This week’s date night was a little gift—literally. For our 8th wedding anniversary, my sister-in-law surprised us with a voucher for Eight Pool Bar (Eight for Eight… get it?) at the Fairmont Hotel. Honestly, could there be a cuter (and so me) present?
So we decided to cash it in for date night! What we ended up with was a chilled, slightly unexpected night out — full of wine, laughs, good food and even a bit of that “holiday vibe” you don’t always get in the middle of Singapore.
Where?
📍 The Eight pool bar, Fairmont Hotel, Raffles City
Directly above City Hall MRT, super convenient.
What?
First impressions: Arriving at the Fairmont was surprisingly… easy. We literally just walked into the lobby, went straight up to the pool bar, and found ourselves with prime seats overlooking the water. No questions asked. Which immediately made us wonder—could we do this at every hotel in town? If so, we’ve just unlocked a dangerous (but brilliant) new weekly date night hack.
Eight Pool Bar has two pools (two circles – like an eight!): one for kids and one for adults. Ironically, the adults-only pool was closed off for aqua aerobics when we arrived, so we ended up sitting by the family pool. At first we thought it might feel strange, but actually, it was lovely. The sound of splashing kids made us smile—it reminded us of our boys, but without the stress of actually having to supervise them. Parenting nostalgia, but with wine in hand. Win-win.
Happy hour runs from 3–8pm so we kicked things off with drinks: a chilled glass of white wine for me and a smooth red for him. Mine was perfectly fruity and cold, exactly what you want while lounging next to a pool in Singapore’s humidity.
We ordered some food to go with it, and it came out really quickly:
* Chicken karaage to start – piping hot, juicy, and surprisingly good for bar bites.
* Chicken burger for him – a proper, hearty size with a crispy chicken breast and all the trimmings.
* Pulled pork wrap for me – soft, tasty, and easy to eat without too much mess (always a win).
It wasn’t fancy food, but it hit the spot—simple, tasty, and exactly the kind of thing you want alongside drinks in a relaxed setting.
What was meant to be a quick, casual evening turned into one of those nights where the drinks just kept flowing. We hadn’t planned to “make a night of it,” but that’s exactly what happened. Sometimes the best evenings are the unplanned ones, when you let yourself lean into the moment.
We never actually went into the pool! But that didn’t matter. Sitting there with our feet up, sipping wine, watching the city lights glow as the sky darkened—it felt special, in the most low-key way.
WOW Tips
⭐️ Don’t skip happy hour—3–8pm means plenty of time for poolside drinks at a good price.
⭐ ️Order a couple of bar bites to share—the chicken karaage is a solid choice.
⭐️ If the adult pool is closed, don’t stress—the family pool side still has a great vibe.
⭐️ You don’t have to swim—lounging poolside with a drink is perfectly valid!
⭐️ Tip from us: if this works at Fairmont, try sneaking a peek at other hotel pool bars too?
Worth it?
Me: 7/10
It wasn’t flashy or dramatic, but it was chilled, easy and fun. Sometimes that’s exactly what you need.
What HE said…
“I felt like an intruder on other people’s holidays at first, but good food and good house wine helped me to relax into the situation.”
7/10
Wrap-Up
Date Night #31 was all about keeping things simple: poolside drinks, quick bites, and a relaxed evening that turned out to be more fun than expected. Thanks to a thoughtful anniversary gift, we discovered that sometimes you don’t need to go far or plan much—you just need the right setting, a few glasses of wine and the right company.
We didn’t swim. We didn’t do anything particularly extravagant. But we laughed, we relaxed, and we ended the night feeling closer and lighter. And really—that’s what these date nights are all about.
Would I go back? Absolutely. And now I’m wondering: is hotel pool-hopping the new best-kept date night secret in Singapore? Watch this space…
Have you ever just walked into a hotel and started using the facilities? Let me know in the comments! And stay tuned for date night next week!
Wanna see?
📸 For photos from the night, check out Instagram.
