You can take a vigorous walk in the parks w/o a mask. Same for other outdoor locations. However, if this is one of your first dates, why in the world would you want to be close to ANYONE without a mask, unless he/she brings the results of one those rapid tests to the meeting.
Try the lehman’s list on shiduchshuk.
Also, it should be noted that many hotel lounges are somewhat open now (you man need to wear a mask to get to your table, but once you’re sitting down they’ll let you remove it). Just make sure to call beforehand.
Why not attend a shuir together (yes you both will be sitted separate), and then get coffee afterwards and go for a walk? Then you have plenty to talk about (example the shuir) while walking and enjoying warm coffee, and that can allow to see if your hashkafa lines up together.
Most museums, etc. that have reopened require masks . Restaurants serving indoors, still ask that you leave the mask on until you complete ordering and only remove it to eat/drink. If this is someone you know or trust, find a big table at an off-hour when its not crowded and distance as much as you can. Any of the bars in hotel lobbies that are open would be good choice since you can often spread out your chairs away from the bar itself.
Or at Fillmore Avenue and Marine Parkway, at the Marine Park basketball court? That was in the Oct. 15 YWN article yesterday, titled “GLARING DOUBLE STANDARD: No Enforcement In Non-Jewish “Red Zone” In Brooklyn”.