Attachment theories and research have brought new understanding regarding the bond between parents and their children for professional therapists and psychologists. Art-based assessments that elicit visual representations instead of words to symbolize emotional expression used in tandem with confidential interviews can be highly effective ways to communicate with children and evaluate and address their unique relationship concerns. One such assessment is the House-Tree-Person that was developed to look at an individual’s reaction to interpersonal relationships, their environment, and their inner psychological issues. This qualitative study documented and distilled themes that arose between nine child participants’ self-reported attachment styles, open-ended attachment interviews, and symbolic drawing elements in their individual House-Tree-Person drawings. Through phenomenological analysis, themes that correlated between the three assessment methods were identified. Though drawing elements were not found to indicate a specific attachment style, symbols did arise that seemed connected to the participant’s developmental age and attachment style. Three significant themes arose from the interviews: desires to be valued and protected by guardian, to be heard and validated, and to be like guardian or their special person. Through triangulation of the three data collection methods, verbal themes and drawing elements reflected secure and avoidant attachment styles self-identified by each child participant. A need for security is a theme that ran throughout all of the participants’ drawings and discussed experiences. This research underlined the importance of ongoing, fine-tuned therapeutic assessment approaches to children. Information regarding what children desire from their caregivers can provide guardians with answers and therapists with of the knowledge necessary to enhance parent-child bonding.