Compensated Dating appears to have originated in Japan where it is still widely practiced today. In Japan it is known as enjo-kōsai and probably has its roots in Geisha culture.

The practice of Compensated Dating is in many ways very similar to Rent a Date but with certain subtle differences though some overlap does occur. Compensated dating is almost exclusively carried out by young girls (and boys) who are still in education. It appears to satisfy the 'Lolita Complex' which some men (and women) find appealing. It is usually but not always an exchange of sexual favours in return for money. Where actual sex is involved it matters little what name it is given. It is prostitution. Although enjo-kōsai is, to some degree practiced worldwide it is predominantly restricted to Asia and in Japan,Taiwan, Korea and Hong Kong in particular.

The money may be used for furtherance of education or to purchase luxury goods. Involvement in subsidised dating is so well known now that it is no longer an exclusively a 'big city' activity. Most towns will have young people tempted by the returns. Anonymity in arrangements is easy using phones (Telephone Clubs), the internet and the use of Short Time Hotels (Love Hotels).

The issue becomes more complicated when viewed through Western eyes and judged by Western morals. The age of consent in Japan is 14 years of age (2 years higher than Vatican City) though it is actually, through a 1999 dictate, against the law to have (paid) sex with someone under 18 years of age. This makes it stricter than most of Europe or the USA.

A survey carried out in Hong Kong in August 2009 amongst young people aged between 12 and 20 found that 34% would consider 'compensated dating' as a full time job. Out of those 34% most would get involved simply to earn quick cash. Only recently has the behaviour become a 'craze' and it is almost fashionable to be 'in'. This disturbing trend suggest a type of moral decay which needs addressing before the situation worsens.