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Ultimate Guide to the Perfect Engagement

Updated on April 7, 2020

The proposal itself should be a reflection of your relationship, and should focus on the person whom you’re asking to spend their life with you. If you’re ready to get engaged, you’ve probably picked up a thing or two about their likes and dislikes over the years. Try to make it as sensory an experience as you can, all tailored specifically for them.

If your fiance-to-be’s idea of a good time is a quiet evening making dinner at home, they probably don’t want a lavish Broadway production for a proposal. Less, sometimes, really is more, and romance doesn’t have to be expensive as long as you make it personal. Above all, the proposal should match your relationship.

How to Plan Your Surprise Engagement

Step 1: Have a ring

"Bring a ring. A piece of jewelry — whether it’s a traditional ring or something creative like earrings, an heirloom bracelet or something else — is a symbolic token of a proposal and engagement. Even when women say it’s okay that you didn’t bring a ring, they wish you had."

The other important point to remember is that a lot of jewelers will allow you to have a proposal ring. This is a ring that has some value but is not the end product, it allows you to have a ring that sparkles and looks great to drop to one knee with but also allows you both to create the perfect engagement ring together. This is a very useful service and some jewelers may not provide it, so make sure you get what you want out of it and that way you can both surprise her and show you want her to be a part of the experience of actually choosing her perfect engagement ring.

Step 2: Find a Venue/Location

If you are renting a venue for your proposal, one of the pro’s in having the surprise engagement party right after the proposal is using the same venue. If you don’t have a proposal venue, then you will want to figure out where to have the surprise engagement party. The venue need not be incredibly fancy or expensive – it can be held anywhere from someone’s backyard to a local museum or even a favorite restaurant.

Step 3: Find a professional photographer

He or she can hang out close to your proposal spot and covertly capture amazing photos of your proposal scene. Expert photographers know how to capture the light, make your setting look even more magical, and position themselves perfectly to get a priceless shot of the look on her face when she realizes what's happening. It's a big trend now to invest in pro photography — these images are way too important to risk losing via dead camera batteries or other mistakes non-pros might make. You can give the engagement photos as a surprise wedding-day gift to your bride! If you want to document everything from the proposal to the wedding, you may want to hire a photographer or videographer to capture the engagement party as well. It isn’t a necessity, and there are other ways of doing it, but if you truly crave the professional photos then you need to plan for it in your budget. The good news is that an engagement party is a good testing ground for the wedding – if your photographer does a fantastic job with the party, then they are probably a good candidate to photograph the wedding as well.

Step 4: Plant the Details of your Day/Evening

Are you going to propose at dinner? Make a reservation early and talk to the maitre d. Are you setting up your room? Talk with the hotel staff and be sure what you want can be accomplished.

Step 5: Look your best.

Dust off that good suit, get your hair cut and make sure you look your best. Nothing makes you feel more like the man than when you’re in a tailored suit looking your best, and she will really appreciate the efforts you have made.

Step 6: Have a Back-Up Plan

Even the best laid plans can sometimes go terribly wrong, due to traffic, weather or something completely unforeseen! With the help of proposal planners and external help these are limited but always have a back-up plan or scenario. This could be something as simple as in front of a fire at home. In this situation the gesture should do the talking and not an elaborate plan.


1) Hire a musician or band

There’s a plethora of musicians and bands for hire. Have one or a few show up for a surprise performance of your fiance-to-be's favorite love song in a park or public location for your proposal. For a really personal touch, ask the performers if they can incorporate your fiance's name into the lyrics.

2) Include friends and family

Surprise your significant other by having family and friends share the moment. Consider involving them in the planning process or even the proposal itself. I only recommend this if you know you can trust them with the secret, you don’t want your carefully planned engagement surprise to go awry because of a chatty aunt.

3) Set up a treasure hunt

Starting with a clue at your home or memorable location (like your first date) lead your fiance-to-be through a tour of the town that ends with your proposal. If you really want to go all out, incorporate little gifts along the way as each clue recalls a memory that you two have created.

4) Offer a Couple’s Photo Session

This is one of the best ways to get some great engagement photos. Tell your partner that you’ve hired a photographer for a romantic couples photo session, but then turn it into a surprise engagement.

If your lovely person loves having their hair, makeup, and nails done send them out for an all-day makeover (or join in to make it a sweet, couples day). She’ll feel like a queen, plus, when you pop the question you'll both be looking your absolute best in the engagement photos.

5) Go on an outdoor adventure

Does your significant other love outdoor adventure? Take them on an epic hike to a favorite peak to pop the question. Or go camping or have a bonfire on the beach, and bring a blanket, marshmallows, materials for s’mores, and of course, the ring.


6) Plan a Trip

Ever heard of a destination engagement?

There's something so romantic about being away together, and alone in your little corner of the world, whether it's in a cabin two hours away or on an island in another hemisphere. Plus, the very nature of being on vacation makes even the simplest proposal spectacular

You suddenly open up a million possibilities of outside-the-box activities: horseback riding, scuba diving, whatever. You can throw in a nice hotel. And most importantly, you get some much-needed smokescreen. She won't necessarily realize that your romantic activities are a prelude to a marriage proposal, she'll just think they're part of the vacation.

7) Make an entire day out of it

Pamper yourselves. Get a couples massage at a day spa, with the works --candelight, low music, and feel good feels.

Plan an evening out at a fancy restaurant and call ahead to order champagne and extra flowers for your table. Candlelight and good food puts everyone in the mood for romance. After you propose the staff can come bring all the celebratory.

If you both love to dance, you can use the dinner as a romantic setup and then actually pop the question later -- plan ahead to have the DJ or emcee dedicate a song to them before you propose on the dance floor.


8) Get a nice hotel room for the evening

Get a gorgeous hotel room which can be the perfect place of comfort and intimacy. You can arrange to have the room set up with candles and champagne while you are at dinner, or you can do it yourself beforehand.

Other ideas include:

  • Slip the ring on her finger while she’s sleeping. Have fruit and champagne ready and then give her the most romantic wake up call she’ll ever receive.
  • Order room service and have the box holding the ring under one of the silver platters.
  • Put together a gift basket of yummy treats, like dark chocolate, coffee, and fresh fruit, and hide the ring and its box among the presents-- say that it is from the hotel, and as she digs in she’ll find the ring.

9) Plan a scene from a romantic movie

Remember in Stepmom when Ed Harris’ character (Luke) proposes to Isabel (Julia Roberts) by presenting a ring box filled with a spool of thread, and he asks her to never give up on "the choice to love each other, even if it's only by a thread.” If you need help, check out this list of best movie proposals by Bride Magazine.

Whether you believe it or not, the night you propose will be one of the most nerve wracking nights of your life. You will be jittery, you will be distracted, you will not seem like yourself to your partner. Bear down and ride it out, because the story of a well-planned wedding proposal is something they will be telling their friends and family about for weeks and will remember forever.

It may be just one day or night of the rest of your lives, but the effort you put into your proposal will show her what she can expect from you for the rest of your lives.


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