-Compliment her. eg, nice outfit, nice hair, etc.
-Talk about her kids. SHow an interest in them, even if you have never met them. I guarantee you this will pleasantly surprise her. Other guys who want to date her are only interested in fucking her, but you are interested in finding out about her kid's interest, level of education, etc. Let her talk about them. Tell her you hope to meet them one day.
- Don't talk excessively about yourself or how rich you are, what car you drive, etc. Let her ask you those questions.
- Up your game in bed. Your last MILF told you she feels no chemistry with you, its a code word for you suck in bed. If you make her cum like crazy, you could look like Jabba the Hutt, but she will call you the next day to look for another fuck session.
- MILF's are good fucks. If you play your cards right, you could have a regular one on the side.
- Good luck and happy hunting.