I grew up in a parish that, while not "chant-oriented," was otherwise very much "say the black, do the red," so I gained some liturgical snobbery from that. Then, when I went to college, I decided to major in organ, as I had always been involved in "church music" in some form or another.
For my first church job, while still in college, I knew as much as, "Haugan/Haas stinks, hymns are better, and we are supposed to do the 'proper' texts for the responsorial psalms; not changing words."
Around that time, I was also becoming friends with some of my fellow Catholic music school undergrads, and we bonded over the musical superiority of our Catholic heritage, and in particular, some of their excitement over things like chant, polyphony, and chant-based repertoire spilled over to me. (H/T to J. Balistreri!)
Also around this time, I came across Aristotle's website (although of course I didn't know that at the time,) along with the NLM blog.
Soon after, I was hired into my next job, by a pastor who was (and still is) passionate for good music and good liturgy, although we literally worked through figuring out what that was, together. We both had to learn, since neither of us really knew. He sent me to the Colloquium in (I think?) 2007. (The last one in DC.) And the rest is history...

Nashville Dominican Sisters of St. Cecilia told me about the Propers. Later a parish priest handed the choir a copy of the SEP. We had always sung devotional chants and "solid hymns" at our parish, but were clueless that Propers existed for the Novus Ordo Mass.

Once we started chanting the Propers at Mass, "traditional" hymns started sounded profane in comparison to the sacredness of chant.

Since you mentioned Canada...
I am fortunate, in that at about 12 years old, we began attending the FSSP parish in Calgary, so that's where I first experienced it! My mom gave me a Liber, my dad has been buying me missals and chant books ever since. I also often attended the Byzantine rite in high school, and couldn't believe that these two places had such incredible music, and yet in the OF we had been at previously sang out of a disposable missalette.

When I moved to the US in 2004 for school, I didn't really know where to go to for "a good Mass", and when I started playing at a Catholic parish, it was to accompany the youth rock band and play a couple hymns on the organ on Sundays. There was no such thing as propers or chant...I even went to a conference from the other organization, and went to their chant intensive. But even that was not the same. I had been reading Mr. Tucker's articles for years (my dad would even clip them out and mail them to me at university...awww) and started checking out the CMAA website more seriously, especially when I became a DM at a rural parish, and encountered resistance to the sacred. Then I was sent to study at the Liturgical Institute (yay!).

The internet and my studies showed me SO much more for the OF, more than I guess I thought was possible. And of course, the internet makes it wonderfully possible to follow all of my colleagues at the LI and actually use their material (thank you Adam). So, inspired by these examples, I decided to actually try and use some propers. I honestly don't know if I'd be able to do the same back in western Canada...though I am in an interesting diocese here :)

It is amazing what this community has produced and made available for use. Thank you to the FSSP/schola/choir in Calgary for their hard work for so many years, and to all of you so much for your efforts!

When I was in highschool I had the privilege of singing with a women's group where the conductor loved good classical music. Chant was part of this. The first one I learned was "Ave Maria". I picked up more chant here and there over the years. In university we sang quite a bit of Anglican Chant in our "Chapel Choir" which I appreciated. I remember going to a World Youth Day Mass in Toronto where the parts were sung in Latin Chant. I was impressed that everyone, from across the globe, could sing them together. We have a new pastor who insists on Chant as the responses at Mass and has a "Gregorian Choir" which sings many of the original Gregorian propers. Now it is ingrained and I love it.

I grew up in parishes that did both contemporary music and traditional hymns, but I always had a greater fondness for the traditional side. In college, I was the only one who sang both with the 'folk group' for Mass and with the concert choir. Was a cantor for many years, doing the full gamut of styles (well, not the really casual stuff).

About a dozen years ago, I found myself increasingly spiritually unsatisfied by what I was doing with a growing feeling that my musical offering was no longer pleasing to Him. Long story short, He pushed me onto a seeming desolate road, where I studied Church documents online and poured over CDs and books (like Dr. Marier's A Chant Master Class). I also remember reading Aristotle's blog with great interest. Then I found the CMAA and my first Colloquium in 2006. That's when I knew I had found what I was looking for.

The little experience I had made me bold (dumb?) enough to volunteer to help with the music at our parish's first-ever EF Mass in 2008. Information I got from online editions of the chant and instruction from those on the forum were invaluable. (I didn't have all the right books and didn't understand many of the written instructions.) While I now have most of the chant books in hard copy, I still use the online editions frequently as well as the web-based sites like CCW. None of this would have gotten off the ground without the online accessibility.

I remember hearing chant and classical polyphony on 33 1/3's as a child. As an under- graduate sacred music major I got an intensive introduction to chant & polyphony from an historic viewpoint. Of course, classes in 16th century counterpoint cemented a true admiration for Palestrina. During graduate school, I had the good fortune of working under and studying with Msgr. Martin B. Hellriegel, who taught me a great love for the chant and sacred liturgy. That was the first time that I was exposed to the sacred chant as the normative expression of worship and adoration. (However, those faithful Germans at Holy Cross were probably as good as, if not better singers of hymns and chorales than any Lutheran congregation in Saint Louis!) It was at that time that the St. Louis Jesuits were holding forth at the College Church. In the turbulent 1970's, things changed drastically. The Archdiocesan Priests Choir gradually dispersed, guitars became the standard in most parish churches and a wave of "puritanism" in music & liturgy spread across the country. It would have embarrassed Oliver Cromwell, who managed to dismantle organs all over England, destroy choir libraries, vestments and anything else that could be construed as "Catholic" or "Anglican." After years of finding sanctuary in
Episcopal churches that appreciated chant & polyphony, I came "home" to a wonderful
parish where I could again use chant & polyphony both English & Latin, along with hymns and settings by Proulx as well as H & H! We moved to California to what I thought
was going to be my "dream Job." However, after a few years on the job, I was forced to
look elsewhere. My crime was getting local university students involved in our program and pushing out our talented volunteers who didn't need to rehearse a lot to sing solos.
They were down-trodden that "Fly Like a Bird" was never done, but a children's choir of 35-40 kids were being "forced" to sing irrelevant stuff that was "condemned" by Vatican II. Needless to say, I found a much better place! A pastor who jokes that not only are we reading the same book, but are frequently on the same paragraph. My first Christmas at
Saint Edward, the pastor gave each member of the choir a Gregorian Missal as a Christmas present! Nearly eight years later, we have a broad musical ministry that includes different choirs, including a children's choir and solemn mass choir that are now able to sing several chant ordinaries. At the Missa Cantata, we now sing the full proper from the Graduale, are in the midst of a multi-year project of learning the 5-part Offertoria of Palestrina, and learn also truly wonderful music by serious contemporary composers. I offer this as a word of hope for those who might be suffering for their art right now. Don't ever give up hope. Great art will always be the exception, rather than the rule. Remember the words that Msgr. Hellriegel used to say to the Children after an intense rehearsal for a great feast: "We don't practice in order to put on a show, but rather, that we might offer the best worship of which we are capable at that moment and so that nothing we do will detract from the worship experience of the person in the pew;
because that person is not a theologian and his or her experience of the Divine comes through the sights, the sounds and even the touch of the sacred liturgy."

The first time I heard of Gregorian chant as actual liturgical music was when my pastor introduced the Jubilate Deo ordinary chants at daily Mass. He told us about Latin being the language of the church, and Gregorian chant being encouraged by Vatican II. I read more about this as a theology student, and experienced it at the same time, since my classes were held at a Twin Cities parish that incorporated chant and polyphony at their main Sunday Mass. I became interested in learning more, and a seminarian at our parish obliged a friend and I by teaching us to chant the Pater Noster and Ave Maria. We also had a small group that chanted morning prayer together before daily Mass.

It wasn't until several years later that I was drawn into authentic sacred music for good. After getting married and moving out of state, then moving our family back, I was in my old parish listening to the "four-hymn sandwich" with an occasional motet sprinkled in, when something told me there had to be more to sacred music than this. As it happened, the organist/music director shortly left for a new job and I helped fill in until his replacement came. Around that time a friend told me to listen to recordings by the Cambridge Singers. Polyphony hooked me then, and chant came next. I dusted off my theology skills and dug into the church documents for concrete proof that there really was more to sacred music than what I was hearing at my parish. Our new pastor was more than willing to go along with my idea of starting a little schola to introduce the singing of proper chants at Mass. I found a group of about a dozen people who wanted in on the scheme. I photocopied the Square Notes article and a Latin pronunciation guide for them, and leaning on recordings from St. Benedict's Monastery in São Paulo, Brazil, we started out with the Communio and sang our first introit on Laetare Sunday as our pastor preached about what the introit is and how it is meant to be sung at every Mass.

That summer I attended the CMAA colloquium in Washington D.C. It was so encouraging to realize how alive the sacred music movement is! Back at my parish, the previous music director returned and much to my amazement seemed to know all about the Church's teaching about Gregorian chant. He continued what my little schola had started and grew a flourishing program whose highlight was singing chant and polyphony in Rome.