Questions: Dating

28, really pretty, 5’4.

She is a doctor, also looking for a doctor that is well to do and 27-32. She even said she is looking for a tiny demographic of guys.

Wants the guy to have a more provider mentality.

Her brother is divorced.

She has been in a few relationships. She likes to be really independent, not good with dealing with relationship stress. Occasionally goes on solo trips abroad. Has needed therapy before.

Because of her age and personality traits do you think she will end up single? I try to tell her to just be realistic and give a guy a chance

I once met a girl on the subway. We had never seen each other before, but she kept looking at me for a few seconds, so I smiled, started a conversation right away, and got her number.

I mean, has anything like this ever happened to you while walking on the street, waiting in line at a store, sitting in a park, etc?

The guy is from a really rich family and only recently started making a lot of money.

The first few dates the the guy paid. Then 50/50 on everything. Is there anything wrong with that?

He would spend hours on the phone everyday and drive to see her a lot straight after work.

Treated her well, caring, emotionally available. Even when broke up he did not insult her. Did gift her but not expensive things.

Girl felt the guy should have contributed more monetarily to make her feel special.