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When I proposed to the woman who is now my wife, it happened unexpectedly. I knew I was going to ask her to marry me sometime, but I didn’t have a lot of money at the time. So I was buying the ring in stages. I had already bought the main jewel and was working on the smaller ones around it. At a family party, a good friend heard that I was saving up to buy a ring and asked if I wanted their old family ring that didn’t fit any more and that looked exactly like what my future fiancé wanted.
Since we were with all the family, I decided now was a good time, and while skipping rocks on the beach, I said, “Oh, look what I found.” I pulled out the ring and asked, “Will you marry me?”
Bros, she laughed! She thought I was joking and had somehow just found a ring right there. Once I assured her it was for real, she hugged me and said “yes,” but there was a little panic there for a second.
Let’s go over some of the best ways to propose and some ways NOT to propose. As with everything, you need to know what she likes. What may sound like a great idea for one person may not get the same reaction from another.
While a surprise, my proposal was at a lake I grew up on and had spent a lot of time with my wife. Plus, it was just gorgeous.
Where have you and your girlfriend spent time together? Do you remember where you met or where you had your first date? Any place that has some special significance for the two of you should be fine. It’s the memory of that special moment and the fact that you took the time to remember it that matters.
But you also don’t want to make the mistake of trying to force something just for the sake of it. If you met when you were backpacking around Italy after college, you don’t need to save up for a European vacation for the two of you again if that’s not in the stars. Instead, you can take her to a museum with an Italian art exhibit, a nice Italian restaurant, or somewhere with a view that will remind her of your time in Italy.
When I gave my wife her first iPad, I actually went and found an old used book from a sci-fi author she loved. I cut out the inside and hid the iPad in the book. When she opened the present, she saw only an old book. She noticed how excited I was and (graciously) said thanks, but I told her to open it. When she opened it and saw her new iPad, she shrieked with joy. It was fun to use her love of books and sci-fi/fantasy as a way to give her a gift.
It’s the same with proposing. What does she like to do? I saw an article online about one guy who knew his girlfriend liked video games, so he literally created a game to propose to her.
The only thing I would caution you about is to make sure the photos of the proposal are going to be something that she’s excited to share. I’ve been to two surprise parties where the woman was coming from the gym. She may have been appreciative, but all the photos were of dressed up people and her with no make-up, no nice outfit, and messy gym hair. Your girlfriend may be a great MMA fighter, but right after a practice bout may not be the best time to ask her to spend the rest of her life with you.
I have ADD and eat quickly, so long, drawn-out dinners are really not my thing. But I know, for most people, it’s very enjoyable. Sometimes there’s nothing more romantic than a nice dinner out with your person, so this could be a good idea for your proposal.
There are a couple of advantages to doing it in a restaurant. The ambiance is usually set, there’s music and wine, you’re dressed up, and there’s magic in the air. You can call way ahead of time and reserve the finest table in the establishment. You can ask the chef to prepare something special like a dessert with the ring in it. Or you can find a quiet corner at your favorite restaurant.
Since the proposal will be in a restaurant, you need to remember that there will be a fair bit of attention, which can be a lot of fun if she’s the type of gal who would enjoy it. People clapping, taking pictures, drinking champagne, giving you hugs, and admiring the ring can all make it a great memory.
If you can’t think of a place she considers special, you can propose with special people around. There really are only a handful of huge life events. For example, graduating, getting married, and having kids. When you can have your favorite people around to help celebrate these moments, you’re creating lasting memories.
When I popped the question to my wife, we were at a family celebration in the town where I grew up, so everyone I loved was all together. I figured that I had no idea when we would all be together again and be able to celebrate, so with permission (I’ll get into that later), I proposed surrounded by family. Then friends started stopping by as the word got out.
Maybe there’s a family reunion or a gathering of friends that would be a great time for you to propose to her. A lot of people choose New Year’s Eve, as they are usually surrounded by friends and/or family as well. You can even get them involved ahead of time if you want. Everybody loves helping out with an engagement.
Proposals don’t have to be big and grand like the ones you see in the movies. They can be small, intimate, and special just to the two of you.
A private proposal has way fewer moving parts and way less things that can go wrong. And let me tell you, when you have that ring, it’s burning a hole in your pocket. You want to propose ASAP so you don’t lose it!
The proposal could be something cute and romantic with rose petals and candles when she comes down from a shower, or it could be a moment where you realize you can’t wait any longer to ask. The best part of the private proposal is that you can be totally you, without any prying eyes, and tell her exactly how you feel about her. You don’t need to wait to get your just desserts!
While I’m here, I also want to do a public PSA on how NOT to propose to someone. A lot of these ways may seem like good ideas, but just don’t. There are so many better options.
Some women may profess that they want to be proposed to in a huge public setting, but it’s a very risky move. A restaurant may be considered a public place, but I’m talking about sports games, concerts, a plane-flying-over-the-beach kind of thing.
There’s a chance that it can go right, but also a chance for it to go wrong. Even if you are totally sure she will say yes, people do a lot of weird things when they are under the spotlight. Don’t bring all sorts of unwanted attention onto her or risk embarrassing her.
I have never seen someone propose to their girlfriend during someone else’s special event, but I’ve heard lots of stories. People show up to a baby shower to celebrate Mary and her impending baby. During the party, her brother, overcome with emotion, asks his girlfriend to marry him. Suddenly, the entire party is hijacked, and all the attention taken away from the one being celebrated. This happens at showers, birthdays, and even other weddings!
I get that your emotions may be all lovey-dovey at this time, and you realize that so many of your friends and family are around. It feels like the perfect time, but I assure you that it is not.
When I proposed, it was a wedding celebration for my brother and his new wife so they could meet everyone on the East Coast. When I was given the ring, I sure as shit went and asked my sister-in-law and brother what they thought of the idea of me proposing. They loved it. But I waited until the next day so it wasn’t at the party proper. You may come across a situation like that as well, but tread lightly.
If you are going to do an outdoor proposal, make sure you are not at a place where you may drop the ring and have it disappear. I know that dusk on a dock may sound like a great idea, but, if in her joy, she accidentally knocks the ring into the water, you’ve got a whole new problem.
Tie a string on it, keep it in a floating box, whatever! If it’s important and slightly dangerous, get a fake/costume ring to use for the proposal and have the real ring safe on land for when the skydiving is over.
I hope this next year brings lots of engagements — I think we’ve all realized how important it is to have someone with us who has our back after this last year. Good hunting, and let me know how it goes!