6 Tips for Executing the Perfect Proposal

Exactly two years ago, Bugsy got on one knee and popped the question! Without any hesitation, I (obviously) said YES!

Looking back nostalgically on that day, it was one of the most special moments of my life (and the most special moment in our then seven-year courtship), not only because the BIG QUESTION was asked, but because he got ALL THE DETAILS RIGHT.  Even though I can’t take credit for this post (boo), I wanted to share the wisdom I gained from being the beneficiary of Bugsy’s hard  work in planning the perfect proposal.  After all, this moment only happens once – so do it right!

1. Public or Private?  Is your soon-to-be fiance a public or private person? If your significant other grimaces at the sight of large crowds or being the center of attention, then don’t plan an elaborate public proposal (i.e. no jumbotron, skywriting, restaurant announcement).  But let me not confuse you.  Proposing in a public place does not necessarily render the proposal itself public.  In other words, even if your person is more of an introvert, you could still propose at a quiet spot in a public park or at a famous monument at a time when you know there won’t be large crowds.

Our story:  I love sharing big moments with the world (I mean clearly –  I blog), so Bugsy knew I wouldn’t mind an attention-seeking proposal and boy did he do it.  After a treasure hunt that led to all of our most memorable date spots in NYC, I arrived at our first date location (a super popular outdoor watering hole) and he proposed in front of all of our closest friends and family (with balloons in hand) while the restaurant played a Vision of Love. For me it was perfect, but for some others, likely frightening. 


2. Location, location, location.  Choose  a location that has or will have sentimental value. What was the location of your first meeting, date or kiss? Is there a place that he/she always dreamed of going together or identifies as particularly romantic? Just remember that the place you choose should be meaningful – whether its reflective of your history or your future.

Our story: Bugsy’s intricately planned treasure hunt took me on a tour around Manhattan to our most memorable date spots and finally led me to our first date location, the Boat Basin, where he proposed.  

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3. Include the people you love.  Whether family or friends are present for the actual proposal or you have arranged for them to meet at a place after the proposal is complete, sharing in the moment at the moment just sweetens the day.

Our story: All of our very best friends and family were present, cheering, crying and cooing.  Some even participated by skype – love you SDP and cousin SX. 


4. Get a photographer.  Whether you have a friend who has a fancy DSLR or you hire someone to take photographs of the proposal, they will be treasured always.  There is nothing like capturing the emotion of that moment in real time.

Our story: One of our close friends photographed our engagement and those pictures were so gorgeous that we opted out of having an engagement shoot and used the photographs from the day for our save the dates – thank you MV


5. Speak from the heart.  What could be more anxiety inducing than asking someone to marry you?  So, give some thought to what you will say before the actual proposal – whether it’s telling him/her when you knew they were the one or why you’ve made this incredible decision.

Our story: Clearly nervous and a little inebriated, Bugsy took me down memory lane and even revealed for the first time that he knew I was the one from the first day we met.  


6. THE RING! This is not the time to make a hasty purchase or to “get creative.”  Do your research (sister, brother, best friend, clandestine google search collection)! Here are four major categories to consider when finding the perfect ring: (1) Metal: Yellow Gold, White Gold or Platinum? (2) Style: Classic, Modern or Vintage? (3) Stone: Diamond or Gemstone? and (4) Quality or Quantity: Does he/she care about the overall size of the presentation or the quality of the presentation.  In short, don’t give the diamond girl/guy a ruby or the sapphire girl/guy a diamond. If you’re not sure, you haven’t done enough research!

Our story: Over the course of our 7 years, I guess I dropped enough (photographic) hints for him to get it right and he did. 

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Happy Planning and Good Luck!


Exactly two years later, celebrating our engagement with the help of a furry friend.

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Happy Engageversary my Bugsy and thank you for providing the most inspirational story for this post. 

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