We’ve Been Together 3 Years, and He Still Won’t Propose

Dear Ani,

I’m 29. My boyfriend and I have been together for 3 years, and we’ve been living together for 2. I’ve brought up marriage at least five times. He always says “someday” or “I’m not ready yet,” but won’t give me a timeline. My friends are getting engaged. My parents keep asking when we’re getting married. I’m starting to feel like I’m waiting for someone who will never choose me. I love him, but I don’t know how long I’m supposed to stay. Is he ever going to propose, or am I wasting my time?

Chelsea Waiting for Someday

Ani’s Response:

Dear Chelsea, Waiting for Someday,

It sounds to me like he has already made a choice. He decided on a girlfriend without the commitment of a wife, and “someday” because it keeps you put without him having to do anything.

The real question you need to be asking isn’t whether he’ll propose, it’s whether you’re going to keep accepting crumbs and calling it a meal.

Here’s what “someday” actually translates to: “Stop asking, but don’t leave because I like having you here.”

Listen, if this man wanted to marry you, you wouldn’t be writing to me right now. You’d be at Kleinfeld’s arguing with your mom about whether off-the-shoulder is “too much.” He would’ve said something tangible, like: “Babe, I want to marry you, but let me get this promotion first,” or “Give me six months to save for a ring,” or literally ANYTHING with a timeline attached.

But no, he’s out here acting like marriage is some mystery he needs more clues to solve. Sir, you’ve had THREE YEARS, and you live together, what more intel do you need? A DNA test? An astrological chart? A sign from God?

After 1,095 days of watching you brush your teeth and seeing you without makeup and navigating whose family to visit for holidays – if he doesn’t know, that’s the answer.

Okay, story time because you need to hear this:

I worked with this woman – let’s call her Sarah – who came to me absolutely WRECKED. She and her boyfriend had been together since they were 15. FIFTEEN. High school sweethearts who went to prom together, college together, the whole Hallmark movie setup.

After college, for two years straight, every time she brought up marriage, he’d hit her with: “Obviously we’re getting married, what are you stressing about, it’s going to happen.

But when she asked WHERE or WHEN it was happening, all she heard were crickets. Then this man gets a fancy job offer in another city, and you know what he tells her? “Long distance won’t work. Let’s take a break until you can move here, too.” A BREAK. After NINE YEARS. Let that marinate.

Now, this should’ve been when Sarah said, “Boy, BYE.” But NO, she convinced herself this was love and that if she really loved him, she’d make it work.

So what does she do? She quits her AMAZING job – good boss, great pay, actual career growth and packs up her entire life, leaves all her friends, and moves to his city. No invitation to move in with him, no ring, no proposal, just his word, “we’ll figure it out.”

She gets there (wants to surprise him), finds a job (nowhere near as good), gets settled in a temporary apartment, and calls him, all excited like, “Baby, I’m here!”

And this man – I CANNOT make this up – says: “I think I need space, I’m not ready for you yet. I realize that before we get married, I want to see what else is out there.”

He wanted to DATE OTHER PEOPLE after she gave up everything, EVERYTHING!!

Sarah spent six months in that city feeling like she’d lost her mind. Crying in a studio apartment WITH a roommate, and that she couldn’t afford, working a job she hated, and wondering how she got so stupid.

But then – and this is where I get emotional and excited – she got MAD. Not sad-mad, PRODUCTIVE mad.

She joined a running group, made new friends, and started remembering who she was before she became a professional “SOMEDAY” waiter.

And then she met someone new in her running club, someone with great abs and a great job, someone who on date FOUR told her: “Look, I’m 32, and I know what I want. I’m dating because I want a wife, not a situationship.”

Six months later? Engaged – Boom, just like that!

THEN – because the universe has a sense of humor – guess who slides into her DMs? The ex. “I miss you, I made a mistake, I’m ready now. Can we talk?”

And Sarah – the SAME Sarah who moved cities for this man, who waited nine years – sends back one text:

“I’m engaged.” With a picture of her ring.

I heard he didn’t take it well; he told her she “gave up too soon.” And that she “didn’t give him enough time,” that if she’d just been more patient, he would’ve proposed. You know what Sarah told me? “I gave him nine years, my fiancé needed six months to know that I was the one. That’s the difference.”

Chelsea, I’m telling you this because I need you to understand something:

You cannot nice-girl your way into a proposal. You cannot be calm ENOUGH, patient ENOUGH, understanding ENOUGH, or perfect ENOUGH to make someone marry you if they don’t already want to.

So here’s what we’re doing:

STOP. ASKING. THE. SAME. QUESTION.

You have asked five times, and he answered five times, and his answer is clear: “Not now, maybe never, but I won’t say never because then you’d leave.”

Have a DIFFERENT conversation.

Sit him down and say: “I need to know if you actually want to marry me, and if you do, what’s your timeline, because mine is X.”

And then – this is crucial – watch what he DOES, not what he says.

Does he get defensive? Does he flip it on you like YOU’RE the crazy one for wanting commitment? Does he say “why do we need a piece of paper?” (RED FLAG CITY, by the way), or does he actually show up like an adult and say: “You’re right, let’s talk about this for real”? His response will tell you everything you need to know about your future.

Then YOU decide:

Can you live with this relationship exactly as it is, forever, with no guarantee that it will change? Can you do another year of “someday”? Two? Five? Nine?

If you don’t have this conversation with him, you’ll be 32 making the same excuses to your family. You will be 35, wondering if you’re asking for too much, or 40, realizing you spent a decade waiting for someone comfortable enough to let you stay.

Here’s the thing nobody tells you:

Waiting for someone to choose you makes you smaller.

You will convince yourself that marriage isn’t that important anyway, and then you become the “chill girlfriend” who doesn’t ask for too much, and, sadly, one day you wake up and don’t even recognize yourself.

You are 29, not 90, asking for clarity in a relationship after three years isn’t pressure, and you are not being difficult!

The right man doesn’t make you beg for commitment.

He doesn’t treat your desire for marriage like you’re being needy, traditional, or dramatic. He says, “Yes, I want this too, let’s figure out the when and how together.”

He doesn’t need to propose tomorrow, but he can have an actual conversation about it without making you feel insane. If your man can’t do that after three years? You need to ask yourself why you’re still there.

And I KNOW what you’re thinking:

“But I love him. But what if he was about to propose? What if I’m throwing away something good? What if I end up alone?”

Those fears are valid, I get it, but what if you stay and nothing changes? What if he proposes in three years because you pressured him, and he resents you forever? What if the relationship you’re waiting for doesn’t actually exist? Which future can YOU live with?

Here’s what I need you to remember and take action on:

You’re not waiting for him to choose YOU, YOU are deciding whether to keep waiting, and THAT’S your power.

He’s chosen comfort and “someday.” Now you get to choose.

Choose yourself.

Choose the relationship you actually want. Choose clarity over “someday.” Choose a man who doesn’t make you feel crazy for wanting commitment.

And if that’s not him? Walk away and find someone who doesn’t make you wait. You deserve “hell yes,” not “someday.”

You deserve someone who sees you and says, “she one” – not someone who arrogantly thinks he can keep you on layaway indefinitely!

You deserve better than that.

Now have that conversation, and pay attention to his response.

Wishing you all the best!

Ani