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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. Your difference in years may elicit some unfortunate assumptions and remarks, but if you truly care about each other, stay focused on how you feel. We have people in their 90s using it! Dating an older man in your 20s and 30s is much different than dating one in your 40s, 50s, and 60s. If his working days are behind him and you're still focused on a job and all the ambitions, woes, and time demands that come with it, you may struggle to connect at the end of the day.

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