So... All of that in red happens after they speak to ('talk to man") the character just one time? If so, that is very easy.
All you need to do is add a verb to the man and type in speak - this should pop up an automatic list of verbs similar to speak to. Click on that. When the player then types 'talk to man' or 'speak to man', your message will appear.
If the player needs to 'talk to man' one time to get some info... then 'talk to man' a second time to get more info... that is a bit different. In my case, I would use flags (but I'm weird like that). When you speak to the man the first time, also raise a flag on him and name it something like speakonce. Then, if you speak to him again, use an 'If' script to check if the flag is raised (which it would be) and print an appropriate second message. Then add else's to it to check for other flags ('speaktwice", "speakthrice', etc)
If you want an ask/tell conversation... like 'ask man about Mary', you'll need to add cases to the ask/tell tab for the man.
If none of this seems like an option, I think you need to change the type of object the person is. There is a tab (maybe object?) where you can change the 'object type'. Change it to 'male character (named)' (<-- something like that) and everything should be fine.I think Quest has a built in check to see if the object can be talked to. If you have a rake in your game, for example, it wouldn't make any sense to 'talk to rake' so Quest has a built in response like 'you can't talk to that'. But if you change the object type to something like a named (or unnamed) male/female, the built in response to that changes to something like "He/She says nothing" - that is, unless you add the 'speak to' verb.
Let me know if that makes sense (sorry if it is not very accurate - I don't have Quest downloaded to computer at school so I can't look at it directly).
Good luck.
And... I like your writing style be the way. I hope you finish your game so I can give it a try!

XanMag