Middle school counselors are involved in cross-gender interactions with students daily. In order to explore middle school counselors' experiences in cross-gender student-counselor working alliances, interviews were conducted with 22 practicing middle school counselors. Selections from the resulting conversations reveal that female and male middle school counselors describe their same-gender counselor-student relationships as less challenging and perceive more challenges in their cross-gender relationships in school counseling. Recommendations are offered for cross-gender relationship building for middle school counselors working with students.