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The Elder Scrolls V: Skyrim Hints
Speech
1 of 4: The main way to practice this skill is to do a lot of buying and selling with merchants.
2 of 4: Travel to every town and look all around for things that are legal to take, then sell them to the local merchants. You can also steal stuff to sell if you've done enough Thieves Guild faction quests to gain access to one or more of their special "fence" merchants.
3 of 4: You can also get Speech practice by buying stuff from merchants, including stuff you just sold them, but you'll lose money in the process.
4 of 4: You might want to do that until you run out of money, use the Money-Making Tips to make some more money, then repeat the back-and-forth routine with a merchant's cheaper items to practice your Speech skill. Note that skill increases will be *very* slow in coming, though. (Just like with the Mercantile skill in Oblivion.)