I will tell you what’s the WORST (as I recall from my dating days):
It’s when a guy asks you out “for a drink” at mid-scale restaurant, and you have to sit at the bar because the restaurant reserves actual tables for people willing to pay for a meal.
Then, after about 30 minutes, the guy asks “do you want to stay for dinner?”
What that tells me is that the guy was willing to pay for a $10 drink, but didn’t want to commit to an additional $15 for dinner until he decided you were “worth it.” Always found that a turn-off.
If you are a professional, college-educated man in his 30s asking out a professional, college-educated woman, take a risk and invite her to dinner right off the bat. All you’ll risk is an extra $15.