Blossoming friendships on walks for singles 

Liz Nicholls

David Jackson will lead a spring walk for singles through Coneybank Wood, 10am-1pm on Sunday, 27th April. We chat to him about his career pivot… 

Every spring, our wondrous woodlands here in the Chilterns hum into life with a carpet of fragrant bluebells. This joyful, seasonal show is certainly not lost on David Jackson, a relative newcomer. 

“I grew up in North Lincolnshire and went to University in London so I only discovered the Chilterns in my thirties,” says David who has lived in Great Missenden for 11 years. “Spring is great and the bluebells and new beech leaves are a highlight. Later in the year I enjoy the wild orchids near Aston Clinton and Whiteleaf Cross. Evening walks are good to see deer.” 

David worked in finance until he was made redundant in 2014 and decided he wanted a different challenge. “One of my passions was trekking in the world’s high mountains, such as the Himalayas, so I booked myself on a navigation skills course, joined meetup and set up Chiltern Walks. Now David organises walks in the Chilterns and walking holidays around the UK. You can join meetup for free and pay for walks and breaks you want to join – visit  meetup.com/chiltern-walks-meetup 

About a year ago, the team from Date in the Diary contacted David to see if he might like to work with them to lead walks for single people. “I’d been organising and leading walks for my group for 10 years and I liked the idea of adding a different dimension that was dedicated to single people,” adds David.  

Date in the Diary events (dateinthediary.com) are designed for like-minded single people, allowing them to meet doing something they love, with none of the pressure of one-to-one dating. If you happen to meet someone you’re attracted to romantically, it’s a bonus, but in the meantime it’s all about genuine friendships and connections. If you wish to continue the social aspect and making connections, Sunday lunch can be booked for after the walk.  

“Last year I attended the wedding of a couple who met on one of my walks,” adds David. “As well as this, numerous friendships have blossomed after people met on my walks. I met many of my own friendship group on my walks. 

“This walk on 27th April goes through one of my favourite bluebell woods in the Chilterns, which explode into glorious colour at this time of year. It takes in a couple of short climbs but much of the walk is through some of the best beech woodland in the area. 

“Many of my walks are suitable for dogs, as long as the dogs are well-behaved around other people and dogs and – because of the wildlife and livestock here in the Chilterns – they must have good recall or be kept on a lead.”