dated vs outdated; well-off vs rich;

[Linh Bui Hoang]

Please tell me the difference between dated and outdated, between well-off and rich and between prolong, delay and extend
1. It was a fashionable film years ago, but it looks ____ now.
A. Dated B. outdated
I am very confused because both words mean old-fashion.
2. He may have a nice house, a nice car and be able to afford to go on nice holidays, but you couldn’t say he was ____
A. Well-off B. rich
Again, well-off and rich both mean wealthy.
3. The police asked the kidnappers to _____ the deadline by six hours
A. Prolong B. lengthen C. extend
This time I don't know what to choose among these three words similar in meaning.

[Gray]

1)
Dated: marked by features of the immediate and usually discounted past

Therefore, 'outdated' is apt here as we are talking about a film which was fashionable years ago.

2)
'be able to afford to go on nice holidays' and the negative tone of 'you couldn't say' makes me favour 'rich' over 'Well-off'. So, he was well-off, not rich. But our answer is certainly 'rich' :)

3)
I couldn't find reason here:( but I think 'extend' is correct.

I heard it many times - extend the deadline, as I rarely complete my tasks at work before the deadline :)
_________________
First lesson - English, not english. I, not i. ~A student of English

[Esl_Expert]

Hello Linh Bui Hoang and Gray,

There is some overlapping in the usage and meaning of the words "dated" and "outdated", but here is how I would describe the difference:

I would use "dated" in Linh Bui Hoang's first sentence. To me that suggests that you can tell approximately when the film was made (and that it was made quite some time ago) simply by watching it. In other words, if something is "dated", you will get a sense of the time it came from.

"Outdated" tends to be used not only when something is old or old-fashioned, but also when it can/will/should no longer be used for the purpose originally intended. Thus, you will hear people talk about old versions of things such as technology, manufacturing methods, machines, information, etc. as being outdated. Newer and/or better forms of these outdated things will have replaced them in the meantime.

[Gray]