Dec 7th

Engagement Proposal Ideas: What Works, What Doesn't

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I love designing engagement rings.  I love hearing about how couples met, hearing about their plans for the future, and the priceless look on a man's face when he sees the finished ring.  There are most certainly times when I become what could best be described as a confidant to men who are planning on proposing.  You may or not be surprised to learn that many men still have no proposal ideas even once they have the finished ring in their possession.  Over the past few decades, I have heard stories of amazing proposals, and have also heard some proposal nightmares.  Here's a compilation of some of the best (and worst) of proposal ideas.

Worst Proposal Ideas:

  • DO NOT, I repeat, DO NOT try to hide an engagement ring inside of any type of food or beverage in an attempt to surprise her.  You will surprise her all right.  With a trip to the dentist, or worse.  Just don't do it.  It sounds good in theory, but is a generally bad idea.  If by chance she swallows it, let's just consider for a moment the manner in which you will have to retrieve it.  This is not a story you want to tell your family, and she may have difficulty wearing, or even looking at, the ring once it is recovered.  If you don't trust me, read it from someone it happened to.
  • DO NOT believe your soon-to-be fiance when she tells you she doesn't want the proposal to be a big deal.  It is, and should be a big deal.  Now if your girlfriend is very shy and doesn't like a lot of attention on her, I don't recommend proposing to her on a giant screen in front of a packed stadium full of people.  However, even if the proposal will be done with just the two of you present, plan something that she will enjoy telling her friends, family, and future children about.
  • Please do not propose during sex.  I thought this was a no brainer.  Apparently not, as I have a customer who did it.  Just don't.
  • Don't propose via social media, i.e. Twitter, Facebook, etc.  I had a client who thought it would be a great idea to propose to his girlfriend by asking her to marry him on her Facebook wall.  Clearly, he did not tell me about this plan, as I would certainly have talked him out of it.  Not only was his girlfriend unmoved by the lack of emotion in the proposal, all of her friends and family began calling her before she even saw the post.
  • It's generally a bad idea to leave the ring somewhere that she will find it when you're not around.  I know a man who did this.  He placed the open ring box in the refrigerator (Don't ask, I have no idea why), and left it in there before he went to work.  She found it when she went into the kitchen for breakfast and called him to ask if he knew there was a ring in their refrigerator.
  • I personally feel like the fortune cookie idea is just overdone.  It is cute, especially if you both enjoy going out for Chinese, but it has just become really popular.
  • Don't mention biological clocks while proposing.  Just trust me.

Best Proposal Ideas:

  • I have a man who brought his girlfriend to his company's holiday party.  At the party, the owner of the company made an announcement that he had to show a video about an important new development with the company.  Of course, the video started and it was a slideshow of the couple, finishing up with the words, "Will you marry me?" on the screen.  The man got down on one knee and proposed right there.
  • One of my all time favorite proposals can be seen here.  An air traffic controller proposes to his girlfriend over the loudspeaker on a plane.  His nerves only make this proposal that much more special.
  • If you're not an air traffic controller, you may still be able to propose 10,000 miles in the sky.  From what I understand, Southwest tends to be the most lenient airline as far as working with men to allow them to propose on a flight.  This is an excellent idea, but if you happen to get a testy flight attendant, it could seriously backfire.  Better to plan this one in advance with the airline.  I am aware of several on board proposals that have gone very well with the cooperation of the flight crew.
  • I had a client who had planned a wonderful vacation for him and his girlfriend to a couples only adults resort in the Caribbean.  Admittedly, I was VERY nervous when he sent the ring (insured, but still..) to the resort after speaking to the staff of the hotel.  The staff arranged it so that when the couple arrived at the hotel, a staff member greeted them with mimosas and hot towels.  The girlfriend's hot towel was wrapped up in a pink ribbon with the engagement ring tied to it.  She was so taken aback that it allegedly took her awhile to convince her that it was a real proposal.  She couldn't figure out how he had gotten the ring to the resort before they arrived.
  • If your girlfriend is one of the few remaining people that reads a newspaper or local magazine (in hard copy form, not online), contact the publisher about placing an ad in the paper asking her to marry you.  Just make sure you're there and waiting with the ring when she is likely to see the ad.
  • Before heading to a show or some type of public event with your girlfriend, contact the staff and ask if they will assist you with a proposal.  Most venues will.  I had a client that managed to convince the cast of a Broadway Show to bring his girlfriend onstage under the guise that her seat number had been chosen for some type of prize.  One of the characters presented her with the ring as her boyfriend made it to the stage and made the public proposal.  Don't use this one if your girlfriend is extremely shy!
  • See if a local radio station will allow you to propose on air.  Many will.
  • Use the element of surprise.  Women are generally somewhat aware of when their boyfriends are getting ready to propose.  Therefore, if you do it at Christmas dinner or on her birthday, she likely won't be completely surprised.  Some of the best proposals occur at a random time on a random day.  These proposals are special because there isn't much to plan, so it's less stress on the man.  Plus, I find men tend to be much more open with their emotions when proposals are somewhat private.
  • With that in mind, don't surprise her at a time when she is:  in the middle of dying her hair, wearing her biweekly mud mask on her face, is complaining that she is fat and bloated, preparing for a friend's shower or wedding (this will constitute stealing the friend's thunder.  NOT OK), taking a pregnancy test, complaining about your mother, crying (regardless of the reason), etc. etc.  You get the picture.
  • Consider hanging a banner over an overpass the two of you frequently travel by.  I have heard of this working in the past.
  • It is possible to hire an airplane to fly over a beach or somewhere else the two of you will be with a banner written with the proposal.
  • I had a client who switched his girlfriend's screensaver to read "Will you marry me?"  He basically stalked her all day with the ring in his pocket, waiting for her to walk in to the screensaver.  She finally did, and he got behind her on one knee with the ring.
  • Propose at a place that is meaningful for the two of you.  Have you had a memorable date somewhere?  Is there a restaurant that is sentimental for the two of you?  Consider proposing at such a location.

I have tons more great (and bad) engagement proposal ideas.  Let me know what you want to hear more about.  Feel free to share your proposal ideas, stories, or plans below.  I will be posting a follow up post with additional proposal ideas, but this post seems to be running a bit long, so I will save that post for another day.  Thanks for reading, and please let me know what you think about these proposal ideas!

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