The first card we drew is the reversed Two of Pentacles, which represents a distrust of the request or a lack of trust. This indicates that while you intend to entrust Chiara with your foreign language training, you may not feel completely comfortable with entrusting her with your training. There may be some concern on your part about the quality of the material she will provide or the way she works. Lack of trust could also be due to other factors such as distance and lack of time to take courses or poor communication between the two of you. In any case, the first card suggests that you should carefully consider whether to trust Clare in this case.
The second card we drew is the reversed Five of Cups. This card represents the opponent's emotional state and is a sign of distrust on the part of the latter. This means that, while you intend to rely on Chiara for your foreign language training, your opponent may not share your opinion and may even question his quality as a teacher. There may also be some prejudice or distrust of her competence and ability to teach foreign languages. You should then consider that possibility and decide whether your opponent's opinion should influence your final decision.
In conclusion, from the tarot it seems that you are carefully evaluating whether to trust Chiara for your training in foreign languages. However, there is also a certain degree of distrust from the opponent that could hinder your decision. So, considering all aspects taken into account with these two papers, the answer is likely to be No: you shouldn't trust Chiara with your foreign language training.