When conducting practice landings at Naval Outlying Field Spender in Milton, Flordia, Jack consistently heard a high pitch, "annoying" voice on the radios. Every time Colleen walked out to the flight line to hot seat into a helicopter, she would see someone with the nametag sticker “Lahey” on the back of his helmet sitting on a stoop. Colleen would make fun of “stoop boy” behind his back. Despite living a block from eachother in Texas, seeing and hearing each other on the flight line, attending each other’s parties, and bumping into each other out at bars in Pensacola, Florida, Jack and Colleen’s paths finally crossed for good on the Blackwater River in Milton, Florida. Jack and Colleen solidified their relationship that night by dancing outside of the post office and taking shots of ranch dressing.

After buying severely overpriced beers at the Hotel Del Coronado, Jack and Colleen walked down to the beach. Jack pointed to the Naval Air Station North Island runway right behind Colleen and asked if she thought the runway was closed. Colleen turned her back to Jack to scope out the runway and sassily called out, “you should’ve known that the runway was closed.” Colleen turned around to the sight of Jack down on one knee. Colleen’s level of excitement and shock was nearly matched by beachgoers exclaiming, “Oh my god, this dude is proposing! Should we take pictures?!” Colleen couldn't believe Jack pulled off such a surprise without her knowing. Jack couldn't believe he kept the ring box covertly tucked into the pocket of his skinny jeans the entire day.