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The Playboy and the Widow

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Forced to trade in his carefree life of expensive sports cars and fancy restaurants, confirmed bachelor and playboy Cliff Howard joins a carpool with station wagon-driving, widowed mother Diana Collins, and unlikely sparks fly.

Mass Market Paperback

First published January 1, 1988

194 people are currently reading
387 people want to read

About the author

Debbie Macomber

909 books20.7k followers
Debbie Macomber is a #1 New York Times bestselling author and one of today’s most popular writers with more than 200 million copies of her books in print worldwide. In her novels, Macomber brings to life compelling relationships that embrace family and enduring friendships, uplifting her readers with stories of connection and hope. Macomber’s novels have spent over 1,000 weeks on the New York Times bestseller list. Fifteen of these novels hit the number one spot.

In 2023, Macomber’s all-new hardcover publication includes Must Love Flowers (July). In addition to fiction, Macomber has also published three bestselling cookbooks, three adult coloring books, numerous inspirational and nonfiction works, and two acclaimed children’s books.

Celebrated as “the official storyteller of Christmas”, Macomber’s annual Christmas books are beloved and six have been crafted into original Hallmark Channel movies. Macomber is also the author of the bestselling Cedar Cove Series which the Hallmark Channel chose as the basis for its first dramatic scripted television series. Debuting in 2013, Debbie Macomber’s Cedar Cove was a ratings favorite for three seasons.

She serves on the Guideposts National Advisory Cabinet, is a YFC National Ambassador, and is World Vision’s international spokesperson for their Knit for Kids charity initiative. A devoted grandmother, Debbie and Wayne live in Port Orchard, Washington, the town which inspired the Cedar Cove series.

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5 stars
314 (45%)
4 stars
175 (25%)
3 stars
144 (21%)
2 stars
36 (5%)
1 star
14 (2%)
Displaying 1 - 28 of 28 reviews
Profile Image for Nicole.
956 reviews
June 20, 2021
The Playboy and the Widow is one of Debbie Macomber earlier books. I have read some of her newer works but this is the first of her early stuff I have read.

Like the other books I have read by Mrs. Macomber lots of humor exists in the story. The writing is simple and the pace of the story flows well. It is a bit predictable but that is one thing nice about the story. Sometimes I just want a fun simple read and Mrs. Macomber always delivers that.

I liked the kids and the growth they showed as they came to terms with their mother dating once again. In some way the two girls were more mature about Diana dating then Diana was. The part with Cliff was a bit unbelievable, suddenly a playboy sees a single mother and forgets all about the beautiful girls throwing themselves at him does not seem real. Other then that is it just a fun light read.
Profile Image for What to read next ........
360 reviews3 followers
May 31, 2023
The Playboy and the Widow , its a sweet read, a little repeative, but a nice easy read. This a very early Debbie Macomber book.

It is a story of Diana , a struggling widow raising 2 preteen daughters.
Diana just isn't ready to give up the ghost of her husband, the thought of meeting and dating other men is just not appetising to her .
By accident Diana meets Cliff. When Cliff comes over to help with a plumbing matter. Cliff was at the neighbour's house when Diana called for help.

Cliff is a playboy, good-looking, has money, an attorney and dates models, and really has no plans to change his lifestyle.

But there is something simple, sweet , and desirable about Diana and her daughters.
Cliff can't get enough, he realises that he is not happy with his life, the way things are .
Diana on the other hand has to decide whether Cliff is worth taking a risk of being hurt and how he is going to fit with her girls.
Profile Image for Lis Sigona.
595 reviews
June 10, 2022
How sweet it is to going back to reading Debbie Macomber’s novels. I took a break finding I was starting to be able to second guess her storylines. But after reading a few other novels for a break, it is enjoyable picking up her writings again. It was nice to see the struggles, the different angles and the overwhelming feelings the characters are dealing with through the storyline. It’s enlightening and refreshing, but it helps in time of despair and sadness to enjoy such light heartedness. Especially in these difficult days.
2,115 reviews8 followers
January 12, 2018
Diana Collins is a widow with 2 daughters. Cliff Howard is a confirmed bachelor. An accidental meeting propels them into something neither is prepared for. The girls love Cliff and so does Diana, but Cliff isn't ready yet for family ties. They have several misunderstandings but eventually all works out.
Profile Image for Emma Inman .
99 reviews
July 9, 2024
This was a short book about two people who weren’t planning on falling in love and their friends didn’t think it would be a good match and it turned out to be a great match. This was a short book and I took it on vacation with me, but it was not my favorite and did not keep pulling me back like many other Debbie books.
This entire review has been hidden because of spoilers.
Profile Image for Carol Ward.
Author 13 books20 followers
May 1, 2024
I enjoyed reading about the trials and tribulations of Cliff and Diana. And I found it rather amusing that best friend Shirley went from warning her friend away from Cliff to claiming responsibility for them connecting in the first place.
Profile Image for erika (riksreads).
319 reviews2 followers
November 30, 2022
The love interest that I was supposed to swoon over was repulsive.. he had a Lamborghini, that's about it.
10 reviews
June 12, 2024
asdabsdh ang standard ni Cliff pero hindi ko na-realize na redflag siya kasi mukha green siya in disguise. AT LEAST NAGBAGO. YUN NA YON MWHEHEHEHE ASJDBASHDJASDJSAKND
4 reviews
November 4, 2024
I love Debbie Macomber’s books and this one did not disappoint. A few twists thrown in but overall a good easy read.
Profile Image for Carol Wilson.
11 reviews1 follower
September 28, 2025
The Playboy and the Widow

A great book! It was funny, romantic and many honest feelings to life. I was hooked right at the beginning and enjoyed so much!
11 reviews
September 28, 2025
I just love her writing!

Always a wonderful book to read what Debra has written. A beautiful story, about a widow and her daughters, A must read.
768 reviews24 followers
May 31, 2009
Sometimes I forget how old I am. This romance was written by Debbie Macomber in 1988, making her heroine right about my age. She is the widowed mother of two girls; he is her age, about 30, and never married. She meets him when she calls the neighbors to ask Mr. to help her with a plumbing problem. He is visiting and picks up the phone (no caller ID in those days). Mr. isn't home, but he comes over, fixes the pipe and claims dinner with her as a payment. The attaction is mutual, and strong, yet he isn't looking for serious and with two kids to think about, she is. He makes a comment about it being the eighties and folks go to bed whenever they want...It is a romance and maybe it is the author, maybe it is the times, but they stay out of bed until they get married.

I like Macomber's books. They are fluffy but fun. I think her writing style has matured since this book, but it was still a fun read.
Profile Image for Carolyn Sisko Porcelli .
21 reviews2 followers
January 11, 2015
This is a great, quick read. A story about opposites attracting. This reveiw has a spoiler. Thirty year old widow, Diana, has two young daughters, 11 & 8. Stan has been gone three years. Diana has a tough life raising her girls. One day, as her leaky sink took over, she called a neighbor to help out. Cliff, a friend of her neighbor, comes over to fix her sink. Shirley, Diana's neighbor, warns Diana of playboy Cliff and she does not want to see Diana get hurt by Cliff. Diana seems to have a connection when Cliff is over that she has not experienced with anyone else since her husband's death. Cliff is motivated, Has feelings for Diana and her girls, Joan and Katie.
This is a good novel. Diana attempts to see that she & Cliff are too different and it could not work out. Cliff is persistent. I take weeks to read a book, but this book got my attention & I finished it in two days. You'll love this love story.
Profile Image for Heidi.
454 reviews11 followers
January 15, 2015
This is a charming tale of a young widow who lost her husband in a plane crash, and a lawyer with a playboy reputation. Both Diana and Cliff are immediately attracted to each other, but endure the ups and downs of a budding relationship.
The book was originally published in 1988, long before internet and cell phones. The version I read must have been an updated version of the original, but still worth reading.
Profile Image for Jordin.
173 reviews22 followers
January 10, 2010
This book really wasn't worth my time but I read it because it's been on my bookshelf for awhile. It felt like Diana Collins was a really self centered person... or maybe she just had her children on her mind... I'm not really sure but I can say that to me she overreacted a lot and it was hard to get through. I kept wanting to quit. The very ending was perfect though. I do applaud that.
Profile Image for Joy Carter.
407 reviews3 followers
May 26, 2015
I don't really have much to say that I haven't already said. I just always enjoy these simple to read, easy to follow plots and stories that Debbie writes. I enjoy reading them day in and day out and the story lines are always different. Debbie makes everyone believe that love is possible for all!
Profile Image for elstaffe.
1,274 reviews4 followers
December 22, 2014
2 stars for actual enjoyment + 1 star for ridiculous eighties tropes/language/references. I am looking forward to pawning this off onto a friend who will appreciate it. In my own words in the annotation at the end: so wow, very virile, such 1988.
5 reviews1 follower
November 28, 2015
Pretty good book overall, however I just felt like there was too much emotional flip-flop from the characters, especially the main character. it seemed like she just couldn't make up her mind as to what she wanted.
35 reviews
Read
September 11, 2009
I related to parts of this book. Good story, romance.
Profile Image for Paola.
15 reviews
August 6, 2015
At first i thought it was the sweetest thing i have read.Well written, you really get into it. but the story is too short and not real at all.
I had greater expectations.
21 reviews1 follower
September 7, 2016
Dana & Cliff are opposites but she goes out with him anyway. Her daughters love him and Cliff is rethinking marriage
7 reviews
March 28, 2017
only problem I had was they tried to make it modern. talked about youtube and Katy Perry. but it was actually written in the 1980's.
Displaying 1 - 28 of 28 reviews

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