I hesitate to suggest a ďfirst stepĒ because that would imply that there is a ďone size fits allĒ approach to sharing the beauty of our heritage with a fellow Jew. There are really no rights or wrongs when it comes to sharing our Yiddishkeit; so much of it has to do with who you both are and what your relationship is like.
However, one thing is clear, the better your relationship is with another person the easier it is to share anything with them, whether about Judaism or anything else. A real relationship, based on care and mutual respect, and sharing your lives with one another is really the only ďfirst stepĒ. Getting together for coffee or lunch and just talking about your lives, your achievements and challenges, creates opportunities for sincere dialogue that will include things that are important to you such as Yiddishkeit.
At the right time, questions are always a great way of opening up a discussion on Jewish issues. For example, have you ever thought of doing any adult Jewish learning? Why do you think there is such a double standard when it comes to Israel? Have you ever thought of keeping kosher at home, or sending your kids to a Jewish day school or camp? How would you feel about your child intermarrying? Questions imply mutual respect and encourage dialogue, as opposed to well-meaning suggestions that could be taken the wrong way.
Depending upon your relationship, your personalities, and your likes and dislikes, there are various ways to share your Judaism with others. The rule is that there is no rule and whatever you do should develop organically through your relationship. However, a combination of any of the following in any order is appropriate:
Shabbat and Yom Tov. Inviting Jews for Shabbat is a great way to engage or deepen relationships and really to show one of the pivotal Joys of Judaism.
Sharing family simchas/celebrations. There is nothing like the depth and meaning of our simchas and it is a great way to introduce people to the joys of our heritage.
Share Torah. Jewish wisdom is the key to our personal growth in life, and sharing that wisdom with others will enable growth, helping to become better spouses, parents and just better people. You can enter into a chavrusa relationship where you learn once a week, or you might begin by sharing Jewish wisdom before the various holidays; this is often a time when people are very grateful to have some deeper more meaningful ideas than what they learned in Hebrew school. (Donít worry if you donít have all the answers, you are not the ďRabbi or RebbetzinĒ and can discover the answers together)
Be a Shadchan/matchmaker. You can also keep your eyes and ears open for programs and experiences that might appeal to your friend, such as a trip to Israel, a Jewish young professionalís program, an NCSY program for teens, or even suggest that they can learn about any topic they might want through the Project Inspire One on One learning program.
Pray. Ask G-d to help connect our brothers and sisters to His beautiful Torah, in the right way and at the right time.
However, that being said, stimulating conversation and curiosity is best achieved by being interested in your guests and asking them questions about their lives and about Judaism. Some hosts have the practice of going around the table throughout the meal and asking people to share a little about themselves and about a Jewish moment or memory that was meaningful to them growing up, or what about your trip to Israel has impacted you the most etc. Also, if you are going to share a Torah thought during the meal, it might also be good to bring it out through questions engaging your guests rather than as a monologue.
Itís best not to tackle really controversial issues at the table, because it isnít really the appropriate forum in which to handle them. Itís better to validate the question and refer them back to their Rabbi for a proper answer.
An analogy that that may resonate with him is the difference between candy and a filet mignon. A child will grab the candy, while an adult whose palate is more sophisticated will opt for the steak. So too with the finest wines; it takes time and somewhat of an investment to acquire a taste for the sophisticated pleasures in life. But once you do, youíll never go back to the sugary bug juice you drank in camp as a child.
And lastly, if your friend actually believes in G-d and that He created us, pose to him the following question: Does it make sense that G-d would create us, custom design us to seek pleasures of all kind, and then hold us back from enjoying them? Thatís cruel. Would your parents do that if they had unlimited resources and could give you anything in the world to enjoy? Isnít it far more likely that G-d created us for pleasure and Judaism encompasses the greatest, most sophisticated, and eternally satisfying pleasures that one can possibly experience? But you canít experience that pleasure standing on the outside, any more than someone can learn to enjoy the true pleasure of wine without the equivalent of a wine tasting course.
Besides, if you actually look at elements which define people and communities as good and healthy contributors to society, religious Jewish communities are high on the list. Their involvement in charity, giving to others in a plethora of ways, supporting a strong wholesome family life, and actively pursuing ethical and personal growth is way beyond anything comparable in the secular Jewish world.
Last and maybe the most important answer to your cousin would be to ask him the following question: You have such a negative view of religious Jews. Do you really know any? Have you ever spent any significant time with them, been over their homes for Shabbat or maybe shared a family wedding or bar mitzvah with them? You can be sure the answer will be a sheepish no. Then the shallow, uninformed and cynical nature of his view will become obvious to everyone Ė even to him!
If itís a holiday not on his radar screen, you can mention how excited you are to celebrate the upcoming holiday and share a bit of what you are doing, or why it is meaningful to you, and/or offer an invite as appropriate.
Of course, personal invitations for Shabbat meals and other family experiences such as Chanuka etc. are also great ways to help him learn more about Yiddishkeit.
With that being said, probably the best way to get some great basic answers to questions of all types is to spend some time daily or weekly on some great Jewish websites dealing with these issues like Aish.com or simpletoremember.com. Just read an article each time. Besides becoming more equipped to answer questions, you will really enjoy it yourself!
First, being a really good ethical, helpful, honest and refined person at work and throughout your life is the most important step in having a positive influence on others, no matter how religious or non-religious they are.
Also, as a result of your sincere and caring relationships developed at work you have an opportunity to share what to you value in your life with others.
Giving Shaloch Manos, home baked Challah to your friends, and other holiday treats as the year progresses is very appreciated by co-workers.
Some are very eager to learn about the holidays on an ďadult levelĒ to make their own experiences more meaningful.
Inviting co-workers for Shabbat meals, Chanukah parties, family simchas/celebrations etc. are all beautiful steps to sharing the joy of your Judaism with others.
Some might enjoy learning with you or someone else about Judaism on a weekly basis.
Look to connect them or family members to Jewish experiences/programs that they would enjoy, like a trip to Israel.