It’s Hard To Fly With A Birthday Cake

I have had this post saved in my drafts for a couple of days now and I can finally post it, woo! Stefan and I originally had this week off together and we were going to head back to his hometown in Southern California to celebrate his birthday. BUT, then he decided to go and get a big new fancy job so he’s currently in training for the next couple months. Since I still have the time off I figured I might as well hop on a plane and keep him company (or hit up the pool while he’s in class studying) so he doesn’t have to celebrate his birthday alone in a hotel room. Now, I should let you know I love birthdays. Well, I love everyone else’s birthday except mine. I never want anything or ask for anything when my birthday rolls around but I love spoiling other people for theirs. This birthday was a little trickier since I was bringing the party from Toronto all the way to Miami! I had to strategically put all the presents in my roller bag as well as my purse, I crammed a Happy Birthday banner in my bag, and since there’s no easy way to pack a cake for an international flight I brought birthday cookies (this should really become a thing!) Thank goodness for the warm Miami weather because I don’t think I would have had room to pack my Canadian fall attire.

Alright, back to the important part of this post… COOKIES! I opted for making birthday cookies for Stefan since there was no way a cake would make it safely to Miami plus this guy loves his cookies. I didn’t want to make ordinary cookies though because it’s a birthday and they should be special! So I decided to make pineapple shaped sugar cookies. I know, it sounds weird when I say it out loud too. Many months ago I told Stefan that if I had to describe him in one form of fruit it would be a pineapple – he’s a little tough and spiky on the outside but he’s soft and sweet on the inside. Also his hair stands straight up like a pineapple in the morning and after he takes a shower. So, I ordered a pineapple shaped cookie cutter on Etsy and of course, it did not come in time SO I had to improvise and channel my inner Martha Stewart. Here’s what you’re going to need to MacGyver your own cookies for that special pineapple in your life:

  • Some sort of hand drawn pineapple shape
  • A piece of sturdy cardboard
  • Penicl/pen/Sharpie
  • Scirssors
  • Cookie dough (and a cookie sheet… and an oven… you catch my drift)


I drew out the pineapple I wanted on a piece of paper and cut that out before tracing it over on a piece of cardboard to make it easier to use as a cut out type thingymabob. I usually like to make my own sugar cookie recipe but my inner sloth was in full effect this week so I opted for the Betty Crocker Sugar Cookie Mix. This is a great foundation for a cookie and it gives you the option of tweaking the recipe to make it a roll out dough. In addition to the dry ingredients in the package, I added:

  • 3 tbsp flour
  • ½ cup butter (melted)
  • 1 egg

Simply mix everything together and voila! I suggest dividing the dough in 2 and chilling in the fridge for a couple hours to make it easier to roll out. Once it was chilled enough i proceeded to roll it out and start the painstaking process of cutting out enough of these damn pineapples to spell out “Happy Birthday”. To my surprise, I only dropped one on the floor while trying to gently move it from the counter to the cookie sheet (insert self high five here).


Bake your little pineapples for 5-7 minutes depending on your cookie sheet and oven. Once out of the oven, let them cool down enough before attempting to decorate them if you desire. I just bought the Cake Mate Decorating Icing in green and yellow and then let Jesus take the wheel. An hour and one cramped hand later I had pineapple birthday cookies! My OCD had to take the back burner on this one because the icing isn’t the most ideal for detail but it got the job done.


Now these pineapples look great in the picture above BUT they didn’t look so hot after the flight to Miami. I was trying to be a nice flight attendant while travelling standby so I offered to gate check my roller bag instead of having it as a carry-on. The cookies did not like that decision. I didn’t notice that half of them had fallen apart until I was trying to set them up in Stefan’s hotel room. Stefan had class the day of his birthday which is a bit of a bummer but it gave me a chance to turn his hotel room into a little birthday celebration. Everything went as planned until I started laying out the cookies and my OCD cried a little bit. Thankfully Stefan took a picture from an angle where you can’t tell how sad and broken they really looked. Have I mentioned how much I love birthdays and this handsome little pineapple I got to celebrate with?



4 Comments Add yours

  1. @kundun66 says:

    Another blog..👏👏👏…LOVE IT kiddo…👍 they tasted great..besides we all know it’s the little things..and this little thing was pretty awesome ..🎉🎁🎈

    Liked by 1 person

    1. jtbosko says:

      I knew he wouldn’t want to eat them right away so I brought the extra regular sugar cookies also so he could admire he pineapples for a couple days, haha!


  2. Kaitlyn says:

    CUTIE! love it. Why I never thought of simply making my own cookie templates is beyond me…all the possibilities….

    Liked by 1 person

    1. jtbosko says:

      Cookies will never be the same! It was a little more of a pain than a regular cookie cutter but that just means that much more love went into them! ❤


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