Outreach: Tearing Apart Families on Both Sides of the Holy Spectrum

from http://www.imamother.com/forum/viewtopic.php?t=36648&highlight=kiruv

I know that there are many people who aren't thrilled that I'm publicly writing against orthodox outreach. Dishonest attempts to cause non-orthodox Jews to leave their current lifestyles and become orthodox are, at best, disrespectful to those Jews and their families. At worst, kiruv can cause irreparable damage to families for years at a time, sometimes for life. Good friends of mine have told me horror stories of their own children getting caught up in irresponsible Jewish outreach and breaking all ties with their families, believing that this new lifestyle requires that they isolate themselves within the orthodox community. While not all outreach professionals outrightly encourage young people to break familial ties, they all promote a lifestyle which, through its stringences alone, subtly pushes people to alienate, or become alienated from, their families. People who are new to religious observance may feel pressured to do everything perfectly and may not have the ability to balance their secular upbringing and family with their new religious lifestyle. In an effort to please their rabbis, mentors, and God, many inadvertently push their secular friends and family away.
     That brings me to the image that I've included with this post. (Click on image to enlarge or read the original post here .) I took this from Imamother, an online forum for married orthodox Jewish women, from a thread entitled "Who Here is Shrewd and Creative? Need to Arrange Kiruv." (Don't even get me started on the use of the word shrewd.) This particular thread is about a woman who wants to be mekarev (bring closer to God in an effort to become more religiously observant) a young woman and is looking for ways to introduce her to someone who might inspire her to become orthodox. (I'm only commenting on the post in the image, but feel free to read the original post. Just to make this easier, everything in blue was stated by "Mummiedearest" in response to the block in white, which is another commenter quoting and responding to a different set of text posted by Mummiedearest. In the quoted material, I included the definitions of Hebrew terminology in parentheses following the italicized word.) Although this conversation is from 2007, I think a lot of what Mummiedearest states is still relevant.
     Mummiedearest, an orthodox woman, states:

I think we have to realize that we are not superior to non-religious Jews.... Why is it that so many baalei teshuva (newly religious Jews) have a hard time fitting in to frum (religious) communities? I get it, let's be mekarev them and once they're frum enough and don't need kiruv, we can shun them with a clear conscience. Kiruv is NOT a project, hobby, or career. Kiruv should be done out of ahavas yisroel (love for fellow Jews), not because of a superiority complex.1

She seems to be appalled by people with little or no experience turning non-religious Jews into their pet projects and by those involved in outreach thinking they're better than everyone else. Even though she doesn't think that all outreach is bad, the fact that she recognizes some of it as problematic is good. It gives me hope that maybe more orthodox people will realize that not every non-orthodox Jew is fair game in what often seems to be a recruitment hunt.
     The following quote is my favorite. While Mummiedearest and I would probably have some key differences in our feelings about God, she makes a great point regarding those who ended up religious despite that never being their intention:

I know people who were pushed to become frum, became frum, married, had kids, and finally said enough. They weren't ready, felt pressured, and eventually left their families to fend for themselves. We have to think of people as people, not chessed (kindness) projects, not "nebuchs,"(poor, unfortunate people,)  not "badly in need of kiruv." Yes, a person's soul wants the closeness to G-d. Absolutely. But the person has to recognize it.2

 While I would disagree on "what a person's soul wants," I have to hand it to Mummiedearest. She's right on point when she states that "the person has to recognize it." A major problem I have with Jewish outreach is that kiruv agents assume that everyone, whether they realize it or not, yearns to be religious. But Mummiedearest, an orthodox woman--notice how I keep stressing her background, feels that the person him/herself needs to recognize this need within him/herself. She doesn't think outreach should be done deceptively and even mentions later on that a person will ask questions if interested and will find her own mentor if she desires one. Mummiedearest seems to see the big picture, the reality of what happens to people who are pushed into religious observance and realize later on that they are totally miserable in this lifestyle. What kiruv professionals often don't realize is that experiences like these tend to turn people off to all Judaism, not only orthodox Judaism. 


1. "Mummiedearest, member since July 24, 2007, New York qtd. in "Who Here is Shrewd and Creative? Need to Arrange Kiruv" on December 27, 2007. Original thread posted by Anonymous on December 26, 2007. http://www.imamother.com/forum/viewtopic.php?t=36648&highlight=kiruv accessed 2/23/2013 at 3:28pm.
2. ibid. 

Lunch & Lure

Yesterday I put up a post in which I mentioned in passing that there are orthodox groups who go after high school and college students in an effort to do kiruv/outreach. Today, while perusing the internet, I found a link to this news story, reported by CBS, in Great Neck, New York. (See video or click the link to see it on YouTube.) Apparently, Torah Ohr Hebrew Academy has been running a Lunch and Learn program for high school students, in which students are given a free lunch and lessons in orthodox Judaism from rabbis who lead this program. Great Neck North High School's policy of allowing its students to leave the school for lunch gives an opening for kiruv professionals to entice Jewish students with a free lunch. Unfortunately, kids don't always realize that there's really no such thing as a "free lunch." In this case, they were served a side of proselytizing with their pizza bagels. Read today's article from The Great Neck Record here. According to The Great Neck Record, a letter from the ADL (the Anti-Defamation League)

stated that they had been contacted by “concerned Great Neck community members” and the ADL believed that while the school permits an open campus during “free periods,” the school cannot treat Torah Ohr, or any religious institutions or practice, any differently than it treats other, non-religious places or activities.” The ADL said that placing restrictions on “or creating special requirements for the temple’s lunch and learn program is an infringement on a student’s right to association and free exercise of religion in violation of the First Amendment of the United States Constitution.”1

When an institution as large and influential as the ADL can force a school principal to retract a parental notification letter regarding the safety of his students, there is something wrong. While I understand the importance of religious freedom and tolerance, I have a huge problem with outreach professionals luring impressionable high school students into religious programs with promises of free food and drink, so that they can preach their beliefs to them. High school students are at an age where they are still getting the tools they need to explore the world critically. Despite their desire for independence, middle adolescents (ages 15-18) are still developing. They are first beginning to figure out who they are and are first developing their own philosophies. They still need guidance when it comes to life planning.2 (Read more about teen development on a child development pdf put out by Iowa State University here.) The fact that Jewish outreach professionals are preying on high school students during the school day is abhorrent and deceptive.

1. http://greatneckrecord.com/2013/controversy-over-free-lunch-at-torah-ohr/ accessed 2/17/2013 at 1:52pm
2.http://www.extension.iastate.edu/4hfiles/VI950902FAgesStages.PDF accessed 2/17/2013 at 2:07pm

Birthright: Focus on OU Israel Free Spirit

     In a previous post, I discussed the importance of knowing the trip provider for those of you who may be going on a Taglit-Birthright trip to Israel. I focused on the Mayanot trip in that post. In this post, I'm just going to quickly discuss the OU Israel Free Spirit providers. As I mentioned, it is very important to understand where your trip providers are coming from. An orthodox organization may provide a great trip, but they also may try to convince participants to attend post-trip stints in yeshiva, or attend further programs either overtly or subtly pushing orthodoxy.

The OU's symbol, found on many kosher products.

     The OU trip is sponsored by, of course, the OU--the Orthodox Union. They're the ones who put the little OU sign on products that they certify as being "kosher" because those products meet a certain set criteria. The OU also provides Jewish services for college students and runs programs for high school students (they sponsor NCSY, the OU's youth movement.) They also publish a magazine, books, sponsor jobs and job training. They work within the orthodox community to help provide people with services that they may need. You can read more about the OU here. They also "sponsor programs and initiatives that inspire and empower Jewish adolescents"1 such as the Birthright Israel trip. They plainly states that "the mission of the Orthodox Union is to engage, strengthen, and lead the Orthodox Jewish Community, and inspire the greater Jewish community."2 Inspiring "the greater Jewish community" already screams "outreach!" to me, but I'm biased, so let's move on. 
     As expected, the OU trip's denomination is listed as orthodox. No surprise there. They are open to participants of varying backgrounds and the trip itself is supposed to emphasize the spiritual connection between the different facets of the Jewish people as a whole--the people of Israel, the land of Israel, contemporary Israel, and Jewish tradition all meshed together. The Birthright site states that

Israel Free Spirit trips are comprised of JSU & NCSY staff, College Jewish Education Professionals and Taglit-Birthright Israel alumni who share a passion for Israel and bring extensive background in informal Jewish education. In line with our mission of maximizing your trip we go beyond the required two staff per trip and usually add a third staff member who is a dynamic educational expert (a campus rabbi or similar) so you get more one on one attention.3

That sounds like a great deal if you want more one on one attention or a trip that will give you access to an orthodox rabbi or orthodox educational expert to give an orthodox point of view if needed. I think that this is great if a student is already orthodox. Providing an orthodox point of view for an orthodox clientele, or even a rabbi who can help students with preparations for Shabbat (the Sabbath) makes sense. I don't find these things to be at all problematic. What I find troubling, however, is who they are affiliated with.
     The OU boldly states to those interested in the trip they provide that "the OU “Israel Free Spirit” trip is a collaboration of NCSY, JSU (Jewish Student Union), Aish, Yachad/NJCD, Yeladim, JACS, MEOR, and many other allied agencies that have pooled their resources to provide you with the experience of a lifetime."4 This is where your eyes should widen if you're a parent of a non-orthodox student, or if you're a non-orthodox student going on Birthright and considering the OU Israel Free Spirit trip. Here's why:

1. NCSY, while a youth group, also does extensive outreach to Jewish public school students. They are a kiruv(outreach) organization. An article about outreach in the OU's Jewish Action online magazine discussing kiruv programs states that "many of these programs serve as a magnet for Jews because they don’t take place in an obviously Jewish site. Thus, programs loosely wear an “Orthodox” or “outreach” label to avoid scaring away Jews who have little connection with traditional Judaism.....That, [Rabbi Steven Burg, international director of NCSY, the international teen organization sponsored by the Orthodox Union (OU) dedicated to connecting Jewish teens to Torah] says, is why NCSY has located some of its most successful outreach programs in places like public schools and cafes."5
2. JSU (Jewish Student Union) is a "club" that is advertised to public schools. Check out their website here. They advertise themselves as an "awesome Jewish club, right in your school!"6 With promises of free kosher pizza and an advisor who will bring pizza, Judaism, and fun, who can resist? At the bottom of their website, they mention that they are sponsored by NCSY. They are an outreach organization.
3. Aish. Aish is short for Aish HaTorah, a major outreach organization with yeshivas and learning programs specifically designed to transform non-orthodox Jews to fully-observant Jews.
4. MEOR. MEOR is an Jewish organization that sets up on or near college campuses. They offer Jewish learning, programs, and holiday and Shabbat observance from an orthodox perspective, all created for college students. Their website states that "MEOR’s goal is to create the next generation of Jewish leaders by investing in students like you on leading U.S. campuses today." They also state that they "focus on in-depth Jewish learning for students who are seeking that opportunity as part of their college experience."7 They are an outreach organization. Read more here. 

These four organizations are kiruv organizations. While the OU Israel Free Spirit trip isn't going to make anyone orthodox, there is no guarantee that the trip providers and additional staff provided don't have ulterior motives. There is no guarantee that post-trip extensions or follow-up won't include subtle or not-so-subtle pushes towards orthodoxy. Be aware of who your trip providers are, and which organizations sponsor them. Future articles on this topic will cover other orthodox Birthright trip providers. I also plan to include more in-depth discussion of the groups mentioned in this post.




1. http://www.ou.org/about_us/#.UR_NMPKQ1hp accessed 2/16/2013 at 1:32pm.
2. ibid.
3.  http://www.birthrightisrael.com/VisitingIsrael/Pages/OU-Israel-Free-Spirit.aspx accessed on 2/16/2013 at 1:48pm.
4. ibid 
5. Lipman, Steve. "The New Face of Jewish Outreach." http://www.ou.org/index.php/jewish_action/article/64253/ accessed 2/16/2013 at 2:18pm.
6. http://dojsu.com/ accessed on 2/16/2013 at 2:24pm.
7.  http://www.meor.org/homepage-features/for-students accessed on 2/16/2013 at 2:29pm.

Edible Outreach: Kiruv Mishloach Manos

Project Inspire's Kiruv Mishloach Manos ad.

Just in case you thought that college students were the only people being wooed with free food and goodies, you should be aware that "less-affiliated" people of all ages and careers are treated equally when it comes to food-centric outreach efforts. (For those unfamiliar with the Hebrew terminology, mishloach manos are gifts of food given on the holiday of Purim.) As with most of these holiday kiruv (outreach) campaigns, the wording in this ad (meant for kiruv agents, not people being missionized) is disturbing and completely undermines the intended recipient(s). In fact, this gift of food isn't just a typical basket of goodies, it's specifically called "kiruv mishloach manos." So, what makes this gift different from all other gifts that a kiruv professional might give during Purim? Let's explore this ad and find out.
     The most noticeable part of the box given to the outreach professional's "less-affiliated co-worker, friend, neighbor, doctor, or lawyer" is the four paragraph explanation of Purim and its customs on the front. In typical outreach fashion, the explanation is simplified. I find the paragraph entitled "Food, Glorious Food" to be most troubling. It states the following:

We give treats of food to one another on Purim. This expresses our respect and love for those around us--that every person is unique and special and that by giving and caring for one another we express ourselves most fully. Only when we are united with our brothers and sisters can true joy be achieved.1

The front of Project Inspire's Kiruv Mishloach Manos package.

While it is true that gifts of food are given to strengthen friendships with one another (according to Jewish belief,) I have trouble believing that this is the reason for this "kiruv" gift. The paragraph also mentions that "every person is unique and special." If this is so, then why the great need to send outreach gifts--gifts that are meant to draw them in, to teach them orthodox observance with the hope of changing their "less-affiliated" lifestyle choice to that of orthodox-style observance? A gift with an ulterior motive is not a gift that shows respect for the recipient.
     As an aside, I'm sure that there will be readers who will find this post problematic. "So, what's wrong with showing another Jew a Jewish custom?" some will ask. I don't think there's anything inherently wrong with sharing holidays or traditions. But, as I've said before, people involved in kiruv/outreach work have an ulterior motive: to get you to change your belief system and practice as they practice. Project Inspire is a program run by Aish HaTorah. Aish is known for their yeshiva programs and their outreach programs to non-orthodox Jews. A book that they put out, "The Eye of the Needle: Aish HaTorah's Kiruv Primer"explains issues related to doing Jewish outreach and gives advice to kiruv professionals.



1. Kiruv Mishloach Manos. Project Inspire. Aish HaTorah. accessed 2/11/2013.

Birthright Israel: Focus on Mayanot

     Chances are that if you're a Jewish college student, or if you're the parent of a Jewish college student, or even if you've been a college student yourself in the past thirteen years, you've heard of Taglit Birthright, a program run by a not-for-profit organization that sponsors free ten-day trips to Israel for the post-high school (18-26 years old) set. Read more at their official site or on wikipedia. Under the Birthright umbrella, students have the opportunity to choose the trip of their choice, each run by different trip providers. This is where it gets tricky. There are about fifteen trip providers, ranging from orthodox to non-denominational. Birthright offers some tips on how to choose your trip provider, however, despite the denominations listed near the trip description, it's still easy to get them confused. Here's why: the trips listed as orthodox in denomination don't appear to be geared towards orthodox college students. They welcome all types of Jews and from what I understand, the programs are generally well-run, informative, and a lot of fun. There may be subtle differences in each orthodox group's particular ideology (some trips are run by Chabad, others by OU, others by Ezra, etc.) but there seems to be a general understanding that most students going on these trips are probably not orthodox and so the trips are run more liberally than one might expect.  Orthodox trip providers have put a lot of effort into not making their program descriptions appear to be orthodox in any way. However, it is not the initial Birthright trip that poses a potential outreach/kiruv issue, but the follow-up after the trip and possible pressure to attend yeshiva programs affiliated with the group's particular brand of orthodoxy that could be problematic. Understanding that this post could be endless, let's focus on one program for now. I've chosen to focus on Mayanot because it is the first orthodox organization listed on Birthright's list.1

     Mayanot, the Birthright program run by Chabad, mentions partying, learning about contemporary issues, exciting tourist attractions, partying, the political, cultural, and "spiritual" dimensions of Israel, and of course, the word that excites even the tamest of college students, partying. And have I mentioned partying? The description is very careful to only mention the word "orthodox" under the heading "affiliation," and states further down that "Mayanot draws inspiration from Chabad spirituality." Nowhere on this site does it say that the Mayanot is actually an outreach/kiruv yeshiva, but if you do a little independent research, you'll find that Mayanot is actually a baal teshuva yeshiva, designed to help Jews become orthodox. Mayanot is run by Chabad and while their Birthright trip isn't making people orthodox, the trip does serve as another feeder for their yeshiva and study programs. This is the link to the Wikipedia site, but you can find this information on their site as well. In the blurb about the sponsoring organization, Mayanot Institute of Jewish Studies, (not quite a name that someone would associate with an orthodox yeshiva,) words such as "academic," "intellectual," and "textual study,"are used--words that sound more like they were taken from a college course catalog than anything linked to an ultra-orthodox yeshiva. This is not to say that any participants on the Birthright trip are ever forced to become religious, however, be aware that ideas on religious issues may be from a Chabad perspective even if it's more like Chabad-lite, (what I'll call outreach that is specifically meant to get non-orthodox Jews interested,) and students may be urged to extend their stay in Israel for an additional three weeks to study on their Post-Birthright Study Program.

     The Mayanot Post-Birthright Study Program draws students in with the excitement of being away from home for a longer period, but also with the insanely cheap price. "Taglit-Birthright Israel participants can apply for a scholarship to join this program for only $99! This includes tuition, room and board for 3 full weeks (normal tuition for this program is $799)" their website screams. (They also offer longer and shorter programs.) Having traveled extensively while in college and on a tight budget, I can tell you that this would have drawn me in. Three additional weeks, all-inclusive? Sounds like a good deal! One of the ways they get to students to commit to the post-trip study program is by presenting potential participants with a sense of urgency, mentioning on their website that  "although applications for this scholarship will be available on your Taglit-Birthright Israel trip in Israel, due to the popularity of the program only those applications that are received in advance of your trip may be guaranteed a spot." How many young travelers, excited and possibly apprehensive about traveling alone in Israel, are thinking "well, I should definitely do this! What's a few hours of study a day when I can still travel and hang out?" But before you sign up for this or any program, stop and ask the trip providers for details.
     Here are a few questions you should ask if you're wondering if the Post-Birthright trip deal is too good to be true. The Mayanot trip may seem like a party and you may have an awesome time. But you should ask these things before you sign up for additional weeks through their yeshiva:   

1. If I do the post-Birthright study program (which is not co-ed,) how long will I be expected to be in the classroom, studying? Will I have free time? Request a typical daily schedule, preferably in writing, with the times outlined so you can understand how your day will look.
2. Will I be expected to adhere to orthodox religious practice even if I don't want to? 
3.  If I decide the program is not for me, am I free to leave? 
4.  What are my financial obligations if I decide to leave the program?
5. Why am I being offered what has been billed as a $799 program for only $99? What are this group's ulterior motives?  

When asked about his experiences with the Mayanot Birthright trip, former participant Eli stated:

They made in obvious attempt to convince us to stay longer by repeating how easy it was to extend your flight. They also brought us to the Mayanot yeshiva before Shabbos where we had to sit through a parsha (Torah portion of the week) class. Most of the participants were secular and were only concerned with going out and partying. Mayanot encouraged that as well, even putting it on the itinerary as a frabrengen (joyous, usually Hasidic, gathering.)

There was an emphasis on Kabalah (Jewish mysticism) and we spent a bit too much time in Tzfat (famous for Jewish mysticism and Kabalah.) We had to hear a Kabalist artist who was a baal teshuvah (returnee to orthodox Judaism) speak about what inspired him and almost everyone felt they had to buy something from him.
Shabbos wasn't as strict as an NCSY2 Shabbaton, but we weren't allowed to swim or leave the hotel (there was actually a warning if one left the hotel they would be sent home immediately and have to pay their return flight.) I guess they were concerned for safety to an extent, but when it wasn't Shabbos they let us roam all around Jerusalem and Tel Aviv at night, so it didn't really make sense to me.
While I definitely felt a presence of kiruv, I noticed more of an effort to convince people to make aliyah (move to Israel.)

As for the Mayanot Birthright trip, be aware that you may be approached to extend your trip to attend Mayanot's yeshiva programs. There are other trip extensions that are not centered on religion. Or students can do what a lot of us did, and just bring a backpack and sleeping bag, and find a youth hostel near places of personal interest. No matter which provider you choose, be sure to research the trip providers and any information the website may contain about post-trip programs.
 


1. Other posts will discuss other Birthright options listed on their site as "orthodox."
2. NCSY is an orthodox youth group sponsored by the OU (the Orthodox Union) who also do outreach/kiruv work.

The following articles might be of interest to readers interested in Birthright

Birthright's Israel: The Political Bias of the Jewish Community's Favorite Program by Nathan Ehrlich. November 28, 2011

Largest Outreach Effort for Alums of Birthright Raises Concerns by Gal Beckerman. August 26, 2009

Birthright Alumni Center Tied to Haredi Outreach Group, by Gal Beckerman. September 2, 2009

Supermarket Soul Saving in the Matzoh Aisle

   I found this in my email today. It's Project Inspire's latest outreach effort, their brand new Supermarket Passover Awareness Campaign. The goal is to reach non-orthodox Jews who are shopping, in order to educate and "inspire" them about the upcoming Passover holiday. And what better place to reach out to inspire them to purchase holiday foods of the kosher variety than the supermarket!
This is not the first time a supermarket campaign has been waged for Jewish souls. For years, Chabad representatives have set up in supermarkets in various locales, giving out booklets about upcoming holidays, kosher food samples, and information about the local community outreach activities. When I first saw this in my inbox, I laughed. It looks like Chabad will have some competition on the kiruv (outreach) front this year. But that's not the main reason I'm posting this. I know I've mentioned in previous posts the problem I have with the way kiruv professionals address the non-orthodox Jewish population. If you look at the photo, you'll see see two instances where the Project Inspire refers to non-orthodox Jews as  "less-affiliated." They "plan to set up tables in supermarkets across the country to reach out to less-affiliated Jews who come to buy their Passover provisions...." You know, because if you're not orthodox, you're less. Less of what? Less connected? Less Jewish? Obviously this is what kiruv professionals are thinking. Certainly, this is the message that those of the liberal branches of Judaism or even those who are secular Jews would get if they were to view this ad. Bear in mind that this message is intended for insiders in this organization. And recall previous postings in which I've mentioned that orthodoxy does not allow for Conservative, Reform, Reconstructionist, or other denominations of Judaism. To outreach professionals, if you're not orthodox, you're not practicing true Judaism.
    The third paragraph mentions the intention to provide the "less-affiliated Jews" with "meaningful hand-outs for their seder"(sic) and is extremely offensive. Project Inspire appears to assume that if one is not orthodox, he/she is not having a meaningful seder and therefore needs to have supplemental materials, specifically the ones that they will provide. They will also provide shoppers with "opportunities for further involvement in outreach programs." The intention here is to undermine whatever Jewish affiliations shoppers have and provide them with something else, something that Project Inspire appears to believe is better.
     Now, imagine this for a second. You're doing your weekly shopping on a Sunday. Maybe you have a kid in tow. Maybe you're alone. You're picking out your five-pound box of Streit's or Aviv matzoh from the huge display because, hey, maybe you celebrate Passover to whatever extent that you do. Or maybe you just like matzoh. (Yes, there are people who do.) A lovely Passover table is set up. A few people are standing around. You're offered some gefilte fish. Conversation ensues. You walk away with a handful of literature and fish breath. But you've also told them, in polite conversation, about your daughter's upcoming Bat Mitzvah at the Reform temple. Maybe you told them that you're an atheist, but you still go to holiday meals with your family. Perhaps you mentioned that your nephew goes to a Conservative Hebrew school twice a week. But whatever information you volunteered in pleasant conversation was interpreted in one way: this is a less-affiliated Jew who needs our help.
     Project Inspire's website has a link to an article by Rav Shlomo Wolbe in which he states that "the only requirement for the coming of the Moshiach [the Messiah] and the redemption is repentance. We have to repent. And what about our brothers…B’nai Yisroel who are far away from fulfilling the commandments? They have to repent, too! And we have to help them come close to repentance."1
     So, while you shop on any of the four Sundays before Passover, remember that when you're offered "food for [your] soul and educational materials about Pesach," it's not because these are just nice people who want you to buy some A&B's fish. They want you to buy into a whole new way of thinking.

1. http://www.kiruv.com/articles/338/rav-wolbe-ztls-vision/ accessed 2/5/2013, 8:18pm

Talking With Missionaries (Yes, That Includes Kiruv People)

Guest Post by Jewish Atheist
When I was younger I got involved with anti-missionary work. It started when I discovered that some friends of mine somewhat deceived me into organizing a concert at a Jews-for-Jesus (J4J) center… also discovering that these friends were J4Js! That encounter actually led me to start studying Judaism more… and ironically led me on the path to becoming very religious. But I always kept an interest in missionaries, the threat they posed to the Jewish community (or at least as I perceived it), and how to argue with them. This hobby of mine was rather unusual for a yeshiva bochur (student), but then again, I’m the kind of person who likes to debate his beliefs. And so I did.
I used to go out to Jewish gatherings (e.g. the Salute to Israel Parade) or any events that I heard would have a lot of missionaries. I would often stop to argue with people preaching to Jews in the subway. (I usually only bothered with missionaries who were targeting Jews.) And amongst my friends I was known as the guy who had answers to their questions.
And that’s what a lot of people think is most important, answers and rebuttals. In truth, that’s only a small part of it. More important, I found, were the assumptions and framework for the debate. Otherwise you can simply get into dead-ends where people just stubbornly accept their own opinion; in particular, one’s own interpretation of texts.
Now that I’m an atheist, I’ve often found that arguing with religious Jews - especially the kiruv (outreach / missionary) types - is quite similar as arguing with Christian missionaries. Very similar.

So here are some thoughts and observations on how to have a meaningful debate without falling into common traps:

1.  Burden of Proof: Religious folk often assume that their beliefs are the default truth and that skeptics must “prove them wrong.” No. They’re the ones making a claim that “such and such is true” so they have the burden of proof to demonstrate it’s true (especially for such extraordinary, supernatural claims). Establishing this is a key component to such arguments. Don’t let rabbis corner you into “proving the ten plagues didn’t happen.” Or “proving there isn’t a god.” That’s b.s. They’re the ones claiming magic exists; let them prove it.
2.  Define Terms!!! Define “god”; define “moral”; define “proof," etc. For instance, it’s very easy for kiruv types to talk about how the Torah teaches morals… but only because they define morals as “that which the Torah teaches”! (And obviously circular reasoning is not very impressive.) It’s very easy to politely disagree and say that you don’t define morals that way, and that if they are defined that way, that you don’t particularly care about “being moral” (aka “doing what this particular ancient text - and interpretation - says). If you can come to a mutual agreement on what it means to be “moral” or an elment of morality (e.g. promoting wellbeing), then one can have a more rational discussion. For instance, on whether it’s “moral” to dress less strictly than the orthodox modesty rules. Or whether it’s “moral” to impose such strict modesty rules. etc. But you can only get to this if you define terms first. (Also: Don’t fall for, or create, simplistic dichotomies. Embrace the gray area. Embrace that things usually exist along a spectrum. e.g. Most people aren’t “good or bad”. We’re all somewhere inbetween.)  
3. Go back to the basics, to the framework: It’s easy to fall into a trap of “I think the text means this” vs “I think the text means that.” Don’t do that. Establish a system for analyzing texts and claims. In particular, look at the assumptions in a belief system’s framework. For instance, when I would argue with missionaries, I’d often begin by asking them if they agree that Judaism existed before Christianity. Which, of course, it did. I then ask, “If Judaism came first, and Jews had their own understanding of the Torah, then why on earth would it make sense to adopt a new interpretation which completely contradicts the standard, historical, traditional  interpretation? Why would it make sense to suddenly understand, for instance, Isaiah 7 as referring to a “virgin” if the word doesn’t imply that and - to my mind, more importantly - that it was never understood as meaning a virgin (nor as a messianic prophecy!). It makes the argument not only about “interpretation” but about a historical perspective, an argument about the structure of Christianity itself, and the validity of its novelty.The same is true of Judaism. For instance, the assumption Orthodox Jews share that the Rabbinic interpretation represents the true intent of the text. E.g. “eye for an eye” isn’t meant literally - and never was. How do they know that? Afterall, we know for a fact that there were different religious groups around at the time who interpreted the text in different ways, and often expressed the opinion that rabbis were just making stuff up and not sticking to the text. E.g. Karaites, Sadducees, and more. (Thus one could argue that the “traditional” understanding of a text may actually just be a very old novelty originating from the rabbinic sects, but not the text itself. {But yes, “almah” in Isaiah 7 would still not make sense for Jesus. Facts and evidence are still important!})) 
4. Fact-check. Amazing how many people - especially kiruv types - make stuff up or present only a very one-sided perspective or just repeat dribble which they naively assumed was true. Question their stats, their facts, and esp their quotations. Double check. Especially if it seems fantastical. Thanks to the internet, this is a LOT easier than it used to be. Take advantage. 
5.  It’s ok to say “I don’t know.” Or, “I want to look into it more.” Don’t be pressured into making stuff up or trying to invent poor arguments which will only make your arguments weaker. There’s no rush. Take your time. Do your research. And be honest if you don’t know. You’ll avoid getting cornered and bogged down by having a weak argument of yours being demolished. And besides, we don’t know everything. And that’s okay. It’s something religious people need to learn to accept instead of - as is often the case - merely using a “god of the gaps” argument.
6. “Is this any different from other groups?” This one question can debunk (or at least lead to some great discussion about) lots of outreach arguments. “Our lives are wonderful!” Okay, but can’t other religious groups say that too? Should I therefore become a Mormon? “We have prophecies that have been fulfilled!” Aside from looking into those “prophecies" again, ask if this is different from other religious groups which claim to have had prophecies fulfilled. You get the idea.
7. Emotions: They get in the way of thinking clearly, which is probably not what you want to happen. So, three points:

• A) Stay calm. Don’t insult. Don’t let them rattle you. The calmer you remain, the better you’ll be able to formulate points, the more reasonable you’ll seem (and probably be,) and it’ll irk those who try to tug at your emotions to evoke certain reactions.  
• B) Don’t get bogged down in long, emotional stories. If the rabbi has a story about Jewish children being identified in Christian orphanages by their recitation of the shema, then just ask him for the bare facts: Some Jewish children were kidnapped and found. Just ask for the facts. 
• C) Environment is important: Whether you realize it or not, your brain acts differently based on the environment you’re in. If you’re on a retreat with other Jews, unfamiliar with the place, and being led by rabbis around a Jewish schedule, it’s essentially already placing you into their environment. It can be dangerous, and I suspect is a huge part of why going to yeshiva in Israel - surrounded by other religious Jews - has such a big effect. If you can, avoid such scenarios - or at least be wary. If the rabbi wants to talk, you may prefer email or a neutral setting so that you’re both on equal ground. 

Well, there you go. Hopefully this will be of some help. And feel free to drop by my blog: JewishAtheist.tumblr.com