The secret to good conversation especially in a dating situation is not made up of cliches or smart comments, it comes naturally when you are speaking to the right personality and it is very difficult when you are speaking to the wrong personality.
This is what makes romantic partnerships a success long term.
Of course it is not all that makes it a success, but if you do not get this part right your chances are very small.
Half the population generally speaking, do not like to talk in terms of personal feelings or emotions and avoid it most of the time choosing instead to speak about non-emotional subjects such as politics, religion, sport, winning, success and achievement.
The other half like to speak of emotional aspects such as how they felt about an event, how a place feels, how music moves them, how art affects them, how pretty or frightening something is, but they do not like to speak only of non emotional subjects because it has no depth of meaning for them.
When the two opposites try to make interesting conversation on a date or at a dating function it will be either difficult or it will become more difficult as it progresses.
When each one describes something there is no connection, they are speaking of the same thing, but in completely different ways so that conversation does not flow easily.
Each person feels increasingly that the other does not care for them, talking seems to be a battle rather than a wonderful sharing with mutual insight.
The non emotional person is called non-disclosing while the emotional person is called disclosing because one will be happy to disclose personal details and feelings and the other will find it very difficult to disclose personal information.
In a work situation you can know a "non disclosing" person for years and not find out about their upbringing or family life other than an occasional comment.
When you work with a "disclosing" person you can often find out half of it on the first day.
So for dating success look for how easy it is to talk with the other person, not just talk to them.
Are you agreeing on almost everything, does the other person seem like one of your good friends or are you puzzled by the way the other person thinks which makes conversation stilted.
This applies to long term relationship aims, not to quick liaisons.
You can get along with almost anyone for a short while and they can be very attractive even if they are the wrong style, but if you want a long term relationship should it work out between you then take notice of this information.
Ease of conversation is the key to a good relationship, you both need to be the same style.