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. This is the story of how I proposed 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, and a growing tug toward something braver. This is the story of how I ended up proposing to my partner.
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.
So I took his silence as rejection. 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 wanted so badly to be chosen that I couldn’t see how much of my power I’d given up to someone else.
It took months of waiting and overthinking before the question shifted.
Not “Why won’t he ask me?”
But “Why can’t I?”
That single flip changed everything for me. But 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’d still been living out a script that said love means waiting.
So I did what I do best: I made a plan.
Step 1: Making the Rings
I signed up for a jewelry-making class to buy myself a few months to think and to make our wedding bands by hand.
(Side note: learning to secretly measure your partner’s ring size while he’s asleep is an art form. It cost me hours of sleep and many failed attempts.)
Step 2: Choose 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 unplugged—to plan a five-course meal that I had no business cooking. My coworkers grew suspicious when I told them not to contact me during this time. I hesitated to share what was happening because of the doubts that echoed as I moved ahead with the proposal:
Would people think I’m weird or desperate?
Would 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 full of encouragement, not pity. This alone softened some of my doubts.
While the doubts never fully disappeared, the regret of not giving our relationship a fair shot was louder. So I kept going.
Step 3: Ask the Question (or Not)
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!”)
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 asking our dog, “Hercules, what is this?”
When he found the crocheted ring box I’d made (because ice cream is his love language), he opened it and saw two rings.
“Are these both for me? One is kind of small…” he asked, voice high with confusion.
I choked. I couldn’t get the words out.
So I simply pointed to the card where I wrote out what I planned to say for 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.” (He always said he didn’t believe in marriage.)
Instead…he said yes!
And just like that, all the waiting, worrying, and self-doubt melted into something soft and surreal. Not because I got a favorable answer, but because I’d done something I never thought I could: I chose myself, and I survived.
The Lessons
I still smile thinking about that night: pulling off the dinner (without burning anything down), 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-worth, 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 you, whether it’s a partner, a boss, or life itself, can only happen after you’ve said yes to yourself.
Reflection Guide Before You Propose
If you’re who’s wondering whether to propose, or simply to take the lead in a new way, 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 big moment? Let’s talk!
If you’re navigating your own “What if?” moment—whether in love, leadership, or life—this is exactly the kind of work we do in 1:1 Authenticity Coaching. Together, we slow down to get clear on what matters most, so your next step forward feels grounded, intentional, and deeply true to you.
Reach out for a free discovery call and let’s explore what it could look like for you to stop waiting and start choosing.
