23 Best Chicago Winter Date Ideas: Fun, Unique & Romantic

Looking for the best, most unique Chicago winter date ideas? Stay right here, because we have over 20 in this guide! We’re sharing tons of romantic things to do in Chicago in winter for all interests and budgets. Foodie? Adventurous? Music lover? Thrill-seeker? We got you.

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When we took a weekend road trip to the Windy City just before Christmas (one of the perks of moving to the Midwest from Arizona!), I had to do some serious digging to find Chicago winter date ideas.

Well…fun, realistic ideas, anyway — things people actually want to do, that don’t cost a small fortune and aren’t the same old-same old.

Surely we could get more creative than dinner and a movie, wine tastings, or an escape room. Right?

Fortunately, yes. This is Chicago, after all, one of the greatest cities in the world. And that’s coming from someone who grew up in New York and typically spends most of her free time hiking and camping, far from any major cities.

From exploring a museum dedicated to ice cream and learning new skills like rock climbing or cooking, to cozying up in a rooftop igloo and playing Whirlyball, we packed over 20 romantic things to do in Chicago in winter into this guide.

Just because Chicago winters are frigid cold, doesn’t mean your love life has to be!

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Best Chicago Winter Date Ideas

1. Go Ice Skating

Bundle up for one of the most fun, romantic things to do in Chicago in winter. This classic winter date idea lets you glide (or stumble!) around the ice hand-in-hand, while enjoying views of the city skyline.

Chicago has several ice skating rinks, each with a unique charm and vibe. They generally open just before Thanksgiving (one of the main reasons the Windy City is one of the best places to visit in the USA in November!) and close in early March.

Admission is typically free, though skate rentals are not. You can also bring your own skates.

As a bonus, if your date is a bit unsteady on ice skates, you get to help him or her (more opportunity for close physical contact!). That alone makes ice skating one of the best first date ideas!

Unless otherwise noted, assume that you have to get tickets in advance for a specific date and time.

Here are some of our favorite ice skating rinks in Chicago.

• Maggie Daley Park Skating Ribbon: Picture-perfect quarter-mile ribbon that requires advance reservations
• Millennium Park ice skating (McCormick Tribune Ice Rink): Skate in front of iconic Cloud Gate, AKA ‘The Bean,’ with free admission and free weekday lessons
• Midway Plaisance Park: Large rink adjacent to the University of Chicago in Hyde Park
• Warren Park: One of the largest and cheapest rinks in Chicago, just north of all the mouthwatering Indian restaurants in Little India
• Navy Pier: Part of ‘Light Up The Lake,’ this outdoor rink situated right on Lake Michigan is open only during the holiday season

2. Try Your Hand at Curling

Another active Chicago winter date idea is curling, AKA ‘chess on ice.’

For those unfamiliar with this unique Olympic sport, in curling, players slide heavy stones across sheets of ice toward a target. Curling brooms are used to ‘sweep’ the ice in front of the stone, warming it up and (hopefully!) strategically altering the stones’ path.

It’s fun and fiercely competitive, and even more so when cocktails are thrown into the mix. Kind of like your best backyard picnic ideas, times 100. Or when you play on one of the city’s most elaborate rooftops.

Here are three places you can be a curler, at least for a few hours. Be sure to make reservations ahead of time!

• Curling & Cocktails at Upstairs at The Gwen: Wildly popular, partially because its theme changes every year and partially because it includes complimentary cocktails and light bites
• Stone’s Throw at The Emily Hotel: Curl from this Fulton Market hotel’s fifth-floor terrace, which also offers fire pits, heated tents, and a themed menu of warm winter drinks
• Kaiser Tiger: Popular West Loop bar that sets up winter curling lanes in huge tents near its beer garden. Players aren’t allowed on the ice and there are no brooms.

3. Starbucks Reserve Roastery Coffee Class (or Cocktails!)

Sure, the Starbucks Reserve Roastery on the corner of Michigan Avenue and Erie is the world’s biggest Starbucks. But leave every.single.thing you think you know about Starbucks at the door, because this place is full of tasty surprises…and more than one Chicago winter date ideas!

We absolutely adore the ‘Princi’ pastries and exclusive coffee specialties—European-quality, and I’m not exaggerating in the least—but that’s not the reason to come here.

Instead, head up to the 3rd or 4th floor (the Experiential Coffee Bar and Arriviamo Cocktail Bar).

At the Coffee Bar, you can take coffee tasting classes. Much like wine tasting, you’ll learn how to identify different smells and flavors, plus learn about variances between roasts.

Up at Arriviamo, you’ll find our favorites: the Art of the Espresso Martini experience, a coffee cocktail bar, and the Barrel-Aged Coffee Bar. If you book the experience, you not only learn to make your own espresso martini, but you also get to enjoy an espresso martini flight!

You have to sign up for ‘experiences’ ahead of time (and they do book out!), but you can also just order drinks at the bar. On our first visit, we tried a cold brew trio flight. We’ve also had ‘The Whiskey Cloud’ and, of course, espresso martinis…all divine and almost too pretty to drink.

If you’re just strolling Magnificent Mile (one of the most romantic things to do in Chicago in winter in its own right, especially when it’s decked out in holiday cheer!), it’s still worth popping in, even without a reservation.

The whole bottom level is the impressive roastery, where you can get exclusive blends. Plus, a low-key coffee date with incredible pastries always makes a great date! Head to the rooftop terrace for surprisingly good views.

Looking for a GREAT hotel with easy access to tons of romantic things to do in Chicago? We highly recommend the Renaissance Chicago Downtown Hotel. It’s right on the river and a 10-15 minute walk to just about anything you want, plus has an L stop downstairs!

4. Take a Couples’ Cooking Class

A cooking class offers a fun way to hone your culinary skills, meet other people, and interact hands-on in a new setting, all while enjoying a delicious homemade meal. Sounds like the ingredients for some pretty perfect Chicago winter date ideas to us!

There are several highly-reviewed options throughout the city, so we recommend choosing one based on the most appealing theme.

As a bonus, most of the cooking schools are in dynamic neighborhoods, near countless other romantic things to do in Chicago in winter. It’s a great excuse to explore outside of downtown!

• The Chopping Block (Lincoln Square): Known for its niche themes (think dim sum and macarons) and non-food offerings, like knife skills and wine tasting classes 
• The Wooden Spoon (Andersonville): Themed Friday night couples’ classes and BYOB
• Get in the Kitchen (Lake View): Chicago’s ‘party school of cooking classes,’ you can sign up for classes like Dinner & Dancing Lessons or Cooking & Karaoke.
• Give Me Some Sugar (Roscoe Village): A great option if baking is more your style, with everything from cookie and cake decorating basics to themes like ‘Boozy Bakes’
• Traveling Spoon (virtual/at-home): Book this one-on-one virtual class to learn how to make authentic Chicago deep dish pizza, perfect for bad weather nights

5. Channel Your Inner Child at The Museum of Ice Cream

Indulge your sweet tooth and have a (literal!) blast exploring the interactive exhibits at The Museum of Ice Cream. This whimsical, Instagrammable museum encourages you to let loose and have some good old-fashioned fun.

Everyone knows the best first date ideas involve lots of laughing and being playful!

Not only will you learn allllll about ice cream, but you’ll also get unlimited ice cream samples (not to mention the perfect excuse to indulge!) and fun photo ops. Where else can you dive head-first into a giant pool full of sprinkles?

You can be in and out of the museum in about one hour, leaving you plenty of time to grab dinner or window-shop on Magnificent Mile, some other great Chicago winter date ideas.

As a bonus, the Museum of Ice Cream is on Michigan Avenue, very close to The Gwen. Load up on sweets here, then head to the hotel’s rooftop curling rink to work them off.

6. Rent a Hot Tub Boat on The Chicago River

It’s no secret that boat tours are wildly popular in the warmer months. Now, there’s a ‘hot’ new way to enjoy them even in the dead of winter.

Chicago Electric Boat Company rents hot tub boats, which are EXACTLY what they sound like.

You can rent the boats for 90-minute outings November through March, and they accommodate up to six passengers. Also, you can BYOB, but (and hopefully it goes without saying!) the driver cannot drink.

You can drive the boat yourself (it’s easy to pick up quickly, similar to driving a golf cart) as long as you’re at least 21 and have a valid drivers’ license. If you prefer to simply sit back and enjoy the ride, you can pay extra to have a licensed captain do the driving.

Either way, you’ll definitely get major brownie points for coming up with one of the most unique Chicago winter date ideas!

Note: The hot tub boats don’t go out in temperatures lower than 25 degrees or if ice is present on the river.

7. Have a Game Night Out

For a more laid-back date night, cozy up in one of the city’s board game cafes. There are plenty of options across the city, and revealing your competitive sides is a great way to get to know each other.

Bonus Round Game Cafe in Lakeview has a full cafe menu (lighter fare), plus beer, wine, and cocktails, and a HUGE selection of 500+ board games. As one of the more unique Chicago winter date ideas, get a ‘mystery box,’ which is a surprise game that you’ve almost certainly never played.

Replay Lincoln Park is amazing for many reasons, from its 100+ vintage arcade games and pinball machines to the lively trivia nights and elaborate themed pop-ups. Think Harry Potter, Mean Girls, Taylor Swift, Stranger Things, and more.

But the real draw at Replay is that most of the games are totally FREE (yay for cheap Chicago date ideas!), as long as you buy a drink. The only exceptions are Skee Ball, Buck Hunter, and basketball.

Irving Park’s Stay and Play Game Cafe transports you to the tropics with its Puerto Rican decor, music, and food. For just $5, you can access the game room, with an ever-growing collection of nearly 800 games. There’s also an awesome happy hour from 4-6:00pm Wednesday-Friday.

Over on the edge of Logan Square and Bucktown, Snakes and Lattes is perhaps the most unique board game cafe in Chicago. Make a selection from the enormous game vault, or rent a themed private room. Snakes and Lattes also offers membership programs and hosts trivia nights.

8. Catch a Live Blues or Jazz Show

Neither jazz nor the blues were invented in Chicago (New Orleans and other cities in The South, like Memphis, hold that honor), but the city has become a mecca for both. Chicago was a pivotal hub for blues post-Prohibition in the 1930s, and a nurturing ground for jazz during the Great Migration.

Catching a live performance is the best way to immerse yourselves in Chicago’s soulful music scene. Plus, the intimate ambiance of many clubs create the perfect date night atmosphere.

• Green Mill: Iconic Prohibition-era jazz club open since 1907 and a favorite hangout of Al Capone. It’s cash-only and does not have a menu or accept reservations, so go early.
• Andy’s Jazz Club: A staple in the Chicago jazz scene, hosting live performances every night of the week and with several big names in residence
• Winter’s Jazz Club: Walking distance from Navy Pier, this is the best pick for romantic things to do in Chicago in winter—tables seat two and it’s a true listening room, so there’s no talking
• Fulton Street Collective: For a cheap date idea, head to this renowned open-to-the-public art collective managed by local legend Chris Anderson
• Buddy Guy’s Legends: Founded by Buddy Guy himself, this blues club is a shrine to the genre and hosts musicians seven nights a week. For unforgettable Chicago winter date ideas, come in January, when Buddy still plays an annual series of shows.
• Kingston Mines: The biggest and oldest continually running blues club in Chicago, with two performances on two stages. It’s also a 20-minute walk from the Lincoln Park Zoo and Lincoln Park Conservatory, two other great date ideas.
• Lagunitas Brewing Company: A true Chicago hidden gem for blues, the small stage here hosts a surprisingly robust lineup five nights a week

9. Play WhirlyBall

Combining aspects of hockey, basketball, lacrosse, and bumper cars, Whirlyball is one of the best Chicago winter date ideas. It’s quirky and guaranteed to have you both laughing all night, especially if you also have a few cocktails!

The Bucktown WhirlyBall location also has traditional bowling, laser tag, and board games, plus a full menu with food and drinks. You could easily make this your entire date, but WhirlyBall games themselves are only 10 minutes each if you have other things planned.

If you’re looking for Chicago date night ideas in the suburbs, WhirlyBall also has locations in Naperville and Vernon Hills.

10. Splurge at Chicago Winter Rooftop Bars

Looking for more ‘elevated’ Chicago winter date ideas? Make reservations for one of the city’s most lavish rooftop bars, where you can sip, savor, and enjoy each other’s company.

You’ll enjoy stunning skyline views, sophisticated winter-themed rooftops, and an upscale, intimate ambiance.

Note that Chicago winter rooftop bars are difficult to get into. Reservations are mandatory, even if ‘officially’ they aren’t.

Also, every bar has its own policies, but plan on having to reserve an entire igloo/table/cabana to get in. It’s worth the splurge, at least once—this is one of the most romantic things to do in Chicago in winter. Here are the best rooftop bars to enjoy this winter.

• Cindy’s: Iconic rooftop bar on the Chicago Athletic Association Hotel’s 13th floor, with panoramic views of Millennium Park and Lake Michigan
• Raised (Renaissance Chicago Downtown Hotel): Stylish indoor-outdoor rooftop terrace overlooking the Chicago River, with a choice of open tables or reservable winter greenhouses
• I|O Godfrey: Trendy River North rooftop bar at The Godfrey Hotel, with a Winter Wonderland theme and retractable roof that allows for year-round access
• Château Carbide (The Pendry): 24th floor rooftop bar that transforms into a pristine winter garden, with an absinthe-focused menu, wooden ‘lodges,’ and private fireplaces
• Upstairs at The Gwen: The home of Curling & Cocktails, one of our favorite Chicago winter date ideas, with iceless curling rinks, cozy fire pits, and a chic vibe

11. Garfield Park Conservatory

On a serious budget, but also looking for romantic things to do in Chicago in winter? Take your date to the Garfield Park Conservatory to escape winter’s chill.

The lush greenery and colorful flowers offer the ideal setting for a peaceful, scenic date. It’s not exactly a romantic Oahu getaway, but hey. And it’s totally FREE! With that said, we encourage you to make a small donation, if you’re able to.

Better yet, the conservatory is open 365 days a year. For those who don’t celebrate Christmas, this is one of the best Chicago winter date ideas.

Stroll around eight indoor gardens and 10 outdoor terraces, marveling at over 600 plant species and stunning architecture. In addition to simply visiting, you can also sign up for special events and workshops, such as beginning beekeeping and Art After Dark.

12. Go Out For a Real-Life Night at The Museum

Put an intellectual twist on your next date night by visiting some of Chicago’s renowned museums. Whether you’re a local or just visiting, the unique programs and events (many of them after-hours or for ages 21+) transform a regular museum visit into a memorable date.

As a huge perk, many Chicago museums offer FREE admission on specific days for Illinois residents with proof of residency. And if you get SNAP benefits (regardless of where you live), you’ll enjoy free museum tickets at several museums all the time with your EBT card.

We love a cheap date idea!

• Adler After Dark at Adler Planetarium: Award-winning ‘sky shows’ and hands-on activities every Wednesday night. FREE for Illinois residents!
• Museum of Science and Industry: A Chicago gem with interactive exhibits covering every aspect of science and innovation. FREE for Illinois residents on several days in Jan-April.
• Nature on Tap at Peggy Notebaert Nature Museum: Interact with critters like snakes and turtles at these 21+ events that include one cocktail. Or, try museum yoga on Saturdays!
• Field Museum of Natural History: Highly regarded as one of the best natural history museums in the world, and one of the largest. FREE for Illinois residents every Wednesday.
• Museum of Contemporary Art Chicago: The doors often stay open late to host a variety of events, from concerts and film screenings to workshops and dance performances
• Museum of Illusions: This hidden gem in the heart of downtown features a series of optical illusions. MOI is also close to other Chicago winter date ideas, like ice skating at Maggie Daley.

13. Cheer on the Bulls or Blackhawks

If you’re sports fans (honestly, even if you’re not), immersing yourself in the electric atmosphere of Windy City sports is one of the best Chicago winter date ideas.

Head to the United Center, home of two iconic local teams, the Bulls and the Blackhawks. The energy and intensity in the arena is contagious, making it an especially great first date. Bonus points if you show up with a jersey for your date!

Local tip: parking runs anywhere from $25-45, but you can also get to the arena via ‘L’ train or bus. On the L, you want the Ashland/Lake Pink & Green lines, or the Illinois Medical District (Blue line). And look for CTA buses 9, 19, 20, 50, and 126.

14. Go to a Comedy Show

One of Chicago’s many nicknames is the ‘home of improv,’ with its comedy clubs just as famous as its jazz scene. Improv and sketch comedy were both born here, and major comedians have gotten their start in the Windy City — Hannibal Burress, John Belushi, Tina Fey, Amy Poehler, and others.

In our opinion, spending a few hours laughing while cozy and warm indoors is one of the best Chicago winter date ideas!

With such a robust and diverse scene, you honestly can’t go wrong with any comedy show or club in town. Here are some highlights to get you started.

• The Second City: The creme de la creme of Chicago comedy, with long-running revues and one-off shows like Twenty Dollar Comedy on Thursday nights
• Zanies: Old-school local institution with a 2-drink minimum, a particularly great venue to see up-and-comers
• Laugh Factory: Fantastic rotation of popular local comics, plus some big-name headliners
• iO Theater: Considered the ‘mecca of improv,’ you can catch any manner of improv show here. Notably, Tina Fey, Amy Poehler, and Jason Sudeikis all got their starts here.

15. Try Indoor Rock Climbing or Bouldering

Too nasty out to go hiking? For adventurous couples looking for a healthy dose of adrenaline, indoor climbing gyms serve as some of the best Chicago winter date ideas. You challenge yourself both physically and mentally, work up a sweat, and even try something new together.

There are tons of options throughout the city (somewhat surprisingly, considering Illinois’ geography!), but First Ascent is hands-down the best, especially for first timers.

First Ascent was started by Chicago climbers and there are several locations. Some have climbing and bouldering, while a couple of gyms offer bouldering only.

16. Explore the Shedd Aquarium

Nestled along Chicago’s lakefront, the Shedd Aquarium offers a particularly engaging date idea.

You can stroll through at your leisure and check out the touch experiences, but to make your visit even more memorable, catch one of the aquarium’s shows. Or better yet, book a tour or one of the Extraordinary Experiences.

Options range from encounters with sea lions, sea otters, belugas, and penguins to shark feeding.

Don’t miss the special events, including Shedd After Hours. These 21+ events include all aquarium exhibits/experiences, plus special animal encounters and live DJs or bands.

17. Rediscover the Joy of Play at Color Factory

Immerse yourself—literally—in vibrant color at Color Factory, an interactive pop-up art exhibition in the heart of downtown Chicago (it’s on the bottom level of the Willis Tower). Walk through the 14 themed rooms, each one its own immersive art installation.

Each Color Factory pays homage to its local city (there are also locations in Houston and New York), so expect fun surprises like a confetti version of Chicago’s flag.

Two things in particular make Color Factory stand out among fun Chicago winter date ideas. It’s full of whimsical photo ops, and hands-free digital photo stations take perfectly-framed pictures. Color Factory even emails them to you, totally free (countless other places charge for similar services).

Also included FREE are a variety of themed souvenirs and treats, including ice cream, pop rocks, salt water taffy, macarons, and more.

Chicago Winter Date Ideas During the Holidays

18. Christkindlmarket

There’s just something about the charm of a traditional outdoor European Christmas market. Festive wooden stalls, twinkling lights and garland, hot drinks, a huge variety of handmade trinkets, and of course, tons of delectable food.

Perfect ingredients for one of the best Chicago winter date ideas!

Christkindlmarket brings these German-style markets to Chicago every November, transforming the city into a winter wonderland. Choose from three locations: Daley Plaza, Wrigleyville, and Aurora, in the suburbs.

All three have different vibes, but each gets VERY crowded, particularly on weekends and the closer it gets to Christmas. Daley Plaza, in the heart of downtown Chicago, and Wrigleyville are the busiest.

When you arrive, order glühwein (mulled wine) or cocoa straight away. This way, you’ll get the coveted souvenir mug and have something to sip on as you stroll around. Help each other pick out some gifts or ornaments and if it’s a first date, consider buying one together, as a souvenir.

Don’t leave without trying at least a few German foods. Perennial highlights include pierogi from Pierogi House, raclette sandwiches from Baked Cheese Haus, potato pancakes from German Grill, and Nutella donuts.

Admission is free, but several vendors only accept cash. There are several ATMs onsite.

Remember the Renaissance Chicago Downtown Hotel we mentioned earlier? It’s just a 5-minute walk to Christkindlmarket and other Chicago Christmas attractions, like Macy’s, ice skating, and several holiday pop-ups.

19. Lightscape at the Chicago Botanic Garden

The enchanting world of Lightscape provides the backdrop for one of the most romantic things to do in Chicago in winter. This magical event transforms the gardens into a winter wonderland of immersive light, color, and sound.

Bundle up, grab your date’s hand, and stroll through the illuminated paths and installations. There are four spots to grab food or hot drinks, including spiked cocoa and themed holiday cocktails.

The Chicago Botanic Garden is north of the city proper, and Lightscape runs from mid-November through early January. It always sells out, so book tickets as early as possible.

Local tip: even after Lightscape ends for the season, the botanic garden is one of the best Chicago winter date ideas. The Orchid Show of Wonders runs February-March. Its theme changes every year, but it’s always elaborate and impressive, like the carousel theme made from 10,000 blooms.

20. Get in the Holiday ‘Spirit’ at a Christmas Pop-up Bar

Christmas pop-up bars have become a HUGE thing in Chicago in the last few years. If you’ve never been to one, it’s exactly what you think: a bar that goes full-on holiday mode.

Not just festive decor, but full-on transformations, with building wraps, ornaments covering the ceiling, themed menus, costumes, and more.

For holiday-loving adults, Christmas pop-ups are hands-down one of the best Chicago winter date ideas. With that said, we DON’T recommend this as a first date idea. The bars are packed and get pretty rowdy, so it’s not an ideal setting for conversation.

There are several dozen across the city (and more every year), but here are some personal favorites.

• Frosty’s (Lincoln Park): The original Chicago Christmas pop-up, Frosty’s is a major party scene with three levels, two dance floors, and multiple bars
• Santa Baby (Wrigleyville): One of the most popular and completely over the top (prepare for a long wait to get in!)
• Elf’d Up (Stretch Bar & Grill, Wrigleyville): Right next to Santa Baby, this Elf-themed bar commits to its namesake, even offering Buddy’s Breakfast Pasta
• Christmas Club (Wrigleyville): A two-story holiday pop-up with multiple bars
• Rudolph’s Rooftop at LondonHouse Chicago (downtown): Beautiful themed rooftop on the 22nd floor, with reservations-only heated igloos
• The Christmas Inn: Holidays on Hubbard Street (River North): Three stories and highly Instagrammable, plus live music and other entertainment

21. Try to Catch the Holiday Train

For a truly unique date night idea, try to find Chicago’s CTA holiday train or bus. The train and bus are decked out in festive holiday decor, and make appearances at stops throughout the city starting right after Thanksgiving.

Santa and his reindeer ride outside the train (or roof of the bus), waving to onlookers. Photo ops with Santa are also available on some days. This beloved holiday tradition has been running for over 30 years.

To surprise your date with one of the most fun Chicago winter date ideas, check out the full holiday train schedule HERE. You can also use the train tracker in live time (look for the candy cane icon).

22. Indulge in a Holiday High Tea Service

For an elegant day date, and certainly one of the most romantic things to do in Chicago in winter, treat yourselves to formal high tea. During the winter months specifically, you’ll find several holiday-themed tea services.

Here are several suggestions, across every price point.

• Mango Pickle ($42 per person): Mango Pickle’s Sunday high tea service include bottomless tea and seven food items, and is one of the most affordable options in Chicago
• Russian Tea Time ($44 per person): Another wallet-friendly high tea, Russian Tea Time is a long-standing downtown tea house
• The Allis at SoHo House ($63-76 per person): Chic, modern high tea experience that pairs tea with champagne and pastries
• LondonHouse ($90 per person): A favorite holiday tea, with adorable pastries and incredible views of the Chicago River
• The Peninsula ($140-150 per person: One of the most iconic afternoon high tea services in the city, with a selection of fine teas and exquisite pastries

23. Cut Down Your Own Christmas Tree

Want to seriously impress your date, or start a new couples’ tradition? Cutting down your own Christmas tree is one of the best holiday-themed Chicago winter date ideas!

There are several places to do it just outside Chicago, but we highly recommend Richardson Adventure Farm in Spring Grove.

It’s right at one hour from the city, and offers a variety of traditional holiday experiences. Not only can you cut your own tree down, but the staff will give you (and your tree!) a ride back to the barn on a tractor.

In the barn, enjoy complimentary cocoa, coffee, and cookies, and browse a variety of holiday decor and wreaths for sale.

If you found this list of Chicago winter date ideas helpful, be sure to save it on Pinterest. You can refer back to it later, plus it helps other people find the guide, too!

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