"You look familiar... have we met before?" I believe is a well, familiar, overused, ineffective and yet evergreen pick up line and question regardless where we are on earth.
In the past (before the 1960s), matchmaking was a common practice in Singapore. My grandparents were match made and only met each other once before the wedding day. It then moved on till people finding their own soulmate from their social circle, or friends of friends. In the earlier 2000s, dating agencies started to sprout where you pay a sum for suitable dates to be arranged for you based on your profile and preferences. (On a side note, some guys preferred to find a bride from neighbouring countries, mostly from Vietnam or China, with the general reason or sentiment being that, local ladies were 'too materialistic'.) Speed dating came along as well, and fast forward to today's tech age, young people from generation Y are more open to finding a date from apps like Tinder and Coffee & Bagel. Well, there is somewhat a stigma among the community to use dating apps because of having to put oneself out in the market and possibly appearing 'desperate'.
Robert plays an "Ah beng", which is a colloquial phrase of referring to a gangster. The typical look would be someone in tight fitting clothes, heavily tattooed, dialect speaking, cigarette in hand. There was a season in the 90s in Singapore where it was common to hear kissing sounds made by guys to get attention when ladies walk by. Local guys are generally not very forward when it comes to approaching a girl of interest, perhaps because of the conservative culture which still exists somewhat.
The phrase, "to go steady", was also widely used to mean to be officially dating. A girl would then be known as the guy's "stead".
Congrats Robert for clinching a date!