Planning dates

Don't plan anything unless you want to plan it all from now on. That's his job.

Mention it to him once and watch if he takes the bait and acts on it

At least not for the first few months. His date ideas will reflect his overall view of your relationship, so letting him plan everything is a good way to vet him. If his ideas quickly become boring or repetitive and he's not trying his absolute hardest to impress you, ditch him.

If you start planning dates early on, most men will start acting like they're the prize and you should chase them. You can't reverse his mindset after that. So whenever you come up with a fun date idea, it's best to ask a female friend instead, or do it alone if you're comfortable with that.

Don't do it. Instead, suggest to him that it would be nice to do the fun thing with him. He should take it from there and do the actual planning. If he doesn't, he's low value.

This is a good test. If he doesn't pick up on your suggestions after you try this once or twice, I guarantee he never will, and then later accuse you of "not communicating."

Unless it's a man's birthday or similar, the woman never plans or pays.

You can start planning NEVER.

Obviously, you're still stuck in a pickme mindset. I'd be careful if I were you. Quite frankly, with your mindset, you shouldn't be dating right now.

imo if you like him enough go for it, his reaction will be what matters. If he just slacks off on the date like "nice she'll do all the relationship heavy lifting" then that's a red flag that he just wants a mom. That you're so excited to plan something and share it with him tells me there must be something about him you enjoy.

Now don't go overboard ofc. A simple "hey here's this thing coming up, I'd love to go to it with you" should be all the signal he needs