non-boring, non-awkward first date ideas in singapore
If you find yourself searching “cafe for first date singapore” or “quiet bars in cbd for dates”, I’ve got you.
You’re probably looking for a place that has a conducive environment, not too noisy, not too ulu, close / in the middle of both of you, without looking too boring, to minimise awkwardness.
What I always suggest, as a dating coach, and as a woman, is to have two places:
The meal / drink
A walk after
This change in environment loosens the both of you up. It can get a little suffocating and the pressure can get quite high if there’s an expectation to keep conversation flowing for a couple hours while sitting down the whole time, so a little walk after helps your food digest + adds some environmental stimulus.
1: classic cafe / lunch date
A cafe is pretty much the default option, so choose one that’s surrounded by some nature or in an interesting environment. Some ideas:
Toby’s Estate + Robertson Quay walk (where my now-husband and I went for our first date) - we walked along the river all the way to Great World City, which is perfect to cool off. Plus, you can take the train home there.
Ramen + Glasshouse at CHIJMES - Ramen is a fast meal, so you may want to sit down for a little more over coffee or matcha. There’s also Dough, and you can take a little open-air walk around CHIJMES or look at bougie shops in Raffles Hotel. Bonus: the toilets in the hotel are nice (very important).
cafe nesuto + walk in / along MBS - Indoor / outdoor options both are fantastic. The walk along the river is beautiful (especially in the evenings), but if it gets too hot, MBS’ high ceilings, openness and water features give it a “not-just-another-mall” vibe.
2: bars
Some bars I personally love:
My perennial favourite, Bar Stories at Haji Lane. They don’t have a drinks menu, so they’ll ask you to describe what you want in your drink - an easy conversation topic. Does she think the drink they made describes her personality? If she were a drink, what would she be? (Note: It can get quite noisy during peak hours so be sure to ask for a counter seat by the bar! This also adds some dimension and interaction as you can talk to the bartenders who are always super friendly and fun.)
Chimichanga Holland Village or VivoCity - Not technically a bar, but the food (especially the fish tacos) slaps. You can walk around HV, or along the Sentosa Boardwalk after (for the VivoCity outlet).
Foxtail + Duxton Plain Park - Foxtail is an intimate rooftop bar (reservations highly recommended). The park is a straight and long path, and brings you to Outram Park MRT. It’s quiet but not deserted (it’s right next to Pinnacle at Duxton), has lots of places to sit, which makes for a really nice atmosphere to talk to and learn about the other person.
3: for those who prefer outdoor (urban) settings
Outdoor escape rooms are the way to go if you like to walk on a date before sitting down and having your meal! There are several outdoor “escape rooms” that have popped up over the years, but I recommend Hidden SG as I’ve gone on trails with them with a date and with my former colleagues - it’s pretty no-fuss and the trails are fun. Plus, everything is conducted over WhatsApp so you don’t need to download an app.
I personally like these trails because while being low-pressure, they reveal each other’s communication skills and how each of you approaches problems differently - something the both of you can talk about after.
Very important caveat: This is not to say that you should use this opportunity to “test” the other person! (Someone once told me he brought me to an indoor escape room to “test” me - immediate red flag behaviour) The goal is to just learn about how the other person makes decisions and observe how you both work together.
Note: Please do have a backup plan for this e.g. an indoor escape room!
4: for the nature lovers
This is for those of you who like to wake up early, enjoy some greenery, and reward yourself with breakfast (and the rest of the day) after.
For the Westies: Jurong Lake Gardens + Taman Jurong or Starbucks - Jurong Lake Gardens has several beautiful sections, including Chinese Gardens and a dog park. The roads are all well-paved and everywhere is beautifully landscaped, with loads of places to pause and take a short break.
Southern Ridges / Henderson Waves + Kyuukei Coffee - Southern Ridges is a classic walk, and you can end it with a lovely sit-down cafe in an artsy area to cool off. Kyuukei means “rest” in Japanese, and it serves great coffee in a fun, welcoming environment.
The Rail Corridor + Springleaf prata at Rail Mall to reward yourselves - or anywhere along the Coast-to-Coast trail that’s central / near the both of you!
Important: Singapore’s weather is famously unpredictable, so please have a backup plan!
5: culture dates
According to CMB’s global CEO Shn Juay, “culture dates naturally slow things down” because they “create shared experiences, ease first-date anxiousness and open the door to richer, more thoughtful conversations”. I bring this up because you can get exclusive CMB-only perks for culture dates if you use your Culture Pass for these experiences. These experiences do force you to slow down and get to know the other person on a deeper, more meaningful level.
6: hawker dates
Even though I don’t personally love this as a first date option because it’s really hot and not conducive to wear a cute dress, I know some who love hawker dates because it’s very low-pressure and “in your natural habitat”. That being said, I still echo going for a meal and a walk, so here are some hawker centres that allow you both:
Ghim Moh Market + Star Vista for Yo-Chi - All the rage now, and actually delicious. Lots of room to sit either in Yo-Chi or at the big open steps at the first and third floors, or other cafe options like Chagee.
Katong Chicken Rice + East Coast Park - A classic, but do note that the queue can get quite long and the seating situation a little chaotic.
Adam Road Food Centre + Cluny Court or Botanic Gardens - the most central location of them all. Cluny Court is a small pet-friendly mall that has some fun, non-typical shops, and Botanics needs no introduction.
bonus: think about your outfit
Most women will spend some time thinking about an appropriate outfit to wear on a first date, because she’ll want to make a good first impression while being comfortable - especially with footwear.
This is especially relevant for the “non-traditional” first dates like the outdoor escape room or a hawker date. If you let her know what you’ll be wearing, down to footwear, it will remove some of the mental load on her - and it will be greatly appreciated.
(Note: please don’t tell her what to wear e.g. “wear a cute sundress” - that runs the risk of being creepy! Just tell her generally what you plan to wear e.g. activewear + hiking shoes, or oversized t-shirt + shorts + white sneakers etc.)
remember: you’re not trying to perform.
The goal of these multi-location first dates is to lower the pressure and make it fun. Both of you are meeting for the first time, so it’s understandable and even expected that there will be some nerves. But remember: the goal is to be yourself, so that both of you can see each other for who you both truly are - that’s the only way to make serious, long-lasting relationships.
If you’re going to bring someone on these dates, don’t forget to check out my article on the best questions to ask on a first date to get to know each other better.
If you’re struggling with fear or self-confidence on first dates, or if you keep worrying about what she thinks about you, my dating deep dive sees you, what’s standing in your way, and targets exactly what we need to do to change that.
about the author
I'm Wan Ting, founder of portmanteau, a dating coach for men in Singapore.
I help good men like you stop guessing and build practical dating skills for serious relationships.
