Any tips on SD game other than it being the wrong way to DHV?

I'm 40+ and so $$ isn't that big a deal and it's an obvious advantage.

1. texted over a couple of days then met and f-closed a 23 y/o same day. cute enough to be seen with but not hot. anyway, a girl being half your age adds a few points, one day you'll understand! good in bed.
Could tell the girl has some self esteem issues so gave her some validation, sent her some flowers. Seems to want to hook up again but not

#2. texted for a few weeks. Some early IOIs but could be playing me. 8 or so in her pics, a 9 in person.
25-ish MILF/baggage. Wearing engagement ring (so she doesn't get hit on at work) but said she never got married. Said she doesn't get out etc. which I have a hard time believing but who knows. Qualified herself a lot about her career but think she's exaggerating. Said outright she has "high standards". Not great body language but very friendly, just hugs and backed away from kiss. We kicked around a couple of ideas for a 2nd date which I'm fine with because I'd like to get out more and she said to text her.
(she's just text me back)


So how can I have some fun with #2? Some playful shit tests? How far to push etc?

Hate to burst your bubble.... But if you are just throwing money at girls to get laid, thats not really game. It's actually not game at all. That's them gaming you. Girls who have sex for money have a name in the streets.......

Hate to burst your bubble.... But if you are just throwing money at girls to get laid, thats not really game. It's actually not game at all. That's them gaming you. Girls who have sex for money have a name in the streets.......

I know the difference

Maybe it got mixed up in there but the point is I didn't pay the girl. There was some pre-selection at work.

There may be something there to keep having some fun with, but it has obvious downsides.