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Or, you know, they might not be. Dating an older man in your 20s and 30s is much different than dating one in your 40s, 50s, and 60s. How to Make a Platonic Friendship Work. That said, extra years of life experience do often lead to greater maturity in relationships, and more life wisdom. You two may not be picking out wedding rings at this point, but if things start getting serious, it's worth discussing what you both think your next ten-to-twenty years will look like. A woman in her 40s or older has plenty of hard-won lessons and accomplishments of her own to tout, of course.

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