Midlife Dating

How to Not Die Alone

Logan Ury · 2021

Ury is a behavioural scientist who worked at a dating app and then went and read the research, and the result is the least sentimental book here. She identifies the patterns that keep people single without their noticing, argues that most of us are terrible at predicting what will actually make us happy in a partner, and is very good on the second half of the problem: not finding somebody but deciding about them. Practical, and it works just as well at fifty-five as at twenty-five.

Our Souls at Night

Kent Haruf · 2015

Addie Moore, a widow in her seventies, knocks on her neighbour’s door and asks whether he would consider sleeping in her bed at night, not for sex but for the company and the talking in the dark. Haruf wrote it while he was dying and it is under two hundred pages. It is the finest book there is about wanting somebody late, and about the grown-up children who take a dim view.

Deeper Dating

Ken Page · 2014

Page is a psychotherapist and his premise is that the qualities we are most ashamed of — being too intense, too sensitive, wanting too much — are the exact places where real connection is possible, and that most dating advice teaches people to hide precisely those things. His distinction between attractions of deprivation and attractions of inspiration is the most useful idea here for anyone who keeps ending up in the same situation with a different face.

Olive, Again

Elizabeth Strout · 2019

Olive Kitteridge, widowed, difficult and in her mid-seventies, takes up with Jack Kennison and discovers that the awkwardness does not go away with age: the bodies, the previous marriages, the adult children, the fear of being seen. Strout is entirely unromantic and entirely warm at the same time, which is rare, and she writes late desire without a trace of embarrassment.

Mating in Captivity

Esther Perel · 2006

Perel’s subject is the tension between the security we want from a partner and the desire that requires a bit of distance to survive, and why the two keep undermining each other. It is aimed at long relationships and it is enormously useful before you start one, because it explains what actually went wrong last time in language that is not about blame. Read it before the third date, not after the third year.

Really Good, Actually

Monica Heisey · 2023

Maggie is divorced at twenty-nine and insists, loudly and to everybody, that she is doing brilliantly. It is a comic novel and it is included here because the dating-app chapters are the funniest and most accurate anyone has yet written: the messages, the catastrophic first drinks, the compulsive checking. Younger than most readers of this page, and the mechanics are identical.

Eight Dates

John Gottman & Julie Schwartz Gottman · 2019

The Gottmans spent forty years watching couples in a laboratory and can predict divorce with unsettling accuracy, so when they set out eight conversations a couple should have — about money, trust, sex, family, growing older — it is worth taking seriously. Structured as eight actual dates with actual questions. Unglamorous, and exactly the right tool if you have decided you are not doing the second one the way you did the first.