July 4th, 2016 Tim & Jen both swiped right on Bumble and it began. Tim was working and living in Vegas between schools and Jen was on her very first Vegas layover. The two started chatting until the next morning when Jen's location read "Toronto" and Tim said "wait your location says Toronto" and Jen said "yeah I'm from Toronto." The relationship almost came to an abrupt end but Jen promised she would bid for more Vegas layovers to visit Tim. The next month Jen was awarded 3 Vegas layovers but before she made it down Tim flew home to Australia for his grandmother's funeral. Tim promised he would be home for the second layover. Some time passed and as Tim's return date approached the two began planning the visit. Then came the day Tim ghosted Jen - or at least she thought. After not hearing from Tim for 24 hours she got a message that read "Well I got denied entry". Upon Tim's return to LAX, due to an incorrect visa form he was denied entry to the US. Tim was detained until he could get onto the next flight to Brisbane, and the border patrol took his shoelaces. For two months the pair chatted daily over messenger and FaceTime. Tim would stay up until 5 am to chat with Jen due to different time zones. Upon receiving his Visa he embarked on his journey back. Jen paid full fare (something she hasn't done since) for a plane ticket to visit Tim. Their first date was a four day Vegas extravaganza beginning with an airport and rental car pickup. Luckily after months of anticipation, it was a Royal Flush.

Tim proposed at Netanya Noosa on Noosa beach. A strategic location picked by Tim and Janine as it was where she and Peter (Tim's Dad) Honeymooned many years prior. After an incredible beachside dinner at Sail Noosa, Tim proposed to Jen on their suites private rooftop patio which was decorated with dozens of tea lights. Tim further sweetened the proposal with the stinkiest cheese plate of all time which much to his dismay Jen enjoyed thoroughly all night. The couple then settled into their private Jacuzzi to enjoy their engagement-eve.