What makes a great date is the quality of the conversation. Keep it intimate at this classy but bold space at the Mandarin Oriental. Inspired by the Pacific Ocean and the culture of Asia's ports, the menu is chock full of beautiful drinks fitting of your date. Try the Mother of Dragons ($26) a blend of strawberry aloe vera and dragonfruit cachaça as well as the Coconut Beaches of Fiji ($28) if you're looking for a romantic getaway without having to leave the city. There are also plenty of plush lounge chairs for both of you to open up and get to know each other through deep chats.
Impress your date at this grand art deco-inspired bar, featuring champagne-hued tapestries that line the ceiling, and intricate gold and bronze balconies that surround the space. But the highlight here is its massive gin tower, which claims to house over 1,000 bottles of gin. You can't go wrong with a gin and tonic or the Atlas martini but have fun and explore the rest of its extensive menu. It even has non-alcoholic cocktails if your dates prefers to stay away from booze.
Perched on the second floor of Sum Yi Tai, the Cantonese restaurant that takes inspiration from Hong Kong's hedonistic days in the 1980s, Mona Lounge is a back-room cocktail bar where the afterparty happens. Sip on a cocktail or two as Chinese jazz is piped in through the stereo and savour the surprises the night might bring. The modern Asian cocktail menu curated by group chief bartender Sam Wong features drinks like Mona’s Tea ($22), a cognac-based cocktail made with oolong PX sherry and Fernet Branca, which is served with salted egg chocolate made by Singapore’s own craft chocolatier, Fossa Chocolate.
Snuggle up to your date at this dimly lit bar and have a conversation over its unique signature drink, the Gibson ($23). A cousin of the martini, this tipple is a conversation starter served with house-pickled onion, ginger and smoked quail egg. Pro-tip: come on Tuesdays to enjoy oysters at $3, all night long. *wink*
Show your street cred by taking your date to this basement bar that's only marked out by a couple of illegible scribblings. The bar's cloud of light bulbs and host of multi-sensory cocktails should help to get the conversation going. If not – there's always Dagger's experimental cocktails that are driven by flavour profiles so you get funky combinations like the Pork Soda, which is actually lighter and more refreshing than it sounds.
Right around the corner from BluJaz is its Latin offshoot, a Mexican joint that, like the mothership, attracts crowds with live DJs and a bustling alfresco area. But, it's the cocktail-friendly Mexican grub that keeps us coming back. The chunky guacamole is prepared with just-right doses of lime and chilli, and a fresh and tangy ceviche is worthy of seconds. Unwind with an after-work margarita in hand that won’t leave a gaping hole in your wallet. The vibe here is streetside chill – go for the outdoor seats along Haji Lane and play a drinking game with your date: each time you spot someone taking an #ootd or wefie in the photogenic area, down one.
There's nothing like a good rooftop to set a romantic scene, but you also don't want to peak too early – save the best for the month-iversaries. Southbridge is a happy medium. This fifth-floor shophouse perch rolls out a view of the Singapore River beneath your feet and the CBD in the distance. Book ahead for one of those seats by the roof's edges, and order a cocktail or two to have with a bit of nosh or an oyster platter.
Sail with your date through the undisclosed sliding glass door down to this basement speakeasy below Uma Uma Ramen – you're hardly a super spy, but in his or her eyes, you'll look cool. In this sleek bar, the cocktails are potent, Japanese whiskeys approachable, and bartenders professional yet tonnes of fun – they'll help you navigate their many rows of top-shelf booze. Uma Uma's steaming ramen bowls can also be ordered late into the night. Otherwise, share one of the many izakaya-style snacks like gyoza, shishamo, edamame.
So your date's better looking than he or she is a conversationalist. Nothing new here, eh? But don't give up yet – if you're still keen to hang, hit up Crazy Elephant on Clarke Quay. The live musicians here croon old-school roots rock, rock 'n' roll and blood-and-guts blues that'll bring the barn (and hopefully your date's guard) down. Who knows – you might just get lucky after a few drinks and conversations held close.