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Dating in Cheltenham

Cheltenham might not be the largest town around but it certainly packs a big punch. With plenty of things to do, this jewel of the Cotswolds is an excellent place for likeminded singles to get to know one another. But if you're currently looking for love, you might be wondering how to connect with likeminded singles looking to make meaningful connections with others...

The good news is that with Rest Less Dating, it's quick and easy to start connecting with singles in Cheltenham, so you can find the perfect person for you.

Being nestled amongst some of the UK's most dazzling scenery, Cheltenham is the perfect place for nature lovers to plan an outdoor date. Although, if you're looking for something a little more intimate or the weather's not great, then there are plenty of great things to do in town as well.

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Featured members from Cheltenham


66 - Cheltenham, Gloucestershire

I can be trusted. I care for people. It would be nice to have a friend to share some of my life with


69 - Cheltenham, Gloucestershire

Hi , I’m a Honest ,loyal , caring with a good sense of humour Enjoy travel and The Countryside . Dining out in...


61 - Cheltenham, Gloucestershire

I am an easy going, nature loving, outdoor person who loves to laugh. I am caring and empathetic and absolutely...


69 - Cheltenham, Gloucestershire

I'm a quiet but thoughtful man, who cares for and appreciates family and friends. Loves his 2 grandchildren....


67 - Cheltenham, Gloucestershire

I am a kind and caring person who loves the theatre, cinema, visiting gardens and national trust places and who...


59 - Cheltenham, Gloucestershire

How hard can it be? Tall, fit, emotionally intelligent, empathic, hard working and self employed, spaniel owner...

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Success Stories

Met 14 months ago and still going strong!
Caroline, 10 October 2023
We swapped numbers after a few days of general chatting, totally out of character for both of us, a 3 hour 15 min telephone conversation, we have chatted every day since, have met for a day out and we both feel we have been together forever. We are very happy together, learning about each other every day and at times, feel like we're 15yrs old again.....And our Match percentage was only 61% and there is 220 miles between us too We are so, so excited to hopefully grow older together.
Dave, 12 September 2023
I met my partner on Rest Less 7 months ago, things are going really well. Thank-you Rest Less another match ❤️
Christine, 22 December 2022

Cheltenham singles

Your perfect idea for a date might involve fresh air, stimulating conversation, and perhaps a little bit of light exercise. Or, you might prefer sampling some tasty food and delicious drinks. Whatever gets you excited, you'll undoubtedly be able to find it in the charming town of Cheltenham.

Cheltenham couldn't be any more perfect for an outdoor date. With loads of stunning nature walking routes winding their way around the surrounding area, you're spoilt for choice if you want to take your date on a romantic hike. Why not consider taking a walk up Cleeve Hill? It's the highest point in Gloucestershire and it boasts spectacular views of Cheltenham town - perfect for sparking a romantic moment.

If you'd like to keep things in the town centre but still want to get some fresh air, then you could consider taking a stroll around the Imperial Gardens; a beautiful, well kept Regency- era garden situated between the Queens Hotel and the Town Hall. There's even a bar where you can enjoy a drink or two on a sunny day.

For a first date that allows you to get to know each other while enjoying something fun, you can't go wrong with dinner and drinks. There are loads of restaurants and bars in the town centre of Cheltenham to suit a wide range of people. Gin & Juice on the Promenade mixes up an especially good cocktail.

And finally, for something a little more lively, why not catch a stand-up show at The Strand's comedy club, or a gig at the Gloucester Guildhall, one of the UK's most interesting and diverse entertainment venues?

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Feedback from members we've helped in the past.

Thankyou. Appreciate prompt and clear response
Anne, 21 September 2023
Many thanks for your very swift and helpful reply.
Gail, 27 June 2023
Thank you for your feedback, much appreciated.
Deborah, 05 November 2023