It takes a certain bit of finesse to flirt with an older women, mostly because mature woman know what they want and don't respond to cheap stunts and gimmicks. The key to attracting women that are older is to have confidence.
MAKE HER FEEL YOUNG by downplaying her age in a clever way. Pretend she's too young to drive or something along those lines. Use your environment to help you brainstorm.
COMPLIMENT HER MATURITY. This one is tricky because some women are sensitive about their age. Say something like: "you don't like younger women because their immature,". Basically find a way to make her feel better about being older without making her feel old to avoid turning her off.
HAVE INTELLIGENT CONVERSATIONS, as that may make flirting with some older women easier. Some women want to make sure you're more than just a vegetable, so do your best to hold down an interesting and intelligent conversation.
COME OFF AS A STUDENT. Some older women like to be a little more dominating and instructive than their younger counterparts. If you are attempting to attract a woman that loves to teach new things, be receptive and you might win her over.
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- Pick up lines are cheesy and don't work anyway so don't work.
- Tap into your youth, because a lot of older women are attracted to the vitality of younger men.
- Be genuine, because any older woman with a level head will detect and dismiss any B.S. straight from the gate. Play towards your strengths, to keep the advantage in your court.