You've got the ring. You know you want to do it. Now comes the hard part: keeping it a secret while planning every detail.

I've helped dozens of guys plan surprise proposals in Boston, and I've seen everything — near misses, last-minute changes, and (thankfully) lots of tears of joy. Here's everything I've learned about pulling off a proposal without your partner finding out.

The Golden Rule: Don't Overthink It

Before we dive into the details, let me save you some stress: your partner is going to say yes because they want to marry you, not because you planned the perfect proposal.

I've seen proposals at fancy restaurants and proposals at a random bench in the park. The reaction is always the same — pure joy, tears, shaking hands. What matters is the moment, not the backdrop.

That said, a little planning goes a long way. Here's how to do it right.

Step 1: Gather Intel (Carefully)

You need some basic information to plan, but you can't exactly ask "where would you like me to propose?" Here's how to get the details without raising suspicion:

Ring Size

The classic move: borrow a ring they already wear (from the correct finger) and take it to a jeweler. If that's not possible, ask a friend or family member if they know. As a last resort, guess slightly larger — resizing down is easier than up.

Date Preferences

Think about what dates might be meaningful: your anniversary, where you met, a birthday. Or pick a random Saturday and make it meaningful by proposing.

Style Preferences

Does your partner want a big public moment or something intimate? Pay attention to how they react to proposal videos online. Do they say "aw, how sweet" or "I would die if someone did that to me"? Big difference.

Step 2: Choose Your Location

Boston has no shortage of stunning proposal spots. When picking yours, consider:

• Privacy vs. Public: Some people love an audience. Others would be mortified. Know your partner.
• Logistics: Can your photographer hide easily? Is there a backup plan if it rains? Is it easy to get to?
• What comes next: A dinner reservation? Champagne with friends? A walk home? Plan the full evening, not just the moment.

Step 3: Create a Believable Cover Story

You need a reason to be at the proposal location, dressed nicely, at a specific time. Here are cover stories that actually work:

• "Let's take a sunset walk" — Simple, believable, explains why you're at a scenic location.
• "I booked us dinner reservations nearby" — Explains dressing up and being in a specific area.
• "My friend is a photographer and needs practice shots" — This one is risky but explains why a photographer is there. Only use it if you're a bad liar.
• "I want to show you this spot I found" — Works if you're genuinely the type to explore the city.

Step 4: Coordinate with Your Photographer

If you're hiring a photographer (and I highly recommend it — you only get one shot at this), here's how the coordination typically works:

Step 5: Handle the Nerves

The day of the proposal, you're going to be nervous. That's normal. Here's how to keep it together:

• Don't drink too much beforehand. A drink to calm the nerves is fine. Three drinks and you'll be sloppy.
• Check your pocket multiple times. The ring should be in a secure pocket you can access smoothly. Practice the motion at home.
• It's okay to be emotional. Your partner will love seeing that this moment means as much to you as it does to them.
• If you forget your speech, just say what's in your heart. Nobody remembers the exact words. They remember how they felt.

Step 6: What to Say

You don't need a memorized speech. In fact, the most touching proposals I've photographed were the simplest — a few sentences from the heart.

Here's a simple framework if you need one:

1. One thing you love about them: "From the first time we met, I knew you were different..."
2. One thing about your relationship: "These past [X] years with you have been the best of my life..."
3. Your commitment: "I want to spend the rest of my life with you..."
4. The question: "Will you marry me?"

That's it. 30 seconds, max. Then get on one knee and ask.

Common Questions

What if it rains?

Have a backup plan. Maybe it's a covered area nearby, or maybe you reschedule. When you book a photographer, ask about their rain policy — most (including me) will reschedule at no charge.

What if someone walks into the shot?

It happens. A good photographer knows how to work around it. And honestly? Sometimes those candid moments with random people clapping in the background make the photos even better.

Should I tell anyone beforehand?

Up to you. Telling close family (especially if you're traditional and want to ask for permission) is common. But the fewer people who know, the less chance of the secret getting out.

What about getting down on one knee?

Yes, do it. It's traditional for a reason — it shows respect and intention. Just make sure you're on the correct knee (traditionally left, but honestly no one will notice).

The Checklist

Final Thoughts

The best proposals I've photographed weren't the most elaborate — they were the most genuine. Your partner wants to see you in that moment. They want to know this is real, that you mean it, that you're nervous because it matters.

So yes, plan the logistics. Pick a beautiful spot. Hire a photographer to capture it. But when the moment comes, forget all that and just be present. Look them in the eyes and say what you feel.

That's what they'll remember.