“You Don’t Think I’m Beautiful” – Dating Over 50

Chuck Epstein suffered two personal crises that dramatically changed his life. After more than three decades writing about finance, he was laid off during the 2008 financial services meltdown. Not long after that, his wife died of cancer.

Epstein left California and eventually relocated to Florida to be near his daughter and grandkids, yet found himself single, alone, and yearning for companionship.

You Don’t Think I’m Beautiful is Epstein’s painfully honest account of dating after 50 (focusing on his 60’s) in a world where online connection spawns equal parts hope, anxiety and disappointment – with barely a dollop of true happiness.

By turns funny and sad, Epstein includes poignant insights about going solo in later life where an “epidemic of loneliness” persists amidst promises of unlimited possibilities. His writings on solitude are achingly beautiful in their yearning for partnership in a world often made for couples.

As a long-time journalist, Epstein includes nuggets from several surveys (there are far more elder women who have never been married than one might think) that spawn a book serving as private journal, dating advice, social treatise, and study of modern romance.

Epstein is often at his best when exploring the nuances of online dating, such as the underground network of social connections that speeds information among the women in Palm Beach County quicker than an old-time party line.

He recounts falling in love for just the second time ever, to a social butterfly so overscheduled that Epstein was often left home alone awaiting her call. Their breakup – and his crucial faux pas – is recounted in agonizing detail. He divines the psychology of happiness, including the theory that many people don’t believe they’re worthy of love, leading them to sabotage even the most harmonic convergence.

“We are our own worst enemies,” he writes, “and we have become too judgmental and overly critical. We focus on the castle on the hill, even when the castle is a mirage. Often, the real castle, with all of its diamonds and riches, is sitting right across from us. Too often we are just lazy or too blinded by our own vanity to reach across the table and hold hands.”

You Don’t Think I’m Beautiful is many things, yet most of all it’s an honest and intimate account of the barriers that often keep older Americans separate and alone despite their longing for connection.



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