What to expect when dating an older woman Should you date an older woman. When I started talking about The Age Gap in my other video , it had a lot of positive and mixed responses. Some women are happy to date younger men and not want a family straight away , for other their biological clock ticks over and they want to eventually have some babies! Learn to choose your battles and the right person to do them with to make love easier and more enjoyable. Read the original article. Notify me of follow-up comments by email.