Sounds like an extreme amount of pressure for your daughter. To not be able to tell you about her life because it upsets you. I "get" how you feel. My H moved out and right in with maggot. But when my kids tell me anything about his new life - I just smile and listen and make no comment. I don't have to like it. But I don't say anything about it. I just listen.
And that's the point. If your daughter doesn't feel she can come to you to tell you what's wrong - who WILL she turn to? Especially in a couple more years when she too is interested in boys.
As for your older daughter - remind her of all her good points and don't commiserate with her. She needs you to be the dad. To love her unconditionally.
C2 - you ARE a good dad. But you your perspective is a bit "off" at times.
I totally was going to write the same thing as Gineen - about your new attitude. And also about the need to do the big trips when money is obviously a stress. No way I'd be taking them to big cities, staying in hotels etc. It costs megabucks.
Go to your local parks. Plan picnics. Keep on swimming. Maybe rent a boat for a couple of hours. Go fishing.
The most important thing to do with your girls is to spend time with them. It really doesn't matter where.