Chesapeake is like the overshadowed younger sibling of Norfolk and Virginia Beach. It’s the third-most populous city in the state, yet it has a reputation for being a bedroom community. As in, the town where your bedroom is, but your work life and social life take place outside the city limits.
This city is more than a sleepy town of commuters, however. Chesapeake is big and bustling in its own right, and it’s time for the community to come into its own.
You don’t have to travel to neighboring cities to meet new people and find dates in Virginia. You can use our list of ways to meet singles in Chesapeake to bring some excitement in your love life and give you a reason to stay in town for the long haul.
Chesapeake Dating Sites
Our dating experts all agree that online dating is the most popular and the most effective way to meet someone these days. That wasn’t always the case, but an influx of users and a rise in success stories has effectively gotten rid of the stigma attached to online dating. According to a 2016 study, 59% of Americans say online dating is a good way to meet people. So why not give it a try? You can use the following high-tech tools to zero in on your type of date.
Best Singles Site
Virginia may be the Mother of Presidents and the Mother of States, but Match is the Mother of Dating Sites. Founded in 1995, it has been around longer than any other dating platform, and the company has learned a thing or two in that time. Today, Match has a tried-and-true match algorithm that hones in on what its members want.
- Relationships: Friends, Dates, and Relationships
- Match System: Browse by zip, age, appearance, more
- Our Experts Say: Match has facilitated the most dates and relationships of any dating site, and its large audience and high success rate make it our top review. Our Review »
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Over 50 & Senior Sites
OurTime is a dating site for singles over 50. After all, there’s no age limit on love. The site’s user-friendly search and matching features help men and women of a certain age navigate the online dating scene with ease. It takes less than two minutes to sign up, complete a profile, and start browsing for local dates.
- Relationships: Dates and Relationships
- Match System: Search by profiles by zip and more
- Our Experts Say: OurTime is well-known in the over-50 dating crowd, particularly because it has a ton of helpful search features and an easy layout. Our Review »
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For Black Men & Women Only
Chesapeake is a racially diverse city. Nearly 30% of residents identified as black or African-American in the 2010 census, and that number continues to grow year over year. Anyone interested in finding a date in the local black community can use the niche dating site BlackPeopleMeet to network with Virginian singles who share a similar ethnic background.
- Relationships: Deep Relationships or Just Casual Dates
- Match System: Search by location, age, more
- Our Experts Say: BlackPeopleMeet.com is the one of the largest and most popular dating sites for black and biracial singles, and the site is used by more than 5 million people a month. Our Review »
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Hookup & Sex Site
Adult Friend Finder is the go-to dating site for singles, swingers, and couples who just want to hook up. You don’t have to make a big commitment to land a romantic date here. Everyone is pretty open about their desires, fetishes, and goals in live chat rooms and video calls.
- Relationships: Hookups Only
- Match System: Search by location, interest, more
- Our Experts Say: Make no mistake: this site isn't about making friends, it's about finding hookups and casual encounters. No adult site has a larger or more active user base of those seeking discreet fun. Our Review »
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Popular Dating Apps
Chesapeake is a coastal city with a big commuter population, so its residents are constantly moving around and covering a lot of ground. That can make dating difficult — unless you have the location-based tools of a dating app behind you. Dating apps can locate dates based on their proximity to you, and that means you never have to look very far to find someone to chat and match with you.
Match.com
- Relationships: Fun Dates, Serious Relationships
- Match System: Browse by location, age, interest, and more
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About the App:
Available via the App Store and Google Play, Match is a fantastic app for dates and relationships. With a user base of 30 million singles, Match is where you’ll have a high chance of success. It’s free to download, create a profile, search for date prospects, and receive compatible matches based on personalized preferences. Free members can also chat with select members and send unlimited likes.
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eharmony
- Relationships: Long-Term Relationships, Marriages
- Match System: Get daily match suggestions
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About the App:
Responsible for 4% of marriages in the U.S., eharmony is among our top picks for relationship-minded heterosexual singles. To become a member, add the app to your phone (iOS or Android) and then take its 29 Dimensions® of Compatibility Matching Quiz. It’s absolutely free to do both these things — as well as receive matches and communicate during other special events.
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OurTime.com
- Relationships: Dating and Relationships
- Match System: Search by age as well as zip, gender, more
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About the App:
Made just for single seniors, OurTime is one of the most well-known niche dating apps. It’s a fun and straightforward app with simple swiping features. Once two people swipe right on each other, they can communicate. For more match options, visit the ConnectMe and I’m Interested pages.
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Chesapeake Singles Bars
Meeting in person is the fastest way to establish chemistry, which is why some singles still prefer the bar scene to the online dating scene. If you’d rather sit back with a drink in hand and scope dates without your phone, then you should head to a Chesapeake bar on a Friday or Saturday night. Many singles turn out in the evening in hopes of meeting someone to share a round of drinks and good conversation with them.
The Eagles Nest Rockin' Country Bar
Just for the name alone, The Eagles Nest Rockin' Country Bar deserves a spot at the top of our list of favorite bars in Chesapeake. This place gives guests a rocking good time seven nights a week. The bar has three spacious dance floors, multiple stages, and a mechanical bull named Sally, for crying out loud. If you enjoy pub grub and signature cocktails, then you're in luck because this menu hits on all the classics. The kitchen stays open until the wee hours of the night (until 2 a.m. seven days a week), and many locals say that the wings are out of this world.
Buckets Bar and Grill
The awesome bar food separates Buckets Bar and Grill from the average Chesapeake drinking establishment. You can get a plate of boneless wings smothered in sauce or chicken nachos piled high with toppings. The bar's Friday specials include $3 drinks and $5 appetizers, and the kitchen's famous wings only cost 50 cents apiece on Wing Wednesdays. Buckets Bar and Grill may not be a fancy place, but it's a friendly place. That's really what counts when you're looking for a date.
Big Woody's Bar & Grill
Big Woody's Bar & Grill is the perfect place to kick back with a few friends and enjoy great food, great drinks, and great company. This neighborhood bar draws people because of its cheap prices, but they stay because the service is just that good. The live music and American fare keeps everyone happy as they unwind after a long day or a long week. You can chill out on the outdoor deck that overlooks the water and take a load off your mind.
Smokey Bones Bar & Fire Grill
Who says chains can't be good? Most often chain restaurants are popular for a reason. In the case of the Smokey Bones Bar & Fire Grill, it's the delicious barbecue. The restaurant's cozy atmosphere and indulgent menu can satisfy just about anyone. You can grab a meal at the bar and start chatting with people who share your appreciation for prime rib, bourbon chicken, and mac and cheese. Smokey's fire-grilled favorites will have you licking your fingers and wondering when you can come back for more.
Branches Tasting Room
We have a lot of grills and restaurants on this list, but not everyone wants a burger and beer to cap off their evenings. Some would prefer a nice glass of wine and a light appetizer to munch on. That's Branches Tasting Room's specialty. This upscale tasting room began as an idea between a father and son to raise the bar in Chesapeake with a selection of award-winning wines. Now many local wine lovers gather here for a quiet conversation in a classy setting. Take a look at the event calendar to find out about upcoming wine pairings, brunches, and tastings.
LongShots Billiards & Darts
The odds are good that you'll find a new friend at LongShots Billiards & Darts. This large and inviting pool hall features 17 billiards tables and eight dart boards, so it's easy to spend hours here playing games and shooting the breeze. Regulars often challenge each other to friendly matches, and you don't have to be an expert player to jump in. The LongShots bar stays open until 2 a.m. from Monday through Sunday. Daters on a budget are in luck because there's no cover charge to get in and games of pool only cost $1.
Chesapeake Speed Dating
Trying to date on your own is like taking back roads from Greenbriar West to Portsmouth, whereas speed dating is like taking Interstate 464. It just saves time. You can jump on an expressway to romance by finding a locally organized speed dating event in Chesapeake. These events don’t come around every week, or even every month, but they tend to attract a large crowd of relationship-minded singles. Keep an eye on Eventbrite’s calendar for updates.
Chesapeake Singles Events
The problem with dating at a bar or club is that you never know who’s single and who’s not until you talk to them. That problem doesn’t exist at a singles event. Everyone there is available and looking to meet someone special. Singles mixers and meetups offer a casual space where men and women can have a conversation without feeling under an obligation to set up a date. If you’re a friends-first kind of dater, a singles meetup should be right up your alley.
Chesapeake Singles Clubs
Some daters make the best first impression on the dance floor. Nightclubs offer singles a chance to show off their moves and make a date without having to say very much at all. They can let the music carry them away and help them build connections within the span of a single song. You don’t have to be a dancing queen to enjoy this partying atmosphere either. The lounge and bar can let you stay on the sidelines and still mingle with outgoing people.
Chesapeake Chat Rooms
Chat rooms have a lot of upsides for singles. For one thing, it’s free to join. For another thing, you can use a handle instead of your real name and retain some privacy. Chat rooms are also low-risk dating environments where you don’t have any pressure to link, flirt, or match with anyone. You can just talk and see where things go. If you don’t see any date prospects, then exit out of the window and move on to the next chat room and try your luck there.
Chesapeake Personals
In the “Escape (The Piña Colada Song),” Rupert Holmes tells a story about how personal advertisements can bring excitement to a drab love life. This old-fashioned form of communication offers a safe way to explore your options and fantasize about a special pen pal. Now dating personals have given this practice an upgrade. Your dating personals profile needn’t go into detail about your drink preferences or yoga habits — you just need to explain who you are and what you’re looking for online.
Attend a Festival, Fair or Community Event
When you’re single, it can be easy to stay at home and get stuck in a rut, but you’re never going to meet someone while curled up on your couch watching Netflix. You have to get out there and make something happen. Which means you have to go where the people are.
Chesapeake hosts many public events where singles can engage with one another in a casual and fun atmosphere. Whether you’re looking fresh produce at the farmers’ market or discovering beauty at an arts fair, you can expand your social network by mingling at community events. Check out Chesapeake’s calendar to find out when and where to go.
The Chesapeake Jubilee offers a weekend of amusement for locals and visitors.
The Chesapeake Jubilee is among the most popular and highly anticipated events in the city. Every May, the event delights attendees with a weekend of carnival rides, games, BBQ competitions, livestock shows, shrimp feasts, and fireworks. This event kicks off the summer season on a high note and gives locals plenty of opportunities to laugh and have a great time.
Dating is at an All-Time Peak in Chesapeake
As the youngest of three myself, I relate to Chesapeake’s struggle to stand out and make a name for itself. Just as I’m more than a little sister to my big brothers, Chesapeake is more than Norfolk’s neighbor. This large and diverse community has flourished in the last few years as more people settle there for more than just the night.
You can make inroads in this lush dating ground by attending events, creating dating profiles, and becoming more socially active in general. Our list of ways to meet people is just the beginning. You can create your own opportunities to connect with singles and get involved if you follow your passion and don’t give up. Good luck!
