The problem with most passive entertainment ideas (music, comedy, movie) is little interaction. And landing with someone you don't know at a restaurant can be awkward, though most escorts are good at making things feel comfortable.
My suggestions
- If possible, 'stack' activities. If you do two things together, even if they are brief, you'll feel like you've shared much more and know the other person better. But they should be in separate locations
- Be willing to spend money, but don't feel you need to
Yes, you'd need to talk to your date and ensure there is a genuine match of interest, energy, and comfort level. And all of these will require some planning since getting the logistics right is 90% of the battle.
Some examples
- Game of pool at dive bar followed by nearby upscale cocktail bar followed by a quick meal at a handy, neighborhood restaurant
- Walk/short hike (if it's a first-time date, this will def need to be a very public place for safety) followed by a meal
- Bowling, PickleBall, Batting Cage, Mini-Golf followed by one or two (dinner/cocktail bar) activities
- Wing lady. OK, This is not for every lady or every gent, but have an early dinner, and then spend an hour (no more, no less) in a nice-ish bar hitting on civvies with your date as your wing lady. Working with a lady can help other ladies feel safe and make you look good; you may end up with a few numbers. But even if you don't, both of you will be so horny by the time it's done (again, you have to be the right people with the right chemistry) that by the time private time rolls around, you'll be sooooo legit ready to go.
Hope this helps!!!