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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


59 - Cheltenham, Gloucestershire, England

I am outgoing, cultured, funny with a dry sense of humour (boring on dark) I am an animal lover and enjoy...


39 - Cheltenham, Gloucestershire, England

Single, currently living in Cheltenham, Cotswolds area. Love life, listening to music and improving my piano...


70 - Cheltenham, Gloucestershire, England

I am sociable and enjoy the company of others. Since the death of my husband 10 years ago my life has become...


73 - Cheltenham, Gloucestershire, England

I think one of my best attributes is deciding to do things, such as holidays, days out, weekends away without...


57 - Cheltenham, Gloucestershire, England

Life is for living and there are so many wonderful things to experience in this world. I have been fortunate to...


65 - Cheltenham, Gloucestershire, England

Writer and property man, I've had two history books published, both about France during WW2, each about 150k...

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We met on the 3rd of June and we are going to France together in 2 days time. We are getting on really well. Thank you.🙏
Véronique, 18 September 2023
We matched then messaged each other using this app and met up after a week and we’ve been seeing each other regularly for 8 weeks.
Karl, 08 August 2023
It was love at first sight - found my soulmate forever.
Rachel, 29 August 2023

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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