Get the awkward out of the way as you messily dig into over-the-top and greasy-in-a-good-way dishes such as the bak chor mee grilled cheese sandwich ($18). If you're on a budget, take advantage of the Beat the Clock promo. Housepours, beers and wines by the glass go for $5 between 5-5.59pm, $6 between 6-6.59pm, and $7 between 7-7.59pm.
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.
Park yourself on the roof of this three-storey complex to enjoy glittering views of the CBD. If that doesn’t impress, there’s always cocktails like the Chinese Mojito ($21) and Date a Gangster ($21) that’ll do the trick.
The craft cocktails at Bitters and Love never disappoint – unlike dates who don’t look at all like their Tinder profile. Ask for a bespoke cocktail and let head bartender Naz Arjuna take care of the rest.
Cosy 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 – you could always just talk about the weather.
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.
Skip the people-watching booth seats at the front for the darkened tables-for-two just past the kitchen at Vasco. This well-appointed Latin American-inspired gastrobar has a transportative effect, so it feels less CBD and more deep-in-Buenos-Aires, and the food and drinks certainly help cement that impression. Pisco, mezcal, cachaca and tequila native to South America feature heavily on the drinks menu, while empanadas, ceviches and Argentinean rib-eye only add to the feeling of being whisked away for an adventure.
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.