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Dating younger women don't have to be intimidating or taboo if you understand you may even find yourself with the love of your life 20 years younger than you! Even if she is young, she could be a mature old soul at the age of 50 inside. A young woman dating an older man is often romanticised but it can be very, very to move in with her year-old boyfriend Shaun (yep, not his name either). There are lots of men who date younger and attractive women. after 30, 40, 50 or 60 not knowing what to do about the lack of attractive women in their lives. Now I am 42 and my dating and sex life has never been better. . Related: 40 Pieces of Unconventional Life Advice For Every 40 Year Old Man.