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Writer Mary Rose Madigan reflects on what it was like dating an older man at 19 years old, and what she wishes she knew sooner. I Dated An Older Man In My 20s - The Pros & Cons, and. There's nothing wrong with dating an older man in your 20s I don't see anything wrong with dating an older man in your twenties. If you like each other, date. The Reality Of Dating A Man 23 Years Older Than You While Dating Older Man Has Its Perks, The Reality Is That Large Age Gaps Can Cause Big Relationship Problems. Ask Annie: How do I protect my feelings while dating older men? From "Dear John" to "All Too Well," we can learn from Taylor Swift's heartbreak when it comes to dating an older man.
