Dating a childish man
He is not looking for confidence, he is looking for love.
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When you talk about these things, it emphasizes the age difference and creates an awkward feeling for both of you.
For instance, you can ask him about career growth or money management because he is likely to be very supportive, offering you advice from his experience, referring you to professional colleagues, or simply pointing out where you can find your best answers.
Additionally, an older man will probably really enjoy talking things over with you.
By asking him about important decisions you're thinking of making, he will not only be able to offer insights, but he will also feel recognized and appreciated.
Even if a man earns much more than you and can easily take care of all your expenses, he will feel stifled if he has to take care of all the bills and expenses, as well as make all the decisions on where to go out for dinner, where to shop, and other simple things.
So stay self-assured, confident, and fairly independent. So avoid talking about past events, especially cultural events, like movies or trends.