a littleshadyit is, with its half grunge, half cowboy décor it is probably not your typical fist date location but that is what’s so great about it. it is a great watering hole, hidden from the busy city, perfect to get cosy over a few drinks. you could go all in and order bourbon, chill with a beer or be a little spontaneous and order a cocktail, whichever drink you decide, it will aid the conversation flow. warning, your biggest obstacle here will be finding the bar– the entrance is a non-descript alley door with no signage, good luck. shadypine saloon shop 4, 356 crown street, darlinghurst, sydney nsw web: shadypinessaloon.com hit the sweet spot: chanoma, sydney cbd the way to someone’s heart varies person to person, the way to my heart for instance is cheese but more often than not, the way to someone’s heart is sweets. this authentic japanese café in regent place is known for its japanese matcha green tea but sticking to the sweet notes, they serve up generous matcha-based parfaits that are great for sharing . you can’t go wrong with the standard parfait matcha comprising of sweet green tea ice-cream with taro balls, pocky sticks and fruit. read our full post on chanoma. chanoma 1/501 george street, sydney nsw phone: (02) 9767 5465 web: chanoma.com.au for the people watchers: the bucket list, bondi beach the perfect venue for a sun-filled afternoon date where you watch the world go by, literally! it is the best spot for people watching and to share a jug of pimms! the only downside is that it gets very busy over the weekends in the afternoon, so i would recommend making sure you know what your date looks like before venturing inside, otherwise that could be quite awkward. the other plus to going here is that there are so many people you can always excuse yourself for the ‘bathroom’ and take a detour all the way home. the bucket list the bondi pavilion, queen elizabeth drive, bondi beach, sydney nsw phone: (02) 9365 4122