10 Creative Date Night Ideas for Every Relationship Stage

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Summer 2025

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The classic Netflix and chill date is starting to feel outdated, and for good reason. Relationships—at any stage—take effort, and one way to show the person you’re dating that you’re invested is by planning a creative or unique date. It’s a great way to keep things exciting, demonstrate thoughtfulness, and above all have a lot of fun.

  1. Attend a Concert or Comedy Show

If you and your partner or the person you’ve recently started dating share a love for the same band or have a similar sense of humor, grabbing tickets to a local concert or comedy show can make for quite an entertaining date. For a first date, consider getting drinks beforehand or after the show to ensure you have time to connect one-on-one. That way, you can enjoy the entertainment while still having a chance to chat and get to know each other better! And if you’re at a comedy show, maybe avoid purchasing front-row tickets—unless you’re ready to be part of their crowd work! 

  1. Arrange a Pickleball Double Date

Double dates can be a great way to ease first-date nerves but they are also a fantastic activity for long-term couples who are looking to switch up their date-night routine. Pickleball is one of those easy to pick-up sports and can be played at any age. Paddles can be rented at most courts. 

  1. Share Family Recipes 

There is nothing more special than when a partner offers to cook dinner for you. Whether you are just getting to know them, or have been together for some time, getting creative in the kitchen is a fun date night and a meaningful way to connect at any relationship stage. Instead of a traditional dinner, take turns preparing the main course and the dessert. One night, you can cook a dish from your culture while your partner makes dessert, then switch roles the following week. Bonus points if you share a family recipe—it’s a romantic way to introduce them to your traditions and roots.

  1. Have a Picnic by the Water

For a romantic and relaxing date, pack a picnic and head to a scenic spot by the water. If you and your partner enjoy biking, rent some for the day and ride to a park with a pond, stream, or a picturesque tree. Otherwise, you can drive or take transit together. Prepare a picnic basket with charcuterie board essentials—grapes, cheese, crackers, salami, prosciutto, and a bottle of wine—and set it up on a cozy blanket. It’s simple, delicious, and effortlessly romantic!

  1. Create Some Friendly Competition 

There is nothing more fun than a little friendly competition. Whether you’ve been married for years or dating for just a few months, activities like axe throwing, go-karting, skating, bowling, or going to an arcade are great ways to flirt with each other, and remind each other how much fun you can have together. 

  1. Pretend to be Picasso For the Night

Many people shy away from painting because they think they lack artistic talent. But whether you’re a Monet or a Picasso, painting can be a fun and creative way to spend time together. A viral TikTok trend had couples painting portraits of each other. This is a great way to get silly and goofy. Just be sure to establish the rules first. Agree to put zero pressure on each other and paint your partner as you see them. The worse the painting, the more laughs you’ll have!

  1. Opt For a Game of Mini Golf or Hit the Driving Range

Mini golf is a fun and flexible date idea, no matter the weather! In the summer, book an outdoor course or head to the driving range. In the winter, try a glow-in-the-dark mini golf course or a virtual driving range. If your partner loves golf, this is a great way to show you care about their hobbies—or even start learning so that one day, you can join them on an 18-hole course!

  1. Book a Drive-in at a Movie Theatre 

Yes, we may have suggested not to have a Netflix date but trust us, this is different. With a drive-in movie theatre, you get to have your own cozy space while still making an outing of it. Plus, you can prepare snacks beforehand to save on costs. Drive-ins are nostalgic and make for the perfect intimate date night, especially if you arrange to watch the sunset beforehand.

  1. Plan a Day Trip to a Winery

Explore nearby wineries, distilleries, or breweries and treat you and your partner to a tasting flight to experience a variety of flavors. If you’re in Toronto, consider a day trip to Niagara-on-the-Lake to visit its renowned wineries or head to Collingwood for a distillery tour. To make the day trip special, you can offer to make them a playlist for the car ride to your destination. Ask for their favourite songs and include them in the playlist ensuring there are plenty of tracks you know they’ll love. It’s a great way to set the mood and make the long car ride just as enjoyable as the destination.

  1. Sign Up For a Pottery Painting, Clay Making or Candle Making Class

For new couples, it’s a great way to see how patient your partner is. For those who’ve been together longer, it’s a relaxing and therapeutic activity to enjoy side by side. Plus, you’ll walk away with a handmade keepsake to remember the experience!

Claire Simpson | Contributing Writer

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