Have you been having a tough time coming across any worthwhile Boston casual encounters? The truth of the matter is that finding people for a hot tryst means knowing exactly where to look. Fortunately, we’ve come up with a gameplan to help you find someone naughty anywhere and at any time.
While you may have assumed that bars like Mr. Dooley’s Boston and Oak Long Bar + Kitchen were go-to places for casual encounters in Boston, you’d be mistaken. In fact, many men have spent hours driving along Route 28 after heading to these bars only to come back home to an empty bed. So if you’re ready to make use of your time, then check out our list of recommendations for both bars and sites. Our list will help you find the naughtiest Boston casual encounters that the city has to offer.
So check out our list and quit wasting time at bars and on sites that won’t get you lucky!
Where Boston Casual Encounters Actually Happen
Here are our favorite online and offline places for meeting people for one-night flings:
@Havana-Club-625544937515451
Havana Club is the perfect spot for salsa dancing with hotties
Have you ever dreamed of dancing body-to-body with a gorgeous woman? How about tons of gorgeous women? Well, you’ll have that opportunity and more at Havana Club. The club is a pretty classy place where singles come to meet, dance and have fun. The club always has high-spirited women who are just looking for a good time.
If you’re not yet confident in your dance skills, don’t worry. The club also offers beginner salsa and bachata lessons. Learn from the pros and then come out on a Friday night to a poppin’ club. The place also serves drinks, so you won’t have to worry about making a fool of yourself while sober. Just strut in with as much confidence as you can you’ll come across tons of beautiful single ladies.
AFF is the most reliable option for most guys to find casual encounters in Boston (try it free)
With an enormous userbase of over 90 million people, AFF is perfect for finding casual encounters in Boston. Let’s get real, finding women who want casual fun can be tough. Even bringing up the topic in person can cause things to go sour pretty quickly. Many women want to avoid looking “easy.” So even if they want something casual, they keep it quiet. AFF helps break down that barrier by keeping things discreet online.
The secret to the site is that all of the users are looking for noncommittal fun. This is the one site that we’ve seen get guys lucky every time. It’s also the only site where you don’t have to look like a male model to get women. Everyone on the site is looking for some type of good time. And with the sheer amount of users you can quickly find your match. However, that’s not even our favorite thing about the site.
If you haven't tried out AFF you're gonna be surprised by how easy casual fun can be to find.
The site also makes it easy to look through users with their unique filtering system. You can filter through users based on age, location, kink, cup size and more. As the site has been around for a few years now, it also has a more legitimate userbase. That means you’ll be less likely to run into fake bot accounts or catfish accounts. The possibilities of finding Boston casual encounters are endless with AFF.
@BukowskiBoston
Bukowski Tavern is a great spot to grab a few drinks and relax
We know that not everyone is looking for a wild night out with dancing. Sometimes all you want to do is kick back with a drink and start up a conversation with a gorgeous woman. Well, at Bukowski Tavern that’s exactly what you can do. This lowkey tavern offers up a wide selection of beers to choose from along with comfort foods.
Although the bar has a “dive” feel to it, that only makes it more alluring. People often spend between 45 minutes to two hours here. That means that if it goes sour with one lady, there’ll be another one coming in just as soon as you finish your drink. The place is cash only, so come prepared. You won’t find anyone that takes themselves too seriously at this hip bar.
Alt.com is great for finding kinkier casual encounters in Boston (try it free)
If you’re a guy who’s interested in the kinkier side of one night stands, then you should try out Alt.com. Bringing up the topic of BDSM in person with a stranger can be incredibly risky. Even bringing the topic up as a joke can quickly make the conversation take a turn for the worse. With Alt.com, you’ll be a part of a unique community that embraces the kinkier side of things.
Alt.com is the largest site of its kind. The site focuses on connecting men and women who are into BDSM, kinks and various fetishes. The best part is that everyone on the site is incredibly welcoming. You won’t have to worry about being judged for your unique interests. We’ve only ever encountered users who are open and friendly while navigating through the site. Another great aspect is that the site has been around for a while. That means that many of the users are real people and not bots or catfish accounts.
Since BDSM and other kinks are so niche, it’s important to take advantage of a platform like Alt.com. This site is your best option for meeting Boston casual encounters who are into the same kinks you are. So give the site a try!
@BostonCityHallPlaza
The Patios is a relaxing beer garden experience
The Patios are the perfect option if you love beer and socializing. This chill beer garden is outdoors and they serve drinks from an Airstream. You can try out some of their craft brews while hanging out with a cool crowd of locals. However, the custom patio areas aren’t the only thing that attracts so many hotties to this place. The beer garden also has a pop-up snack shop where you can satisfy most cravings.
If you want to challenge a beauty to a little competitive fun, then try out the mini-golf stations. The summertime is obviously the best time to head to this place. You’ll come across charming women who are far from pretentious or snobby. This is the perfect place to meet down-to-earth women who are just looking for a bit of naughty fun.
The Boston Craigslist casual encounters forum was once a solid option
In the not too distant past, the Boston Craigslist casual encounters was a popular option for one-night flings. The message boards were filled with personal ads all looking for Boston casual encounters. While tons of people were getting laid, there was a serious catch that many people neglected to bring up.
While it was free and easy to use, this wasn’t where you’d find the highest-quality flings. Since users didn’t have to disclose any personal information, many just pretended to be somebody else. You’d think you were talking to a local hottie in the Boston area and then meet up in person to be gravely disappointed. You can imagine the disappointment of that sort of situation.
These days, the Boston Craigslist casual encounters section has been removed. While you might still come across a few potential ads throughout the site, they’re not really worth searching for or responding to.
Listen to absolutely unreal live music at Wally’s Cafe Jazz Club
If you enjoy the idea of kicking back to amazing live music in cozy surroundings then Wally’s Cafe is the best place for you. This old-school jazz and blues club has some of the best live music in the city. If you’re lucky, you’ll catch performances by some of the most talented locals and students that the city has to offer. However, that’s not the only great thing about this place.
Our other favorite thing is the crowd that it attracts. You’ll find women from all different backgrounds frequenting this place. This makes it the perfect place to introduce yourself to your next Boston casual encounter.
The Apps Dating Experts Recommend To Regular Guys In Boston
If you're not using at least one of these apps you're going to struggle to find anything casual around town. Post-Covid, almost all of these connections are happening online first. If you're not giving these a shot you're missing out. They are where most guys have the best results:
| Site | Our Experience | Our Rating | Free Trial Link |
|---|---|---|---|
Best Casual Encounter Site  | Experience Highlights
| 9 | Try AFF For Free |
Great If You're Handsome  | Tinder Highlights
| 8 | Try Tinder |
2nd Best For Most Guys  | Experience Highlights
| 8 | Try Passion |
Locanto in Boston has lots of available options
With Craigslist out of the picture, Boston Locanto has stepped up as an alternative for one-night stands. Similar to Craigslist in nature, Boston Locanto also features message boards where people can post personal ads. The personal ads vary, but most users are looking for casual encounters in Boston.
While the premise is a good idea, our biggest issue is that the site has no way of verifying a user’s identity. There’s a lot of catfishing that goes on and you can never be sure if that hot girl you’re talking to is actually her. To avoid being led on, we recommend trying out one of the other sites on our list. Locanto in Boston should honestly be a last resort choice.
Durty Nelly’s is an Irish pub with great music and even better people
Durty Nelly’s is so much more than your typical Irish pub. This place has a fantastic crowd of people that are always friendly and inviting. So if you happen to be on the introverted side, then this is a great place for you. Everyone is always socializing and super friendly.
If you happen to come out on any night, be sure to choose one with live music. The bar often hosts an open mic night on Sunday nights and you don’t want to miss it. Durty Nelly’s is a great place to meet new people and come across your next fling.
