How to Propose like a Gentleman

How to Propose Like a Gent.

There comes a moment in most relationships where you feel this overwhelming rush of “knowing” course through you. You look at her one day and think, “I’m going to make you my wife.” This thought often comes as a surprise, but is immediately followed by a thought similar to “and it’s gonna be awesome.”

If you’re having the, “we’ve been together for so long, I guess I should marry her” thought, I have some tough news. You should do the opposite. Do not marry someone because you think it’s the right time or right thing to do. You’re not buying a car, my friend. In that situation, you can just wake up one day and decide to go pick up a new truck because it was time. This, however, is a much bigger deal. Get your head out of your ass.

This is a personal story of my take on how to propose like a gentleman. There are a million ways to do it, but I’m a hopeless romantic, so this is the story of how I did it. I’m going to tell the story of us, but I’ll also point out the few things you want to do to make your proposal amazing, meaningful, and memorable.

Remember the Details

how to propose like a gentleman
According to Pinterest, this is what women ask for in a proposal. Simple and true.

However you choose to note them is your choice, but make sure you remember/record some details. What kinds of things does she admire in other proposals or love stories? What’s her favorite local spot, or vacation spot? Who are her best friends? What do her friends have to say about her idea of romantic surprises? – You can reveal your intention if you like (we’ll talk about that next). Would she prefer a ring that’s more traditional or more unique? Take some notes (even if they’re mental notes) because they’ll make a world of difference when the day you decide to drop to one knee comes.

From the moment we met on December 3oth, 2012, I knew I was going to marry her. The very first night, I wrote a little note on a piece of paper and dated it. Every day, until the day I proposed, I wrote a little love note to her. These totaled 867 notes when that day came. (The video below details a little more of that story) I knew she didn’t want any flash mobs, so that was good for me (I don’t like them either).

Declare Your Intentions / Get the Blessing

I knew her grandfather was the most important man in her life, so I spoke with her Grandma on the phone before we headed up to Ohio, and let her know I needed a moment with Grandpa, man-to-man. I told him my intentions, and asked for his blessing. I’m a man of tradition – what can I say?

how to propose like a gentleman - the sharp gentleman
Every note – Relive Photography

You may not need to get her parents’ blessing, and in some cases that’s not possible, but I still stress that you declare your intentions to the most important person in her life (whomever that is) for three reasons:

  1. You put your intentions out into the world, and it makes them real
  2. You now have a supporter in your corner, always looking for ways to help you carry out your plan – even if it’s just having a beer and trading stories together.
  3. It will mean the world to her to know you are a man of your word, and that you honor a tradition like getting the blessing. Trust me.

Even if there are no parents to ask, involve her closest friends instead. You are asking to share a life with someone, and having an open dialogue with the people she’s closest to will provide a great space to be honest and vulnerable – two qualities a gentleman knows are invaluable to his character.

I worked with Jami’s friend Monica for a couple of months before the proposal to coordinate the day’s activities. She was incredible. She made everything possible because I could rely on her to take care of things on one side of town, while I took care of the rest on location. She also provided a distraction for Jami while I put all the pieces in place. She made sure Jami looked great, had great nails, and was “coincidentally” ready for photos.

BONUS: How to pick the perfect engagement ring to match her style <– Click this!

Get Friends & Family Involved

how to propose like a gentleman - the sharp gentleman
The final note – Relive Photography

Even in the smallest capacity, it will still make a big impact. We have family all over the country, so I let them know the day before that I was going to pop the question. This allowed them to be cheerleaders through social media, eagerly waiting for updates so they could celebrate with us. As a bonus, after we finished at the local harbor (which is one of our favorite spots), we headed to a restaurant for another surprise detail. I had 40 of her friends and family waiting there to surprise her and celebrate with us.

Some couples may not want friends of family involved, and that’s a perfectly acceptable thing too. If you’re able to get a select few involved (again, that may be as simple as letting them know you’re doing it, and to check Facebook for updates and pictures), I still vote you do it. When it feels like the whole place is cheering for her, she’ll be cheering right along with them. It’s actually a pretty magical thing when a group of people all band together and celebrate someone else’s happiness.

how to propose like a gentleman - the sharp gentleman
The moment! – personal camera

I worked on my proposal for a little over two months. I knew I was going to marry Jami for two-and-a-half years. Sometimes you just know. Sometimes you don’t but you stay curious and you explore together. Contrary to popular (albeit stupid) belief, relationships are not difficult. Love is not hard. When you settle for things you feel you deserve instead of focusing on the relationships you truly want, you end up struggling with that disparity. Focus on who you are and the relationships you truly want, and they’ll show up.

Before I met Jami, I declared my intention to fall madly in love. I wanted a wild, permanent, ridiculous love, and I wasn’t going to settle for anything less. That knowing made it possible for our love to bloom. When I met her, I already knew what I wanted, who I wanted, and the man I needed to be to make that happen. After that, it was just a matter of putting small pieces together until the whole picture emerged. Your dream girl is out there, gents. If you’re lucky enough to have found her, be the best man you can be, and propose like a gentleman.

Here’s how I did it.

Here is the video of my proposal to the girl of my dreams: (turn your volume down – it’s a little loud)

how to propose - the sharp gentleman
After dinner and storytelling – personal camera

Side note: The fountain you see in the beginning of the video was broken for a couple of weeks before that day. It had also rained almost every day for the three weeks prior. I needed that fountain running, and I needed it to stop raining to make my plan work. I mentioned the fountain in passing to a friend of mine, and he happened to know the people in Public Works. After a phone call telling them what I was planning, they rushed the part, fixed the fountain, and it came to life that afternoon.

Just another instance of getting a few people involved to make your magic moment happen.

BONUS: How to pick the perfect engagement ring to match her style

If your proposal was awesome, please share it in the comments below! I’d love to hear some other perspectives on proposals and what you did that seemed to make all the difference to her.

***Photos and video were done by our amazing friend, Laura Parent of Relive Photography. She’s an incredible woman with such a cool, calm, creative vibe – it made our pictures and our event wonderful.***

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The Author

Blake Hammerton

Blake Hammerton

Blake Hammerton is the founder and coach at The Sharp Gentleman, and helps men earn more respect while gaining confidence in who they are. He is a certified relationship coach and loves writing about men's fashion, style, character-building, relationships, travel, adventure, and more.