Here's Exactly How to Know When to Propose

Your knees are weak and you have a serious case of sweaty palms and heavy arms. Are you about to go into a rap battle like Enimem in 8 Mile? Nope, you’ve decided to propose — and you have no idea how to do it.

No need to panic. Though deciding to propose is a huge (and emotional) life decision, it’s not something you have to fret over. Instead, think about the process logically by breaking the whole proposal down, step by step.

We know, we know: Easier said than done. Luckily, we’re in the diamond engagement ring business and have heard a thing a two about marriage proposals, so let us help with this guide to planning the perfect proposal.




when to propose man holding ring box

Step 1: Decide if you're really, really ready to propose

We’ve all heard stories about people who got engaged just a couple weeks — or even days — after meeting. While that doesn’t mean the marriage won’t work, it’s a sign that perhaps the couple hasn’t thought things all the way through.

But that’s not you. You’ve been with your significant other for months or years and know you’re ready to make the big commitment. While that may be true, ask yourself the following questions:


  • Have you had the big, uncomfortable discussions? It might not be romantic to ask about your partner’s views on certain life milestones — like kids and their views on sharing money — but these are necessary conversations to have before walking down the aisle.

    You need to be on the same page about whether or not you’ll have kids, whether or not you’ll share a bank account, and what your future goals are. Otherwise, miscommunication — or no communication — on these factors can lead to serious resentment or divorce down the road. Be sure you’re on the same page (or at least willing to compromise) before you decide to propose.

  • Do you communicate well? Every couple has arguments, but it’s how you communicate — and come to a resolution — that’s important in a healthy marriage. If you fight a lot, hold grudges or just don’t work out disagreements, that’s a sign that you should probably rethink the proposal for now. That doesn’t mean fighting = dealbreaker, but you should try to work things out via a therapist before you decide to propose.

  • Who is paying for the ring? You’ve probably discussed marriage at least once or twice by this point, but do you know the specifics of her wishes? Decisions on the cost, style, and who is paying for the ring should be out in the open before you decide to propose.



when to propose man on one knee in front of family

Step 2: Decide when you’re going to propose

While a spontaneous proposal might work in the movies, you should probably do a little planning before popping the big question.

There are a few factors you should consider before deciding on a date:


  • How long do you want to be engaged? Think about an ideal length of time (months, years) between your proposal and the wedding and then work backwards to find a date.

  • Do you want to involve their family? Many people propose over the holidays because it's the easiest way to ensure their family can be present for the special occasion. If that sounds like your future wife, then planning it over the Thanksgiving or Christmas celebrations is one way to do it.

  • Do they have a favorite season? Does your significant other love a certain time of year, like the first day of fall or New Year’s? It might be special to them if you made their favorite season or event part of the big question.


Step 3: Set the proposal date

Alright, you’ve thought things through and have a date in mind. Awesome!

Now it’s time to commit to the date and use it as the jumping-off place for all your planning — like arranging for her family to be there, or even doing something as spectacular as creating a vacation around the proposal.

Whatever you do, just make sure it’s something that will be special to you and her. You don’t have to include anyone — or do anything fancy — if that’s not how you are as a couple. If you know she would be happy if you propose on a “random” Saturday night, then go that route. If she (and you) would love a fancy party, go for that.

Ultimately, it’s important to go with your gut.

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