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Before Asking Her to Marry You, Do This

Engagement season lasts from November to February, but like the diamond on a bad ring, the sting of rejection lasts forever. Here's how to know if it's meant to be

When my boyfriend proposed, I couldn’t think of a reason not to get married. We’d been dating for eight years, and our life together felt cemented and harmonious; we’d even bought a house. We were, generally, conflict-free. Why wouldn’t we take it to the next level?

So I immediately said yes. And the moment I accepted, I felt a queasy rush of existential dread wash over me, a sinking feeling that made me want to retch. In that instant, my future life with him flashed before me and I knew I couldn’t do it.

I realized I harbored serious concerns about his ability to grow up, save money, act like an adult and consider purchasing real plants over the fake ficus he enjoyed so much. It was a valid relationship, but one I had outgrown. I’d just been too scared to see it.

Still, it took eight years and that proposal to know it. Had he not asked, I might’ve gone along for a few more years only to end up in the same place. We broke up six months later.

Then, a few years later, I got married. I moved fast, followed my gut and took a leap of faith — everything I didn’t do before. And that didn’t work out either.

Both times, I did it wrong: I spent too long in a relationship I should’ve ended the first time, and I jumped too quickly into one I should have let play out more first the second time. Which is why you should consider a few things before you ask your partner to marry you, and a few more things before saying yes.

Here’s how you know it’s the right time — and the right move.

Accept That There’s Always a Risk

Engagement season lasts from November to February, but like the diamond on a bad ring, the sting of rejection lasts forever. That’s why it’s important to go into a proposal scenario with a relatively high degree of confidence. To be sure, there is no one surefire way to know if she’ll say yes — even if you put in the time, take it slow, procure the perfect engagement ring (or “pre-ring”), book the perfect candlelit dinner and hire the perfect mariachi band to play “Moon River.”

Make Sure You Really Want to Marry Her

I don’t mean to sound cynical, but I know enough divorced people to know that many of them have a shockingly similar story on hindsight: They realize they got married because they thought they were supposed to. Everyone was doing it; they’d been together a long time; and they felt pressured by family, society and/or their partner to bite the bullet. Because of that pressure, and because they generally did want to marry someone, they couldn’t see the red flags this someone was presenting and they couldn’t separate that pressure from whether the relationship really met their present needs.

Men and women can both succumb to this pressure, but men tend to have a bit of a reputation for stumbling into the pressure of generic milestones with blinders on. After all, there’s a famous Sex and the City episode about how marriage, for men, is often like driving a taxicab.

The more traditional, romantic Charlotte says marriage is fate.

“It’s not fate,” the cynical Miranda spits back. “His light is on.”

“What light?” Charlotte asks.

“Men are like cabs. When they’re available their light goes on,” Miranda responds. “They wake up one day and decide they’re ready to settle down, have babies, whatever; then they turn their light on. The next woman they pick up, boom. That’s the one they’ll marry. It’s not fate. It’s dumb luck.”

Which is why you should be sure you’re really, truly, madly in love with this lady, not the next lady you started dating after you turned 35, nailed a promotion and got bored with Tinder. Don’t treat marriage like last call at a bar, frantically scanning the room for any takers because you’ve gotten desperate.

Make sure you like being with her. The sex is great. You enjoy your activities. You aren’t trapped watching The Bachelor every night when you’d rather watch PBS. You’re not booking vacations to Belize when you want to go to Berlin. You actually like her as much as you love her. You know how you both feel about children, finances and division of domestic labor. And make sure that’s mutual, unequivocally, if you want her to say yes to taking your hand.

Make Sure She Thinks Your Relationship Is Actually Stable

Most of the rejected proposal stories floating around involve men getting dumped when they propose because they obviously had no idea how bad the relationship really was, or how the woman actually felt. You might think things are going swimmingly but you’re ignoring her protests and complaints. Don’t let your satisfaction be the only metric.

Weather the Critical Waiting Period

Knowing you’ve both fully immersed in each other’s lives gives you a better shot at getting a yes. Most people get engaged after approximately two years, and also after they’ve lived together, then marry about a year and a half later. That’s not an exact science, but it’s long enough to move past infatuation and lust. This is a critical waiting period.

Get in a Fight — a Big One

You might get a yes if you’re still the in honeymoon phase of courtship, but that isn’t necessarily a good thing. Make sure you’re proposing to someone you’ve weathered a few storms with.

In other words, I hope to God you have fought like hell at least once. I hope to God you do not fight like hell constantly. You want the conflict porridge that Goldilocks chose. But more importantly, you need to be able to live with whatever conflict style you have, because you’re going to be repeating it for every issue until one of you drops dead. (To change it, you’ll need therapy, and most people don’t do counseling until the relationship is permanently damaged.)

Your relationship should also have a pleasing, agreeable autopilot, meaning you’re both comfortable in how it feels in the every day, and that your autopilot does not feel crushingly boring. If you’re constantly breaking up and she’s always angry with you, a proposal is like trying to put a Band-Aid on a gunshot wound.

Talk About Getting Married

It seems obvious, but if you aren’t having some pretty straightforward conversations about wanting to get married, then you’re taking a huge risk by asking. It doesn’t mean you have to plan out the proposal itself, although that’d be fine if you did, it just means that at the very least, you both have admitted you’re on the same page and want to be together, and also married. Then you can worry about how to surprise her in the most wonderful possible way, after you’re sure she’s down to be surprised.

Stories about women looking to put the brakes on a proposal they can sense coming (but don’t want) demonstrate how oblivious perfectly decent men can be when they get the idea in their head to propose. It’s not that they don’t love these blokes, it’s that they simply haven’t discussed marriage, the future and the commitment enough for the women to feel ready. Often they resolve it by revisiting the idea of marriage at some point in the future, but not without him getting rejected first. This is entirely preventable.

Consider the Hints She’s Dropped

Does she swoon a little when a friend gets engaged? Are you attending more and more weddings together where she seems a little misty eyed or hopeful? Has she outright told you that you’re both not getting any younger? Most women who want to marry do these things, because they’re sick of waiting on you to ask.

Consider Your Hangups — and Hers

By the time you propose, you should have some idea if you’re really her person or if you’re a substitute for the one who got away. If there are unresolved relationships for her that keep coming up, whether because she’s still enmeshed or constantly compares you to another partner, that’s a good sign she’s not over her past.

Don’t Do It in Public

Finally, if you haven’t dealt with all of the above and you’re just going to wing it anyway, you do so at your peril if you do it in front of a live audience. At the very least, for everyone’s sake, don’t take your shot in public, at a wedding, with her parents, in Times Square or at a football game. Public proposals run the highest risk of embarrassing mortified stammering nos, even if it’s just because she’s not the public type. Remember, you want the diamond to last forever, not the story of your public humiliation, embalmed in viral meme juice for eternity.