Annapolis singles: Naval charm, waterfront dates, and a surprisingly tight pool
About 3,950 singles live in Annapolis, with a population of about 39,000 people. It’s a small capital with a harbour feel, so dating here tends to be part scene, part radius search. More options come from the nearby towns around Maryland, fast.
3,950singles in Annapolis
Which sites are worth it in Annapolis
What are you looking for in Annapolis?
Searching for
Beyond the usual Tinder, Bumble & Hinge, why don't you try:
Adultfriendfinderi9
★★★★★
130members in Annapolis
30 ♀ · 100 ♂
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
★★★★★
40members in Annapolis
10 ♀ · 30 ♂
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 Annapolis
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 Annapolis
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 Annapolis
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 Annapolis
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 Annapolis
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 Annapolis
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 Annapolis
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 Annapolis
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 Annapolis
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
★★★★★
940members in Annapolis
350 ♀ · 590 ♂
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
★★★★★
1,180members in Annapolis
500 ♀ · 680 ♂
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 Annapolis
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
★★★★★
310members in Annapolis
50 ♀ · 260 ♂
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
★★★★★
50members in Annapolis
20 ♀ · 30 ♂
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
★★★★★
180members in Annapolis
30 ♀ · 150 ♂
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 Annapolis
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 Annapolis
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 Annapolis
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?
Maryland: 46%
About 3,950 singles live in Annapolis, and that number tells you the main thing: you can date locally, but you should not pretend the pool is huge. Walkable and social, yet small enough that you will notice repeat faces pretty quickly.
So the first move is usually online. For short-term, adult-focused matches, AdultFriendFinder is built for people who want to skip the long warm-up. For discreet connections, Ashley Madison fits better, and if you want a more openly no-strings setup, BeNaughty gives you that lane.
Annapolis works best when you keep one eye on the waterfront and the other on the map. Annapolis gives you an easy first-date rhythm, but the real range comes from places like Severna Park, Crofton, and Odenton. That’s where the extra matches are hiding.
How dating feels in Annapolis
This is a place where people know the name of the street, the marina, and often the person behind the counter. That can be nice. It can also make everything feel a little too visible, especially if you want discretion. A lot of locals end up mixing a small-city social circle with broader search settings so they are not stuck dating the same six profiles forever.
For that reason, the strongest picks are the ones that match your intent. SDC makes sense if you are looking for swingers and open-minded couples. Heated Affairs is the cleaner fit for affair-minded dating. And if you want an added layer of privacy, Victoria Milan stays in that discreet lane.
Where people in Annapolis actually end up meeting
You will get the best results by combining local face-to-face life with nearby-town reach. Annapolis is compact, so people drift between the harbour area, the downtown core, and the larger Maryland corridor. That mix gives you enough variety without making every date feel like a project.
Stay local, and keep expectations realistic. Good for a quick coffee, a walk, or a low-pressure drink. For more breadth, widen the search and let the surrounding towns do some of the heavy lifting.
- Use one mainstream profile for visibility, then a discreet site if your goal is private dating.
- Keep your search radius open enough to include nearby Maryland towns.
- Don’t wait for the perfect match to appear in one zip code. In a place this size, that gets old fast.
One more thing: if you are looking for something very specific, test a second site rather than forcing one app to do everything. That saves time, and in a town like Annapolis, time matters.
Top 8 First-Date Ideas in Annapolis
- City DockClassic Annapolis energy, easy to walk, and simple to leave if the vibe is off.
- Main StreetPlenty of casual places to grab a drink or coffee without making the date feel formal.
- U.S. Naval AcademyGood for a scenic walk and a date that feels a little more memorable than a standard coffee stop.
- City MarinaWater views do a lot of the work for you and keep the mood relaxed.
- Susan Campbell ParkOpen, public, and good for a short meet-up before deciding whether to extend the date.
- West StreetA good pick if you want more restaurant and bar options without driving far.
- Quiet Waters ParkWorks well if you want a calmer first date and a bit more breathing room.
- Maryland State House areaCentral, easy to reach, and useful if you want to combine history with a short walk.
FAQ
How many singles are in Annapolis?
About 3,950 singles live in Annapolis, so the pool is real but not massive. You’ll usually do better if you search both locally and in nearby towns.
Which dating site works best for Annapolis singles?
It depends on what you want. AdultFriendFinder is good for adult casual dating, Ashley Madison for discreet connections, and BeNaughty for a more open no-strings approach.
Is Annapolis too small for online dating?
No, but you should not expect endless local volume. Annapolis works best when you use radius search and stay open to nearby Maryland places.
What kind of dating works best in Annapolis?
Low-pressure dates work best here. Coffee, a walk, or a waterfront meet-up usually fits the city better than anything overbuilt.
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.