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The Lady Always Wins

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It's all fun and games.

Nobody has ever come close to taking the place that Virginia Barrett had in Simon Davenant’s heart. As a child, Ginny was his best friend and comrade-in-arms. As a young lady, she became his sweetheart. But when his parents discovered their growing affection, they threatened to cut Simon off without a penny if he married her. And when Simon planned an elopement, Ginny refused: She wasn’t going to marry a poor man. Ever.

Until someone loses a fortune.

In the seven years since they last saw one another, Ginny has been married and then widowed. Simon has built an empire as a railway financier. When they meet again, there’s still that same delicious, playful attraction between them. But only Simon knows how tenuous his second chance really is. Everyone believes that Simon is wealthy. In truth, his company has been taken over by a hostile competitor and he is ruined. He knows from bitter experience that Ginny won’t marry a poor man. And so he has three days until the news becomes public—three days to seduce, woo, and marry the woman he cannot forget, or risk losing her…and this time, for good.

71 pages, Kindle Edition

First published February 22, 2012

62 people are currently reading
833 people want to read

About the author

Courtney Milan

68 books5,484 followers
Courtney Milan writes books about carriages, corsets, and smartwatches. Her books have received starred reviews in Publishers Weekly, Library Journal, and Booklist. She is a New York Times and a USA Today Bestseller.

Courtney pens a weekly newsletter about tea, books, and basically anything and everything else. Sign up for it here: https://bit.ly/CourtneysTea

Before she started writing romance, Courtney got a graduate degree in theoretical physical chemistry from UC Berkeley. After that, just to shake things up, she went to law school at the University of Michigan and graduated summa cum laude. Then she did a handful of clerkships. She was a law professor for a while. She now writes full-time.

Courtney is represented by Kristin Nelson of the Nelson Literary Agency.

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5 stars
256 (16%)
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546 (34%)
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602 (38%)
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150 (9%)
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Displaying 1 - 30 of 175 reviews
Profile Image for UniquelyMoi ~ BlithelyBookish.
1,097 reviews1,760 followers
December 12, 2013

Courtney Milan is one of those authors who never fails to deliver. Her tales are romantic, witty, sexy, and always have a lesson to be learned with true love as the ultimate reward.
From the cover:

IT’S ALL FUN AND GAMES…

Nobody has ever come close to taking the place that Virginia Barrett had in Simon Davenant’s heart. As a child, Ginny was his best friend and comrade-in-arms. As a young lady, she became his sweetheart. But when his parents discovered their growing affection, they threatened to cut Simon off without a penny if he married her. And when Simon planned an elopement, Ginny refused: She wasn’t going to marry a poor man. Ever.

…UNTIL SOMEONE LOSES A FORTUNE.

In the seven years since they last saw one another, Ginny has been married and then widowed. Simon has built an empire as a railway financier. When they meet again, there’s still that same delicious, playful attraction between them. But only Simon knows how tenuous his second chance really is. Everyone believes that Simon is wealthy. In truth, his company has been taken over by a hostile competitor and he is ruined. He knows from bitter experience that Ginny won’t marry a poor man. And so he has three days until the news becomes public—three days to seduce, woo, and marry the woman he cannot forget, or risk losing her…and this time, for good.
Ginny and Simon are a delightful pair and their teasing banter and efforts at one-upmanship made this a fun, witty story. Then toss in their undeniable passion for one another and a lovely happily ever after, and you have Courtney Milan’s winning recipe for a truly enjoyable read!

My thanks to Ms. Milan for providing me with a copy of this book in exchange for an honest review. As always, it was a pleasure!
Profile Image for Zero.
809 reviews24 followers
March 24, 2023
Ginny and Simon were childhood sweethearts. Simon's family didn't think that Ginny was good enough for him, so they threatened to cut him off if they married. Simon asked Ginny to elope with him, but she wanted stability and wanted to wait. Somehow they didn't communicate well, and she ended up marrying someone else.

Even though some of the story doesn't make perfect sense, I ended up liking this novella. I think it's a decent second-chance romance, if you can suspend disbelief about the reasons for their initial separation.
Profile Image for Ashley.
3,513 reviews2,382 followers
December 4, 2015
This was one of CM's more fluffy outings, but it was very well done for what it was. Very silly, very bantery (the MC's have unique sense of humor, and the dude is a bit of an ass). It still has ad a bit of a backbone (the 1800s railroad boom, specifically, and some musings on poverty), and as always with CM, rings true emotionally with even her silliest characters being emotionally complex.
Profile Image for -ya.
518 reviews63 followers
August 24, 2016
3.5-stars
The setup for this second chance at love is cleverly done. I just wish it were a full-length novel.
Profile Image for Wollstonecrafthomegirl.
473 reviews255 followers
December 31, 2016
I made my way through a lot of Milan's novellas this year (possibly all of them?) because I bought a collection of them at the start of the year and I've rationed them out across 2016.

So that's my context for this review. Milan is a hell of an author and, within that, a fantastic novella author (I think probably the best novella author? If anyone wants to make a submission to the contrary, please do shout out some recs in the comments) and so I grade on that curve.

This was probably the weakest one I have read. The writing was still great. The backstory between our H/h was deftly created in few words. The characterisation of Simon, at least was very well done. The sex was amazing.

But, the story let it down. I suspect too much to do in a paucity of words (and I think this was even shorter than the others I've read). It just didn't hang together for me at the end. I think what Ginny had done had to be flagged in the sections from her POV otherwise it doesn't make sufficient sense. And Ginny's heartbreak at Simon's plan really didn't make sense because she must have known his reality and/or she simply could have said: 'guess what!' It just made for wholly unnecessary drama and undermined Milan's attempts to create a character for Ginny.

However, writing still great and I inhaled the whole thing in the course of one bath and for that reason it's 3.5 stars rounded up to 4.
Profile Image for Katrina Passick Lumsden.
1,782 reviews12.9k followers
June 26, 2014
You can't go wrong with Milan. You might think the two protagonists are hopelessly infantile, but that's sort of the point; they were hopelessly infantile at one point. To see this much character evolution in a novella is nothing short of miraculous.
Profile Image for Lisa.
328 reviews83 followers
March 27, 2013
Simon Davenant was crushed when his childhood sweetheart married another, just to have money since his father was going to cut him off if he dared marry Ginny. Now, seven years later, Ginny is a widow and he has three days to make her fall back in love with him before his new found wealth disappears. But Ginny had her reasons for marrying for money and when they come up, it about undoes Simon's plans. I enjoyed the banter between this couple, how they were always trying to one up each other and the ultimate one up comes at the end and was a nice little twist, which you don't always get in a novella. Another enjoyable story for one of my favorite authors. Seriously, Courtney Milan could write the phone book in a way that would be enjoyable :) 4 stars
Profile Image for Shannon.
3,111 reviews2,565 followers
January 1, 2015
This is free on Amazon right now ... which was definitely a good thing.

So far my least favorite of what I've read by her. I think I just wanted more: as I do with most novellas. There's never enough characterization or development of the plot for me to care about anything.

For some reason I don't feel like this was a complete waste of time though.

YMMV
Profile Image for Gwen (The Gwendolyn Reading Method).
1,730 reviews473 followers
February 9, 2016
heh. ridiculous little story, but also a cute little story. Not where I recommend starting with Courtney Milan but if you're well into her roster, it's a fun, if presposterous, side note.
Profile Image for Kaethe.
6,567 reviews533 followers
October 29, 2022
There are quite a few authors whose books I enjoy: I only read for pleasure, so. There are very few writers whose works are all favorites: not only do I buy everything Milan publishes, I sometimes buy multiple copies of her works, since she often contributes to fundraising bundles and such. Her causes are as well-considered as her writing. When I know what's coming in a reread it's delightful because of the anticipation.. I'm like rhe grandfather reading The Princess Bride.
Nor is it possible to complain that she isn't more prolific, because the books are all so clearly worth the time she spends on them.

I confidently recommend Milan's work to anyone who doesn't think they could appreciate 21st century romance.

Personal copy, obviously
Profile Image for Lynn_G.
1,114 reviews27 followers
October 21, 2022
short and sweet second chance love story

Ginny & Simon’s story was very short but Courtney Milan managed to pack so much into it: humor, strong emotion, star-crossed first loves brought back together after seven years apart, and all the while the reader is given vivid details which brings the characters and setting to life without any tediousness.
Profile Image for Sometime.
1,718 reviews172 followers
July 18, 2018
Why do I keep reading second chance romance? Every time, I hope that this will be the book I love and every time I am disappointed. Really, this is a "me, not you" situation with my intense dislike of second chance.

As always, Milan's writing is perfect. She is a capable writer. But the plot was just annoying to me.



The ending was very sweet and had a nice surprise twist. If you like second chance and aren't turned off by the typical things that come with the trope, you probably really like this book.
Profile Image for Christina (A Reader of Fictions).
4,574 reviews1,756 followers
September 5, 2018
Milan's novellas don't work well for me as a general rule, and this one's no exception.

The Premise: Childhood sweethearts went their separate ways because his parents were going to disinherit him if he married her, and she refused to marry him without money. Now that she's a widow, he returns, claiming to want to seduce her and break her heart in vengeance, but actually planning to marry her despite the fact that he fully expects to lose his fortune forthwith.

Milan tries to set up the fact that these two commonly would play weird contests together, so that it's totally okay by both of him when he shows up and tells her he's going to seduce her and break her heart in the next three days. Let's just say that didn't convince me. I also find it really strange that, if that's the game, she would promptly have sex with him but whatever.

The whole point is that it does a sort of Down with Love thing and keeps shifting what the actual game is. But unfortunately the basis of this romance is a man who was willing to lie through the teeth to the woman he claims to love, and he does it fully knowing it's garbage. Of course, since it's a romance, everything conveniently resolves, but I was frankly disgusted by this ship.

The only plus I have for this is the fact that the heroine isn't shamed for not wanting to risk everything for love. Her pragmatism is upheld, though this does get really dark for a novella.
Profile Image for rameau.
553 reviews199 followers
February 24, 2013
Novellas about two people reuniting after years of separation and falling madly in love in a matter days apparently work. The fact that there is history and that the characters are only relearning to know each other helps to brush aside the insta love elements, and lets the focus remain on fixing what went wrong in the first place.

Still, a novella is never long enough and the time jump skips over the teasing and more interesting parts of the courting. Hurried, sweet love story, just like any other Milan novella.
Profile Image for Gaufre.
467 reviews26 followers
August 2, 2020
A lesser simpler Courtney Milan, which is still an ok read because, well, Courtney Milan.
Profile Image for Michelle K.
657 reviews65 followers
March 29, 2013
Another fabulous heroine by Courtney Milan
http://anotherlookbookreviews.blogspo...


Courtney Milan writes the best historical heroines. They're always so smart and admirable. I know so many readers love a hero but for me, the heroine makes or breaks a story. Even though The Lady Always Wins is a novella, the heroine Ginny is just as commendable and memorable as though I had read about her story in a full length novel. I just adored her.

Ginny and Simon were childhood friends, adolescence sweethearts and then parted ways desolately before they had a real chance to have their love bloom into a mature romance. Courtney Milan provides excellent background history and writes entertaining flashbacks to their first meetings.

Due to the circumstances placed before the juvenile couple, Ginny married another man and Simon sought out to build his fortune and make a name for himself. I felt their heavy disappointment seep through the pages even though their story was recollected by the couple from years past. The span of time apart did not soften the hurt. Clearly they never got over each other and they were in each other's thoughts daily.

With Ginny's recent status as a widow, Simon wasted as little time as possible to pursue Ginny. Although The Lady Always Wins is a novella, I felt it was the perfect length for Ginny and Simon's story. From the moment they see each other after being apart for years, they immediately slide into the easy and fun banter that they both enjoyed from the past. It was if no time had passed. I LOVED their smooth transition into the little game of Simon seducing Ginny by a deadline. It fit this couple perfectly. In fact, when I finished reading The Lady Always Wins, I went right back and re-read it.

The Lady Always Wins is a gem and only .97 on Amazon. A delightful read that is sure to put a smile on your face.

Teasers: beetle meeting, check-mate, tulips, fake meteor shower
Profile Image for Blackjack.
483 reviews200 followers
January 2, 2017
I thought this novella could easily have been a longer story and its short length was a bit of a detraction. Having said that though, I really enjoyed the friction and dynamic between the main couple. Ginny and Simon were childhood frenemies. The adored each other from the ages of 10 onward, though competition was at the forefront of how they always interacted. Incidentally, the childhood beetle story is wonderful and one worth remembering for how to respond to bullies. I love that Simon continues to taunt Ginny with beetles right to the very end. I'm a fan of frenemy romances and despite its short length, this one is right up there. It takes a bit of time to get the rhythm of Ginny and Simon's back-and-forth verbal exchanges, but they are sharp and meaningful.

Simon thinks he understands Ginny better than anyone as a teenager, but he misses a key part in that Ginny fears poverty on a level of desperation that Simon cannot truly fathom, having never been poor himself. When his parents threaten to cut off his funds if he marries the "unsuitable" Ginny Barrett, Simon wants to thumb his nose at his family and marry the love of his life anyway. Ginny does not see things in the same light and is willing to walk away from Simon, despite believing that she's unlikely to love another man ever. The story actually begins some years later with Ginny living in the same town as a young widow and Simon returning as a wealthy self-made railroad entrepreneur. Knowing that Ginny is now single, he has decided to strike while the iron is hot and win her back. The second-chance courtship is intricate though because this is a couple that struggles to be open and transparent. Much of their interactions are coded and each tries to hide the depth of their feelings for the other. I think in another writer's hand, the games could feel tiresome but Milan does a nice job of balancing posturing with humor. There are a number of surprises that I did not see coming, but as is typical with Milan's fiction, the hero is in the end utterly devoted and supportive and swoon-worthy!
Profile Image for Francesca the Fierce (Under the Covers Book Blog).
1,886 reviews504 followers
June 4, 2013


You know what I need to realize? That when I read a Courtney Milan book I should expect the unexpected! This little novella took me on a ride and made me feel all sorts of different things. I liked and disliked the characters at times and never saw the twists coming! I loved every second of it!

Simon Davenant has been in love with Ginny since they were kids. They had a teenage romance and, because of her lesser position in society and her lack of money, his father didn’t think it would be a good match for them to marry and did everything he could so he succeeded in separating them.

When Simon thought to come back for Ginny it was only to find out she had married another man and wouldn’t take him if he didn’t have his title and his money. Now that she’s widowed, he’s come back for her to fulfill of a promise he made her on their last parting. That he would come back for her, make her fall in love with him, and then stomp on her heart.

Aren’t you already fascinated when the story is starting out like this? But that’s how Milan always keeps you on your toes. Things are not what they seem in so many levels and the twists in such a short 70 page novella are great.

THE LADY ALWAYS WINS is witty, funny, sexy and emotional. I connected with her characters from the very first page. Quick but very satisfying read! I would highly recommend it.

*Review copy provided by author
Profile Image for Jen Davis.
Author 7 books727 followers
April 14, 2013
Whenever I am looking for a historical romance novella, Courtney Milan always hits the spot. This second-chance love story was no exception.

It's been seven years since Ginny broke Simon's heart. She refused to marry him, instead marrying another man. But now her husband is dead and Simon sees his chance to reclaim the only woman he has ever loved. When Ginny turned him down years ago, it was because his parents threatened to disown him. He had no trade and she didn't want to live in poverty. Now, he is independently wealthy, at least for now. But a looming business calamity threatens to take all that away, so he figures he must seduce Ginny quickly and secure her hand before he is financially destroyed and she has a reason to turn him down again.

It's amazing that in less than 70 pages, Milan can make me feel so invested in her characters. At first glance, you might think Ginny is the lesser member of the relationship... after all, she chose her husband for money. But we see she is so much more than that; and Simon bears his own responsibility for their separation. Ginny is practical and pragmatic, but she also loves Simon utterly and completely --even after seven years apart. Just as he loves her. There are some books three times as long that don't make me feel connected to the characters and their feelings even half as much.

I really enjoyed the romance --and the surprise twist at the end. Good stuff.

Rating: B+

*ARC provided by author for review
Profile Image for Jennifer.
459 reviews16 followers
June 10, 2013
Although this was cute and sweet, it was not quite on the level of The Governess Affair, which is one of my shining examples of all-time favorite novellas (also written by Milan). She is quite good at building tension quickly and finding just the right fit between her leads, but ultimately I felt the story, perhaps the characters, lacked quite the level of connection I wanted them to have. Perhaps falling back on the idea that they've known each other for years and have all this history together, while it definitely works sometimes, worked instead against this book for me because I wanted to read about more of those important moments between them - not just read about them remembering the moments... I'm sure it's just a matter of personal preference. As always, it was superbly written and Milan continues to be one of my very favorite authors of this genre.
Profile Image for Susan.
153 reviews15 followers
May 11, 2014
Simon Davenant and Ginny Croswell
1845, England


Courtney Milan really packed a lot into the 60 pages of this novella. For once, I felt satisfied after reading a short romance. You really felt the love and, more importantly, the friendship between the two characters and I loved the banter and gamesmanship between this couple. Perhaps because it was a novella, the story did not dwell tediously on any feelings of betrayal or revenge but quickly segued into a sweet reunion between Simon and Ginny.

I also love a story where the hero is smitten, which Simon definitely was.

Profile Image for Karen.
454 reviews71 followers
March 9, 2013
This one ended up being really sweet. At the beginning, the guy seemed a little too arrogant and the woman a little too one-dimensional, but I should've known Courtney Milan wouldn't leave me hanging like that. Because by the end (after the story took a rather delightful turn I wasn't expecting), the characters had sorted themselves out, and I couldn't help sighing with happiness over the way it all worked out. Milan always shines in her novellas, and this one is no exception.
Profile Image for Amanda.
Author 11 books129 followers
August 13, 2016
The Lady Always Wins is for people who...

...enjoy historical romance
...like the rekindling of early love
...love a good Courtney Milan story (who doesn't, really?)
...don't mind a little game playing
...even when that game playing leads to a little heartbreak too
...but ultimately love prevails
Profile Image for Dabney.
484 reviews68 followers
April 7, 2013
Ms. Milan is my favorite novella writer. This one is great fun.
Displaying 1 - 30 of 175 reviews

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