One of my first online pen pals was a girl living in Madison, Wisconsin. We met on a Harry Potter discussion forum — because that’s what you did in 2004 — and began sharing stories from our lives. I told her about the sunny beaches of Florida while she told me about freezing Midwestern winters.
I asked her once what there was to do for fun in her town, and she answered, “Haha, nothing. It’s such a cheesy place.”
My friend couldn’t wait to grow up and escape Madison, but Wisconsin’s capital is hardly a social desert. It has an estimated population of over 280,000 people and a population density of 3,500 people per square mile. It’s packed with people to meet and things to do, if you know where to look.
In honor of Emily, proud Hufflepuff and Madtown native, I give you the top nine ways to meet interesting people in Madison, Wisconsin.
Madison Dating Sites
Dating has changed a lot since Madison’s founding days in 1829. In those days, single men and women had to rely on family connections and horse-drawn carriages to meet new people. Now you can simply log into a dating site and find thousands of date prospects at your fingertips. Online dating is the modern single’s best friend because it puts them in touch with a wide dating pool and helps them narrow that pool down to the most desirable candidates. We recommend trying out the following free dating sites next time you’re in the mood to flirt.
Best Singles Site
Match is hands-down the best dating site for relationship-minded singles. Since 1995, this platform has honed its match algorithm and highlighted important personality traits and interests in its in-depth profiles. You can look through dozens of personal bios in your search for love in Madison.
- 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 »
- Browse Free: View Photos Now
Over 50 & Senior Sites
The cold climate may not be ideal for seniors in Dane County, but the local dating scene isn’t nearly so inhospitable. Singles over 50 can use a niche dating site like OurTime to meet warm and friendly people in the same age group. This mature dating environment makes singles of a certain age feel comfortable building friendships and picking up dates online.
- 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 »
- Browse Free: View Photos Now
For Black Men & Women Only
Only 7.3% of Madison’s population identifies as African-American, so seeking a date in the black community in this predominantly white town poses somewhat of a challenge. However, BlackPeopleMeet can meet the dating needs of black and biracial singles with its diverse national database.
- 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 »
- Browse Free: View Photos Now
Hookup & Sex Site
When singles want to hook up, they can depend on Adult Friend Finder to be their wingman in the online scene. This sex-oriented dating site facilitates fast-paced connections between naughty singles, swingers, and couples. If you’re looking for some no-strings-attached fun, you can create a profile on AdultFriendFinder and browse through millions of hot photos for free.
- 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 »
- Browse Free: View Photos Now
Popular Dating Apps
Dating apps bring the online dating experience to the palm of your hand, and that makes them as good as gold to modern singles. You no longer have to wait until you’re near a computer to like a profile or send a response to your online crush. All you have to do is download the app and start swiping and matching to your heart’s content. Many popular dating networks have begun adapting to the mobile age and offering dynamic platforms that combine new-school technology with old-school charm. We’ve listed reviews for a few of our favorites below.
Match.com
- Relationships: Fun Dates, Serious Relationships
- Match System: Browse by location, age, interest, and more
-
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.
- Browse Free: View Photos Now
eharmony
- Relationships: Long-Term Relationships, Marriages
- Match System: Get daily match suggestions
-
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.
- Browse Free: View Photos Now
OurTime.com
- Relationships: Dating and Relationships
- Match System: Search by age as well as zip, gender, more
-
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.
- Browse Free: View Photos Now
Madison Singles Bars
All right, maybe technology isn’t working for you, and you’d rather meet people in person. I get that. Sometimes it’s easier to establish chemistry and build a relationship in person than in a series of text messages. If you’re looking to get your flirt on in Madison’s dating scene, you can always hang out at a neighborhood bar, brewery, pub, or winery. These casual spots offer a ton of opportunities to enjoy yourself and make conversation with someone new.
The Old Fashioned
Named after its favorite drink, The Old Fashioned is a classic American tavern serving classic Wisconsin fare. We're talking artisanal cheese plates and buttery sandwiches topped with aged cheddar. Monday nights are cheeseburger nights here, so you can enjoy buy-one-get-one-free deals on its local grass-fed beef burgers. You can also stop by for affordable tacos on Tuesdays, fish fries on Wednesdays and Fridays, or BBQ ribs on Thursdays. If you make friends and become a regular here, be sure to check out the Big Shot program, which offers exclusive discounts to returning customers.
The Mason Lounge
The Mason Lounge looks more like a quaint living room than a bar. People can lounge on squishy couches and recliners or choose a table near the bar. The bartenders treat everyone like part of the family and can always provide a drink recommendation to anyone overwhelmed by the extensive selection of beers and liquors. The Mason Lounge doesn't serve food, but it does host improv jazz nights to add to its laid-back, devil-may-care ambiance. "My concept was to be nothing like any of the other bars that had been in that space," said the owner Bryan Richgels.
The Great Dane Pub and Brewing Company
The Great Dane has cultivated a winning reputation as the best locally owned brewery in Madison. Its beer garden, rotational menu, dart boards, and pool tables can keep anyone entertained for an evening. Since 1994, this beloved bar has featured a 10-barrel brew house, a casual billiards lounge, and an outdoor seating area where people can congregate freely. The Great Dane's food is amazingly delicious and affordable, so definitely check out the burgers, pretzel sticks, wings, and other pub grub here.
HopCat
The open and friendly atmosphere at HopCat has won over many a Wisconsinite over the years. And if the cool vibes don't get you hooked, the extensive menu surely will. You can find seasonal brews on tap and plenty of home-grown grub on the menu. These juicy burgers are packed with flavor. Plus, HopCat puts on live shows on weekend nights to help people relax and get into a partying mood. "I'm a lover of sitting at the bar, so that's where you'll find me at HopCat," said Patti T. in a Yelp review. "I love the selection of beers."
Madison's
Located on King Street, Madison's is a two-story bar that serves artisanal cocktails and the best wings in the city. You definitely should come here hungry because everything on the menu is incredibly filling. Take the Madison Burger, for example. This monstrous meal includes two four-ounce beef patties on a butter roll with cheese, dijonnaise, pickles, and thick-cut bacon (optional but encouraged). Madison's brings in a local DJ every weekend and a live band every Thursday to get everyone on its two dance floors.
Blue Velvet Lounge
The Blue Velvet Lounge's bartenders know how to pour a smooth drink that packs a punch. This retro martini bar is a great place to have a few drinks and light up the dance floor with someone special. Whether you're into passion fruit drinks or boozy ice cream cocktails, the Blue Velvet Lounge has something tasty to satisfy you. This sophisticated bar and lounge doesn't serve food because its signature drinks are enough to attract a lively crowd. "If you haven't been, go," said one Facebook review. "It's a classy little lounge with a variety of fun and delicious martinis."
Madison Speed Dating
Don’t have time to go out every night of the week and pursue multiple dates at once? Then speed dating may be more to your liking. This time-saving event gives singles a chance to sort through dozens of date prospects in an evening and select only those with whom they feel a genuine connection. If that person feels the same way, you’ll exchange contact information and can go on a longer date another time. Thanks to speed dating, Madison singles don’t have to waste more than five minutes on incompatible dates.
Madison Singles Events
If you spend your days surrounded by couples, attending a singles event will be like entering a whole new world. These flirtatious events lead to so many dating opportunities and romantic moments that it’s well worth the price of admission. You can find a meetup centered around an activity, or you can attend a general singles mixer around town. We recommend Lock And Key Events, which organize parties for 80+ men and women at local bars, restaurants, and other venues.
Madison Singles Clubs
The club scene appeals to many singles because it gives them a chance to make a great first impression without saying a word. They can let their dance moves do all the talking for them. Madison has a thriving nightlife, populated mostly by college students and young professionals, and it’s easy to get into the swing of things by making a trip downtown. Whether you’re dancing up a storm at the High Noon Saloon or relaxing by the bar at the Blue Velvet Lounge, Madison provides a wealth of entertainment in a social atmosphere.
Madison Chat Rooms
I know from experience that you don’t need to see someone in person to make a friendly connection with them. As long as you have something in common — a fandom, perhaps — you can build a relationship one conversation at a time. Online chat rooms give singles the ability to bond with one another and discover common interests in a casual environment. You can hop in and see what people are talking about, and it’s easy to add your two cents or exit out if you don’t see anyone worth chatting up. We recommend the following local chat rooms for Madison residents looking to meet someone on the fly.
Madison Personals
Placing a personal ad for a local date used to be this involved process of contacting a newspaper, paying a fee, and haggling over wording. Nowadays, it’s much easier to put yourself out there on a dating personals site. You can create a free account using a valid email address and then post a bio that communicates what you’re looking for in the dating scene. Whether you’re interested in making a friend or finding a hookup, you can state your case and seek a like-minded personal on a dating personals website.
Attend a Beer, Music or Cultural Festival
The City of Four Lakes is a cultural hub in the Midwest. Many organizations host concerts, food fests, and other extravagant events for the community throughout the year. Singles can spend a day mingling at local events to make new friends and have a great time while they’re at it.
The Monona Terrace plays nighttime movies during the summer months.
The Monona Terrace Community & Convention Center livens up the downtown area by hosting free rooftop concerts throughout the summer. Hundreds of people show up to these events. Check out the community programs and event calendar to find out what the convention center has going on right now.
Since 1987, the Great Taste of the Midwest beer festival has been the delight of Madison residents celebrating the end of the summer. The event features over 190 brewers in Olin Park. Every August, this sold-out festival creates a lot of hustle and bustle in the city streets. It has the distinction of being the second longest-running event in North America, so it must be doing something right.
Fall Madly in Love in Mad City
I lost touch with my Wisconsin pen pal by the time we reached young adulthood, so I don’t know where she ended up. Maybe she went to school out of state and never looked back, just like she’d planned. Or maybe her hometown’s natural charm and cheesiness grew on her as she matured, and she found something to love within its borders.
Wherever she is, I hope she’s met worthwhile people who make her days a little brighter. If that’s your goal as well, you can always get out there and meet fantastic folks in and around Madison. The city may be a bit cheesy, but it’s got a lot of heart, and that’s what counts.
