cover image The Arrangement: A Love Story

The Arrangement: A Love Story

David Winkler. Rare Bird, $26 (298) ISBN 978-1-64428-268-7

“I didn’t consider myself that cliché man in the crush of a mid-life crisis, chasing young girls,” writes 50-something film producer Winkler, a self-identified “sugar daddy” and ethical nonmonogamist, before spilling the tedious details of his transactional relationship with Jordan, an Instagram model 20 years his junior. The two met in 2017, on Seeking Arrangement, a dating site that connects typically well-off men with typically attractive women in search of a “monthly allowance” (“The website frowned on ‘Pay Per Meet’ dates,” Winkler notes, “as it was too akin to straight-up prostitution”). What first was an avenue to attain “all the perks of a relationship without the drama” quickly devolved into a volatile open relationship. As Winkler excavates his anxieties about sex—which, inconveniently, affected his virility—he describes being blindsided after discovering Jordan’s ongoing struggles with depression. Later, stunned by the impact of #MeToo on his Hollywood peers, Winkler pantomimes progressiveness as he reflects on the unequal power dynamics inherent in paying younger women for dates—for a couple pages. Readers who enjoy accounts of men’s public midlife crises might find a thrill in this naked confession, but those in search of insights on nonmonogamy will have better luck elsewhere. This misses the mark by a mile. (June)