One good way to encourage conversation whilst on a date is to have some props. If you have an interested watch, piece of jewellery etc, your date is likely to ask you about it. Note: whilst the prop should be different, it should still be tasteful. If you are unsure, perhaps get some advice from friends or relatives about what they think of your dating prop.
It is even better if there is a story to go with the dating prop. If your date brings it up, you will be able to tell a story about how interesting you are, without bringing up the topic yourself. Another good reason to go on a holiday.
You can also use the idea of dating props in your house. If you have some interesting props placed around your house, this should also generate conversation pieces. If you found that African face mask whilst trekking around the African countryside... all the better.