Red Flags In Lana Del Rey's Relationship With Jeremy Dufrene

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.

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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.

Dating as a celebrity is tough, and many beloved A-listers have their fair share of past exes and flings — including Lana Del Rey. "Lana's dating history indicates a penchant for serial monogamy," Susan Winter exclusively tells Glam. Looking back over Del Rey's checkered relationship timeline, the star has never stuck with the same beau for more than two or three years at the most. She's also been known to jump into doomed romances with both feet, as many of these past relationships sparked engagement rumors. In 2013, Del Rey wore a massive diamond ring that hinted at an engagement with then-partner Barrie-James O'Neill. In 2020, the same rumors popped up about Del Rey and musician Clayton Johnson. And in March 2023, Del Rey was reportedly betrothed to artist manager Evan Winiker.

None of these engagements panned out, suggesting that Lana Del Rey loves freely and fiercely — but perhaps for a limited time. Del Rey isn't ignorant of her own behavior, either. As the performer told Harper's Bazaar in late 2023, "I'm definitely not in love right now. ... But give it a week. My history, sure, it's coming for me at some point." How self-aware, not to mention prophetic.

Now, even though Del Rey has seemingly settled down with new spouse Jeremy Dufrene, Winter warns that this dating pattern could spell trouble if Del Rey isn't ready for an extended commitment. "Is each incarnation of a new partner simply a refinement of her selection process? Or could it indicate a greater unconscious preference for relationship churn?" Winter asks. If it's the former, then maybe the "Young and Beautiful" singer has finally found the right fit in Dufrene. However, if it's the latter, then their spur-of-the-moment marriage may be in for some challenges ahead.

Lana Del Rey isn't the only one potentially bringing relationship baggage into her new partnership. Reviewing Jeremy Dufrene's romantic history, it seems that the gator guide has a will-they-won't-they dynamic with marriage itself. Dufrene has been married once before and shares three children with his ex-wife. After they split — a divorce that is reportedly amicable — he reunited with Kelli Welsh, whom he'd originally dated as a teenager.

Dufrene proposed to Welsh in 2012, but the wedding never materialized. Instead, the duo continued on as long-term fiancés until finally splitting in 2023. Long engagements aren't unheard of, but more than a decade without tying the knot suggests some kind of hang-up in the relationship. Publicly, Welsh has taken on the weight of that decision: Apparently, she felt unable to go through with the marriage after losing her father and not having him there to walk her down the aisle. But in the wake of that years-long engagement, it still seems beyond strange for Dufrene to turn around and marry Del Rey so quickly after taking their romance public.

While Welsh expressed happiness for the couple, she told the Daily Mail, "I am in shock because we were engaged for 12 years, and he got married after one month." Perhaps, after years in limbo with Welsh, Dufrene was eager to take his new relationship to the next level — a hastiness that might indicate its own issues down the line. Susan Winter shares exclusively with Glam that Del Rey seems predisposed to "relationship churn," but Dufrene's dating history doesn't bode well for the couple, either.

Unfortunately, money problems are one of the most common reasons behind divorce. While this may seem manageable when one spouse is a minted global superstar, Susan Winter wouldn't count out finances as a stress point for Lana Del Rey and husband Jeremy Dufrene. "Though Jeremy runs a successful business, the economic disparity between [him] and Lana is extreme," Winter exclusively tells Glam. "This imbalance has been known to create friction within a marriage. When one partner dramatically outpaces the other financially, resentment, insecurity, and jealousy can arise."

Just how pronounced is the disparity? When Dufrene was still married to his first wife, they lived with their kids in a house valued at $340,000. Compare that to Del Rey's real-estate portfolio, which is valued at $6 million, and her personal net worth sits at a whopping $30 million. That kind of difference may make Dufrene feel like he's stumbled into a rags-to-riches story, even though he had a perfectly respectable lifestyle pre-Del Rey.

It can be tough to navigate financial dependence in a relationship, even when one partner makes more than enough to support a household, and it seems unlikely that Dufrene's finances will ever be able to compete. Once the whirlwind magic of their globe-trotting honeymoon period wears off, Dufrene may need to find other ways to feel like he's contributing meaningfully to their life together — for his own self-worth and peace of mind.

Finances aren't the only place where Lana Del Rey and Jeremy Dufrene come from different worlds, and with their unique backgrounds, it could be tricky for this duo to meet in the middle. "Lana's a sophisticated New Yorker who'll need to adapt to a down-home, country lifestyle," Susan Winter exclusively explains to Glam. So far, it seems like this hasn't been too much of an issue — Dufrene has shown a willingness to travel with his wife and adapt to her schedule, from supporting Del Rey at music festivals to stepping out with her at celebrity weddings. Similarly, Del Rey has been spotted spending comfortable downtime in Louisiana, whether it's relaxing on a sunny porch or going out to eat in New Orleans with Dufrene.

However, this kind of compromise and gap-bridging isn't always easy or sustainable. Dufrene's roots, business, and children are all in Louisiana, tying him in place more than Del Rey may be prepared for. "Although it may feel like the grounding she needs to steady her fast-paced career, it could just as easily become the divide that distances her from Jeremy," Winter says. "What appears as 'charming' at first glance, can become stifling in day-to-day life."

There's something charming about an odd couple, but in real life, opposites don't always attract. Relationships are often plagued with signs that romantic partners are too different to stick it out together, and relying on "opposites attract" couldn't even save beloved couples like J.Lo and Ben Affleck. Susan Winter explains how these personality mismatches can go from a selling point to a stumbling block.

"Extreme attraction is born of opposites. We see an aspect within another that yearns to be expressed within ourselves. But extreme opposites require a lifetime of negotiation," Winter cautions in an exclusive chat with Glam. Certainly, there are plenty of opposites to tally between Lana Del Rey and Jeremy Dufrene — which means a lot of negotiation to come. Success for the duo and their future together will likely hinge on factors like patience, flexibility, and dedication. As Winter adds, "Couples must work mightily to sustain relationship equilibrium. Sometimes that work becomes too much for the partnership to sustain."