Human attachment describes the establishment of contact between two or more people leading to a closer interpersonal relationship. For measuring attachment, the use of nonverbal assessments tools including art and drawing tasks has been shown to be an alternative to conventional assessment approaches. The present study aims at evaluating the internal criterion validity of a new digital drawing tool for measuring interpersonal attachment. 68 participants took part in this pilot study and were separated in groups of two. After completion of a 10-item subscale of Social Orientation (SO) they were asked to sit opposite to the other and to hold eye contact during a three minute drawing period. Moving the pen to the upper section near the partner stood for thoughts about the other, while moving to the lower section closest to the subject implicated thoughts about oneself. The mean distance of the resulting time series of the two subjects were calculated, using the mean Euclidean distance, and compared with the difference in the SO values via linear regression. Taking all differences together a moderate correlation of r = 0.298 was observed, which however slightly missed the level of significance (p = 0.09). We were able to find small evidence for the criterion validity of IU digital drawing tool. For future studies, other measures of similarity in the time series, i.e. the Manhattan Distance are discussed as an extension to foster the present results.