How long?
How often?
100

How long was Art's dinner with Betty?

Probably about half an hour.

100

How often do the two sisters dine at this restaurant?

Probably quite often. They know it well and prefer to go there on special occasions.

200

How long was Art's dinner with Liz?

A few hours. 

200

How often does Betty see Art?

Quite often; probably almost every day.

300

How long have Betty and Art been dating?

Not too long at all; probably for a month or two.

300

How often does Art dine at this restaurant?

He's never been to this restaurant before.

400

How often does the sommelier have a customer like Art? 

Probably this is the first time he has had such a customer.

400

How often does Art drug women?

Never; he's never done it before.

500

How long did it take Art to take a shower this morning?

Quite a long time; maybe half an hour or more.

500

How often does Art jump from trees?

This is his first time.