[Ask April Masini]

Don’t “drop hints”. Be clear and let there be no misunderstanding what your intentions are — to date his mom. It’s understandable that he won’t be happy about this, but if you’re okay with his being unhappy, then you can at least know you didn’t go behind his back and lie to him. Age is one thing, but having the character and maturity to be up front closes any age gap. 😉