My goodness, but aren't there a lot of blogs out there that are being run by people who were very interested in Torah Judaism at one point in their lives but were subsequently turned off by bad encounters with Jews who didn't walk their talk in the kiruv process.
So here, on my own, I'd like to share the lessons I've learned over the years in the hopes that people out there who may be disillusioned with Torah Judaism right now might take another look at it and give it a second chance.
I'll start up front that I do not work for any kiruv organizations although I attended services at an Aish HaTorah shul once in 1993 and I'm friends with the Chabad emissary in my town. I want to be absolutely clear: I'm committing the following to print because I believe that Torah Judaism has the potential to provide a wonderful life for its devoted adherents, if it's practised properly and the participant isn't under certain delusions regarding what it is and isn't.
(Also, I hate writing "him/her" so "him" will refer to both, okay?)
1) Recognize that the reason for someone to become a Baal Teshuvah is because Judaism believes that a person is in this world to perfect himself spiritually. The way to do this is through the performance of mitzvos and living life in the way God intended for us to. That is the reason a person should become a ba'al teshuvah. Not because frum Purim parties rock, or because one might be feeling lonely and wants to identify as part of a group, or because one is seeking out a religious group that might be all-moral and all-holy. Those are lousy reasons because the person will ultimately be disappointed and then wind up leaving Judaism. God is perfect, everyone else is flawed to a greater or lesser extent and understand that will prevent a lot of heartbreak.
2) Realize that frum people are, unfortunately, just like everyone else. Yes, a Torah lifestyle should lead to a higher level of morality. Yes, one should practice what one preaches. Yes, wearing the outfit of an observant Jew in public means one should behave in a manner befitting what that clothing implies. But in real life, it doesn't work that way. The same person who is medakdek to make sure he only eats mehadrin food and waits 6 1/2 hours after meat to eat milk (not like those meikels) may have no scruples about cheating another person in business, Jewish or not, fooling around on or beating his wife, or doing all manner of anti-social activities. Don't look at frum Jews and say "I want to be like them!" That's another straight road to heartbreak. A ba'al teshuvah shouldn't be going through the process to become like someone else. God made you an individual for a reason and to be a good Jew you don't have to give up your individuality for the sake of some mythical community standard no one holds to anyway.
3) Learn for yourself. Don't let others spoonfeed you information because everyone has a bias and will only tell you those things that they want you to know. Yes, lectures and shiurim are important sources of Jewish knowledge but they're not the Torah from Sinai, just part of the package. For example, Rav Dovid Gottleib has posted dozens of the lectures he gives to Ohr Samaeach students on the web. Rav Akiva Tatz has stuff at the same site. I've lost count of the times I've heard both these very intelligent men make statements about something in halachah or haskafah that isn't as black and white as they're making it out to be. Judaism is never simplistic and each person has an obligation to learn about that complexity for themselves. If the ba'al teshuvah is looking for a simple way, "do this and don't do that", then he will eventually be told to do something that his inner moral sense objects to and he'll be faced with a lousy choice - do something that feels wrong because somebody said so, or abandon the path with all the attendant bitterness it brings.
On that note, I have some specific recommendations(assuming minimal or basic Hebrew skills):
a) The basic foundation of Judaism is the Torah. Learning Mishnah, Gemara or other works is a waste of time without a basic knowledge of Chumash. Reading the Chumash straight without a decent commentary is also a waste of time and while Rashi is the de rigeur commentator that one must learn at some point, he might not be the best for the introductory level student. My recommendations include the Artscroll Stone Chumash because its commentary is general enough for the beginning and intermediate reader. Yes, the Chumash will insist on a version of history that doesn't fit the facts of archeology and geology but one shouldn't let that be a barrier. Everything our Sages said is true. We just don't understand their words and after misinterpreting them, we blame them for these "errors". After a couple of times through that, one can try the Metzudah Rashi Chumash. As opposed to Artscroll's, this one minimizes the supercommentary on Rashi so the reader can spend more time on what he picked up the set for in the first place.
b) My father always said that someone who learns Gemara gets an insight into the brains of Judaism but in order to see its soul, one must learn Tanach. Having done that, I can't agree with him more than I already do. Gemara will teach a student what is and isn't allowed and it does have its share of Aggadah and inspirational stories but Tanach is the history of our people, warts and all. For those who condemn Reform and Conservative as easily as they take in air, an exposure to Tanach will teach that our ancestors were, at times, much worse than anything the heterodx amongst us are like today. What we were meant to be, and what we were, is all laid bare within the pages of Tanach and it gives a learner a good reminder that the point of observing halachah isn't simply to see how many chumros and minhagim one can accumulate in one's lifetime but rather to bring a sense of Godliness to this world. Behaviour that does that is the right thing, and behaviour that doesn't is wrong, no matter what "the book" says.
c) Mishnah and then Gemara follow this. Well, come on. The Talmud is the foundation of Jewish life today and not learning it leaves a huge gap in one's knowledge base. In addition, being ignorant of Talmud allows unscrupulous individuals to take advantage of the new Baal Teshuvah. Yes, there are some statements in the Gemara that might be seen as problematic but with proper perspective and interpretation many of those problems can be reconciled. Not knowing what the issues are in the first place won't help the new Baal Teshuvah overcome those difficulties. The Artscroll Talmud is a great way to start. If one has a functional knowledge of Hebrew, bypass that and go to the Kehati Mishnayot and the Steinsaltz Talmud. They're easy to read, well laid out and full of god commentary.
d) Halachah - don't start with halacha digests like Artscroll's or Feldheim's. Remember these books are written by authors with an agenda and they'd never see the light of day if they brought a balanced approach between lenient and strict opinions. The primary sources are the best and with Feldheim's Mishnah Berurah translation you can learn a lot that later sources just might miss. Also it's a great way to pick up Hebrew. Hebrew is important because in the English books with Hebrew footnotes (eg. Rav Eider and Fuchs) one can often find leniencies and opinons that somehow didn't make it into the English section.
In short, you are responsible for your own education, not someone else.
4) Never EVER forget - a truly observant Jew does what he does because of his relationship with God. I had a friend who lived in a Chareidi neighbourhood and stopped going to shul for 2 years because he was sick of the hypocrisy he saw around him. I finally convinced him to try going back because the bottom line for him was that he wasn't supposed to go to shul for social purposes or to win the approval of his peers. He was supposed to go to shul because it's a place to daven. God, being all-mighty and omniscient, can form a 1-on-1 relationship with every Jew, no matter how crowded the room. Why not daven at home then? Because there's something special about answering to the kadish, Borchu, and kedushah. But going to shul wasn't for others, it was for him and his personal relationship alone.
5) One's ties to one's family (assuming they were close in the first place) and one's friends from before the Ba'al Teshuvah started "the process" are important. They are part of what defines a person. There are some within the kiruv world who will try to convince the new Ba'al Teshuvah to cut as many of those ties as possible as he heads into his new lifestyle. Unles one comes from a bad family, chalilah, like abusive parents, one should remember that the honouring of one's parents isn't limited to frum ones. True, the halachah is clear that if a parent asks a child to do something against the law, the child is obliged to refuse but the halachah is also clear that this refusal must be done as respectfully as possible with the child making clear that the only reason for it is that it is against Jewish law, not because of any questioning of respect for the parent. Those who maintain a good relationship with their parents will find that their parents will come to accept their decision to become more religious over time. I know of Ba'alei Teshuvah who simply keep their own set of dishes in their parent's home and eat certain foods when there to keep up their relationship.
What's more, I have found that keeping one's family and old friends close is a good barrier against fanaticism. If a Ba'al Teshuvah starts looking at his parents and friends and thinking "Tsk, such ignorance" or the like, there's a good warning right there that learning has ended and brainwashing has begun. Be self aware. Be yourself.
Have Ba'alei Teshuvah been hurt because they've been rejected by "frummies", or told their kids can't attend a certain yeshivah because of their past, or been cheated by a trusted figure in the religious communities? Unfortunately, this happens all the time but it is not because of the observance of Jewish law but rather its non-observance that this happens. Remembering that is so important so that one doesn't not reject God and his Torah simply because some of his self-proclaimed representatives are jerks.
May we all find peace and contentment in our relationship with God and not reject that which has the potential to give us Life Eternal.