Planning a Proposal? Read These Guidelines First . . .

Planning a Proposal?  Read These Guidelines First . . .

by Gina B.

It’s wedding season, which means that established couples who aren’t planning nuptials are at least forced to think about it.  Some men are sitting tight, hoping the season passes quickly without uncomfortable questions or additional pressure.  Others are inspired to propose!

Guys . . . when you propose, please keep in mind that you are staging an event that will be forever remembered.  Several hundred people will ask, over the course of your lives, what method you used to ask her to marry you.  Having said that, please be thoughtful.  Make it dynamic.  Make it a beautiful experience.  Make it a story worth bragging about and repeating.  And please make sure that the proposal you plan will be something that your future fiancée will love.

I don’t have the wedding bug; I was inspired to write about this topic after having recently witnessed an extremely awkward public proposal.

The boyfriend and I were at a birthday party in one of our favorite cities.  The party was lavish – set in a beautiful sprawling home.  It was catered with an endless assortment of amazing food and complete with a full staff of friendly and accommodating servers and bartenders.

Most guests – about 60 people – were gathered in the living room when the birthday cake was presented.  As soon as the song was sung and the candles were expired, another server emerged with an entirely different cake.

Cake fiend that I am, I was originally excited about the potential flavor of the new cake, which was an explosion of red with floral design (please be red velvet!  PLEASE!?).

As the server walked past the birthday boy to another area of the living room, I noticed that she was attempting to mask the lettering on the cake.  She handed the cake to an anxious looking man, and I could finally see the message written in white icing:  “Will You Marry Me?”  At that time, a borrowed toddler emerged from the crowd wearing a cute (albeit stained) red t-shirt that mirrored the sentiment on the cake.

I forgot all about the potential deliciousness of the cake (particularly after the toddler had been breathing on it).  The prospect of witnessing a live proposal was infinitely more interesting!

The fiancée-to-be had a wide-eyed look on her face with the hint of a smile.  I would say she was shocked (others might describe her as pissed).
The proposer took the cake from the server and performed a balancing act
on one knee, holding the cake in one hand and the closed ring box in the
other.  After attempting to prevent the toddler from face-planting into the cake, the proposer awkwardly eked out a quiet proposal and handed her the jewelry box, still closed.

In the meantime, everyone in the room – most of whom were strangers – was clamoring to listen and learn if she had accepted.  She looked at the curious crowd with a frozen smile and confirmed that she said yes.   (She didn’t fool me.  I knew that smile.  That was the very smile that my mother occasionally wore in public to mask her true desire to kill either me or my father.)

Someone asked if she was surprised, and her reply was a somewhat dry “Yes, I was definitely surprised.”

Personally, I was concerned about the ring (because, really?  One of the exciting parts of a proposal is getting a cool new piece of jewelry.)  I hadn’t seen the ring, and more importantly neither had she!  I witnessed her wrestle it unceremoniously from the box and cram it onto her finger without as much as a glance.

I was also concerned about her reaction.  When a woman is proposed to (by the right person), she is generally elated.  She can’t stop staring at the ring or hugging her guy.  She might immediately grab her phone to spread the news.

This woman exhibited none of those behaviors.  I wondered if she would have accepted were it not for the audience.

However, toward the end of the party she had loosened up and appeared to be happy.   It could have been the champagne, but I concluded that she was happy to be engaged – although she might have wished that the setting and methodology had been different.

So, guys . . . in case you’re thinking of popping the question, here are a few guidelines to consider:

  1. Make sure you’re ready.  If you can’t imagine life without her,
    propose to her.  If you’re thinking of proposing because of timing, biological clocks, shared children or family pressure, take some time to be sure that you’re being true to yourself.
  2. Plan. Imagine her best possible reaction and put the components in place to elicit that response.
  3. Make it all about her.  While an announcement on the Jumbo Tron during a sporting event is a grand display, make sure that she feels that a Bulls game is an appropriate place to declare your eternal commitment.
  4. Add a personal touch.  What are some of the memorable things you’ve done together?  What has she always wanted to do?  Be creative and incorporate some of those into your proposal.
  5. Use a prop. A few of my friends have been proposed to with the assistance of custom photo albums including collections of pictures taken during the relationship.  Years later the Proposal Book remains a cherished keepsake. (Bear in mind that the book does NOT take the place of a ring.)
  6. Propose with a ring, and present it proudly.  Why? Well, aside from the obvious reasons, please know that the first question she will be asked after announcing that you’re getting married is “where’s the ring?”  Having a ring lets us (and our friends and families) know that you’re serious.  Even if you plan to upgrade at some point, propose with something.
  7. More about the ring.  Get her what she wants, within reason.  She’s going to have to wear this ring for a long time (unless you replace it later), so make sure she loves it.  Granted, we’re not in the best economy and it’s understood that most men can’t afford the 4-carat doorknobs that cause most women to salivate.  Prioritize the cost.  Don’t spend so much on the ring that your contribution to the purchase of a home could be jeopardized.  At the same time, don’t spend less on the ring than you would to service your car. Definitely research her preferred cut, etc.    If you don’t know, enlist the help of one of her friends (preferably one who won’t blow the surprise).
  8. Be happy and enthusiastic.  Don’t be afraid to become emotional and sentimental.

Have you experienced creative proposals?  We want to hear about them!

Filed under: Marriage, Men, Proposal, Wedding

Tags: Gina B.


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  • Great article! I started my business because some men really need help planning the perfect proposal.

    Michele Velazquez
    Marriage Proposal Planner

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