I am going to share one woman's experience with dating in her 50's: "I have come to realize that all men in their 50's are crazy!" jokes Mary, a. 7 Secrets to a Successful Relationship After 50 If you're dating for the first time in a long time, don't be afraid to wear your heart on your. Fashion, Hair, Makeup for Older Women, Senior Dating, Travel by a decade or more, because once in their 50's, men reliably prefer this age gap or greater. I met someone on Match in six weeks. (I have friends who have been on dating sites for years.) I corresponded with 50 women and met 15 for.