How I Proposed to My Partner (as a Woman)
...and how to know if YOU'RE ready to ask.
I never thought I’d be the one to propose.
But after years of waiting, I realized love isn’t about being chosen, it’s about choosing yourself. This is the story of how I ended up proposing to my partner (as a woman) and what it taught me about courage, clarity, and authentic partnership.
If you’ve ever wondered whether you could be the one to ask, this guide shares what I learned, what surprised me, and the questions to ask yourself before deciding if it’s right for you.
The Proposal
It didn’t happen in a single flash of inspiration.
It was more like a quiet build: a mix of frustration, longing, friendship, and a growing tug toward something more.
Back then, we were three years into our relationship. I loved him deeply. He was steady, kind, and saw me through some really rough moments. But I also found myself in an emotional loop I couldn’t quite name: I wanted our relationship to move forward, and he… didn’t seem to.
I told myself to be patient.
I hinted (too many times) at engagement scenes on TV.
I even made a Pinterest board filled with wedding ideas and “accidentally” left it open on his iPad… hoping he’d take the bait. He didn’t.
It stung. I took his silence as rejection, as a message that maybe I wasn’t desirable enough, or that he didn’t see a future with me. Every time I tried to talk about commitment, he’d stay quiet, and I’d spiral louder.
I’d been waiting to be chosen for so long that I lost sight of the truth:
“I always have a say in my own story.”
It took months of overthinking (mostly because I had no one I could talk to) before the question shifted for me—from “Why won’t he ask me?” to “Why can’t I?”
That reframe flipped everything for me. At first, the thought made me laugh: me, proposing? For someone who prided herself on defying gender roles and rejecting “quiet Asian woman” stereotypes, it hit me that I was still living out a script that said love for a woman means waiting. And I was tired of it.
So I did what I do best: I made a plan.
Step 1: Make the Rings
First, I bought myself some time—mostly because I had no idea what to do next.
As a woman, there isn’t exactly a blueprint for proposing. There’s no guide for what it should look like. For me, engagement ring shopping and getting down on one knee didn’t fit, so I decided to create my own symbols.
I enrolled in a six-month jewelry course to make two rings: one for him, one for me.
That part of the process became its own kind of ritual.
Leaning on my practical side, I figured, we’ll need wedding bands eventually, so why not start there? But more than that, I wanted the rings to say something about who we are.
I’d quietly rummage through his old ring box when he wasn’t around, taking mental notes about the styles he gravitated toward. He’s not one for flash, so I kept his ring simple: clean lines, something that felt timeless, and white gold because it would easily match the earring he already wore.
Mine, though, was different. I designed a twisted braid in warm gold: a modern take on a ring I inherited from my Burmese grandmother. The braid felt symbolic: two strands that are distinct yet stronger together. It also represented continuity, carrying something from my past into my future. (Keep reading to see the finished rings!)
I didn’t realize it then, but sitting at that jeweler’s bench was the start of something bigger. I wasn’t just shaping metal. I was shaping what partnership meant to me.
Looking back now, that’s what authenticity has always been about: the quiet courage to create meaning where no rulebook exists. It’s the same practice I bring into my coaching—helping people design lives, relationships, and businesses that reflect who they are deep inside, not just who they were taught to be.
Step 2: Pick the Date
I chose to propose on his birthday—the perfect cover story! If he saw me sneaking around, he’d just assume I was planning a surprise dinner.
I took three days off work (a radical move for a workaholic who never unplugs) to plan a five-course meal that I had no business cooking. Let’s be real, I’m more of a foodie than a chef.
My coworkers grew curious when I told them not to contact me during this time. I hesitated to share what was happening because of the tender doubts that still echoed in my mind about proposing:
Would people think I’m weird or desperate?
What if people think I wasn’t loved enough to be proposed to?
Was I doing this because I wanted to, or because I’m afraid to be single again?
When I finally admitted I was planning to propose, their responses were the opposite of what I expected: full of encouragement, not pity. This alone softened my doubts and put some wind under my sails.
Step 3: Ask the Question
By the time the day arrived, his office had flooded (of course), meaning he was home all day, completely ruining my timeline!
I asked him, as casually as I could, to leave his own apartment for a few hours to go wander the streets of New York or head to boxing class without me. And after he left, I cooked, I plated, and I grew more nervous.
When he returned, he humored me with mock surprise. (“Oh, I didn’t know!” with a knowing smirk.)
After an impressive dinner (if I may say so), I shyly handed him a small gift box with a card. He opened it slowly, chuckling, and asked our dog, “Hercules, what is this?”
When he found the ring box I’d made (I crocheted one of his favorites: ice cream), he opened it and saw two rings.
“Are these both for me? One is kind of small…” he asked, voice peaked with confusion. He looked to me for clarification.
I choked. I couldn’t get the words out.
So I pointed to the card where I had written what I planned to say in my proposal. (Thank goodness for Plan B.)
He read the card. Silence. I had fully prepared for him to say, “This is sweet, but I need to think about it,” since he always said he didn’t believe in marriage. Then…
He said yes!
I couldn’t believe it, so I asked him to repeat himself. Just to be extra sure, I added, “No take-backs, ok?”
In that moment, all the waiting and worrying gave way to something grounding—my first glimpse of self-trust.
The Lessons
I still smile thinking about that night: pulling off the dinner (without burning anything), the tender look on his face when he realized what was happening, and the flurry of supportive texts from my coworkers who’d been quietly rooting for me.
And I still laugh at the memory of him turning to our dog, genuinely confused, asking, “What is this?!” before it all clicked.
Looking back, proposing taught me more than I could have imagined about love, self-trust, and alignment:
That taking time off for something deeply personal is not only allowed but necessary.
That what we fear people will think of us often is our own self-judgment projected outward.
That it’s never as weird as we think it is. Most people find bravery contagious.
That I’m happiest with my choices when I take the time to understand my hesitations and act in ways that reflect my authenticity.
And maybe most importantly, that someone saying yes to me, whether it’s a partner, a boss, or life itself, can only happen after I’ve said yes to myself.
A Reflection Guide Before You Propose
If you're wondering whether to propose, here are a few questions to sit with before you decide.
Why now?
What’s truly motivating this moment? Clarity, love, frustration, timing, or longing?
What does commitment mean to me right now?
Am I asking for validation, partnership, reassurance, or shared direction?
How do I want to feel in this moment and how do I want my partner to feel?
This centers the experience in connection, not performance.
What stories about love, gender, or worth am I carrying?
Notice what expectations you might be ready to release, and what values you want to lead with instead.
If they say no (or not yet), what truth will I still stand by?
Your courage isn’t defined by the outcome, it’s revealed in your willingness to ask.
How can we co-create what commitment looks like, instead of inheriting a script?
This question matters for everyone: men, women, queer, nonbinary, anyone who wants to love more consciously.
How do I want this decision to reflect who we are, not what’s expected of us?
That’s the heart of authenticity: shaping life in your image, not in tradition’s shadow.
Planning your next chapter? Let’s talk!
If you’re in a “what if?” moment—in love, leadership, or life—but not sure where to start, Authenticity Coaching can help. Book a free discovery call and start shaping your next milestone around who you actually are. It’s time to say yes to yourself!
