Lana Del Rey shocked the world with her wedding to Louisiana airboat captain Jeremy Dufrene, but while their marriage has been something of a whirlwind, their acquaintance is a story five years in the making. The couple first met in March 2019, when Del Rey and her friends booked a bayou tour with Dufrene at the helm. "Jeremy lemme be captain at Arthur's AirBoat Tours," the "Summertime Sadness" singer captioned a Facebook post at the time.

The next step in their relationship isn't completely clear, but most signs point to a reunion at Louisiana's Hang Out Fest in March 2024, which Del Rey followed with another of Dufrene's boat tours in May. By August, Del Rey and Dufrene were spotted holding hands -- not in Louisiana, but at the Reading and Leeds Music Festival in Wetherby, England, where Del Rey was headlining. By early September, the couple was publicly attending events together, and by the end of the month, vows had been exchanged.

Following such a quick path to wedding bells, what could be waiting next for this couple? Pairing a world-renowned singer-songwriter with an alligator tour operator sounds like the premise of a romance novel, but in real life, the discrepancies in such a match could prove difficult to navigate. To find out whether Del Rey and Dufrene are facing smooth sailing or choppy waters, Glam spoke exclusively to relationship expert and bestselling author Susan Winter. From their personal dating styles to financial differences, Winter broke down some of the biggest obstacles that may cause friction between the newlyweds.