Resentful? I wouldn't go that far. I am concerned about the costs and somewhat annoyed that she is not that concerned about my financial situation.
She is significantly older than me and well-established in her career. She make about $20k more a year than me, plus she has a defined benefit pension plan, a 401 k, a traditional IRA, and a Roth IRA. She also contributes to Social Security. I basically have a 401k and a tiny Roth IRA (they add up to about $15k -- all I have saved for retirement!).
I am doing what she likes to do because what I like to do would not be considered a date. I like to go fishing, ride my bike, cook food together, and take part in community organizations -- stuff like that.
In order to make room in my budget for the dates I am going to go fishing much less, probably much, much less. That is the place in my expenses with the most room to wriggle.