Pairing people
 Recruiting people
 Building a community
So Penn has SNL (Sunday Night Learning). Its a great communal learning event, and it features free food on a night when Hillel is closed. Most of the religious people come and many people who don't normally commit time to Jewish learning make it a point to come. Having a set chavruta (=accountability) is a great factor as is the 1/2 hour of food and schmoozing before the hour of learning. People at Penn always brag about how amazing it is, and I see those rumors have made it all the way over to Princeton ;)
I just checked through the attendance sheet (yes, they keep one) of a recent SNL: there were 110 people. Out of those, there was 1 person (nonJewish) who came for the first time (invited by a friend), 4 people who were becoming more involved/interested in Judaism (through a h2h meal, being friends with people in the OCP, involved in Aish) and 3 somewhat to-very-involved CJC (conservative jewish community) members. The other 102 people were Orthodox.
So as you can see we're not all that great at reaching the wider Jewish community either in this regard. Two years ago I went to the heads of SNL and I said "Hey, I'm meeting all these people and having them at Shabbat dinners and they want to, or might want to, learn more abotu Judaism. How about I bring them to SNL and we can pair them up!" I was ready for them to jump up and down and shower me with praises for the greatest idea ever, because being able to provide for people like that, and pairing up religious veterans of torah study with interested beginners is what many people love most about SNL. "Actually no", they said, "SNL is really only for Orthodox people. We wouldn't want to have to water down people's Torah study to learn with someone who doesn't know anything, if this is their only learning of the week. The people who aren't orthodox who do come - they just slip through the cracks." They suggested I teach a class for the people I knew were interested.
I was furious - I ended up going to their SNL board meeting and pitched my cause - only half of them were for me, and half were against - so it didn't really happen. Listen, I understand the value of people learning seriously - but these beginners are often the most serious about learning, depth and breadth. Gemara isn't the only Torah that counts, and if it really is important to people, I'd hope they could find another time during the week to do it. So instead I started my Hebrew-learning chavruta program, which started with 5 pairs and this past year we were up to 8 or 9 pairs. But I went around asking friends who go to SNL who they'd rather learn with and many of them (not all) said they'd much rather learn with someone I brought in, and they'd reschedule their other chavruta. So I and others have often just been bringing people to SNL - theres always someone for them to learn with, or triple up. This year the head of SNL said she'd be willing to work on splitting up some religious chavrutas and freeing up some people to learn with new people. But then she had to meet with the CJC cho-chairs, and then she had to meet with the whole committee, and then she had to meet with the Reform heads, etc. Of course it never happened. For next year, hopefully we/Ariel will think of a more sustainable, agreeable model.
Okay, that was way too long, and I didn't mean to vent. I should share some positive things we've learned: For the hebrew thing/when I would bring people to SNL, I invited people who I've had at meals/met through other forums who expressed an interest in Judaism. Meals are great but they're more social/communal and not too much depth, text-based, learning, etc. I'd try and push it if I saw people were interested. Like "Hey, I see you had a great time at Shabbat dinner, l gotta tell you about this thing on Sunday nights..." I think having it at the same time as other people is key, so its not just a text study, but its part of a larger framework of Jewish life. Food is also a good draw, as well as a complement to the intensive intellectual study. Though maybe at Princeton people are more serious and would be satiated with just studying ;) Teaching Hebrew is a great draw for people - whether bc theyre going to Israel on Birthright or want to learn how to pray. And teaching Hebrew is not just aleph, bet, gimmel - at least with me, it invariably turns to the meaning and context of words, ideas, and a much larger scope than just reading. But its also good because after 5,10 weeks, people can walk away with a distinct skill - and then walk into services, or Israel, etc. In terms of getting people to come, its probably harder to get people to come to a learning thing than a shabbbat dinner - and even with Shabat dinners I've found personal invited are much much more effective than random emails/signups. That being said, when we had the shabbat table on Locust Walk, signing people up for Shabbat dinners, we also asked people if they wanted to sig up for a hebrew learning program or a weekly partnered-learning program. Less people, but still some did sign up and some of them ended up coming. We never really did it, but if we just sent out an email to CJC or the reform community, I'm sure some people would come. And many more would probably want to but would be too afraid to. But emailing is at least the first step. Asking in person and explaining why they'd enjoy it and that it's open to them and saying you'd go with them the first time - that's probably the next step. One could put up signs around campus or the Quad with some cool catch phrase and logo and "Free Pizza!" or "come learn the secrets of Kabbalah" but that could start getting a little weird, not exactly what I'm comfortable with... I try and set chavrutas up with people who go well together - like cool kids with cool kids, science nerds with science nerds. It's hard to tell exactly and some people go well with everyone, but I try and match interests, if possible. Make sure the religious people you pair up are good kids - know what they're talking about, personable, good role models, know how to relate to others. My guess is that most people are good like that. Don't have to be the most religious/smart people, but I try and go for those most passionate about their Judaism. I found that just asking religious students if they'd want to learn with a new person at SNL was enough to enlist them - they ones I wanted would almost always say yes (maybe it's bc i was friends with them and they were involved in H2H stuff already). I know Princeton's community is smaller and maybe you can't be as picky, but if they're not into it, they're probably not the right person. In terms of what to learn, at SNL they leave out selections of articles in english on the parsha/current events/Jewish philosophy. I've used those a few times with people, and they could be good, but could be random. I've done Pirkei avot with two people -that's great because each mishna is short, and has so much in it that anyone can relate to and build off of, even with no religious background. I've also just learned Chumash starting with Genesis/Beresishit, that was with two different people who knew nothing and wanted to learn the basics. SNL also has a sheet of different areas you could learn (i.e. bible, talmud, law, philosophy, etc.) I would also just talk with my chavruta the first session, or the first half hour and find out what was bothering them/what interested them.