its real tone emerges. The people on this forum are suspended in emotional purgatory—some hopeful, others exhausted, many quietly realizing they’re waiting for something that may never arrive.
One of the first posts I clicked was titled, “How to stop hating him and yourself?”—so, you know, light nighttime reading. A woman wrote about spending five years with a man who swore he was “gonna” propose. Gonna turned out to be a stand-in, a sentimental IOU he handed out every time she got too close to leaving. “It was what he felt he had to say to not lose me,” she explained.
I stared at the screen, imagining Olivia across town, probably brushing her teeth next to the man she hopes will someday wake up and choose her. And then there was me—lying in bed, doomscrolling strangers’ heartbreak.
The Waiting to Wed subreddit, which I am now addicted to, is basically a graveyard of the same story told a thousand different ways:
“Five years living together, no ring, no ambition.”
“Is it worth staying if one person will always compromise on marriage?”
“Eleven years together and still no ring…”
“My boyfriend is totally fine wasting both our time?”
Scrolling through it feels like eavesdropping on the group chat of every woman who’s ever spiraled in the shower at 2 a.m. And beneath all the anecdotes and heartbreak, there’s a pulsing gender imbalance that you can’t unsee. In many heterosexual relationships—yes, even in 2025—men still control the proposal timeline. They decide when they’re ready, whatever that means, and the woman just…waits, all while performing emotional contortions to appear patient, cool, and understanding. If you want to marry before having children, though, there is a timeline, whether you like it or not. Waiting has consequences—both biological and emotional. Time becomes a currency, and suddenly everyone is charging interest.
Although rare and not something I’ve seen within my own circle, I have come across a few examples online of women proposing to men. Recently, I saw a TikTok of a woman who had been with her boyfriend for 14 years and finally decided to propose to him herself.
People in the comments were genuinely distressed. “You could not waterboard me into proposing to a man,” one person wrote. Another said, “He hasn’t proposed because HE DOESN’T WANT TO.” Strangers demanded to know where her friends and family were, anyone who might stage an intervention.
Historically, men have done the proposing because marriage was never just about romance; it was about power and property. Men were expected to be providers, and proposing signaled that they had the financial stability and social authority to claim a wife. Women, meanwhile, were merely transferred from one household to another through marriage. In that context, a proposal wasn’t a mutual decision; it was an offer backed by resources and legitimacy. Women didn’t propose because they weren’t positioned to define the future that they were being folded into.
That history cast a long shadow. I just turned 30. I’ve never been engaged. I’ve had a handful of serious relationships and exactly one where I could picture myself doing the whole house, kids, joint bank accounts thing. I’m not panicking, but I do feel…aware. Thirty is the age where time dilates. Twenty-something waiting is spacious, exploratory, forgiving; 30-something waiting feels more like a negotiation with the future.
So how long is too long to wait?
Here’s the terrible, liberating truth: There is no magic number. Five years is too long in one relationship and perfectly fine in another. Two years can feel like forever to someone who knows exactly what they want or way too soon for someone whose parents hate each other. I’ve watched friends wait 5, 7, 10 years, entire chunks of their 20s and early 30s, only to emerge furious with themselves for giving away time like it was an infinite resource. And I’ve watched others bail too early, later realizing their partner wasn’t unwilling, just unready.
So many people aren’t waiting out of patience; they’re waiting out of hope. They wait because the alternative means losing the relationship, uprooting the life they’ve already invested years into, starting over at an age when society says you should already be settled and very good at making charcuterie boards.
The question haunting the subreddit isn’t really “How long should I wait?” It’s “How do I know this will ever happen for me?” And underneath that: “Why does my partner get to decide the timeline of my life?”
Ultimatums get a bad rap, but there’s a very real difference between a threat and stating your needs. Telling the person you love, “I need a plan for our future,” isn’t dramatic; it’s grown-up. It’s the bare minimum for two adults who, in most other meaningful ways, have already committed to each other.
There’s no universal rubric, but maybe the real question isn’t “How long is too long to wait?” but “If I stopped hoping for a proposal tomorrow, would I still want to be here today?”
If the answer is no, then babe…what are you waiting for?