How do statistical regression results compare to intuitive, visually fitted results? Fitting lines by eye through a set of points has been explored since the 20th century. Common methods of fitting trends by eye involve maneuvering a string, black thread, or ruler until the fit is suitable, then drawing the line through the set of points. In 2015, the New York Times introduced an interactive feature, called ‘You Draw It,’ where readers are asked to input their own assumptions about various metrics and compare how these assumptions relate to reality. This research is intended to implement ‘You Draw It,’ adapted from the New York Times, as a way to measure the patterns we see in data.