Meet the 24-year-old, who travels the world with her 56-year-old fiancé

When 24-year-old Allana Luke joined Tinder in October 2020, she had just come through a bad breakup. Tired of men her age, she was looking for someone more mature to spend time with. Two years later, Luke lives in a mansion with her now-fiancé, 56-year-old Jeff Winn, and their three dogs, Bentley, Aston and Porsche.

“It was more of a joke at first,” said Luke, who lives in the UK news week. “I figured I’d bump up the age range and see what happens.”

Luke changed the age range to 25-60 and was inundated with matches, but it was Winn who caught her eye. Unlike most other men she came into contact with, Winn chose to play hard.

“He was a bit vague,” she said. “He sent me a message saying, ‘If you want to contact us, text this number.’ I thought I had to do the work here.”

Allana Luke and Jeff Winn drink champagne
Allana Luke, 24, and her 56-year-old fiancé Jeff Winn sip champagne in the kitchen of their mansion, where the couple had their first date.
Allana Luke

Their first date was at Winn’s mansion — a former girls’ school he had renovated — where he cooked her venison stew with champagne. Within days, the couple were vacationing together in Marbella, Spain, staying at Winn’s villa for two weeks.

The couple have been inseparable ever since and got engaged in June.

“I talk to friends about their relationships, and some of it’s just so petty,” she said. “You just don’t get that with an older man. The stuff that 20-year-olds fight about, that’s just not the case with us.”

Can relationships with a big age gap ever work?

A recently opinion poll of Cougar Life found that 39 percent of Americans have dated someone more than 10 years older than them. In a survey of 1,005 adults, the researchers found that 57 percent would be willing to date someone over 10 years older, while 49 percent would be interested in someone over 10 years younger.

Emotional maturity and financial freedom were seen as the top benefits of dating an older person, while physical attractiveness and outgoingness were seen as the top benefits of dating a younger person.

Professional matchmaker Kara Bell spends her days creating couples that click. She said like any relationship, age gap romance has its pros and cons.

bell tells news week: “For the younger partner, a large age difference can offer stability.

More specifically, women who want a father figure-like relationship and financial stability in their relationship tend to date much older men.

“For the older partner, dating a younger person can make that person feel young and offer a different perspective on life in general.”

However, an age difference can also lead to a conflict of values ​​or competing life goals and desires.

“One might just be establishing himself in his career while the other is nearing retirement,” Bell added.

“It can also lead to the younger partner becoming the caretaker sooner than expected, which can lead to resentment and a loss of independence.”

Allana Luke on the bed with birthday presents
Allana Luke is celebrating her 24th birthday with a present from her fiancé Jeff Winn.
Allana Luke

Mistakes to Avoid in Age Gap Relationships

Mistakes to avoid in an age gap relationship include not discussing the future, invalidating each other’s experiences, and not being willing to compromise.

“Communication is the foundation of any relationship,” Bell said. “The early recognition and discussion of challenges can therefore prevent resentment or misunderstandings in the future.”

She said the judgment of friends and family can also cause friction between age-gap couples, but there are ways to get them on board.

“The support of family and friends can also help ensure that any relationship, but particularly age-gap relationships, lasts,” she said. “So show them the mutual love and respect you have for each other.”

Winn’s family — including daughter Nina, 23, and son Josh, 21 — love her stepmother-to-be. However, she was recently mistaken for his daughter on a recent hike to Machu Picchu.

“The guide was from South America, and when he realized I was Jeff’s girlfriend and not his daughter, he just shook his hand and said, ‘Well done,'” Luke said.

Since the beginning of the relationship, Winn has showered Luke with expensive gifts, including a Rolex watch, pink car, diamond earrings and trips around the world. However, Luke said it’s not a one-way street as she treats Winn as often as possible. Luke believes this devotion to her father is why Nina and Josh trust her more than Winn’s ex.

“I buy him gifts, and he’s never had a girlfriend who’s done that, so maybe some of his ex-boyfriends were gold diggers,” she said.

Despite the over 30-year age difference, Luke said she’s the maturity in the relationship, calling Winn a “young soul.”

She also describes him as “very down to earth” and someone who “loves bargains”.

She never really relates to people her age and enjoys the company of Winn’s friends and family, especially his daughter.

Luke and Winn visit Machu Pichu
Allana Luke and Jeff Winn are pictured on a recent hike to Machu Picchu, where Luke was mistaken for Winn’s daughter by a local guide.
Allana Luke

“Nina and I are the same age, so let’s go dancing together,” she said. “We regularly go to his parents’ house for dinner. We’re just normal.”

Her family and friends accept their romance, but Luke sometimes has to deal with trolls online.

“If there’s a photo of me and Jeff and Jeff looks particularly older, someone will direct message me about abuse,” she said. “But it’s just jealousy. We just laugh at them.”

Although sometimes referred to as a gold digger, Luke would not change anything about her relationship with Winn.

“People sometimes ask questions like, ‘Are you only with him for his money,'” she said.

“But they’ll also ask him, ‘are you only with her because she’s young and beautiful,’ so it goes both ways.”

If you have a family problem, let us know at We can ask experts for advice, and your story could be featured on Newsweek. Meet the 24-year-old, who travels the world with her 56-year-old fiancé

Rick Schindler

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