From Simple Miss to a Bride His Rebellious Ward Forbidden Love Older Man: Teasing the Butler Older Man: The Mistress' Faithful Servant (Part 1) Older Man: On the Way to London (Lady Lily #1) Older Man: Playing in the Garden (Lady Lily #2) Older Man: Lonely Days with the Butler (Lady Lily #3) Older Man: The Explorer. Exude confidence. If you really want to date an older woman, then you have to be secure in who you are. If you have low self-esteem or feel like you can't hold your own in a romantic relationship, then you will have a hard time dating an older woman. Older women who date younger men aren't looking to have a new son or . A list of famous men who married older women. It is traditional for younger women to marry older men, but several famous men have flipped the script and married old.