I began learning Spanish about 7 years ago while I was still a University student. I'll explain the process from start to finish.
1) I had a spanish girlfriend (this was brief and hardly beneficial due to the length of time) but it motivated me to learn spanish.
2) I bought a bunch of books from Chapters. Most of which I never read except one with greetings. (Relatively useless)
3) I download a free government program they use to teach government workers. I printed the text and went along with the audio. I never completed the course as it was incredibly boring. (
http://fsi-languages.yojik.eu/) They have a bunch of language classes available for just about any language you'd want to learn.
4) I began to take spanish classes (2 years in university) - This is where I saw my first big jump in improvement. I participated more than anyone, I didn't care if I seemed like a nerd. I wanted to learn. The book we used was I believe called "Imagenes." It was readable and definately more enjoyable than the fsi government language course.
5) Before embarking on my first extended vacation in Cuba I downloaded a program by Words Galore. It may look lousy but it's fantastic. Around 10,000 spanish-english flash cards with voice. You can mark the cards you know, do tests, change number of repetitions, speed etc. I STRONGLY recommend this program. "http://wordsgalore.com/"
5) I got a dose of reality. I arrived to Cuba with my A+ spanish skills for my first extended vacation in 2011. I went for 2 months. I could say a lot of things but I had 0 group comprehension skills. It's one thing to listen to other gringos saying spanish words another thing to be in a group of native spanish speakers. I was a completely bozo in group conversation, many times to the point where I'd just tone out. During this time I had 2 girlfriends who I spent about a month each with. They were at the time the 2 best looking girls I'd ever been with. By the end of this trip I had some limited comprehension skill but was far from perfect. It was a combination of the girls but also the music that got me even more focused. On one of my last nights there I had the opportunity to see Gente de Zona in concert, it was by complete accident, but the vibe at the concert was absolutely unbelievable. Here's one of their big songs at the time...
https://www.youtube.com/watch?v=N2fJf5ZQvWQ
6) I continued talking on the phone daily with the girl I was dating when I left. (This was expensive) but long run it was well worth it as I kept my spanish exposure high. I also almost exclusively began listening to spanish music (mostly reggaeton). Now I don't know about you but even people who think they speak decent spanish can hardly understand what's actually being said in Cuban Reggaeton. But it forced me to really listen.
7) I continued to take frequent trips but the next big one was in 2012. I went to Havana and Holguin for 2 months each in the Summer. I briefly studied spanish at the university of Havana but I found it detracted from my social life as at the time I enjoyed going out 5 or 6 times a week and with early morning classes Monday to Friday after falling ill in the bathroom the 2nd week in, I decided to ditch the classes. I made tons of friends during this time, partied way too much but more importantly I was constantly exposed to group type atmospheres. I went to dozens of concerts as well. All the time I was in spanish speaking mode. By the end of this trip my comprehension was very good but still my ability to understand spanish reggaeton was limited. I loved the beat of it but understanding the lyrics was tough. Again the quality of chicks I was with was increasing.
8) I took another big 4 month trip in 2013. I spent much of this trip in Havana about 3 months as opposed to 1 month in Holguin. The first month was truthfully a struggle. I was spending more money than I wanted to and wasn't getting the results I'd like. I had a lot of people visit me during this trip. There was a ton of partying in the first month or two but really not very tangible results. My spanish was getting increasingly better though. At the start of the 3rd month I pulled the two best looking girls I'd ever pulled at that time. One I dated short term whereas the other I ended up in a LTR meanwhile during all of this I had a couple year relationship with another Cuban girl. I was constantly exposed to spanish during this time and became exposed to a side of Cuba most don't get to see.
9) I took several more long trips and honestly after a while you are just used to talking and thinking in Spanish. I wouldn't say I have a great use of abstract tenses as in every day speech people don't use about 95% of what you learn, but I'm able to communicate quickly, confidently and understand just about anything. As my spanish has improved, the quality of girls has without a doubt substantially improved. I was in my worst shape during my 2013, 4 month trip. To be frank I was completely out of shape yet was getting the best girls I'd ever had in my life. I think spanish was the main reason for this. With that said while spanish may have allowed me to date a couple points up there were a couple other factors that I also believe helped...
1) Cultural awareness
2) Ability to relate
10) The ability to relate theme is something that is incredibly hard to fake. I have to be honest and say if I went to Thailand or Phillipines I probably wouldn't relate one bit to the girls. I have 0 interest in their television, their music, their food. But I became enamored with those things in Cuba.
11) I have continued practicing my spanish during frequent trips as well as well as by emailing and calling friends. One of the keys to maintain your ability is to keep using it in day to day life. I also still listen almost exclusively to spanish music though I no longer listen to exclusively reggaeton and enjoy casino, merengue, pop, romantic etc.
Because this is game related forum I'll list the things I think are highly important in order of importance.
1) Language
2) Ability to relate
3) Cultural Understanding
4) Game - I think this is a marginal advantage. You just need reasonable amounts. The marginal advantage past a certain point is pretty limited and the 3 above factors are much more important if you want to access top tier non pro or gringo hunter chicks.
5) Appearance (This can slide up and down the scale but assuming you are better than 2/3 men in America you should be fine. Aka, be a reasonable weight, dress reasonably well and groom yourself. Age also falls here.)