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I was having breakfast the other day with a friend who was giving dating advice to his son. For purposes of his anonymity, I am going to call just call him "Son. My friend said, "Son, you're 18 years old, so I am going to tell you how you date.

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Dating is confusing, anything arranging from break ups and asking someone out in high school can be very uncomfortable. Some say the younger girls are more tempting while others think the relationship is better with the older partner who has more experience. I explore the answer to this question.

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I keep that side of myself hidden from most people—along with many other aspects of my personality—and it can be difficult for me to date because nobody really sees me inside, just my appearance. The same with our friends. But a year age difference seems to be very controversial.

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We all remember when year old Ashley Olsen made headlines for reportedly dating year-old Bennett Miller, the director of Moneyball. And, yes, I know some younger men date older women. Kyle Jones, a year-old Pittsburgh guy, was in the news for having a relationship with year-old great-grandmother, Marjorie McCool.

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In reality, several factors play into which site or app works best for any particular person. Age is a big one, as can be the type of relationship desired. Crunching the numbers highlighted a few clear winners for each group.

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In it, Ms. Gadsby takes on the fragility of masculinity — and at one point drills into Pablo Picasso, who, well into his 40s, had an affair with a teenage girl. Seething, Ms.

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When I was 25, I spent a year dating a man 20 years older than me. The Older Man was also my editor, which added a power imbalance to the mix—a dynamic we all know can be equal parts problematic and irresistible. I wonder: What do we gain and lose from dating someone of a different generation? The Older Man was a peculiar person.

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