How To Propose: Tips for Popping the Big Question

Men: if you’re reading this, you’re most likely ready to make one of the biggest decisions of your life. And because you’re taking the time to research, it means you want to make it as special and original as possible.

Just to reiterate, how you pop the question can really set the tone for the engagement and the marriage. We know it can be a nerve-wracking experience planning it all. Trust us — we’ve been there. The key is to remember to always stay calm and confident.

Now, we won’t tell you exactly how to propose. That wouldn’t really be in keeping with our originality theme. However, here’s some helpful advice that will help slow your heart rate.

Tips for Preparing Your Proposal

Planning a proposal isn’t just about the moment you get down on one knee—it’s about everything that leads up to it. Here’s how to prepare like a pro:

Timing is Everything: Think about when to propose. Should it coincide with a special anniversary, holiday, or milestone? Or maybe it’s better as a spontaneous surprise. Choose what feels right for your relationship.
Read the Room: Before popping the question, make sure you’ve had conversations about marriage and the future. If you’re on the same page, the proposal will feel natural and exciting.
Talk to the Parents: While not everyone feels the need to ask for a blessing, it can be a meaningful nod to tradition. Consider discussing it with her parents if you think she’d appreciate the gesture.

Choose the Perfect Engagement Ring

We understand that times are tough and that rings are expensive. However, if it all possible, have some sort of ring with you when you pop the big question. Even if it’s just a temporary cheapie, a loner or a family heirloom ring — have something!

How to Create a Unique Proposal Experience

There’s nothing wrong with asking her to be your wife over a simple dinner. But why stop there? You’re asking her to be your wife — show her why she should spend the rest of her life with you. (Surely, she already knows why, but going the extra mile may earn you a get-out-of-jail-free card the next time your poker night runs late.)

Seasonal Inspiration

Think about the season or time of year:

Winter: Propose at a cozy cabin or while building a snowman together.
Spring: Take her to a park in full bloom or a garden picnic.
Summer: Plan a beachside proposal or a fireworks display.
Fall: Use the stunning autumn leaves as your backdrop, or go apple picking together.

Public vs. Private

Some people dream of a public proposal, while others prefer a private moment. Consider her personality and preferences when planning how and where to propose.

Proposals with a Surprise

If you love surprising her, think outside the box! Organize a treasure hunt leading to the big moment or enlist local businesses to create a memorable experience.

Take a Knee

Why do we get down on one knee? Nobody knows. Just do it! You don’t want to know what the backlash will be if you don’t. So don’t even mess around with the idea.

Involve the Family in the Proposal

We know that this day is about you and your girl. But including both families, if possible, is a very nice gesture. If you’re planning something elaborate, they may even be able to help you with part of the plans.

Virtual Involvement

If some family or friends live far away, consider involving them virtually. Set up a video call so they can witness the moment in real-time.

Keepsakes for the Day

Create small keepsakes, like personalized “proposal announcements” or cards, to send to loved ones. It’s a unique way to share your happiness with everyone who matters.

After she has said yes, surprise her with a get-together with her closest friends and family. This is a great way to cap off a very big day.

Feeling the Proposal Nerves

Relax. Go grab a beer and think about this: She wouldn’t have put up with you this long if she didn’t know you were the one. Whatever way you ask her will be perfect. Be confident and remember, You Da Man!

After the Proposal: What’s Next?

Congratulations, she said yes! The hard part is over, but there are still a few things to think about to keep the momentum going.

Engagement Announcement: Decide if you want to share the big news online, with a photo of the ring or the proposal moment. A fun caption and a personal touch will make it memorable.
Celebrate Together: Plan a romantic evening or weekend getaway to enjoy your first moments as an engaged couple.
Engagement Photo Shoot: Book a photographer to capture this special time. Use the photos for save-the-dates or your wedding website.
Start Wedding Planning: While you don’t need to dive into details immediately, discuss general ideas about what you both envision for the big day.

TMR Recommendation: If planning an engagement night party, consider inviting or flying in some of your fiancée-to-be’s closest out-of-town friends. We know she’ll have had a day full of surprises, but imagine if her best friend who lives across the country could be there to help her celebrate the occasion. You’re sure to be looking at some major brownie points, not to mention tears of joy.