Chesterfield singles: Plenty of choice, but you still have to cross the suburbs
About 4,850 singles live in Chesterfield, out of around 48,000 people. A solid pool for a town this size, but the real trick is that West County dates usually spread out fast. Convenience means you need to pick a service that reaches past Chesterfield and into the neighbouring suburbs.
4,850singles in Chesterfield
Which sites are worth it in Chesterfield
What are you looking for in Chesterfield?
Searching for
Beyond the usual Tinder, Bumble & Hinge, why don't you try:
Adultfriendfinderi9
★★★★★
160members in Chesterfield
40 ♀ · 120 ♂
Casual dating for adults, singles and couples
Try Adultfriendfinder for free
Review
Key facts
For casual datingFor open relationships & swingingCasual datingHookupsSwingersErotic adventures
Pricing: Average
Men / women: 77% / 23%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
AdultFriendFinder's strength is in its vast membership base all over the globe. If you are someone looking for casual fun, this site might work well for you. Check it out now.
Ashley Madisoni8
★★★★★
30members in Chesterfield
10 ♀ · 20 ♂
Dating site for discreet relationships and privacy
Try Ashley Madison for free
Review
Age distribution
Key facts
For serious datingFor fun & flirtingFind loveFlirtingSerious relationship
Pricing: High
Men / women: 70% / 30%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
Ashley Madison creates a dating environment for people exploring discreet connections on their own terms. If you want to meet like-minded individuals who value privacy and personal choice, this might be the platform for you. Join Ashley Madison today to exper…
Kasidiei7
★★★★★
10members in Chesterfield
Adult dating for couples and singles who want erotic fun
Try Kasidie for free
Review
Age distribution
Key facts
For casual datingFor fetish & BDSMFor open relationships & swingingSwingersBDSMErotic adventures
Pricing: Average
Men / women: 74% / 26%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
Kasidie is organized and reliable in making sure that its members meet up and interact in real life, rather than just fooling around online. The events and parties hosted on the site let people find other like-minded individuals personally.
Flingi7
★★★★★
10members in Chesterfield
Casual dating site for singles wanting hookups
Try Fling for free
Review
Age distribution
Key facts
For casual datingHookups
Pricing: High
Men / women: 70% / 30%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
The site is so confident that it'll find a hookup or fling for you that it even guarantees a hook up in 3 months, or else you'll get 3 more months for free. If this dating site interests you, sign up for free today!
eharmonyi6
★★★★★
10members in Chesterfield
10 ♀ · 0 ♂
For singles who want serious relationships
Try Test winner for free
Review
Age distribution
Key facts
For serious datingSerious relationshipFind love
Pricing: Average
Men / women: 47% / 53%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
eharmony is a matchmaking site for singles who are looking for serious commitments. It provides an in-depth knowledge of your match through the required personality and character tests. If you are looking for a long-term relationship and would want to settle …
Victoria Milani9
★★★★★
10members in Chesterfield
Private affair dating for married and attached people
Try Victoria Milan for free
Review
Age distribution
Key facts
For casual datingCasual datingAffairsHookups
Pricing: High
Men / women: 60% / 40%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
If you are a married or an attached individual seeking to spice up your sexual game by engaging in an affair, then Victoria Milan might be the safest site to sign up to.
BeNaughtyi9
★★★★★
10members in Chesterfield
Casual dating for singles after hookups and casual dates
Try BeNaughty for free
Review
Age distribution
Key facts
For casual datingFor fun & flirtingHookupsErotic adventuresCasual datingFlirting
Pricing: Average
Men / women: 75% / 25%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
This is a popular place for setting hookups and meet-ups within a few minutes. People here are very responsive. If you identify yourself with these characteristics, BeNaughty will not disappoint and deliver what you are looking for. Sign up now to try it your…
Red Hot Piei7
★★★★★
10members in Chesterfield
Casual dating for singles, couples and groups
Try Red Hot Pie for free
Review
Age distribution
Key facts
For casual datingFor open relationships & swingingCasual datingHookupsSwingers
Pricing: High
Men / women: 63% / 37%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
RedHotPie may be a good place to try if you are looking for many types of adult fun. It has plenty of features that are rarely offered on other dating sites. Sign up now and who knows, it might help you find your date in an instant!
EliteSinglesi7
★★★★★
10members in Chesterfield
10 ♀ · 10 ♂
Dating for educated singles wanting serious relationships
Try EliteSingles for free
Review
Age distribution
Key facts
For serious datingBest for highly educated singlesSerious relationshipFind love
Pricing: High
Men / women: 50% / 50%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
EliteSingles is a great choice for singles who are actively seeking a committed relationship. It is designed for educated and career-focused singles; many of its members have a higher level of education. If you think you're ready for a serious commitment, the…
iDatesi6
★★★★★
10members in Chesterfield
Casual dating and hookups for singles aged 20 to 35
Try iDates for free
Review
Age distribution
Key facts
For casual datingFor fun & flirtingCasual datingFlirtingHookups
Pricing: Average
Men / women: 73% / 27%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
iDates was created to appeal to both men and women generally between ages 20 and 35 who are fond of meeting new people. You can flirt and use the entertainment factors on the app with matching functions. iDates is best used for casual dating and hookups.
Swing Lifestylei3
★★★★★
10members in Chesterfield
Dating site for swingers and open relationships
Try Swing Lifestyle for free
Review
Age distribution
Key facts
For casual datingFor open relationships & swingingSwingersCasual dating
Pricing: Average
Men / women: 73% / 27%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
Besides interactivity, SLS also offers swingers special features such as erotic stories, DVDs, adult toys, and more. Even though the website could benefit from a little renovation, the developers made sure that their functions served their crystal clear purpo…
Tinderi0
★★★★★
1,100members in Chesterfield
410 ♀ · 690 ♂
Dating app for singles who want relationships, hookups and flirts
Review
Age distribution
Key facts
For serious datingFor casual datingFor fun & flirtingFlirtingHookupsSerious relationship
Pricing: Average
Men / women: 63% / 37%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
Tinder has pretty much revolutionized the online dating scene with its swipe function. Overall, though, this dating platform is confirmed to be legit and accessible. You can also check out other Matchmaker Sites that might be a better fit.
Bumblei0
★★★★★
860members in Chesterfield
360 ♀ · 500 ♂
Dating app for singles wanting matches and new relationships
Review
Age distribution
Key facts
For serious datingFor fun & flirtingSerious relationshipFriendshipFlirting
Pricing: Average
Men / women: 58% / 42%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
Bumble aims to give women more control in their dating choices and its mechanics have been overwhelmingly accepted by both genders. The app continues to provide a safe dating experience for all of its users.
Tawkifyi3
★★★★★
10members in Chesterfield
Online matchmaking for singles after serious relationships
Try Tawkify for free
Review
Age distribution
Key facts
For serious datingSerious relationshipFind love
Pricing: Very high
Men / women: 55% / 45%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
Tawkify is one unique online matchmaking service provider. It does not have too many frills and the service is easy to understand. It is perfect for young singles who are always on the go and only have little time for dating. For these reasons, joining Tawkif…
Taggedi0
★★★★★
280members in Chesterfield
50 ♀ · 230 ♂
Social dating for friendship and dates
Review
Age distribution
Key facts
For serious datingSerious relationshipFriendship
Pricing: Average
Men / women: 83% / 17%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
Tagged started out as a "social discovery website" but eventually tried to step into the online dating industry. The transition wasn't done properly and the website is now an awkward mix of a dating service with underage members and a gaming website with adul…
Badooi0
★★★★★
260members in Chesterfield
90 ♀ · 170 ♂
Dating app for younger people looking for love or casual dating
Review
Age distribution
Key facts
For serious datingFor casual datingSerious relationshipCasual datingFriendship
Pricing: Average
Men / women: 65% / 35%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
Badoo does a good job connecting members who are attracted to one another. With its Encounters feature, the matching of members is sped up and done so with utmost efficiency. However, Badoo may not be the best for people who are searching for a lifetime partn…
Candy.aii8
★★★★★
270members in Chesterfield
50 ♀ · 220 ♂
Virtual dating for adults who want AI companionship
Try Candy.ai for free
Review
Age distribution
Key facts
For casual datingChatErotic adventures
Pricing: High
Men / women: 82% / 18%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
Candy.ai offers a detailed platform for creating your own AI companion, combining intimacy and fantasy. With advanced customization, secure data storage, and smooth interactions, it's ideal for virtual relationships. Explore the future of intimate virtual com…
SDCi9
★★★★★
10members in Chesterfield
Swingers platform for couples and singles in the lifestyle
Try SDC for free
Review
Age distribution
Key facts
For casual datingFor open relationships & swingingSwingersErotic adventures
Pricing: High
Men / women: 67% / 33%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
If you're a swinger looking for real fun and excitement, then SDC might be the home for you. It's more than that, as it offers parties, events, travels, and other exhilarating features. This home for swingers actually values your privacy. Want to try out the …
Secret Benefitsi8
★★★★★
10members in Chesterfield
For singles wanting transactional sugar dating
Try Secret Benefits for free
Review
Age distribution
Key facts
For serious datingFor casual datingFor fun & flirtingSerious relationshipFlirtingCasual dating
Pricing: Average
Men / women: 75% / 25%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
Secret Benefits gives both the Sugar Baby and the Sugar Daddy a simple and straightforward platform to find and arrange dates. Thus, if you are into sugar dating and would like to experience this fast and no-fuss service, try the site today!
WooPlusi6
★★★★★
10members in Chesterfield
Dating app for plus size singles wanting long term relationships
Try WooPlus for free
Review
Age distribution
Key facts
For serious datingFor fun & flirtingAffordableSerious relationshipFriendshipFlirting
Pricing: Cheap
Men / women: 60% / 40%
Where demand is highest
The darker a region, the more often this provider is searched for there. 100% marks the region with the highest demand; 50% means half as many searches.
WooPlus proves to be a viable place for plus-size women and men's romantic partners. Most users of the site are not afraid to show off their curves. It is highly recommended for plus-sized singles to experience using WooPlus.
Where is interest in online dating strongest?
Missouri: 46%
Chesterfield sits in West County, so dating here is less about bumping into someone on one busy main street and more about how far you are willing to drive for a first coffee. Radius search matters here. A decent app can pull in people from Ballwin, Wildwood, Kirkwood, and Maryland Heights without making you waste an evening on dead matches.
For something more casual, Adultfriendfinder is the obvious short-term pick. It suits a place like Chesterfield because people here often split their time between home, work, and the car, so direct intent saves a lot of chatting that goes nowhere.
For discreet side connections, Ashley Madison is the more relevant option. In a suburban area like this, privacy matters as much as volume, and that is where it has the edge.
For something a bit more upfront and flirt-heavy, BeNaughty gives you that quicker pace. It is better when you want to move past the polite small talk and see who is actually available nearby.
Chesterfield itself does not have the density of a downtown scene, so the winning move is simple: widen the search, stay realistic about distance, and use apps that fit your goal instead of trying to make one service do everything.
Nearby towns worth checking: Ballwin, Wildwood, Maryland Heights, Saint Charles, Saint Peters, Kirkwood, O'Fallon, Hazelwood.
Top 8 First-Date Ideas in Chesterfield
- Central ParkAn easy low-pressure start, with walking paths, open space, and room to keep the conversation moving.
- Chesterfield AmphitheaterA simple place for an outdoor walk or a summer event, with enough activity to avoid awkward silences.
- St. Louis County LibraryQuiet, public, and surprisingly good for a short coffee-and-books date if you both like low-key plans.
- Faust ParkPlenty of space to walk, talk, and decide if you want to extend the date without pressure.
- The Butterfly HouseA built-in conversation starter, and it feels more memorable than another standard coffee meet-up.
- Spirit of St. Louis Airport Observation AreaA casual spot for plane spotting and a short, easy date that does not feel forced.
- Riverwoods ParkA relaxed outdoor option with trails and enough scenery to keep things light and comfortable.
- Historic Downtown ChesterfieldGood for an easy stroll, a little people-watching, and a flexible first meet-up.
FAQ
How many singles are there in Chesterfield?
About 4,850 singles live in Chesterfield. Enough to give you choice, but not enough to ignore the nearby suburbs.
Which dating site fits Chesterfield best?
It depends on what you want. Adultfriendfinder fits casual dating, Ashley Madison fits discreet connections, and BeNaughty works if you want a faster, more flirt-first pace.
Do I need to search beyond Chesterfield?
Yes, probably. Chesterfield works better when you include nearby towns like Ballwin, Kirkwood, and Maryland Heights, because the local pool spreads out quickly.
Is Chesterfield good for casual dating?
Yes, as long as you use the right service. Casual and discreet platforms make more sense here than trying to rely on one small local pool.
Founder of DatingScout and Author of the book "Online Dating for Dummies"
Chris founded DatingScout 17 years ago, and today he is one of the leading Online Dating Experts. He is the author of the book "Online Dating for Dummies" and the author of the Internet's largest online dating study analyzing 20 Million Profile Pictures with artificial intelligence. Chris Pleines holds a master degree in media science and appeared in numerous television interviews and publications to give expert advice as well as tips about online dating.