Good Minds Suggest—Amy Webb's Favorite Books About Dating

Posted by Goodreads on February 4, 2013
Online dating is a playground—or bugaboo—for millions of modern singles. Disillusioned by the terrible dates she met on sites like and, digital media expert and single woman Amy Webb decided to use a strategic and mathematical approach to figure out what she was doing wrong. As CEO of Webbmedia Group, Webb helped the city of Chicago modernize its library system. Surely, solving her dating woes would be just as easy! As chronicled in her humorous memoir, Data, A Love Story: How I Gamed Online Dating to Meet My Match, Webb developed her own algorithm to weigh certain traits she sought in a life partner. She also studied her competition by logging on with several fake male profiles. She reveals her practical findings about photos, profiles, and dating—and the story of how she met her husband. The now happily married mother of one shares her favorite books about dating and relationships.

High Fidelity by Nick Hornby
"This is one of my very favorite novels, a book that I reread probably once a year. Main character Rob Fleming tries to unravel the reasons his previous relationships and dates failed via top five lists, mix tapes, and prolific, nerdy pop culture explanations. Rob fears commitment, death, and even his girlfriend at times, but that's all mitigated by his desire to find a lasting, comfortable relationship. Really the only thing I don't like about High Fidelity is the 'Top Five Episodes of Cheers' list, since it doesn't include the pilot."

The Little Book of Heartbreak by Meghan Laslocky (Goodreads Author)
"Meghan is an intrepid journalist who's spent the past few years diving deep into messy, strange romance traditions and truly awful dates. She manages to untangle Greek love spells, tragic funeral pyre breakups, the tale of Abelard and Heloise, and even Norman Mailer's six marriages in a way that's informative, sure, but very, very funny. If I was going through a breakup, I'd want this book at my side."

Clearly, I Didn't Think This Through by Anna Goldfarb (Goodreads Author)
"This book is based on Shmitten Kitten, Anna's dating blog that's become something of a cult phenomenon. Anna is brutally honest, and whether or not we feel comfortable doing it, she invites readers to laugh at her numerous missteps. Her story about one particular bad, late date (Alvin) and her parents calling the police to request a missing person investigation—all over the course of one evening—left me in happy tears."

Good in Bed by Jennifer Weiner (Goodreads Author)
"I really appreciated the honesty and realistic take on relationships in this novel. I may have read deeper into this book than others because of my background as a journalist, but so much of this story was visceral and tangible. The dialogue is realistic, the various twists and turns are heartbreaking, and it has a wonderful, satisfying ending. This smart story is more than a book about breakups and renewal. It's about empowerment in the toughest of circumstances—dating and otherwise."

How to Win Friends and Influence People by Dale Carnegie
"This may seem like an odd choice for a dating and relationship book list, but I absolutely have to include it. When I look back at the data I analyzed and the trends I saw among successful daters, they were unwittingly practicing most of what Carnegie advises: remember details about people, don't usurp the conversation, find the interestingness in everyone you meet, and the like. In fact, all of Part Two: Six Ways to Make People Like You is an excellent primer on how to ensure you land a second date with that someone special. Who would've thought that Carnegie, all these years later, would be an expert on both business and love?"

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message 1: by Barbara (new)

Barbara Newhall Amy, your list looks terrific. Wish there had been so much helpful (let's hope) advice out there when I was dating back in the '60s and '70s.

Too bad it never occured to me to read "How to Win Friends and Influence People." I thought it was something my dad, a businessman, would was supposed to read.

I'd like to add "Why He Didn’t Call You Back" by Rachel Greenwald to your list. She actually goes out and asks guys -- what a thought -- what they liked and didn't like about the women they met for the first time.

Rachel has changed her title to something less scary -- “Have Him At Hello: Confessions from 1,000 GUYS About What Makes Them Fall in Love… Or Never Call Back.” But I like the original title.

You can read more about Rachel's book at:

message 2: by William (new)

William Torgerson High Fidelity, one of my favorites!

message 3: by Heather (last edited Feb 21, 2013 10:54AM) (new)

Heather Mcculloch Books from @thesinglewoman are good as well.. 1400322316 is her new book coming but she also has a ebook available too...

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