Love letters to Derbyshire woman shed new light on a heart-breaking wartime romance

The Canadian’s correspondence, which was censored, was sent to Dot Preston’s wartime home in Eckington where she originated from.

These 11 letters and associated wartime memorabilia are now being put up for auction by Dot’s daughter Karen Plummer, a retired musician who lives in Chesterfield.

Written between 1942 and 1944, the postal artefacts shed new light on a heart-breaking love story that has intrigued visitors to National Trust property Beningbrough Hall in York for decades.

For years people wondered why the names ‘1942 Gipsy – Olie’ were scratched into wood above a fireplace at Beningbrough. The graffiti dated back to the time the Royal Air Force was stationed there in wartime but no one knew who the couple were – until a chance visit in the late 1980.

Karen, 69, said: “Gipsy (Dot Preston) was my mother. She knew she only had a short time to live and one of her last wishes was to visit Beningbrough Hall where she was billeted in 1941 as an 18-year-old. I took her back there in 1987.

“The staff were thrilled and gave us a tour. One of the guides, Eric Downer, showed her the names etched above a fireplace in the drawing room and asked, ‘Do you know who Gipsy was?’ She knew nothing about it and nearly collapsed. She said: ‘That’s me. I didn’t know he (Olie) had written anything.”

The shock was so intense that in ‘A Beningbrough Love Story, 1942 Gipsy – Olie’, by Alan Bott, Eric recalled that Gipsy started weeping and needed time to compose herself.

“Mum never spoke about it much but you could see that there was something inside her that was unfulfilled,” said Karen, 69. "She kept the letters in a drawer all of her life and I’ve kept them safe since she passed away at the age of 67 in 1990. I decided I had to do something with them. I don’t want her story to be forgotten.”

The letters were written on small pieces of official paper and one of them had lines blacked out by censors.

One of them, dated December 20, 1944, provides an indication of how the romance would play out. Olie wrote: ‘Dear Dot – Haven’t heard from you for some time. Hope all is well. Say Dot, I heard today that there is a possible chance that we might be going directly back to Canada. If you get any information about this, will you please send it on to me. Would you send me a photo of yourself, just in case I don’t see you again. Merry Xmas to you. Love Olie’.

Other memorabilia includes a 1941-1942 picture of 35 Squadron and PoW objects including rare escape committee items, German pass cards and French money. Karen does not know when or how Olie gave Gipsy the items. She remembers playing with the foreign money as a child but had no idea where it had come from. She hopes the memorabilia, which includes a note from renowned RAF pilot Wing Commander Leonard Cheshire, may be bought by a museum when it goes up for auction on September 24, 2021.

Canadian airman Sgt Harry Olsen was Gipsy’s first love. They met in 1941 when she was working in the kitchens at Beningborough and Olie, from Winnipeg, was an RAF tail gunner with 35 Squadron. It was ‘love at first sight’.

They’d only been together about three months when he was posted to RAF Pocklington in Yorkshire.

On June 8, 1942, Olie’s plane was shot down over Holland. Gipsy was so devastated she had a breakdown, according to Karen. She thought Olie must be dead. It wasn’t until July 13 that word came through that he was a prisoner of war.

Olie was 26 when captured. He faced solitary confinement, prolonged interrogation, poor food and inadequate conditions. Sometimes the men slept together for warmth. He was a PoW at Stalag Luft VI at Heydekrug, Lithuania, and later at a labour camp in Essen, Germany. But he had something to pull him through those dark days – Gipsy. They managed to exchange censored letters which he wrote in pencil.

Eventually Olie was liberated. He returned to England on May 10, 1945 – but never met Gipsy. She said he was in such a state he couldn’t remember her home address. He tried to contact her through the RAF record office but by the time she received his letter it was too late. He left for Canada on July 8, 1945. There was no way she could afford to go there. They never met again. It was heart-breaking. Gipsy revealed: ‘We both finished up needing treatment for our nerves’.

With an ocean dividing them, they went on to marry other people.

There is one strange coincidence that warms Karen’s heart: “Mum went on to have two daughters and Olie had three children. They both, unbeknown to each other, named one of their daughters Karen.”

Charles Hanson, owner of Hansons Auctioneers, said: “This story brings a tear to the eye. It is so poignant, so touching. It reminds us all of the terrible pain and sacrifices the generations that came before us had to endure. Let’s hope Olie and Gipsy are together again in spirit.”

The lot, which is estimated to raise between £400 and £600 will be offered in Hansons’ September 24 Medals, Militaria and Firearms Auction.