'Know yourself, know your target, a thousand battles fought, a thousand won' - Sun Tzi.
One thing a fellow Singaporean male must know is that Singaporean culture is not liberal American, but conservative Asian culture, & kids are taught to be conservative since young, to protect themselves at all times, & kids are precious to parents in our nation's 2 kids/family household, thus the proven & necessary culture & traditions to be conservative.
Should a male citizen approach a female citizen using American style openess - ' Hi, can I be your friend' - chances are close to nil, as her DEFENCES would be up, to protect herself, as the male citizen is a STRANGER.
To counter this, make use of FAMILIARITY technique. Let her get familiar with you first, through simple & seemingly INNOCENT coincidences. Find out her daily times & schedules such as bus, mrt or personal transport arrival at work & to home, at at office lifts, cafeteria, etc. However, do not, DO NOT be a stalker. It is unhealthy & will only eventually destroys one's mind. So keep it simple & stay out of her privacy rights.
Purpose:- To create an innocent opportunity to meet her. When the opportunity arises, just give her an innocent gesture of a smile & nod of greeting, as a form of natural Human courtesy.