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How to propose after being together a long time - Surprise Proposal Ideas

Updated on January 25, 2012

Proposing after a long courtship

In any relationship there are certain milestones that pass. When you are in the inside of that relationship the significance of those moments may go unnoticed.

One milestone that does not go unnoticed is marriage and the traditional events that lead up to it.

There is still a vestige of a traditional chronology that leads up to a union. Depending on ones background, religious beliefs and romantic leanings this chronology may vary.

In my case, I missed all traditional opportunities to propose. Every expected occasion and opportunity to propose was overlooked.

The eventuality of my permanent union was assumed and agreed on. It was known that we would marry but only I knew what circumstances must be fulfilled for me to be comfortable for that assumption to be actualized.

sweep her off her feet

How to do a surprise proposal
How to do a surprise proposal

To be clear, I consider marriage to be a legal and/or religious compact and consider romance and love to be completely free of such my delay was never one of uncertainty of my destiny or desire to remain "uncommitted" Commitment takes place in the heart and mind; legal papers and precious metals are mere trinkets in comparison to that truth.

But my thoughts and ideals are my own, they shouldnt lead to me robbing my potential lifemate of the joys of a romantic proposal and a story worth sharing with her friends.

So as someone with a penchant for the dramatic I endeavored to create a modest but memorable proposal event. This is my story on how I proposed after a long courtship.

Manafacturing the surprise proposal

Surprise and effect are best created via the use of contrast. Or at least that's whats motivated my planning. Since I was expected to propose and expectations were high I wanted the event to come as a complete surprise. I hoped to create an event that would overshadow the years of waiting.

When to propose: picking a date to propose

I decided that making this year ' a Valentine to remember" would be a great idea. But, simply proposing on Valentines Day seemed unoriginal and unimaginative. So instead I did quite the opposite. In 2011, Valentines Day occurred on a Monday, on that day I arranged for a babysitter, I scheduled for a chauffeured Town Car and made dinner reservations. I then called, my potential life-mate and told her that I would have to skip Valentines Day this year as I would have no chance to make it to the florist and I had lots of work deadlines pending, so would have to work until the wee hours of the morning and even a simple home dinner would be to much of a time expenditure.

How to surprise proposal - The Towncar
How to surprise proposal - The Towncar

Committing to the Proposal

Of course, skipping Valentines Day completely is not a wise thing for any male to do. This is why this section is called "committing," to the proposal. The following days had moments where my perceived lack of romance certainly colored the atmosphere. I know from experience that "what did he do" is part of the post Valentines Day conversation among groups of Women at the office and now at the virtual water cooler of Facebook.

It would be exaggerating to say I was in the dog house for the week, but I certainly could see the door to it.

The restaurant looked better at night
The restaurant looked better at night

The Big Day

Nobody knew of my plans, not a soul. But in order to arrange a trustworthy babysitter I did admit to my targets Mother that I had "Surprise Valentines Day Plans" if you see the above picture you may be able to guess that its quite easy for me to arrange a babysitter from among the family members. I also scheduled a "Night on the Town" package from a local limo service, I opted for a Town Car not for budget reasons but rather to be less ostentatious. The restaurant I made reservations at was selected due to the high level of service and the quality of the decor. I knew the waitstaff would be affording of my request.

Getting my target ready for her surprise dinner date was a problem. When our Babysitters (her parents) "stopped by" I took the opportunity to slip away and get dressed up, shirt tie, shiny shoes the whole nine, I even shaved. I intentionally kept the scruffy I work from home look all week to add to the "contrast".

Gentle persuasion failed, we were unable to get the target to get dressed up and try on makeup and such without spilling the beans a little. It was a shame to have to break some of the surprise but I would have been killed if I dragged her to a fine dining restaurant without allowing for her some preparation. It was nice to see the complete surprise on her face to see I had not forgotten "Valentines Day" after all.

"Get dressed to match, the Town Car will be here in a half hour," I said.

The rest is a blur and I can only say that my use of contrast worked. Extreme surprise existed. She was positively glowing on the car ride there and at that point she only thought this was a Valentines Date. I got many warm and loving kisses and we enjoyed our ride to the restaurant.

Is it still appropriate to order for a woman?

I had researched the restaurant in advance and had made sure the menu would fit her vegetarian palate, one will often find that more upscale fine dining restaurants have very limited "filling" vegetarian friendly meals . This restaurant had a fitting "small entree" and a great reputation for its dessert menu. So in keeping with my plans when the waitress arrived I ordered the complete meal for us. This is out of the ordinary for us and was intended to limit any stress of ordering.

The meal was amazing, beautifully presented, well balanced and perfectly cooked. I don't think I tasted a bit of it. Taking a cue from a million movies I had slipped away and arranged for the waitress to deposit the ring in my targets Dessert. Sure, its been done in the movies, I know, but don't know anyone who has done this in real life and I even worked in the industry for near 10 years.

As the dessert and my future approached I kind of choked on the lines, I felt it would have been contrived to truly write and practice my proposal but in retrospect I would have. The ring arrived sitting beautifully in some mango ice cream (the contrast of the Emerald in the orange mango was perfect!) and I was rewarded by some slightly teary eyes a great barrage of kisses and something along the lines of "I cant believe you"

She said yes - and the rest of the night is boring in comparison.

Picking out the right ring to propose with

I got lucky. My fiance did not want a traditional diamond ring. She much preferred the contrast of an emerald and diamond ring and wanted a ring that had history and life to it. Both of us are ethically opposed to supporting "blood diamonds" and that may be something you may want to broach before selecting an engagement ring. Ive actually heard quite a few times that some are slightly disappointed by the traditional engagement ring as it suggests the guy picked it out didn't clue in on what made the bride unique and recognized her taste.

I had no issues of that nature, my ebay watch list has been filled with "suggestions" from my fiance for over a year now! I had to change my password just to buy the ring! Yes, it fit perfectly and no, I did not buy one she specifically picked out.

Below is a sampling of "Edwardian Emerald and Diamond Rings" which is the variety that most intrigued my beloved.

"I may not be a smart man, but I know what love is."

Fun Ways to Propose - Ideas for a memorable proposal

Fun proposals are not unique to the big screen. Check out some of these fun examples from the interwebs.

Not sure about the backdrop!

How to propose after being together a long time
How to propose after being together a long time

Fun real life Wedding Proposals

In this fun real life proposal video, the suitor uses the famous Love sculpture as a backdrop to getting down on his knee. Too bad the Videographer didn't frame the shot a little better. I cant criticize as I forgot to take my video camera out of my pocket to catch the big moment myself. But some things are best kept organic and in the memory anyway.

In this fun transcript and audio of a real life proposal done via an airplane loudspeaker. A very well done and public proposal. On the plus side, if she had said, No, he wouldnt have had to face her!

Fun Movie Proposal Videos

Its movie scenes like these that made me get the evil eye on more than one occasion for not having had popped the question yet!

Facebook and the Modern Relationship - THE relationship status change

Is it really official if Facebook doesnt know? Its been a week and i still havent got around to calling anyone yet, but 40 some replies on facebook shows the news got around.

My Fathers comment is the best, "Im glad Im on FB so  got to know" .. lol .. I called him the next day.

The ride home

I didnt go as far as creating a mixtape to choreograph our return journey from the restaurant. But, luck was on my side and one of my favorite yet rarely heard songs began to play over the system as we sat in our post-proposal glee.

Seemed fitting at the time...

Many many men,
Can't see the open road.

Didnt arrive in time - perhaps you can work them in?

Comments, ideas, complaints - let me at 'em

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    • misslong123 profile image

      Michele Kelsey 

      4 years ago from Edmond, Oklahoma

      I am going to vote this article up and pass it along to my fiance (about to be my husband). He glossed over the proposal, and we are getting married in a couple days. I always dreamed of a fancy proposal. You had some great ideas. I am passing this along to my facebook friends! Thanks! :)

    • That Grrl profile image

      Laura Brown 

      6 years ago from Barrie, Ontario, Canada

      This was a nice idea for a post. I enjoyed reading it too. I added a link back to this post on my Romance feed on the site.

    • lakeerieartists profile image

      Paula Atwell 

      7 years ago from Cleveland, OH

      Congratulations, and best wishes. My sister had a well thought out romantic proposal like this one, and it is a memory that no one ever forgets. To both of you and your extended family. :)

    • lorlie6 profile image

      Laurel Rogers 

      7 years ago from Bishop, Ca

      Extend my appreciation to your lovely lady on her-and your-taste, won't you? Diamonds and emeralds are the very best combination of gems-I used to have an engagement ring like this, but that's not to imply your marriage will end up like mine!

    • sunforged profile imageAUTHOR


      7 years ago from

      Thank you everyone! its been a fun lovey dovey week, lol

    • sofs profile image


      7 years ago

      Congrats!! and best wishes... a great story there!

    • wavegirl22 profile image


      7 years ago from New York, NY

      The Grinch who ignored Valentines day . .NOT ! turns out to be the most romantic prince charming ever! A is one lucky little girl, all I can think about is how many times she will get to tell this fairytale of how her dad proposed to her mom .. for sure a classic in the making and one your great grandchildren will be telling.

      Mazel Tov to you and J !!!!

    • frogdropping profile image


      7 years ago

      Huge CONGRATZ Sunforged and Mrs Sunforged to be, awesome news. Had you been a little quicker you coulda coubled up with RK in Vegas ;)

    • Lily Rose profile image

      Lily Rose 

      7 years ago from A Coast

      Congratulations, Josh! What a great story, and to have it recorded in a hub is a great "keepsake." Ayla is beautiful! So when's the big day?

    • CASE1WORKER profile image


      7 years ago from UNITED KINGDOM

      what a romantic man you are, so glad she said yes

    • dotty1 profile image


      7 years ago from In my world

      fab hub love the subject :-) best of luck to you Dx

    • Sandyspider profile image

      Sandy Mertens 

      7 years ago from Wisconsin, USA

      Oh how wonderful. I am glad she said yes.

    • Edweirdo profile image


      7 years ago from United States

      Well done, Josh! Sounds like you pulled off a great surprise proposal :D

      Best wishes to you and your lady (and that adorable baby girl!)

    • profile image


      7 years ago

      I want a billboard proposal, but I don't think it's going to happen after 27 years. Lovely Hub.


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