How to Propose: 5 Things You Should Know Before Popping the Question

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William Barton Avatar by  William Barton | Last Updated:  Sep 03, 2020
diamond ring

I know where you’re at right now.

You’ve made the decision to pop the question. That’s the important part.

But now you’re wondering how to do it right.

What kind of ring do I get? Should I propose at a baseball game? Attach a banner to an airplane? Or just keep it simple?

Things only get worse when you ask your friends for advice. They’ll give you conflicting information in the same sentence, leaving you more confused than when you started.

The act of proposing has been hyped up so much, it’s easy to lose track of what’s important—making sure the moment is special.

When I proposed to my wife, I did a lot of things right. But there were a few things that I could’ve done better had I gotten a little advice when I was planning.

I want to lay that advice out for you here because you only get one shot.

So let’s get planning and make your special moment perfect.

So, You’re Going to Propose

Good for you. Getting to this step was one of the hardest parts for me. But once you’ve made your decision, planning out the details can either be fun or a real headache.

I don’t regret how my proposal went, but if I were to do it again, I would change a few things. For one, I went too fast because I was nervous. I’ll cover my thoughts on what you can do to slow down and make the moment count.

In college, I worked at a fancy restaurant that overlooked the Pacific Ocean. We saw a fair amount of proposals there, including some epic fails. Let’s make sure your proposal ends up with a yes at the end.

5 Things You Should Have Locked Down Before Proposing

1. Getting the Perfect Ring

I thought getting the perfect ring would be simple. I was so naive.

We’re not going to cover all the intricacies of diamonds here—frankly, there’s too much to cover and it can be overwhelming.

There are 4 C’s to look for when buying a diamond:

  • Cut
  • Color
  • Clarity
  • Carat

In a perfect world, you’d just pick up a ten-carat, perfectly cut, absolutely clear diamond and call it a day. But there’s that thing called budgetary restraint. Unless you’re Jeff Bezos, you have to make some concessions when buying a ring.

Unfortunately, it’s hard to know which concessions to make.

Rather than rehashing the information that’s already out there, I’m going to break down how I bought my wife’s engagement ring and why I made the choices I did.

Get a Good Idea of What She Wants

Chances are she has a Pinterest board full of what she wants. Also, it’s totally fine to straight-up ask what she’s looking for. If you’re anything like me, you’re terrible at keeping secrets and asking prodding questions on the sly. So don’t be afraid to ask.

Set a Budget

Setting a budget for your ring is important. Back when I bought mine, I was a 25-year-old high school teacher, and I thought my budget was pretty high at $3k.

Don’t go into debt over this purchase. You’ll have plenty of time to spend money on your wedding. Starting a committed relationship with a mountain of debt is a recipe for trouble.

Be Prepared to Go Over Your Budget

She’ll probably be wearing this engagement ring for the rest of her life. So if you blow the budget and go over, don’t stress. I went over my budget by almost double and it stressed me out. Four years later, my wife still wears the ring every day and it looks beautiful.

How to Buy a Ring

Everything you see here comes from With Clarity, an online engagement ring store.

I went the traditional route of going to fifteen different jewelers, being lied to, getting some valuable info, having an anxiety attack, and drinking a flute of champagne. I spent so much time and energy looking for the perfect ring.

When I went through With Clarity to recreate the ring I bought, I actually became a little angry with how easy it was.

It literally took me twelve minutes to find a similar ring. And it was $700 less expensive, too. I would pay $700 to have my engagement ring buying memories wiped a la Eternal Sunshine of the Spotless Mind.

Here’s what I got:

diamond shape metal collection

You start by choosing the general shape of your ring, the material it’s made of, and the shape of the diamond.

I went with an oval solitaire with an 18-carat gold band.

an example finished ring

(Pro tip: long diamond shapes like the oval, pear, and marquise will make your soon-to-be-bride’s finger appear longer and thinner. Classic cuts like round, princess, and cushion will make her fingers appear fuller. Both are great choices, but chances are she has a preference.)

This is where things get nutty.

options available at With Clarity

If you’ve done any research on diamonds yet, you’re probably familiar with the 4 C’s—carat, cut, color, and clarity.


Let’s start with carat. This is basically the size of the ring.

(Pro tip: There’s a disproportionate jump between a 0.98-carat ring and a 1.00-carat ring. If she’s the kind of person who says “close enough” a lot, consider going just below your target. You can save the scratch for getting a clearer, more sparkly ring. If she’s a perfectionist, don’t try and shave that 0.02 off. Just get the full carat.)

carat range example

Diamonds are gems—they don’t play by the rules. You’ll be looking at a range of sizes.


best diamond cut options

The cut determines how the light bounces around in your diamond. A huge, clear diamond with a subpar cut won’t have the same sparkle as a smaller diamond with a perfect cut. With Clarity only showcases diamonds that have Good, Very Good, and Excellent cuts. All of these make for a sparkly ring.

In my experience, the sparkle is much more important than you’d think. Four years ago, I had no appreciation for diamonds. Now I get it. The Very Good and Excellent cuts do truly stand out.

diamond cut grade good with clarity
diamond cut grade very good with clarity
diamond cut grade excellent with clarity


Diamonds range in the purity of their color. Ever wonder how a two-carat and a one-carat diamond can have the same price tag? Colorless diamonds cost more while yellower diamonds cost less.

The range of colors, high to low, goes D-L.

Here is a D compared to an L:

clean clear diamond on black background
yellow diamond

Can you see how much more yellow is in the L grade in the second image?

When you’re shopping in person, you’re limited to what the jeweler has on hand. But when you’re going through With Clarity, you can see a huge range of diamonds and really get specific with what you want.

I ended up going with an F color rating. It’s not perfect, but it’s still great quality.


clean clear diamond
heavy inclusion diamond

See if you can spot a difference between these two diamonds here.

If you can, then you understand diamond clarity.

If you can’t, check this out.

detailed markings on heavy inclusion diamond

All those marks are called inclusions. The scale can be confusing, but it basically goes from “large inclusion,” to “no inclusion.”

In my opinion, there’s a great middle-ground in the VS2- VVS1 range. The two diamonds above are the same cut, carat, and color, but the clarity is way different. That explains the $8k price difference.

For my budget (that ended up being around $5-6k) I went with a VVS2 inclusion.

vvs2 diamond spec

Basically, that means it had a small inclusion, but it was hard to see even through a magnifying glass. I’m sure it affects the look of the diamond, but if I didn’t have a jeweler over my shoulder trying to explain for five minutes how to see the blemish, I wouldn’t have noticed it.

So all-in-all, if I were buying my engagement ring again, it’d look something like this:

my perfect diamond through With Clarity
Clean Clear Diamond

I ended up with a 1ct sparkly diamond that was clear and didn’t have any noticeable blemishes. It’s not technically perfect, but I felt these concessions really led to the most value for what I got.

I recommend checking out With Clarity—everything I just laid out for you took me at least thirty hours to learn and several trips to different jewelers. Plus, I had to judge whether or not I could trust the jeweler I was shopping with. Were they trying to get a quick sale or were they genuinely interested in getting me the right ring?

I got lucky, but you can take luck out of the equation.

With Clarity has a 4.5 star average on Wedding Wire, a 9.99 score on Reseller Ratings, and 4.8 stars on Google.

Take a look at their home-try on program. You can make sure you love the look of the ring before you buy—a great comfort when you’re about to lay out serious cash.

2. Where to Pop the Question

Go Somewhere Special

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There’s a bar out in the California desert called the Big Rock Inn. It’s shabby, beat up, and looks filled with tumbleweeds. I went in once just to see if it was as biker-gangish as I thought.

It was.

There was a guy who’d had a few (dozen) too many. He got down on one knee and started to slur out a proposal. All she said back was, “you can’t keep doing this.”

That’s not the sort of proposal you want.

Don’t propose at a desert dive bar.

Here are three great places to propose instead:

a. Where you Went on Your First Date
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Go back to where it all started. It’s simple and classic.

b.) A Dream Travel Destination
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Taking a trip soon? Vacations are always great, though they’re obvious candidates for proposals.

If you’ve been together for a few years and you’re taking a romantic vacation, everyone will assume you’re going to propose. She’ll probably assume, too.

c.) Out in Nature
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Plan for a hike and a picnic and pop the question at lunch. Nature, particularly any place with a scenic view, is an excellent place to propose.

We just recommend not proposing after a long weekend of camping and also staying away from the beach. Fancy engagement rings plus sand and water don’t add up.

Don’t Propose Near Water

Waterfalls, lakes, oceans, ponds, swimming pools, big puddles—don’t propose near water.

3. How to Bend the Knee

When it was time for my proposal, I didn’t know I needed to practice taking the knee. But at first my wife thought I was just tying my shoe, so she didn’t look down. I had to call her name twice.

Take a full step back, get a good deep breath, and then get down on one knee.

You may already be thinking ahead to what you’ll say, but the whole act is a presentation. The moment needs time to register in your soon-to-be fiance’s mind. So taking a breath and a step back is a signal for her to stop and pay attention.

4. What to Say

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Some guys like to say a few words, while others just stick to the big question.

I think it’s a nice touch to give a brief speech while you’re down on one knee. Whatever you do, take your time and slow your talking down.

You’ll likely have some nerves that can cause you to rush through the whole process. Practicing what you’ll say helps you propose smoothly and with major suave.

Knowing what to say is actually the easiest part. Just be yourself, lay out how you feel in a few sentences, and then pop the question.

5. What to do Afterward

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Now the nerves are gone and she’s said yes (unless you proposed at the Big Rock Inn after drinking 38 beers).

It’s time to have fun. It’ll be a lot to process for both of you, even if she knew it was coming.

A classic move is to call the parents and let them know. Just keep the conversations brief so you can both celebrate, too.

My wife and I ended up calling all our friends to see if they wanted to meet up and celebrate with drinks. It ended up being a solid rager with plenty of cigars and champagne. I had originally planned for a fancy dinner, but we were so excited we wanted to share the moment with everyone we knew.

So I recommend the same approach to you. Have a plan like reservations at a restaurant, or some other special activity, but don’t be precious with those plans. You may find that the moment calls for something spontaneous you hadn’t thought of.

I also recommend holding off on social media posts until the following day. You’ll get a ton of phone calls and you don’t want to spend this particular evening chatting one-on-one with friends.

Besides, only the most special people in your life should know first. After immediate family and best friends know, then you can broadcast your announcement.

Ready For Your Big Moment?

Really, it’s a bit like skydiving (which I also recommend only doing once). The moment leading up can be daunting, but when you’re back on the ground, the exhilaration is amazing.

Don’t overthink your proposal. Keep things simple and be yourself. It’s what got you two this far in your relationship.

Proposals are hard to mess up if you follow a few guidelines.

You’ve got this.