This week’s date night was a little bit different — and a little bit fancy! It was actually a birthday treat from our very good friends (thank you again — you know who you are!). They treated us to dinner at Napolizz at Anson, followed by cocktails (well, mostly mocktails) at the award-winning Jigger & Pony. Definitely a night of indulgence — minus most of the alcohol!
Where?
🍕 Napolizz Pizza – 101 Anson Road, #01-08, Singapore 079905
🍸 Jigger & Pony – 165 Tanjong Pagar Road, Amara Hotel Lobby, Singapore 088539
What?
We kicked off the evening at Napolizz, a relaxed and stylish Italian spot tucked into Anson House in the heart of the CBD. Born from a pizza takeaway, it has evolved into a sit‑down restaurant celebrated for its authentic thin‑crust pizzas and hearty pastas.
The décor felt modern yet cozy, with comfortable seating, warm lighting and a casual energy that suited our birthday‑friend‑double‑date perfectly.
We began with potato wedges, which might sound simple, but were perfectly crisp and served with a surprisingly addictive chilli mayo. Then came the caprese salad, fresh and classic, with creamy mozzarella, fresh basil pesto and juicy tomatoes — light enough to make us feel like we could handle a main course (or two).
We shared a Napolizz pizza — the kind with that slightly charred, chewy crust that tastes like it came straight from Naples — and a ravioli dish so generously sauced that it didn’t exactly look fine-dining fancy… but wow, it was delicious. The sauce was rich, creamy, and full of flavour, and yes, we may have mopped up every last drop with the pizza crust. Classy behaviour? Maybe not. Totally worth it? Absolutely.
From there, we took a short stroll (always nice to walk off the pasta!) to Jigger & Pony, a bar that’s regularly ranked among Asia’s 50 Best Bars AND World’s 50 Best Bars — and you can see why. Walking in feels like stepping into a 1920s speakeasy: low lighting, plush leather seats, jazz music humming in the background, and bartenders who know their stuff.
Despite being an award-winning cocktail bar, only one of the four of us was actually drinking tonight — which turned out to be kind of perfect. The mocktails were every bit as creative as the alcoholic options.
Here’s what we tried:
🍋 Yuzu Whisky Sour – for the token drinker of the night; tart, aromatic and beautifully balanced.
🍏 Apple & Cedar – (non-alcoholic) light and crisp with a touch of sweetness; like sipping autumn in a glass.
🍊 Blood Orange & Raspberry – (non-alcoholic) zesty, refreshing, and gorgeously pink; equal parts tangy and elegant.
The staff were friendly and knowledgeable, happy to walk us through the menu and make recommendations. It felt refined but not pretentious — more like you were part of something special rather than just out for a drink.
Even without alcohol, the vibe was sophisticated, fun and just the right side of fancy. A lovely chance to catch up with friends, laugh a lot, and enjoy a night that felt properly “grown-up” but still relaxed.
WOW Tips!
⭐ Get the ravioli at Napolizz – the sauce is just delicious!
⭐ Jigger & Pony’s mocktails are just as impressive as their cocktails — ideal if you’re skipping the booze but still want to feel fancy.
⭐ Book ahead if you’re heading to Jigger & Pony; it’s small and gets busy quickly.
⭐ For a perfect combo: casual dinner, classy drinks, and a leisurely evening walk between the two.
Worth it?
Absolutely. This date night ticked all the boxes for a proper catch-up: comforting, delicious food, flowing conversation, and an atmosphere that made us feel a little indulged without being over the top.
It’s a reminder that the best nights out don’t always need to revolve around alcohol—good company and a thoughtful setting are more than enough.
8/10
What HE said…
“7/10 – This would be higher, but it’s my fault for going to a cocktail bar during a sober month. The mocktails were excellent and I think I would have enjoyed it even more if I had a cocktail. Warning: very trendy place.”
Wrap-up
Saucy, sophisticated, and slightly sober just about sums it up! A night that reminded us that great company and great food are all you need for a memorable evening. Whether you’re toasting with cocktails or mocktails, sharing a pizza or mopping up ravioli sauce, it’s the laughter and conversations that make it special.
Do you have any good cocktail bar recommendations? Post it in the comments! Stay tuned for next week’s date night…
Wanna see?
📸 For photos from the night, check out Instagram.
