You probably already know this, but if your problems are big, you should try a therapist instead of self-help based on an advice from internet. (Although the advice given on this part of internet is usually better than average.)
Doing something is better than doing nothing. Unless you use it as an excuse for not doing more. (As in: "Nothing can fix my problems. What, CBT? No thanks, I tried one exercise based on an advice from internet, and it did not fix my problem. What, visiting a CBT therapist? I am telling you, I already tried an advice from internet, and it did not work.")
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Just a note: Different people have different dates. Probably the worst (but usually the first that comes into mind) kind is the "awkward silence in a romantic restaurant" kind of date. This works best in Hollywood movies, and perhaps for experienced seducers who don't feel any anxiety and can easily manage social situations. (For them, this is good signalling, but that's precisely because it is costly. And I don't speak about the costs of the dinner here.)
As an alternative, I would recommend a "doing something fun together" kind of a date. Something that (you can pretend) you would do alone and have fun doing it, too, but today you altruistically decided to offer her an opportunity to join you and have fun too. (Feel the difference? You are not begging, you are offering.) Do a short internet research: is there any gallery exhibition, or music concert, or public lecture, or whatever interesting in your town the next week? (Or simply ask other people what interesting activity would they recommend you the next week. You don't have to explain why you need it. Maybe there is an information service you can call for exactly this info.) Choose something that interests you, so you will be relaxed, and later you can talk about it. She may also feel less pressure on this kind of a date.
(Beware of other-optimization, et cetera. If romantic dinners work for you, just continue doing what works. Although trying something new in addition probably would not hurt.)
A friend suggested exactly this before I asked her out. But, uh, I almost never go to galleries or lectures, or concerts unless I really really like the band, and I don't particularly want to change that.
I'm starting to think there may be other activities (video games at home? hikes? board games unfortunately don't really work as an "I'm going to be doing this anyway, join me if you feel like it" thing) that will work for me, though.