Now, I must preface this post by saying I was never the type to learn languages, but rather learn about languages. In other words, I'd rather just read about a language's grammar, phonology, and history instead of putting in the effort and time in studying a language to the point where I can actually use it in my day to day.
I'd been interested in languages even prior, but my first experiment in learning a language came at the age of 14: I chose to study German. Already a formidable task, German's inflections, weak and strong declensions, and somewhat daunting vocabulary where words like "calculus" get translated to "Infinitesimalrechnung" (well, in English what we refer to as "calculus" is actually one calculus out of many, and specifically "infinitesimal calculus" which reflects in the German word for it... meandering aside). I was a maverick however. I eschewed the structure one traditionally uses to learn languages, systematizing it to maximize intuitiveness for a completely random approach. I'd read out of a resource randomly whenever I needed to know something and then try writing something in the language. What also helped was the fact both of my parents had formerly lived in Germany for years, and spoke the language (though they moved back over 15 years ago, so their German is rusty), and that gave me an opportunity to speak it. It had even become a code for when we're both in public and need to discuss something in private.
I'm now a student doing a foreign languages degree (well, it's foreign languages + some other stuff, disclosing more would pretty much dox me), and I studied French and German. Yes, I went back to studying German again! Turns out, being a maverick wasn't the best course of action in learning a language. I suppose chuunibyou got the best of me. However, it did pay off (somewhat), as speaking to my German professors, they had mentioned to me I'm at a B1 or B2 speaking level (well... not very good for having began studied German again at 18...) My French at the moment is much better than my German, which has become rusty.
Another experiment that wasn't as successful was the time I tried studying Latin as a 15 year old. German gave me the confidence to do it. After all, I'd been through all sorts of noun and verb inflections, weak and strong declensions, what's the worst that could happen? It hit me with all sorts of things: 6 cases, more than German's 4... but it isn't too hard to know when to use them, right? Then, you have the locative, which only really works with a few nouns, usually place names. But what cut me down to size was the declension system: 5 declensions you have to recognize, and each declension has its own special suffixes for the 6 cases. And let's not forget the conjugation system.
You see, in French, as we were taught, verbs fit into 3 categories: the first group (verbs ending with -er), the second group (verbs ending with -ir), and then the third group where all the misfit verbs are. For the first two categories, the endings are the same. For example, "aimer", to love. "j'aime, tu aimes, il/elle/on aime, nous aimons, vous aimez, ils aiment). For the second group, you have the verb "finir", to finish. "je finis, tu finis, il/elle/on finit, nous finissons, vous finissez, ils finissent). The two most important verbs in French are of the irregular class. "être" (to be) and "avoir", to have. That's simplifying it a bit but that's the gist of it. Now, Latin has that category for irregular verbs... however, there are 4 regular categories for verbs. FOUR. And let's not even get into the mood matter, with indicatives, subjunctives, and imperatives... and this is all scratching the surface.