Engagement Rings · Proposals

How to Propose: Ring, Timing & Planning (2026)

By Tushar Leclerc · 8 min read

Last Updated: October 8, 2026

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A proposal looks like one big moment, but most of the work happens before it. Get three things right in advance, the ring, the size and the budget, and the day itself is the easy part. This guide keeps the planning practical and spends most of its time where the real decision is: the ring.

Before you propose: three things to settle

Everything else is detail. Settle these first:

• The ring. Shape, setting and metal, chosen to her taste. If you are not sure of her style, more couples now propose with a placeholder and choose the final ring together, which is a perfectly good plan.
• Her ring size. You want it close enough that the ring fits on the day. Methods below.
• A budget. Decide what you are comfortable spending before you look, not after you fall for something. Our guide to how much to spend on an engagement ring walks through the real numbers.

Choosing a lab-grown diamond changes the maths in your favour here: the same budget buys a noticeably larger, better-cut certified stone, so the money goes into the diamond she sees rather than the mining premium she doesn't.

How to find her ring size secretly

You do not need her finger in front of you to get this right. In rough order of reliability:

• Borrow a ring she already wears on the correct finger and have it measured, or trace the inside circle on paper. This is the most accurate method.
• Ask the people who know. A close friend, sister or her mother can often find out, or already knows.
• Compare it to your own finger. Slip one of her rings onto your finger and mark where it stops; a jeweller can read the size from that.
• Guess and resize later. If all else fails, aim slightly large. A ring can be adjusted after the proposal far more easily than a too-small one can be forced on.

Our step-by-step ring size guide has a printable chart and the string method. Every Riona ring is made to order in her exact size, so once you know it, the ring is built to fit.

Choosing the ring

This is where the decision really sits, so give it the time. Three things carry most of the weight:

• Shape. The single most personal choice. Look at the rings she already wears and the shapes she points out. Our diamond shapes guide compares all ten side by side.
• Certification. Buy a diamond with an independent IGI report, so the quality is confirmed rather than taken on trust.
• Setting and metal. A solitaire shows off the stone; a halo makes it look larger; a split-shank frames it. White, yellow and rose gold each change the whole feel.

The best proposal rings are not the biggest, they are the ones that look like her. A thoughtfully chosen one-carat ring in her shape lands better than a larger stone in a style she would never pick. Here are engagement rings across every popular shape to start from:

Round SolitaireFrom $1,105 Oval Split-ShankFrom $1,339 Emerald SolitaireFrom $1,087 Cushion SolitaireFrom $1,087 Pear HaloFrom $1,209 Princess SolitaireFrom $1,120 Marquise SolitaireFrom $1,087 Asscher SolitaireFrom $1,087 Emerald Split-ShankFrom $1,530 Marquise Split-ShankFrom $1,503

Want something unique to her? We build custom engagement rings to your exact design and size.

Proposal ideas: at home, out and holidays

The best proposal idea is the one that fits the two of you, not the most elaborate. A few directions that reliably work:

• At home. The most personal option and the easiest to control: cook the meal you had on an early date, set up photos and candles, or propose in the spot your relationship started. At-home proposals are private, relaxed and need no audience.
• Somewhere meaningful. The place you met, a favourite view, the restaurant from your first date. The location does the emotional work for you.
• A getaway. A weekend away removes everyday distractions. Decide in advance whether you want it private or captured by a photographer.
• Holidays. Christmas, New Year and birthdays carry built-in romance and gathered family, which is why a Christmas engagement is so popular. The trade-off is that the date is no longer a secret, so plan for the expectation.

Whatever you pick, keep it simple enough that you can actually enjoy the moment rather than managing a production.

The proposal itself

When the moment comes, less is more. A few practical notes:

• Keep the ring secure and reachable. A pocket, not a bag someone else is carrying.
• Say the short version. A sentence or two from the heart beats a long speech. Say why, then ask.
• Think about photos. A hidden friend with a phone, or a photographer at a distance, captures a moment you cannot repeat. Agree it in advance.
• Set the mood with music. If you want a song playing, pick one that means something to you both. Popular proposal songs include "At Last", "Can't Help Falling in Love", "Make You Feel My Love" and "A Thousand Years", but your own song beats any list.

Then stop planning and be present. The ring is in your hand and the preparation is done.

After she says yes

A few things worth knowing for the hours and days that follow:

• Let her share it first. Give her the moment to tell the people she wants to before it goes public.
• Insure and keep the certificate. Hold on to the IGI report; it is what you insure and appraise the ring against.
• Resize if needed. If the fit is not quite right, that is normal and fixable.
• Which finger. The engagement ring goes on the fourth finger; our guide to which finger and hand a ring goes on covers the tradition and the exceptions.

A famous proposal: Jackie Kennedy's ring

For a little inspiration: when John F. Kennedy proposed to Jacqueline Bouvier in 1953, the ring was a Van Cleef & Arpels design in the toi et moi ("you and me") style, reportedly pairing an emerald with a diamond of similar size set side by side. About a decade later, in the early 1960s, it was reportedly redesigned with added smaller diamonds around the two stones. Jackie Kennedy's engagement ring is still one of the most searched of all time, and the two-stone, emerald-cut look it helped popularise is easy to echo today, in a white IGI-certified diamond rather than a coloured stone, if that side-by-side style appeals.

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