Hailee and Tyler met in 2012 at Men's Warehouse when picking up a suit for Taylor's prom. Tyler originally tried to sweep Hailee off of her feet by showing her a 10 minute Youtube video, however she was not interested the video (or him). Tyler continued to pursue Hailee by asking a friend for her number. Hailee and Tyler text over the summer while she was at her dads, and met up as soon as she made it back to Cleveland. During the day, Hailee and Tyler hung out with family and returned to his house. Once back at Tyler's, he asked Hailee if she would be his girlfriend. Since this was the first time they truly hung out, Hailee was a little hesitant. She decided to say "yes" that day, but she would end the relationship if it wasn't what she expected.
In 2016, Tyler asked Hailee for her hand in marriage during her birthday celebration at the Downtown Houston Aquarium. Tyler hired a scuba diver to carry a sign down into the tank. Tyler was shaking as the diver dove deeper into the tank. She eventually flipped over the sign that read, "Hailee, will you marry me." It was this moment that Hailee realized exactly what was going on, as she hadn't met anyone else with that spelling.