Don’t worry about longish posts – I think I get some kind of internet prize for doing the same thing, as you’re about to discover lol.

“In regards to actually conversing with a native, when would you recommend doing this?”
For me, I went on Kijiji (which I think is specific to Canada, so if you’re Stateside you’ll have craigslist I guess) and found a Japanese tutor. I pay $20 per session but she’s quite fluent in English so if she says something I don’t understand she is able to explain it. This of course is pretty dependent on where you live – I’m in the country’s capital so there’s a lot of diversity here, which makes it relatively easy to find a native speaker. Otherwise, check out japan-guide.com; you will have to weed through some folks but if you pop an ad up in the classifieds (it’s all free) that you’re looking for a speaking partner, you will find someone. You can start out written at first. Think about what you want to say, and fill in the blanks as you go. Get a lot of it wrong and then you will be corrected. That was my experience with it, anyway. From there you’ll also be able to find people who are willing to go on skype or google hangouts, and you just use what you know. You’re going to encounter things that you don’t know how to say, and you’ll have to learn how to say it. As to when you actually do this, it can be at any time in your language learning journey. It’s going to be uncomfortable as hell but when you start to do it more, your confidence will build and you’ll be more open to making mistakes and not knowing how to say stuff. Necessity is the mother of invention as they say, and in this case swap invention for language learning.

You can also try, and this is scary but worth the risk, chatroulette or one of those other webcam things. The trick is to put that “Japanese” is one of your interests. It eliminates most of the penises you have to see and you’ll get thrown at people who are willing to chat. I’ve made a few friends doing that. There’s also mylanguageexchange.com and italki.com which both have some decent potential. You’re going to get a lot of people that are, as you have experienced, “more interested in flirting than learning” but if you keep at it you WILL get people that don’t suck.

“And one other thing :P, I typically consider myself a pretty sociable guy, but at the idea of trying to converse with a someone in a different language makes me kind of nervous. Any tips on this?”
I have a fairly mild social anxiety, so I can completely understand your apprehension here. I get nervous striking up ENGLISH conversations with strangers lol, let alone Japanese. As far as tips, this is a bit tricky. I try to live by this question: “will I regret this later?” – and I’ve never thought “yes” after talking to someone. (It’s also useful for weight loss! “Will I regret not eating this chocolate later?” NOPE. Just putting it out there haha). Sure you’ll feel like an idiot but afterward you feel good because you made yourself do something. It’s productive and it feels good emotionally to overcome the fear. So, you just kind of do it. Be aware that you might not feel good about it the first few times. You’ll feel like you just made a fool of yourself, and if you’re like me you think they’re judging you. But remember, most people will be happy that you’re making an effort to learn THEIR language. (Imagine it like someone is new to English and they come to you and, in broken English, ask for something; do you think “wow this guy’s an idiot for trying to speak a language he didn’t grow up with”? No, you do your best to understand and appreciate that they made the effort). If you’re more comfortable to start out just writing to someone, do that first. As I said before, I didn’t start using my knowledge until very recently and because of that I have zero confidence in it. Your being nervous comes from having no confidence in your language skills, so you need to build that confidence, which you will do by being uncomfortable a lot of the time at first. It’s actually good to have someone whose English is stronger than your Japanese, because like with my tutor, things can be explained to you. For some inspiration, check out the YouTube channel “Other Ways of Life” and look at his “Rejection Therapy” videos.

Now – all of this said – you still want to learn vocabulary. Grammar is important too, for sure, but there’s more vocabulary than there is grammar. So, as Strangeluv said, grab that 6k deck. You still want to spend a bit of time on grammar, but you will pick up a lot of it over time through regular or semi-regular usage. You should also check out the Tofugu 500 sentences pack if you haven’t. There’s some pretty advanced/weird stuff in there but going through each of the sentences you pick up a lot. I’m cutting myself off now because I could actually write all day about this.

How’s that for a lengthy reply? ;)

And thanks for checking out my channel!!