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  dating an older man in your 20s and 30s is much different than dating one in your 40s, 50s, and 60s. As often as possible, i will go to her house and we will sleep together and hangout and just have fun. On the weekends when we both do not work, we go out on dates and such.   a 17 year old girl dating a 31 year old man may raise an eyebrow but a 31 year old woman dating a 45 year old man probably wouldnt. According to some, you can determine your appropriate dating age range by only dating someone who is within a fifth of your own age. Hollywood ladies man jack nicholson is famous for dating younger women. I have met several women over the years, some were very special relationships but never lasted. Having said that, a guy at 41 squiring a woman of 23 is far more controversial than a 71-year-old man dating a 53-year-old woman. Yes, its legally permissible for a 19-year-old and a 29-year-old to date each other, or to date (have sex with) anyone 18 or older (in most states). The thing is, that someone who wants to date a person who is a lot younger than their own self is.   true, another factor is judgment from other people, who may see a 44-year-old going to dinner with a 25-year-old and make judgments about which one of them is drowning in student loan debt.   we interview a couple for our new series strange relationships. We talk to an 18-year-old girl named stephanie, who is dating a 68-year-old man named rick.

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