Interesting the comparison to separation anxiety.
When my hubs was going out, mostly I tried to just get a lot of lovin' beforehand, and then during the process do things I enjoyed (or try to!) and sit with the feelings a lot. I did a lot of dissecting of what was going on with me. Was I insecure, was I comparing myself to them, was I afraid to lose him.. etc. I'm not going to claim it was easy, but it was useful to see where the feelings were coming from and then talk to him about it so he could see what I was thinking and reassure me about them.
Would it be possible to both go out at the same time? Maybe just for a dinner and some convo kind of date, not too long, but not too short either. The 30 minute thing seems like it would be pretty hard on your dates, but maybe not. Maybe if you are both with the people you find interesting, and both know it won't lead to sex (for now), you can focus on the date itself, and then when you get home talk about what went on for you two, talk about each other, be together. I know that for me finding out through experience how much hubs' feelings for me grew because of his other relationships really helped me.
Interesting, too, because my hubs is thinking he won't feel upset by me finally getting to go out on my own. I am hoping that is the case and it is entirely possible as he has a completely different way of framing things than I do. I also know it is possible to feel stuff you never expected, and things you thought you would be okay with suddenly... aren't.
I think it's important to remember that while the feelings are valid, and need to be experienced, they need to be taken with a grain of salt. Yes, get some insight into where they are coming from and no don't make big decisions just because you're feeling badly at the moment.
Change is not an easy thing.