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Totally Free To Place A Profile and connect with hundreds of thousands of singles like you now!his dry sense of humor kills you, and dang those eyes!And then you learn that the same year you graduated college, he was wrapping up his freshman year—of high school.Dating someone younger—whether you’re two or three years his senior or are talking cougar territory—certainly can work (look at Eva Longoria and her 4-years younger beau), but being an “older woman” in a relationship does tend to come with certain perks and downfalls.If you want to make things work, be sure you can handle the following. Men reach their sexual prime in their twenties due to a spike in testosterone, while women typically reach theirs in their 30s and 40s.