Set boundaries re: the dinner dates and charge him, mostly so he knows there are no feelings there and doesn't get his heart broken.
I think some people need to be less paranoid about "stalkers", "psychopaths" etc. The reality is, that statistically, people close to you are people that are most likely to cause you pain, suffering and drama in your life. People you choose as boyfriends, partners, family members, friends.
99% of clients - even pains in the ass - are not going to cause any real drama in your life. The one's that fancy you, fancy you but know that you are unavailable. Some are infatuated. I've had clients tell me that they love me and are obsessed with me and write me long two page letters describing my favourite bones and facial angles. It's fine, he reiterates that it's from a distance and in a harmless and respectful way like an obsession a celebrity as a teenager. Most clients are asking personal questions as they think of you warmly, they think you are a nice woman and are interested in who you are and want to learn more about you so they have something to talk about. Clients are people, people that pay for sex. It doesn't make them more or less likely to have negative personality traits. If you think that it does, it might be time to reassess how happy you are in your line of work (IMO) as that's very chip on the shoulder.
There are clients here girls discuss where clearly, they have personality traits that are very off (they are controlling, jealous, try to woo them with gifts, invade their personal life, cannot take rejection etc); be on guard with all - people - like that in life, not just clients. Realistically, these are going to be men you date, not clients.. (or time wasters, ugly mugs, men that don't pass your screening).
He is probably just lonely, fancies you and enjoys your company. It's basically where you want him, that's a gravy train for $ Sincerity and empathy will earn you good money, just be careful not to take on the feelings and emotions of others too much.