Plan Like a Pro: Unique Date Ideas Around Singapore | merewards

17 October 2025 by Grace Kho

Are you adventurous, a foodie, or someone who loves art? These are things you can discover during dates when you are trying to get to know someone better. Whether you are planning or suggesting the date, consider switching things up. Most times, first dates are usually a dinner or a chat over coffee, but this does not have to be the norm. A little creativity can make the date more exciting while still giving you the chance to connect on a deeper level.

In this story, we suggest activities you can try on your first date or even your 100th. They do not have to be expensive or take place at a fancy restaurant. Most of these activities are fun and active, and instead of just listening to someone talk about themselves, you get to see their personality in action.

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Squash

A little competition on a first date can be a fun and interactive way to connect. Why squash? This game lets players move side by side in close proximity, creating plenty of chances for light conversation. A friendly match also reveals how your date handles winning or losing, adding a playful yet insightful touch to the experience. To make it even more exciting, set a fun rule such as “whoever loses has to answer a question.”

Playing a sport together is also budget-friendly and a great workout, making it perfect for both friends and couples.

Outfit Shopping for Each Other (Set a Budget)

This trend has been making waves on social media, with influencers asking strangers on the streets to style them for different events. So why not turn it into a date activity? Set a budget before starting the challenge and have fun discovering each other’s fashion sense before heading out for dinner in your new outfits.

This activity is bound to spark laughter and a bit of friendly competition. You can even set fun rules like “winner gets the outfit for free” or “dress each other in themed looks such as beach day or concert fit.” It is simple yet meaningful, making it a great idea for both new couples and those who have been together for years.

Cultural Pass Activities

Photo credit: Klook website

If you haven’t heard about Singapore’s $100 Cultural Pass, you’re missing out. This initiative encourages citizens to explore and appreciate local culture, and it offers plenty of activities that are perfect for dates.

Try something hands-on like the SOS Spice Blending Workshop, where you’ll learn about different spices and even create your own blend. To make the date even more special, head home afterward and impress your date with your culinary skills.

Other great options include art jamming, pottery making, or visiting museums. These are fun, meaningful, and creative date ideas that every couple should try at least once.

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Photowalks

Let art take the lead in your date by sharing your love for different art styles, photography, and nature. If you enjoy being creative and capturing moments, invite your partner on a photowalk adventure. Planning one is simple and it can be as easy as pretending to be tourists, visiting iconic landmarks around Singapore.

During your photowalk, you will get to unpack each other’s creative sides and even your dating styles. Bonus points if you manage to capture beautiful shots of each other and exchange them afterward. Helping one another take photos or acting like tourists can be a fun and lighthearted way to ease first date jitters.

Kayaking at Pulau Ubin

Kayaking as a first date is like having dinner without food. It is intimate, peaceful, and full of conversation. With plenty of kayak rentals available, choose one that allows both of you to paddle together, such as an open-deck double kayak. This activity gives you the chance to talk freely without worrying about being overheard or needing to raise your voice in a noisy diner.

At Pulau Ubin, for instance, you can explore mangroves, listen to the sounds of nature, and enjoy quiet moments together. Some parts of the route are secluded, creating a romantic atmosphere where you can have deeper conversations while gliding under the shade of trees. Kayaking in doubles also encourages teamwork, helping you build chemistry and connection, perfect for couples who want to take their relationship to the next level.

In Singapore, our love for food often makes dinner the go-to date idea. While it is the most common choice, adding a little challenge or team activity can reveal much more about a person than just conversation. If you are planning a first date, we hope these suggestions help you get to know someone better and maybe even spark something special. Wishing you all the best and may your date go well!

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