The story of Yehuda and Tamar is a puzzle. How could a Tzaddik like Yehuda get involved in such a lowlife situation? The Medrash says that Yehuda wanted to pass by Tamar, but the Malach of Ta'ava was sent by Hashem to trap him, which caused Yehuda to go against his good sense, and detour towards Tamar by the road. So great was his passion burning, that he gave her three valuable royal items as a pledge for a single goat (see Ibn Ezra and Abarbanel).
The Meforshim say that when there is an enormous potential for good (like Malchus Bais Dovid and Moshiach Tzid’keinu) then the Satan and all the forces of evil fight back furiously. It was Min HaShamayim that Malchus Bais Dovid should Davka come out this strange episode (including the sins of: ע רָָׂׂ וְאוֹנ ן Er and Onan who were enticed L'maala Min HaTevah to sin). Similarly, we have Malchus Bais Dovid coming Davka from Bas-Sheva (the mother of Shlomo) with whom Dovid sinned.
R’ Shlomo Wolbe Zatzal said that a Yid should be Dan himself L'kaf Zechus (especially these days). Of course, preventing even the smallest sin is of utmost urgency. Yet, when a person feels broken about his unfortunate Kin'ah, Ta'ava, Kavod, Ka'as, etc. situation; he should suspect that maybe it was Min HaShamayim like by Yehuda... "But it’s not the real me!"
“The real me is far from forbidden desires, since I’m a Tzelem Elokim; and especially myself who is loaded with so many Maalos”. It is a Mitzva Rabba to constantly review your Maalos! Then you don’t fall into the danger of looking down at yourself and deciding that you are no good, Chas V’shalom. א לָׂתְ הִ יָׂר שׁ עָׂבִ פְ נ יָׂע צְ מ ךְָָׂׂאבותָׂבָׂיג Don’t consider yourself a Rasha, no matter how low you have fallen!
And then you decide that since you are so special (and indeed: כ לָׂ א ח דָׂ וְא ח דָׂ ח י בָׂ לוֹמ רָׂ בִ שְׁ בִ ילִ יָׂנִ בְ ר אָׂה עוֹל םָָׂׂסנהדריןָׂלזָׂא every person has a Chiyuv (obligation) to say: “The entire universe was created just for me”) thus you are important, as if you are creating Malchus Bais Dovid, and the Yetzer Davka starts up with YOU! I’ve told many people who have loads of unhealthy guilt feelings (which doesn’t help Teshuva; it just helps for more and more useless depression) that maybe they were really forced by a Malach, like Yehuda.
The more positive you are, the easier it becomes to do Teshuva. However, if you can’t shake off your unending guilt mode (which is really a Yetzer Hara, unless it has a Tachlis) then you should be happy that you have a conscience, since according to the Slonimer Chasidim, the difference between a person who doesn’t feel guilty about his sins and a person who does feel guilty, is like the difference between heaven and earth.
