Surprise Party Planning for Newbies

My biggest undertaking by far this holiday season was the surprise welcome home dinner I planned for my brother, who recently moved to Israel but was able to manage a return trip to Canada for Christmas and Hanukkah. This was the first surprise party I ever planned solo (earlier this year, I helped coordinate a surprise sushi send-off for one of my good friends going to grad school in New York, but her very sweet boyfriend did most of the leg work).

Given the relatively small guest list, I thought it’d be easy as pie, especially for a self-proclaimed Martha Stewart In Training. Fast forward to a thirty pound cake (or so it seemed by the time I finished hauling it around), a last minute helium balloon order and my repeated vow to never plan another event in my entire life, and I was singing a different tune. In hind sight, it was all good fun, and the stress was largely self-induced due to my perfectionist Scorpio tendencies, but I thought I would share a few tips I gleaned from the experience:

1.) Plan (really far) in advance
I’m not just talking about logistics. If you’re planning a surprise party, you need to lay the ground work for proper deception. For me, this involved requesting my brother set aside his first night back home for a “sibling dinner”. Having lived in Israel myself, I knew firsthand how difficult it was to track down decent Mexican food over there, so I proposed a night of nacho snarfing to celebrate my brother’s return. He immediately agreed, even though his visit was still a couple months away. I attributed this advanced planning to my excitement in seeing him after such an extended period of time. He didn’t suspect a thing (at least not yet).

2.) Don’t be shy
At the start of my event planning adventure, I was only connected with a couple of my brother’s good friends on Facebook. Since he’s a social butterfly, I knew he would enjoy having more people there, which meant creeping his friends list for names I recognized and messaging them out of the blue. This wasn’t particularly difficult due to my rather schmoozy line of work, but I noticed the surprise element definitely required more frequent (and personal) communication than just setting up an event page on Facebook and blasting it off to everyone and anyone, as I normally would have.

Another challenge was planning an event slap dab in the middle of holiday season; if my brother were visiting any other time of year, the guest list could have easily doubled in size. After some initial disappointment, however, I began to look at the event in a whole new light: in a way, it was more special, precisely because everyone had worked so hard to be there. My appreciation and fondness for my brother’s wonderful friends grew throughout the event planning process and I ended the evening with a profound feeling of gratitude above anything else.

3.) Stick with the tried and true
I knew I would have enough to worry about with simultaneously planning an event and keeping my brother in the dark; I didn’t want to add vendors to my list of possible stress inducers. I selected Milagro Cantina for the location because I had eaten there before and knew they had a solid menu, killer guac and decent service. It also wasn’t too far away, which turned out to be a major plus when a massive cake entered the equation.

The cake was a complete splurge and unquestionably the greatest expense of the event, but it was worth every cent and more. Custom designed by Crystal Nethery of Mrs. Nethery’s Cake Emporium in Oshawa, it came to life after nearly two months of e-mail exchanges, during which I conveyed my vision for a sugary tribute to my brother’s favourite childhood movie, The Lion King.

I knew about Crystal and her tremendous work because of a cake she made for a friend’s wedding I attended over the summer. While wedding cakes are notoriously tasteless and more often suited as a piece of décor than dessert, Crystal’s creation was so good that I actually had to track down the bride and ask who made it. By the end of the evening, the cake had been demolished as guests went back for seconds and thirds. I decided then and there that, when it came time for me to plan a party of my own, Crystal absolutely had to be in charge of the cake.

Sure enough, when my brother finalized his travel details in the fall and I had the green light to officially start planning, Crystal was one of the first people I contacted. I knew the cake would be delicious, but in my massive expectations, was still not prepared for masterpiece I saw when she brought it to my front door. Crystal even had to shake off some passerby who had stopped in the street to admire it.

Needless to say, I was thrilled. In fact, here is the e-mail I sent her, word for word, after the cake was delivered:

Hi Crystal,
I just wanted to let you know that my parents and I are literally in AWE over your beautiful masterpiece. It completely exceeded my expectations and I can’t stop looking at it. You are such a phenomenal talent and it was so wonderful working with you. I can’t wait to see my brother’s face when he sees the cake tonight. I actually feel bad calling it a cake because it is, quite simply, a work of art. I will not hesitate to recommend you to all my friends and family, and we will hopefully have many more happy occasions in the future to celebrate with your remarkable cakes!

Bottom line: stick with suppliers you know and trust and save the experimentation for a less stressful occasion. You do not want to simultaneously be worrying about one of your guests blowing it and whether or not the food will be good.

**If you do wind up commissioning a custom novelty cake from Mrs. Nethery’s Cake Emporium, I absolutely recommend her famed chocolate-banana marble flavour. It is seriously one of the best things I’ve eaten all year. She also offers vegan cakes! You can reach her at (tell her Rachel sent you!)

4.) Do you research
Having worked in the wedding industry for a few years now, I knew that not all venues would be down with having outside food brought in. The restaurant did charge a moderate fee for this privilege (which put me slightly over budget), but the cake was ultimately granted safe passage to the surprise party. I feel compelled to mention that the staff at Milagro were very gracious about bringing out dessert plates and a cake knife, even though they were clearly being used on an item not produced in their kitchen.

Make sure you call your venue far in advance to inquire about outside food policies. For some places, this will not be permitted, and it’s better to find out before you’ve made a reservation and/or purchased a cake, cupcakes, macarons, whatever. If you’re ordering a custom designed cake from a local baker, be sure to also budget for delivery fees (or alternatively arrange to pick it up in person). Mine were slightly higher than expected because Crystal had to trek all the way from Oshawa with Simba in the passenger’s seat!

5.) Play it cool

(Drawing by the marvelous Allie Brosh of Hyperbole and a Half)
This one was definitely the most challenging for me, since I come from a family of expressive creative types. I tend to subscribe to the “go big or go home” school of thought, which makes it even more difficult for me to keep a lid on something I’m particularly excited about. However, I’ve been pranking my close friends and family members since I was a kid, so I’ve managed to perfect my poker face, even if I’m a ball of nerves underneath. My advice? Stick to the basics; elaborate stories and explanations can sound suspicious if you’re a novice surprise planner. Just think of all those movies where the criminals unwittingly give themselves away by providing too many details and sounding super guilty. If you need a solid alibi, blame your therapist (or gynaecologist, if applicable); the person you’re trying to surprise will likely be too polite or uncomfortable (or both) to ask any further questions.

6.) Cover your bases
I know it sounds kind of ironic for someone who works in bridal fashion, but I was a pretty hardcore tomboy growing up. I idolized Mia Hamm, Mulan and Sporty Spice, and for most of elementary school, refused to wear a dress (there are actual photos of me in full-scale track suits à la The Royal Tenenbaums. I know – super embarrassing). I particularly loved sports; when I was in the fourth grade, I took up soccer, and after scoring my first goal, I came home to discover a massive, hand-drawn poster taped to my bedroom door. My dad (who is an excellent illustrator) spent hours working on it. Since then, I’ve picked up the habit of creating little door signs for people in my immediate family to celebrate particularly grand achievements, as well as birthdays or their return home from traveling.

Even though I was preoccupied with the surprise party, I was worried that neglecting my little sign-making tradition would clue my brother into all my elaborate scheming. Lesson: do everything you would normally do under the circumstances. It will help avoid red flags and enable you to continue your surprise planning undetected.

7.) Get help – you will need it!

One thing I definitely didn’t bank on ahead of time was how physical the job would be, even though I only had a cake and balloons to decorate the space. For starters, the cake was not only heavy and also exceptionally detailed. Earlier in the day, a minor snafu caused the translucent waterfall gel to smudge, which was fortunately abetted with some impromptu knife work by yours truly.

Then came the actual storage: the cake was delivered to me without a box and Crystal said I didn’t need to keep it in the fridge, which fortunately expanded our options when it came to stashing the thing until the party. My room was a no-go, being a permanent “nursery” to two mischievous felines (even though they’re now 1.5 years old, they still spend a lot of their time in my room because it was where they first settled in when Toronto Cat Rescue dropped off the little cherubs at 5 weeks old. It’s their comfort zone and they basically freak if the door’s closed). Any common area in the house was also out since there was the risk of exposure, even though my brother was more or less conked out from his 12 hour flight for most of the day.

I definitely didn’t regret my earlier decision to bring our other brother into the fold, since his room provided the perfect cover. More importantly, he was an invaluable assistant when it came time to transporting the cake (a particularly agonizing production which involved re-purposing a massive cardboard box from a recent holiday gift delivery). I also needed him to open the multiple doors in the entryway at Milagro while I carried the cake to its final destination. Our dad, meanwhile, shuttled us to and fro (I don’t drive and taking the cake on the public transit was absolutely out of the question), the latter including a last-minute stop to pick up an impromptu order animal-printed helium balloons from the The Little Party Shoppe near Yonge and Eglinton.

Bottom line: if you’re planning a surprise party, you will definitely benefit by cluing in a couple other people you trust, because no matter how diligently you plan, there will likely be some last minute blip that will require their assistance (especially if cake and decorations are involved). Just make sure they’re not prone to blabbing and you’re good as gold.

8.) Prepare for stares
I’m definitely more comfortable buzzing around behind the scenes than having all eyes on me, but if you’re setting up a party in a public place, you will almost certainly have an audience (especially if there’s a novelty Lion King cake involved). I was approached by no fewer than five people who asked to take a picture of Simba, and even the servers couldn’t resist commenting (one of them inquired if he should rustle up a few children’s menus, before I explained to him that it was an adult party).
9.) Lay off the texting
I arrived super early at the restaurant to set up, which logistically made sense, but psychologically was torture. In my restlessness, I nearly ruined the whole thing by excessively texting people who were with my brother before the dinner, imploring them to cause delays until a couple more guests showed up, requesting information on their whereabouts and basically acting like a neurotic Jewish mother, even though I’m a 20-something whose only children so far are completely covered in fur. The phones were bleeping off the hook, and my brother could have easily figured everything out if my champion partners-in-crime didn’t blame the unusual high volume of texts on work and school. In sum, as anxious as you get sitting there, waiting for your guest of honour to arrive, resist the urge to text and focus on your zen, or whatever.

10.) Check your expectations 
I think, at some point, everyone attempting to plan a surprise party has that hopeful vision of their guests joyfully shouting in unison as the unsuspecting person walks through the door. Balloons and confetti drop down from the ceiling as if by magic; there are tears and hugs and rivers of champagne à la Baz Luhrmann’s The Great Gatsby. It’s only natural to yearn for a movie-moment surprise (you’ll certainly be losing enough sleep over it, trust me) but never doubt reality to play out much differently.

At my brother’s little shindig, no one even shouted surprise – it was much more organic and low-key – but I could tell by the look on his face that he was completely stunned. He did later admit that he suspected I may have been in cahoots with his best friend from university, who is basically one of my favourite people ever, but he had no idea I had coordinated an actual surprise party, with multiple guests and a cake. I should also mention that he was equally surprised by his friends who couldn’t be present for the big reveal due to scheduling conflicts but hustled to be there later in the evening.

11.) Get your camera on
Last year I helped out behind the scenes of a Cuban-inspired bridal shoot with a couple of wedding industry pals (Jan Ng from Willow Rose Events and Michelle Belsky from Magnolia Studios, if you’re looking for a bomb wedding planner or photographer, respectively). One thing I learned from this experience was that it’s incredibly difficult to shoot on the go, and that was with a stockpile of fancy photography gear in tow.

For my brother’s surprise party, I only had my iPhone, which meant that the quality of the images I was able to capture were pretty shoddy by comparison (especially when you factor in the dim restaurant lighting and my neglecting the flash button in the midst of the excitement). Because the single most gratifying element of surprise parties is seeing the look on the person’s face when they first walk in, I would definitely suggest bringing along an actual camera, or – if you have room in your budget – springing for a professional photographer to document the moment of glory.

It may seem excessive for a little dinner party but I have seen firsthand what talents like Michelle are capable of, especially in the wedding industry, when you have only a split second to capture a couple’s first kiss or a mischievous glance between groomsmen. So many wedding photographers now specialize in candid photography, which would be perfectly suited for a surprise party.

12.) Be tupperware-ready 

One regret I had of the evening was that I didn’t bring any tupperware. There was enough cake left over to feed a small army and it would have been nice to send everyone home with a slice or two, especially considering Crystal’s cake was supremely moist and fresh for several days after the event. Over the past year, I’ve gone to an usually high number of dinner parties, and am always so touched when the hosts package up leftovers for everyone to take home.

13.) Remember the most important details
A few days after the dinner, I was watching Boardwalk Empire with my brother. I told him that I wish I had thought to make Nucky Thompson-style corsages for all the boys to wear at the dinner, but then quickly consoled myself because it obviously would have clashed with the Lion King theme. He didn’t even blink (after nearly two and a half decades, he’s pretty used to me and my obsessive compulsive party planning).

The fact remains that I’m an extremely visual person with a knack for little details (which is probably why I love pretty parties and weddings so much). I could have easily done a lot more with my brother’s surprise party: DIY animal place card holders, leopard printed straws, the works. As fun as it is for me to indulge my inner Martha Stewart, however, I know that the real life and soul of any party isn’t in the clever, thematic décor – it’s the people.

My brother’s welcome home dinner wasn’t incredible because of the zebra striped balloons (which I don’t think anyone even noticed). It was incredible because of the people; his friends who re-arranged their holiday plans, took time off work and drove across the city to welcome my brother home. And that was the most important detail of all.

Rachel’s Resources
Venue: Milagro Cantina
Cake: Mrs. Nethery’s Cake Emporium
Balloons: The Little Party Shoppe

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