Modern American Jews increasingly seek spiritual fulfillment outside their tradition or abandon it entirely, signaling a critical shift in the rabbi's role from traditional teacher to spiritual mentor. Through seminars entitled "Exploring Jewish Spirituality" in a suburban Conservative synagogue, participants documented and analyzed significant spiritual moments in their lives, engaging with poetry, literature, art, and music to facilitate deeper spiritual exploration. The research revealed that while congregants readily identified profound spiritual experiences—particularly during lifecycle events, nature encounters, and meaningful human connections—they often hesitated to label these as religious experiences. Spiritual mentoring emerged as a vital bridge, helping congregants understand Judaism as a meaningful framework for their deepest spiritual experiences rather than merely ethnic affiliation or ritual observance. The findings demonstrate that rabbis must develop specialized skills in spiritual mentoring to address fundamental questions of religious meaning, requiring both personal spiritual development and formal training. This approach creates a pathway from universal spiritual experience to particular Jewish religious practice, offering a promising strategy for revitalizing contemporary Jewish engagement and retaining spiritually seeking congregants within the tradition.