A lot of people give me a hard time about doing Heart to Heart - "I don't feel right forcing/tricking people to be Jewish", "kiruv makes me really uncomfortable", "I don't like asking people to do things" "This is the rabbi's job", etc. I never really understood them, because I never felt that any of those things were really an issue. When I'm talking with this random person who I just met or inviting an acquaintance to a Shabbat dinner, kiruv/forcing/tricking is probably the last thing on my mind - or theirs. When I was sitting and talking with a new friend at a Shabbat table and connecting with them on a real level, all I was really thinking about was the person in front of me. And I would usually found that people were more than happy and thankful to join me for Shabbat dinner or let me know about something that interested or was bothering them with Judaism - I just needed to ask. Sure, it makes you a little uncomfortable and definitely makes you feel vulnerable, but the genuine exchange that occurs is probably worth it.
It was something that bothered me, not being able to explain it to people (other than telling them to just try it themselves). And then I saw this video and I realized that I found my answer: http://on.ted.com/Amanda (warning: slighting NSFW). Amanda Palmer talks about the music industry and street performance and crowd/couch surfing and a lot of crazy things - but if you switch music for Judaism, asking for inviting - and she's talking about Heart to Heart. About profound encounters, about empowering people, about inviting people to connect with you, and about the fear and beauty of encountering and asking something of a stranger. And if she can do it, and be so successful doing it - so can we. And so can you. So get out there and genuinely encounter someone new on the city's street! Go out there and invite someone for Shabbat dinner!