ReTest is a novel testing tool for Java applications with a graphical user interface (GUI), combining monkey testing and difference testing. Since this combination sidesteps the oracle problem, it enables the generation of GUI-based regression tests. ReTest makes use of evolutionary computing (EC), particularly a genetic algorithm (GA), to optimize these tests towards code coverage. While this is indeed a desirable goal in terms of software testing and potentially finds many bugs, it lacks one major ingredient: human behavior. Consequently, human testers often find the results less reasonable and difficult to interpret. This thesis proposes a new approach to improve the initial population of the GA with the aid of machine learning (ML), forming an ML-technique enhanced-EC (MLEC) algorithm. In order to do so, existing tests are exploited to extract information on how human testers use the given GUI. The obtained data is then utilized to train an artificial neural network (ANN), which ranks the available GUI actions respectively their underlying GUI components at runtime---reducing the gap between manually created and automatically generated regression tests. Although the approach is implemented on top of ReTest, it can be easily used to guide any form of monkey testing. The results show that with only little training data, the ANN is able to reach an accuracy of 82% and the resulting tests represent an improvement without reducing the overall code coverage and performance significantly.