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Wednesdays just got a little more interesting 👀 Let Timeleft’s personality algorithm match you with five strangers for an unforgettable dinner.


Here's your plan for a fun dinner with five strangers, followed by drinks nearby. Enjoy

Dinner with Strangers 😅

Experience a unique dining event at Kama - Wicker Park with Timeleft. Get matched with strangers for lively dinners every Wednesday.

Group Dinner

✅ Before you go
• Dinners are every Wednesday in big cities all over the WORLD! 

💪 Pro tips
• Some restaurants might not be able to split the bill 6 ways, so bring cash to pay for dinner!
• Go in with an open mind and don’t over think it! My biggest tip is just to be curious + ask questions ❤️
• I felt safe the entire time but just a reminder to always keep track of your belongings/drink and before you head to the restaurant, tell a trusted friend what you’re doing + where you’re going!

Book a dinner with Timeleft 📍

I'm about to have dinner with five strangers so…

I can't remember the last time I made a friend

who wasn't from work or school, if ever??

I filled out their personality quiz and the day before they

sent a few hints about who would be at my table,

they sent the location of the restaurant,

But the Timeleft algorithm worked its magic because our

table hit it off immediately and the restaurant was fire.

I met such cool people and we had lots of spirited conversations,

but the app does have a game to break the ice if needed.

I kept forgetting to film because I was having so

much fun and didn't want to be on my phone.

After dinner, we wanted to keep the good vibes going

So luckily they do this thing called “The Last Drink,”

 the name of a bar within walking distance

where you can chill and meet up with more people who use the app.

This was the best Wednesday night I've had in a long time.

So next time someone tells me not to talk to strangers,

I'm gonna tell them to book a dinner with Timeleft.

Here's your plan for exploring tennis history, shopping collectibles, enjoying coffee, and relaxing at a vineyard. Watch the video 👇

Newport, RI is the ideal day trip destination, offering the perfect blend of coastal charm and fun-filled adventure. Stroll through boutique-lined streets, sip coffee with stunning harbor views, and enjoy dining and games at a local vineyard! 

Ultimate Day Trip to Newport, RI 

Explore tennis history at the International Tennis Hall of Fame by strolling the grounds or diving into the museum's exhibits and legacy.

Tennis museum visit

✅ Before you go
• The museum is open 7 days a week 10 am - 5 pm! 

💪 Pro tip
• Visit their website to see if you're eligible for discounted tickets! 
• https://www.tennisfame.com/visit/hours-and-admission

International Tennis Hall of Fame 

Browse nostalgic baseball and Pokemon cards at PB Collectibles in Newport and chat with owner Paul for the best recommendations!

Card Collecting

✅ Before you go
• The shop is open 7 days a week, 11 am - 5 pm. 

💪 Pro tip
• Talk with the owner, Paul, for great recommendations! 

PB Collectibles 

Grab a specialty coffee at The Nitro Bar—try the Wilbur with coconut and cinnamon—and enjoy a vibrant spot perfect for a quick caffeine break in Newport.

Coffee Drinks

💪 Pro tip
• Get the Wilbur for the perfect coffee with coconut and cinnamon! 

The Nitro Bar 

Enjoy farm-to-table dining, wine flights, and lawn games at Newport Vineyards—plus vineyard views and a relaxing outdoor area. Try the White Merlot Rosé for a treat!

Wine Tasting & Dining

✅ Before you go
• Book a high top table in their restaurant that offers farm to table dining! 

💪 Pro tip
• Try the White Merlot Rosé for the perfect glass of wine with a fruity aftertaste! 

Newport Vineyards 

or someone who just loves wine with a view,

Rhode Island is a dreamy coastal escape you need to check out.

so consider this your go to must do list for a perfect adventure.

stop at the International Tennis Hall of Fame.

This is where the very first US nationals,

for free or snag a museum ticket for a deeper dive into tennis history.

Stop into PB Collectibles for a major hit of nostalgia and

pick up a set of your favorite baseball or Pokemon cards.

When there's a line out the door and a disco ball inside,

We took ours to the waterfront to enjoy the view.

When it was time to leave the dreamy boats behind,

The overlook is the perfect lunch spot for flights,

we headed downstairs to check out their gift shop

and see the kettles where the beer is made.

I could have spent all day in their outdoor

area where you can build your own charcuterie board,

They also offer tasting tours for those that want

to learn more about wine and their property.

Here's your plan for a free wine tasting followed by a fresh, farm-to-table dinner date night. Watch the video 👇

Here’s a perfectly paired date night in Dedham 🍷🍽️ Start with a free wine tasting then head right next door for a farm-to-table dinner loaded with fresh, local flavor.

Free Wine Tasting + Dinner Date 

Enjoy free wine tastings every Thursday from 5-7 PM at Satellite Bottle Shop in Dedham, featuring unique themes and expert guidance from friendly sommeliers.

Wine Tasting


• Free wine tastings every Thursday from 5-7 PM! Check out their instagram (@satellitebottleshop) to see what wines they’ve got open. Sometimes they’ve got winemakers visiting as well 🍇

• If you’re a wine enthusiast or just looking to expand your palette, consider joining Satellite’s Wine Club for a hand selected monthly delivery! More details on their Insta.

• As you leave the wine tasting, be sure to grab a 10% discount card to use next door at Few and Far! 

Free Wine Tasting at Satellite 

Enjoy a seasonal, farm-to-table dinner at Few and Far in Dedham, with a menu that changes weekly and optional wine pairings for a memorable dining experience.

Farm-to-Table Dinner

Few and Far is a sister restaurant of Forage in Cambridge! It’s literally right next door to Satellite. 

• Don’t miss their Wednesday wine dinners- 3 courses with 3 wine pairings for $60/pp. It’s different wines and a new menu every week! Check their Instagram (@fewandfardedham) for details. They always have a vegetarian option which I love! 
• They also do a stellar Sunday brunch. 

Dinner at Few and Far

Here's an idea for a date night with a free wine tasting,

followed by a farm to table dinner right next door to each other.

If you're curious about exploring different wines but don't know where to start,

Satellite Bottle Shop in Dedham has got your back.

They have a free wine tasting every Thursday 

from 5 to 7 p.m. and it's always a different theme.

You could taste your way through a series of chilled reds,

I've learned so much about the world of wine

by chatting with their knowledgeable sommeliers.

They're so friendly and always take the time

to recommend wines based on what you're into.

Satellite's curated selection of natural wines

so it's a great way to support your local businesses as well.

grab a 10% discount card to apply right next door at Few and Far

which is a sister restaurant of Forage in Cambridge.

you know exactly where to grab the bottle.

the focus is on seasonal vegetables and farm to table dining,

Our favorites were the grilled halloumi with slow roasted tomatoes,

and this delectable dessert called the chocolate nemesis.

If you're looking for a more immersive wine and dine experience,

don't miss out on this door to door date night in Dedham.

Here's your plan for enjoying delicious dinner and laughs at a comedy show afterward. Watch the video 👇

Enjoy dinner in East Cambridge and then a comedy show in Somerville!

Dinner and a Comedy Show

Savor delicious Italian fare like cacio e pepe arancini and n’duja pizza for dinner at Gufo in East Cambridge, perfect for foodies seeking a cozy spot.

Fine Dining Dinner

✅ Before you go
• 

💪 Pro tips
• order the cacio e pepe arancini 🤤
• try the n’duja pizza!! 🌽

Dinner at Gufo

Enjoy hilarious performances from local and touring comedians at Goofs Comedy Club in Union Square, Somerville—perfect for a night of laughs and affordable drinks after dinner.

Comedy Show

✅ Before you go
• the venue is intimate, don’t be nervous if you get seated in the front, and have a good time!
• get there a 10 minutes early if you want to ensure your party is seated together.

💪 Pro tips
• $4 drinks!!!
• they told us at our show that if you have a 9:00 ticket, you can use that same ticket to get into an 11:00 show for free all month!! Ask about this on your way out for clarification.

Walk to Goofs Comedy Club

If your ideal night out involves good food and a good laugh,

One of my favorite spots in East Cambridge is this restaurant called Gufo.

It was my friend's birthday and we were in celebration mode,

and I ordered the cacio e pepe arancini  

which is literally my favorite thing on the menu.

But corn might be one of the best pizza toppings.

Then after dinner we walked about 20 minutes

to go to Goof's Comedy Club in Somerville.

I didn't end up filming any of the performers because it was my

first comedy show and I wasn't quite sure if that was OK,

great time laughing with the local and touring comedians.

Grabbing another drink here and watching the show

Here's your plan for a $5 brewery tour with unlimited beer tastings and fun games afterward. Watch the video 👇

Take the $5 brewery tour at Harpoon Brewery that includes unlimited tastings at the end! 

Brewery Tour & Unlimited Tasting!

Take a $5 guided tour of Harpoon Brewery in Boston's Seaport, ending with unlimited tastings of all their beer varieties!

Brewery Tour & Tasting

✅ Before you go
• You can get tickets ahead of time here: https://order.toasttab.com/online/harpoon-beer-hall-boston. We showed up without tickets and were still able to get on a tour! 

💪 Pro tips
• I recommend trying all the beers they have on tap, even if it’s something you usually don’t drink! 

Harpoon Brewery Tour 

Enjoy beer, fun games, and Monday night trivia at Harpoon Brewery's Beer Hall in Boston's Seaport neighborhood—perfect for a relaxed outing with friends.

Trivia & Games

✅ Before you go
• Beer hall hours: 
Sunday: 12PM – 8PM
Monday – Thursday: 3PM – 8PM
Friday – Saturday: 12PM – 10PM

💪 Pro tips
• They also have trivia every Monday at 6pm! 

Games at Harpoon 

I've never been on a brewery tour like this before.

So let me tell you why Harpoon Brewery is so unique.

My boyfriend and I wanted to check out the brewery,

and then we found out that they have tours for only $5 a person.

So we waited about half an hour for the next tour

to go out and enjoyed a little bit of cider.

they tell you about the operations of the brewery,

You get to try every single type of beer they have onra too.

but it was fun to try different types and see if I liked it or not.