Planning the Perfect Proposal Through Espionage & Intrigue


James Bond, George Smiley, Jason Bourne, and Patrick Scardino???  While you’ll probably recognize the first three clever, resourceful, and secretive characters, the last one may be an enigma to you.

Pat is just like you and me. He doesn’t own an Aston Martin or have a spy camera in his Montblanc pen. What he does have is a curious mind, a big heart, and a desire to delight his significant other, Julianne.

Now Pat and Julianne had been dating for a few years, and discussed the possibility of making it “official,” but Pat still wanted his proposal to be a big surprise. So he took some clues from the masters of intrigue, and decided to employ some simple tools used by all successful spies…


Step 1: Prepare for the "op"

When Pat and I first met, he was armed with photos of rings that his girlfriend loved. He had asked her sister, Jaclyn, to assist in the fact finding mission, and she provided key details that helped him narrow down his choices. He discovered she wanted a classic, 4-prong platinum diamond ring with French pave-set accent diamonds on the shank. He was totally open to my guidance on the specifics (for example, selecting the center stone), but his main goal was to give Julianne the ring of her dreams.

Step 2: Check in with HQ

The “how and when” of the proposal is where a lot of would-be proposers get stumped, so take a page from Pat’s book. Pat had planned a surprise weekend getaway for the two of them, and all Julianne knew was to pack a bag for warm weather. He informed her boss that he wanted to whisk Julianne away early that Friday afternoon, and asked her to plan some “meetings” so the extra time off would be a surprise as well. (Her boss was so supportive that she even wrote fake agendas for the meetings!)

Step 3: Lay the trap and wait

Now these two love-birds are very fond of San Luis Obispo, as it is Julianne’s alma matter and her little sister currently attends school there. It was also the perfect get-away spot for Pat’s plan, as he could use a visit to her sister as a part of the ploy. Not wanting to rush things, he stashed the gorgeous engagement ring in his backpack, and their first adventure was a fun night of partying with Julianne’s sister and some other good friends from the area.

Step 4: Confuse your prey


The next morning, Pat suggested they go for a hike (which, admittedly, was a bit strange, as they were both nursing a bit of a hangover). Julianne acquiesced, and they were soon on their way to what would turn out to be the most memorable hike of their lives!

As they walked along the lovely San Louis Obispo coastline, Pat found a romantic spot and suggested they take a bit of a rest and look at the view. Unfortunately, other hikers found this spot just as lovely, and it seemed as though every time he was about to pop the question, one or more hikers would traipse through and ruin the moment. Eventually, there was a break in the action and Pat spotted his chance. He looked Julianne in the eyes and told her how much he loved her, and that he wanted to spend the rest of his life with her. She gave an enthusiastic “Yes!” and the tears began flowing from both of their eyes.

The case of the disappearing family

After many hugs and kisses, Julianne wanted to share the exciting news with Pat’s and her family. She whipped out her cell phone and started dialing, and dialing, and dialing….

Strangely, after numerous calls, not one of their family members had answered their phone! (Unbeknownst to Julianne, Pat had secretly arranged for the families to be unavailable.) Slightly crestfallen, she returned with Pat to the Spyglass Hotel and they prepared to start their first day as an engaged couple.


Without family to share in their good news with, Pat suggested they have a lovely brunch at the Dolphin Bay Resort.  Julianne agreed and, expecting a quiet table for two upon their arrival, the floodgates opened again as they were greeted by each and every one of their immediate family members! A joyous celebration ensued, and continued into the day as the families ventured to some of the couple’s favorite wineries.

Smiley’s Friends…

Having had their personal and family celebrations, it was now time to let their closest friends in on the secret. As they drove back to San Francisco on Sunday afternoon, word started to spread like wildfire.

But Pat had one more surprise hidden up his sleeve…

During the drive Pat casually suggested that they stop off at the Columbus Café in SF before they went home. (The couple first met at this locale some four years earlier.) Expecting a mellow evening, Julianne was once again taken aback as a huge rush of friends came out of the shadows to welcome them with open arms.

The spy retires (or does he?)


Having done his duty for king and country (and the wine/cocktail industry), Pat reluctantly put away his 17 passports and fake mustache as he and Julianne ended their memorable weekend with a well-deserved night’s rest.

The Debrief: 3 key lessons learned from a master spy

  1. Secrets are allowed, even encouraged, when they are used for good and not evil.
  2. Know your mark. When choosing a ring, do your research! You may like Art Deco, but your partner may be a modernist. Put yourself in her/his shoes.
  3. Enlist the help of suspecting (or unsuspecting) friends and family to make this an event that includes all of the special people in your lives!