A growing evidence base supports the value of peer recovery support specialists (PRSS), particularly due to shared lived experience with participants (recipients of PRSS services). Little research has examined whether congruence on certain aspects of “peerness” (e.g., demographics, experiences) matters for PRSS-participant relationships. Results from this pilot study suggest that PRSS-participant alignment on past experiences (e.g., prior incarceration, choice of drugs) may not be needed to establish good-quality working relationships. However, similarities on factors related to current life stage (e.g., age, family relationships) and/or recovery process (e.g., overall pathway, spirituality) may be more important.