Before you ask, no, Catchfly is not a speakeasy bar, but it does feel like it. Located at the basement of 12 Ann Siang (that’s below Screening Room and Coriander Leaf Grill), the American-style bar is cosy and dimly-lit – which certainly helps to set the mood. Oh, and because you’re in the basement, your phone’s connection will be spotty, but the upside is that you definitely won’t be disturbed by a work call. The drinks here are grouped into four categories: Revitalizing; Smooth; Adventurous, and Forbearing. Popular choices include the Honey Badger ($22), if you’re in the mood for something light and refreshing, and if you like your drinks strong and smokey, there’s the Choke and Smoke ($24).

Catchfly is at 12 Ann Siang Road, open from 6pm – 12:30am Monday to Thursday, and 6pm – 2am on Friday and Saturday.

If you want a bite, Catchfly also has a small but decent food menu, which includes snacks like spiced edamame ($12) and truffle shoestring fries ($12). There’s also mains, including Lamb Chops ($28) and Sriracha Chicken Sandwich ($23), which let’s be honest, would be something you’ll probably want to get after three drinks.

Catchfly is at 12 Ann Siang Road, open from 6pm – 12:30am Monday to Thursday, and 6pm – 2am on Friday and Saturday.

With plush leather seat booths, white brick walls, and industrial-chic décor, Club Street Social is undeniably hip, and a little bit boujee as well. It works perfectly for that post-work weekday date, especially if the both of you work in the CBD vicinity. The restaurant-bar recently launched an all-day menu that’s designed for sharing, and you know what they say, food always helps to bring people together. You have to try the Scotch egg ($11), a boiled egg with a satisfyingly soft middle that is wrapped in pork sausage and topped with a housemade red onion chutney. The beef short rib fritters with housemade horseradish sauce ($15) is good too. And remember to save some space for desserts, because their churros ($10), which is served with vanilla mascarpone and balsamic strawberries, is to die for.

Club Street Social is at 5 Gemmill Lane, open from Monday to Friday, 10am – 12am, Saturday, 11am – 12am, and Sunday, 11am – 4pm.

Drinks-wise, there’s a small but decent selection of cocktails. Try the Monkey Mate ($22), and trust us when we say that they’re not stingy with their pours here. There’s also wines, draft beer, and bottled beer if cocktails aren’t your thing.

Club Street Social is at 5 Gemmill Lane, open from Monday to Friday, 10am – 12am, Saturday, 11am – 12am, and Sunday, 11am – 4pm.

There are many things that we took away from Aziz Ansari’s Master of None, one of which is that tapas is a great option for date nights. With dishes ranging from $9.90 to $25 and wines starting from $35 per bottle (available by the glass as well), Tapas Club is an affordable, no-frills tapas restaurant that is conveniently located in town.

Tapas Club is at #02-13 to 15, Orchard Central. Open on Sunday to Thursday and public holidays, 12pm – 3pm and 6pm – 11pm; and Fridays, Saturdays and eve of public holidays, 12pm – 3pm and 6pm – 12am.

Highlights include the Patatas Bravas, deep-fried potato cubes drenched in spicy brava and aioli sauce, and Gambas al Ajillo, prawns sautéed with garlic and served with a side of bread. We also loved the Pan Con Aceite y Vinagre – toasted homemade bread served with olive oil and balsamic vinegar pearls imported from Spain. If you’re hungry, there’s also paella. For something a little different, try the Fideua Negra, a squid ink noodle paella with cuttlefish and aioli.

Tapas Club is at #02-13 to 15, Orchard Central. Open on Sunday to Thursday and public holidays, 12pm – 3pm and 6pm – 11pm; and Fridays, Saturdays and eve of public holidays, 12pm – 3pm and 6pm – 12am.

Craft beer in a hawker centre? Why not? Plus, the bottles range from $6 to $15, which is super wallet-friendly. The obvious downside is that there’s no air-con and it can get hot, but hey, there’s nothing stopping you from coming down in the de facto Singaporean girl uniform (i.e., tank top, shorts, and slippers). You might want to give your date a heads up first though.

The Good Beer Company is at #02-58 Chinatown Complex. Open from Monday to Saturday, 6 – 10pm.

It’s hard to go wrong with a classic cocktail bar. Jigger & Pony at Amoy Street does amazing cocktails – you have the classics, like the Old Fashioned and Negroni, and the bar’s own creations like the Corpse Reviver #101 and Yuzu Whiskey Sour.

Jigger & Pony is at 101 Amoy Street. Open from Monday to Thursday, 6pm – 1am, Friday and Saturday, 6pm – 3am.

And if the night takes a good turn, you can bar hop and check out the other cocktail bars in the area, like Sugarhall (which is right next door)!

Jigger & Pony is at 101 Amoy Street. Open from Monday to Thursday, 6pm – 1am, Friday and Saturday, 6pm – 3am.