As teenagers start to grope for their identity, they will inevitably go to their parents with more requests for possessions and permission.
Not all of the requests will be possible to accede to. The trick to saying "no" to a teenager and have him toe the line is not to state it immediately, say experts and parents.
This applies to seemingly innocuous situations such as hanging out late to even obvious ones such as trying smoking, says housewife Tonia Goh, 47.
"Particularly for teenagers, conversation ceases the moment you blurt out a quick 'no'," says Ms Goh, who has four sons aged seven to 16. "By asking me for permission, they are letting me into their life and space, so I capitalise on that and avoid passing judgment so quickly."
Instead, she probes the reasons behind their requests - such as wishing to feel accepted within a social group - and discusses the pros and cons of each decision.
The word "no" tends to escape well-meaning parents' lips too quickly, say counsellors.
Ms Iris Lin, 33, who heads the youth division at Fei Yue Community Services, says: "You hear teenagers telling their friends: 'No need to ask, parents sure say no', then they go on to do what they like."
Particularly as the child is leaving the "structured cocoon" of primary school and moving on to secondary education, he enters a stage of building his self-identity and esteem.
"For teenagers, they no longer want to be known as 'Mr and Mrs so-and-so's child', but prefer to assert their own mind, heart and personality, and find a group of peers to which they belong," says Ms Lin.
Fitting in with social circles also brings accompanying troubles - parents say they often grapple with their teenager coveting things that his friends own, such as a pet.
Corporate communications specialist Pauline Teo's 13-year-old son and 10-year-old daughter have pleaded with her for a pet cat. But she has had to put her foot down as her daughter has a sensitive nose.
Instead, she offers a compromise - the family feed cats in their housing estate and visit cat cafes.