it's funny that you both think that guilt is a bad thing, I thought that it is actually a good thing. [...] I was wishing to feel that remorse that most frum people felt but I didn't.

So for example, there's no need for guilt if someone from my shul is going home hungry, but there IS appropriate guilt if I had invited that person over and then forgotten!

Getting back up after a fall
If we experience a fall, we must never let it get us down. Getting depressed is exactly what the Yetzer Hara wants, and it leads to a vicious cycle of continued falls. (Listen to this powerful 5 minute audio clip from a Shiur of Rav Ben Tzion Shafier).
The truest test of an eved Hashem is davka when Hashem takes everything away from him, such as when he falls and feels nothing; no emotion and no Hislavus. Hashem does this purposefully sometimes, because that's a person’s moment of truth where he can ask himself honestly, “am I an eved Hashem because it's my nature and/or because it keeps me emotionally happy, or do I serve the Almighty because that's His will and nothing else?”
The Lechevitcher Rebbe (a student of R' Shlomo of Karlin) once went as far as to say that even if a person just killed someone and the knife is still dripping with blood, and he feels unable to stand up and daven Mincha (the afternoon service) with all his strength and heart, then he has not yet tasted from the waters of Chassidus!
The Be’er Mayim Chayim says that in the army, when they would want to test a great soldier to see if he's fit to be a general, they would put him on a wild horse that was impossible not be thrown off of. The whole test was only to see how fast he would get back up after he was brutally thrown down and wounded.
27. Charata vs. Yiush
It is important to understand the difference between “healthy” guilt/regret, as opposed to depression/despair. There’s a simple test we can do to know which of them are motivating us. If we see that we want to get stronger again, then it’s a sign that our “bad” feelings are those of
healthy guilt and positive regret. If, however, we feel that we just want to give up, it’s a sign that we are experiencing despair and depression, and we must quickly find a way out of these harmful feelings before they lead us to a vicious cycle of continued falls.

Kedusha, I started listening to the shiurim and so far so good. Thanks again for bringing the shiur series to my attention. I'll let you know how I like it as I progress...