It is always an uphill battle. Eventually you overthink things less and less and rejection phases you less and less.
IMO, the best way to think of it is like an RPG. Right now you are at level 1 in terms of talking to women romantically online as well as talking to women romantically face to face. The goal shouldn't be to tackle some of the harder things, but instead focusing on making women laugh, getting phone numbers, realizing what they like/don't like, etc.
Dating online is good because you have a lot more time to think things through. On the flip side, real life is good because you can get a lot of experience a lot quicker. You can meet 5-10 women per night (pre-covid), while with online dating, matches are less frequent and the responses are slower.