Don't be so tough on yourself (and the girls by the way), OP.
Some good rules of thumb I use:
- Are you having a nice conversation (more than a few lines) with the girl, even if only in Tinder?
- Have you seen many pictures of the girl without photoshop in IG or FB and she looks good?
- Would you go to that type of restaurant or bar with your friends in a normal night?
- Are you in the mood to eat out?
- Will you be comfortable in paying for her dinner without any expectations that you will bang?
If answer is yes to all questions, just do it... I often go for dinner dates with girls, with very interesting outcomes, and I think it doesn't hurt me, quite the opposite: they will be more open to drink (and it can be followed with the bar drinks after), you will play some gender roles there (even if soft) with you serving drinks, talking to waiter etc, eating makes ppl feel comfortable as well.
Some good rules of thumb I use:
- Are you having a nice conversation (more than a few lines) with the girl, even if only in Tinder?
- Have you seen many pictures of the girl without photoshop in IG or FB and she looks good?
- Would you go to that type of restaurant or bar with your friends in a normal night?
- Are you in the mood to eat out?
- Will you be comfortable in paying for her dinner without any expectations that you will bang?
If answer is yes to all questions, just do it... I often go for dinner dates with girls, with very interesting outcomes, and I think it doesn't hurt me, quite the opposite: they will be more open to drink (and it can be followed with the bar drinks after), you will play some gender roles there (even if soft) with you serving drinks, talking to waiter etc, eating makes ppl feel comfortable as well.