DaMoshe, thanks for covering a lot of the ground. I’ll shed some more light on what happened in my case.
When I was in elementary school (it was the first day of 6th grade), as DaMoshe posted, I once said something about wanting to go to college. The Rebbe replied (in front of the entire class), “College? Only shkutzim go to college! You’re going to sit in kollel!”
I went home that night, and my parents asked me, “How was the first day of school?” I told them, “Apparently Tatty is a sheigitz, and Mommy is a shiksa!” The principal got an interesting phone call that night!
he next day, my Rebbe confronted me, and told me I was chutzpadik for telling my parents what he said. I was thrown out of class. The Rebbe repeatedly embarrassed me publicly throughout the school year.
When I was in 9th grade, I had a Rebbe who would also humiliate me. He told me he was doing it to make me a better masmid. Other kids in the class picked up on it, and I had a miserable year. I decided that if that was what went into being a masmid, I wanted no part of it.
Throughout high school, I didn’t really try to learn very much. I switched schools after 9th grade because I refused to go back to the yeshiva I’d been in. I got excellent grades in my general studies, but barely passed any tests in Gemara, I constantly skipped seder, etc. I was in a dormitory, which was closely watched, so there wasn’t much opportunity for other things. When we had an off-weekend, I’d go out and meet up with girls. I wasn’t careful about various things like Shabbos and kosher. I didn’t do things openly, but if I forgot to shut my alarm clock on Friday, I’d turn it off on Shabbos, or I’d adjust the AC in the summer if I needed to. I didn’t wait between eating meat and dairy at all – if I wanted a chocolate bar 10 minutes after a burger, I ate it.
After high school, my parents convinced me to spend one year in beis medrash. The Rosh Yeshiva caught on to what was going on, and decided to have a talk with me. At first he wanted to expel me, but his boss (the top RY) wouldn’t let him. When he heard I was going to go to college, suddenly he wanted me to stay. He told me, “If you go to college, you’re flushing your whole life down the toilet! You’ll never be a good Jew in college, because college doesn’t go together with being a frum Jew. You could learn all you want, but if you’re in college, it doesn’t matter – you can’t stay frum!”
I told him I definitely wasn’t staying in yeshiva, and that was that. I decided that if nothing I did would matter, then I might as well enjoy myself, so I completely let go. No more Shabbos, no more kosher, I started dating a girl who was in a sorority.
I went to Touro College only because they had a good program for what I wanted, and it fit with my (part time) work schedule. I made some friends there (including DaMoshe!) who were nice, Modern Orthodox people. I was also coasting my way through half a day of yeshiva at the time only to get the college credits. After some time, I realized that I wasn’t any happier than I’d be in yeshiva. I saw that a lot of my college friends seemed very happy and fulfilled with their lives, so I decided to give Judaism a try again – but not the yeshivish version. That’s how I went into the Modern Orthodox philosophy.
That’s just a condensed version. There are more details, but this is all I can write right now. College doesn’t make people go OTD. They go OTD because they don’t have a firm foundation in Judaism. That can happen anywhere – even in yeshiva.