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My last 5p: How one homeless man鈥檚 generosity led to him marrying the love of his life

In 2013, Toni Osborne was struggling, emotionally and financially. Pennies short of keeping her electricity on over Christmas, she went to ask her local shopkeeper for help. But then a homeless man, Jack, offered Toni his last five pence. This simple act of giving would alter both their lives in profound ways…

In this episode of Sideways, Matthew Syed explores how the effects of a seemingly small moment of generosity can ripple outwards, with significant consequences.

“I was homeless on and off for a very long time.”

Jack and Toni

Jack Richardson had been homeless for years. “My mum died of lung cancer when I was about 13 or 14 and I went into care,” he recalls. Then at 16, he made the decision to go it alone. “It was probably one of the worst mistakes of my life,” he states. “I moved around an awful lot… I’d start to get things together and then I’d get overwhelmed, often with a bout of clinical depression… and I wouldn’t be able to keep up with anything.”

In 2013, Jack was begging and sleeping in an underground car park, in a room used by a hotel to store furniture. “There were rats,” he states, “and if you don’t keep your hands out of the way when you’re asleep, rats will gnaw at the ends of your fingers.”

On her way to the shops that night, Toni walked through Jack’s car park. When he appeared, asking for money, she broke down.

“I stopped and asked a woman for money and she burst into tears. I absolutely panicked,” recalls Jack. “I’m autistic and I don’t really deal well with very emotional people. I just wanted her to stop crying.”

And so, to Toni’s amazement, Jack pulled a 5p out of his pocket and handed it to her. “That just blew me away,” says Toni. “Here’s this person who’s got nothing, who’s sleeping on the streets, giving me, a person who’s got a roof over my head, money so that I can put the electric on.”

Thanks to Jack’s generosity, Toni wasn’t in the dark over Christmas.

“When you’re very low down, you don’t often get the chance to feel really good about yourself,” says Jack. “And putting someone’s lights on over Christmas for the bargain basement price of 5p, you can curl up in your damp sleeping bag at night and that’s a bit of warmth.”

For Toni, Jack’s small but hugely powerful gesture “meant the absolute world.”

“I just gave him a really huge bear hug, thanked him profusely, and said may this good karma come back to you.”

鈥淓very couple of weeks we鈥檇 get chatting. And we became friends.鈥

After their brief moment of connection, the pair went their separate ways. It was the middle of January when Toni bumped into Jack again.

“He’d just been given a badge in order to sell The Big Issue,” Toni recalls. “So I gave him a massive hug and said, brilliant, you got your karma, I’m really happy for you.”

Toni would regularly walk past Jack’s pitch. “Every couple of weeks we’d get chatting,” says Jack. “And we became friends.”

Then one night, when he returned to the car park storeroom, Jack found it boarded up. Gone was his sleeping bag, cutlery, clothing and prized bin liner full of second-hand sci-fi books. “Just all the things I owned in the universe,” says Jack.

So he found himself on Toni’s doorstep, asking if he could stay the night. And at his lowest point, Toni was able to help him out. Just as he had done for her.

“Initially I said to him, give it a week or so,” says Toni. “If things work out OK, I don’t mind you staying here until April, when the weather’s better.”

“I caved in and asked him if I could kiss him.”

The pair settled into a routine. And then, Toni realised that something was changing. She had developed feelings for her new housemate.

“I genuinely thought, I don’t stand a chance. He’s going to want someone closer to his age,” Toni recalls. “I really fancied him, and that just increased the more time went on. And after about two or three weeks I think I caved in and asked him if I could kiss him.”

“I was so shocked,” says Jack. “And, of course, said ‘yes’. I didn’t see myself as someone anyone would want… My hair was always a mess and I was radically underweight. I was not in a good place physically, psychologically, emotionally, and so it came as such a shock.”

A year went by. “We fell head over heels,” says Jack. “Absolute infatuation. And it deepened and grew and I knew very quickly that I wanted to marry her.”

"Our love deepened and grew, and I knew I wanted to marry her."

How the ripples of one simple act of giving turned into a cascade of generosity.

Photo © Judith Parkin

鈥淗e got down on one knee on the top of Park Street.鈥

Jack proposed in the middle of the street, at 2.30 in the afternoon, in front of everybody. “I said ‘yes’,” states Toni.

One of his customers said to him, 鈥淚f you can fall in love while you're living in a car park, then there鈥檚 hope for all of us.鈥

And then it “just went a bit crazy,” she recounts. First, The Big Issue ran the story. Then a journalist in the South West got hold of it. “The next thing we knew, it was in all the newspapers.”

Jack’s initial act of generosity had started a ripple effect. And the ripples turned into waves. Offers and gifts came flooding in from people who’d read about them or knew them.

“This lovely woman donated £500 to me to get a wedding dress,” says Toni. The jeweller at the bottom of Park Street offered to do their rings. A local vicar arranged the church venue. On the day there was an award-winning choir, professional photographer and abundant flowers – and it was packed to the rafters.

For Jack, all that generosity had a big effect.

“It’s left me with a sense of responsibility,” he says. “The sense that I’ve been the mysterious benefactor of something magical and it would somehow tarnish what I was given if I didn’t pass it on.”

He does pass it on, by reminding people where generosity might lead you. One of his customers said to him, “If you can fall in love while you're living in a car park, then there’s hope for all of us.”

After seven years, Jack and Toni are still very much in love. Jack may have lost his beloved books, but he’s now working on his own sci-fi novel with the help of a generously donated laptop.

“I’m amazed. Humbled is the right word,” he says. “Everything that’s happened since the wedding has just confirmed that in a life of sometimes questionable decision-making abilities that marrying Toni was definitely the right thing to do.”

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