Dating a guy 20 years older than you

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If Mary Kate or Ashley was approachable and not icy fashion prodigies, I would love to ask how they make it work. After it ended, he talked to a lot of people about our relationship -- and what happened through the grapevine was unexpected. Women judged me as having an ulterior, economic motive: “She just dated him for his money,” or “She thought she could get ahead.” In our society people are so quick to judge a young, naïve woman -- never the older man who perhaps should’ve known better too. I have a friend who’s been married to someone for more than a decade who is 20 years older than her. In my case, the age gap was actually a cavernous black hole defying space and time. Another lesson in dating: a fling with someone in your professional/personal circle is more often than not bad news. He’s old and sick now, and she takes care of him (even financially), but she’s still partying and sleeping around. I sometimes imagine what would have happened if I had stayed with my older man.

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Do you like to feel the occasional rush of adrenaline and stimulation?

Anyone who’s been in a serious long-term relationship knows the journey isn’t without certain challenges, and when you’re dating an older man—we’re talking a decade or more—things can get even trickier.

I know this firsthand, as I’m 25 years old, and I’ve been dating an older guy nearly 15 years my senior for almost four years.

(It will never be exactly the same for two different people.) Assess Your Proclivity for Indulgences While many behaviors in the extreme form represent a problem or even an addiction, some of those same behaviors can be harmless if not taken to the extreme.

Consider a list of activities that fall on the hedonistic end of the behavioral spectrum: drinking alcohol, gambling, shopping, traveling, and spending, for example.

Woman B: Twenty-seven and he recently turned 42 (we're still together). We discovered we had a lot of interests in common and became good friends. Most of the men I dated more casually at the time were in their 30s. It also made me feel special — this man seemed so much more worldly than the men my age, and the fact that he was interested in me seemed too good to be true. Woman D: Originally I think I was flattered that somebody who had experienced so much of life was interested in me.

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