Every now and then there are situations in which we are not sure how to proceed and thus are seeking for help. For example, choosing the best product out of dozens of different brands in a supermarket can be difficult, especially when following a specific diet. There are, however, also people who have problems with decision making or sequencing actions in everyday life, e.g. because they suffer from dementia. In such situations, it may be welcomed when there is someone around noticing our problem and offering help. In more private situations, e.g. in the bathroom, help in shape of a human being cannot be expected or even is not welcomed. Our research focuses on the design of mobile assistive systems which could assist in everyday life activities. Such a system needs to detect situations of helplessness, identify the interaction context, conclude what would be an appropriate assistance, before finally engaging in interaction with the user.