My second "major" transgression came a few weeks after the first. So first I was tearing toilet paper. That summer I volunteered at a local hospital (I was a blood courier! coolest job ever). Every day we volunteered, we got a $5 voucher for a free lunch. There were no kosher options though. Actually, scratch that, there were kosher options, and for the first week or so, I ate reheated frozen dinners. I remember once that the reheated kosher meat thing had purple on the edges...ew. Meat should not be purple.
Anyways, a few weeks later I was eating at the salad bar. I knew that the utensiles they had weren't kashered, and they were probably cutting veggies with the same knife they were making chicken salad out of. I even had the pasta salad once in a while, and I freaked out once when I figured out that what I thought was tuna-pasta salad was actually chicken-pasta salad. My second major step, then, was eating non kosher vegetarian food (and fish) outside of the house. I stayed at that level of observence (kosher-wise) until the end of 2003...so that was around 6 or 7 years where I didn't go further beyond the realm of kosherut.
My shabbat observence stayed around the same as well..I was tearing toilet paper, but not doing much else. That stayed the same until my senior year of high school..which i'll go into later I guess.
Oh and I guess there was one other thing i was majorly transgressing on at the time...the whole shomer negiah thing. I had a secret boyfriend when i was 15...he was modern orthodox, and sometimes when i told my parents I was going to the hospital, I would take a bus to his house instead. His father had passed away before I met him, and his mother worked full time. So during the day we would spend hours making out in his apartment. We didn't have sex, but we did pretty much "everything but".
Eventually my parents found out about him, and I got grounded for about 4 months, becuase as my parents said, I wasn't allowed to date unless it's for tachlis (marriage) and i clearly wasn't going to get married at age 15. Also they found out that his mother had converted and his father was a cohen..which apparently makes him a bastard or something? (cohen's are not supposed to marry converts). Thus started the long line of boyfriends who weren't jewish enough for my parents, even though up until this year, they were all jewish. The next one had a non-jewish father, the one after that had converted to judiasm, the one after that was adopted and didn't re-convert when he had his bar mitzvah or anything. Out of the 7 or so guys I would call "boyfriends" I think only 2 were fully jewish enough for my parents- and those were two of the shortest relationships I had. Interesting.