Yom Kippur 

The Gemara (Taanit, 26b) states that Yom Kippur and the 15^th of Av are the happiest days of the year because on those days they made shidduchim. 

However, on Yom Kippur people go through so much suffering (I.e. starvation). Therefore, why does the Gemara (Taanit, 26b) consider it the happiest day of the year?
 
Additionally, what’s the reason why they would make shidduchim specifically on Yom Kippur (and the 15th of Av)? A large part of Yom Kippur is spent praying. Wouldn’t it have made more sense to set aside a different day to make shidduchim in order so that there would be more time?

Furthermore, the Medresh states that the holiday of Yom Kippur will always endure (even after Mashiach). However, out of all the holidays, why in specific will Yom Kippur endure? 
 
Further, how does one avoid feeling like a hypocrite on Yom Kippur? Many people often make promises on Yom Kippur that they don’t end up fulfilling!?!

Lastly, the Gemara (Yoma, 20a) states that on Yom Kippur man has no yetzer hara. However, if we have no yetzer hara then how is it that we sin?

Rabbi Yochanan Zweig explains that after Adam ate from the Tree of Knowledge of good and bad he received a yetzer hara which gave him needs. Meaning, Adam suddenly had uncontrollable desires to do evil. Rabbi Zweig explains that people often do things (even to themselves) in which they have no desire for just so that they should be accepted by society. As a result, most of the things in which the yetzer hara persuades people to do don’t even give them any pleasure, as they merely act in a manner so that they could feel as though they have a place among society. Therefore, Rabbi Zweig explains that every time one sins they don’t even gain 100% pleasure, as they naturally feel bad for sinning.

Further, Rabbi Zweig explains that a person could still sin on Yom Kippur without a yetzer hara, as Adam sinned before he had a yetzer hara when he ate from the Tree of Knowledge. What then does the Gemara (Yoma, 20a) mean when it states that we have no yetzer hara on Yom Kippur? Rabbi Zweig explains that on Yom Kippur were liberated from our internal needs and pleasures. Meaning, on Yom Kippur we don’t feel addicted to worldly pleasures. Similarly, we could learn this out from the numerical value of the word “satan” (evil inclination) which is 364, as one day a year (Yom Kippur) we don’t have a yetzer hara. As a result, on Yom Kippur we have the ability to be totally in touch with ourselves, as we don’t have our usual internal craving to do evil. Therefore, anything we say on Yom Kippur is what we really want. Throughout the year our yetzer hara forces us to do things we really don’t want to do. On Yom Kippur, however, there’s no pressure from the yetzer hara so we could do what we truly want to do. Thus, any promise we make on Yom Kippur means that we really want to fulfill that commitment, so even if we don’t keep those promises during the year were still not hypocrites, as the yetzer hara simply persuades us to break those promises. 

Furthermore, Rabbi Zweig explains that Yom Kippur is the happiest day of the year because on that day we could do whatever we want without any pressure from the yetzer hara. Meaning, even though we can’t enjoy all the worldly pleasures we nevertheless don’t feel deprived without them because we don’t have a yetzer hara. Therefore, Rabbi Zweig explains that Yom Kippur is the happiest day of the year because we don’t have the force of the yetzer hara driving against us and causing us to feel as though were not in control of ourselves.

Similarly, Rabbi Zweig explains that Yom Kippur is the perfect day for shidduchim because on that day were totally in touch with our real wants and desires. As a result, we are clear minded and know what to look for. Additionally, on Yom Kippur we are all able to realize who we really are (what are interests are, etc.)-so our spouses will be able to see the kind of people we really are (instead of who we are during the year when we are often controlled by the yetzer hara). Therefore, even though a large part of the day is spent praying it is nevertheless the best time to find our real soul mates.

Lastly, Rabbi Zweig explains that after Mashiach comes we will have no yetzer hara and our state of being will be the same as that of Yom Kippur. Therefore, Rabbi Zweig explains that the Medresh says that the holiday of Yom Kippur will always endure.