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Should I be a little worried that I'm level 19 and I don't see much improvement with myself? My matches lately have been pretty down in the dumps, although I do get paired up with some pretty interesting team members that are a bit harder to deal with at times. But poor teammates and bad team compositions can't be the major reason why I keep on getting into matches that end up in defeats, right? It's a tad disheartening.
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Because of how the ranking system works you will always lose about half your matches. In the short term you can lose games because of bad teammates, but in the long term your rank (and thus which matches you're placed in) is determined by individual skill.
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Also, is getting a Rylai's actually a good option for AP Teemo? I often go with Frozen Mallet but I don't know if that's better than Rylai's since I usually already have Nashor's and Malady before it.
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That depends on how AP teemo works. I do not believe that Rylai's procs off of poison dart, and if so, then no, a mallet would be better.
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And how should I go about learning how to jungle? I know how it works on a few champs in theory, and I watch a lot of streams from TheOddOne, so I've picked up a few tips and tricks there, but at level 19, is this a safe time to learn how to jungle?
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As said above, many champs have a hard time jungling without runes. Warwick, Udyr, Fiddle, and certainly more that I'm forgetting can jungle without runes without issue (though Fiddle is a slow jungler with no AP)