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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

CosmicbeautyCosmicbeauty
6
49
Cosmicbeauty

72 - Cheltenham, Gloucestershire, England

Fun to be with according to my friends and happy . Love entertaining and company . I have a positive look on...

CheerfulchappieCheerfulchappie
2
2
Cheerfulchappie

67 - Cheltenham, Gloucestershire, England

I like to think I'm a reasonably good looking, educated fellow (now retired) living in Gloucestershire. Although...

millbrook61millbrook61
10
3
millbrook61

64 - Cheltenham, Gloucestershire, England

Friendly, sociable, optimistic glass always full type of guy. Enjoy travel , walking, countryside, coast, wild...

ShirltheGirlShirltheGirl
4
0
ShirltheGirl

65 - Cheltenham, Gloucestershire, England

I've been on my own since 2019 and I love the freedom that gives me ... but that doesn't mean I wouldn't like a...

sweetcheekssweetcheeks
1
2
sweetcheeks

66 - Cheltenham, Gloucestershire, England

Caring, and fun loving personality. Enjoys working hard and playing hard, good food, good wine, movies, walking...

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...

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The profile process is great, and very thorough, and being specific about what you're looking for makes it easy to see who's a match for you. We had a 90% match rate, and once we started talking it was clear that we were destined to be together, and this platform gave us the nudge we both needed. I can't thank you enough, I can honestly say that I have never been happier.
Carol, 07 September 2025
I met three very pleasant gentlemen but number 4 was the one for me. We have now been together for nearly four years and are in the process of setting up house together.
Alison, 26 May 2025
Many thanks. Online dating is under rated.
Kevin, 03 August 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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