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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

CreativeDreamCreativeDream
4
47
CreativeDream

64 - Cheltenham, Gloucestershire, England

I have my own take on life, I live it to the full and take nothing for granted. I’m house and design obsessed...

KL61KL61
2
2
KL61

64 - Cheltenham, Gloucestershire, England

I’m a well travelled guy who’s still curious about life. My kids say I’m a bit of a social butterfly. I like all...

Elf33Elf33
4
21
Elf33

66 - Cheltenham, Gloucestershire, England

I’m fun to be with and don’t take life too seriously. I’m up for new adventures as well as relaxing at home. In...

ToKnightToKnight
4
8
ToKnight

71 - Cheltenham, Gloucestershire, England

I am interested and I think interesting, usually I surprise people as they think I am a lot younger than my age.

IainBikerIainBiker
10
0
IainBiker

60 - Cheltenham, Gloucestershire, England

I love going to gigs and travelling whenever possible, I’m comfortably off and looking for someone to enjoy life...

Happy1_ereHappy1_ere
3
47
Happy1_ere

61 - Cheltenham, Gloucestershire, England

I’m kind and genuine. I’m easy to get on with and have a happy disposition. I’m very down to earth person that...

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Success Stories

We spoke on 18th July and we are so in love. We are soulmates.
Al, 06 January 2026
I've got engaged to a lovely lady and we have just celebrated a year together despite being 180 miles apart.
Jon, 16 January 2026
I met my match first time we are very happy thank you for giving me a second chance in life
Adrian, 20 May 2025

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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Thank you so much for helping I really apreciated it. I am not an expert in using date apps I am learning how to use it. My gratitude to all of you.
Luci, 13 January 2026
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