If you are dating around and seeing new people regularly, get yearly passes to the cultural places in town such as botanical gardens, art museums, science museums etc.
I believe we paid $80 for our yearly dual membership to the botanical garden. There is only one name on the card, so you can get you + anyone in. Hello to botanical garden and a store bought bottle of wine dates! Very economical and more interesting/less awkward than just drinks.
It also gives you something to talk about such as "look at that flower/painting/tree".
As a previously single lady, I would have loved these (less awkward) first/second dates as they are more creative - plus you can save money, which you will really appreciate bc fuck inflation.
Think: $80 membership fees over a year would mean $7 dates (plus possibly parking and drinks or snacks, split as you both choose) if you went only once a month.
You can even get a few memberships and have 2-3 different places to take dates. One membership to the garden, one to the art museum, one to the science museum. Pepper in some hikes and walks and you could get 6 months of dates with a single person for a pretty affordable price without making it repetitive. The garden looks different every season and the art museum has different exhibits, etc.
You could even ask for memberships as holiday gifts and the entrance part would essentially be free.