To analyze how emotions and imagery are shared, processed and recognized in Guided Imagery and Music, we measured the brain activity of an experienced therapist (“Guide”) and client (“Traveler”) with dual-EEG in a real therapy session about potential death of family members. Synchronously with the EEG, the session was video-taped and then micro-analyzed. Four raters identified therapeutically important moments of interest (MOI) and no-interest (MONI) which were transcribed and annotated. Several indices of emotion- and imagery-related processing were analyzed: frontal and parietal alpha asymmetry, frontal midline theta, and occipital alpha activity. Session ratings showed overlaps across all raters, confirming the importance of these MOIs, which showed different cortical activity in visual areas compared to resting-state. MOI 1 was a pivotal moment including an important imagery with a message of hope from a close family member, while in the second MOI the Traveler sent a message to an unborn baby. Generally, results seemed to indicate that the emotions of Traveler and Guide during important moments were not positive, pleasurably or relaxed when compared to resting-state, confirming both were dealing with negative emotions and anxiety that had to be contained in the interpersonal process. However, the temporal dynamics of emotion-related markers suggested shifts in emotional valence and intensity during these important, personally meaningful moments; for example, during receiving the message of hope, an increase of frontal alpha asymmetry was observed, reflecting increased positive emotional processing. EEG source localization during the message suggested a peak activation in left middle temporal gyrus. Interestingly, peaks in emotional markers in the Guide partly paralleled the Traveler's peaks; for example, during the Guide's strong feeling of mutuality in MOI 2, the time series of frontal alpha asymmetries showed a significant cross-correlation, indicating similar emotional processing in Traveler and Guide. Investigating the moment-to-moment interaction in music therapy showed how asymmetry peaks align with the situated cognition of Traveler and Guide along the emotional contour of the music, representing the highs and lows during the therapy process. Combining dual-EEG with detailed audiovisual and qualitative data seems to be a promising approach for further research into music therapy.