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Sims don't like talking about things that don't interest them. If they won't talk to somebody for more than a few seconds, it means that person is talking about something they don't care about.
You can manipulate your sim's interests legitimately, via the magazines, or cheat their interests to where you want them, via the
supersculpture from Some Sim Things, or you can keep searching for a sim whose interests match yours.
I use the supersculpture nowadays, but I used to keep lists of the top 5 interests of every sim in the neighborhood, so I'd know who to have talk to whom.
Oh, and the pre-made sims usually don't have any interests at all until you take them away from their house for the first time, which may be the source of your problem, if they're the people you're trying to talk with. Before I start a new neighborhood, I make sure Claire and Ginia and the rest all have interests by having them visit Old Town for five minutes. Or I use the supersculpture to give everybody a few interests that most people talk about in real life, like Weather. :-)
I've made some mods for The Sims 1 -- yes, The Sims ONE :-) -- which you can find at
http://corylea.com/Sims1ModsByCorylea.html