Again, unless he pays for them. Also his most recent conquest Gina is also mentioned by the unknown red haired man in ep 5 as being important enough to discuss the winter retreat with her. That either means she's his daughter and he probably has no wife, or he has hired her as an escort/sugarbaby. If the latter is the case, it could possibly mean that Tommy also hired Gina for the evening. We know she does get around and doesn't seem to be interested in getting satisying grades during the exam, that could mean she already has a way to get enough money/being cared for should she get kicked out of school.