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Five Dates with the Billionaire

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A USA TODAY BESTSELLER'I'm insisting you date her. Five dates together, then I'll have this surgery.'Billionaire CEO Connor Stewart is being blackmailed. By his own grandmother, no less, who is refusing to have life-saving surgery unless Connor dates Mia Simms, his dull and dowdy marketing employee.For Violet's sake, Connor agrees to the crazy scheme. There's no risk of breaking his 'short-term only' rule with Mia Simms; she's not the kind of woman Connor is interested in ... and he's sure she's hiding something. He just doesn't expect it to be delicious curves and a firecracker personality.Mia Simms is hiding something, and it's much more dangerous than her looks. All she wants to do is live life in the safety of the shadows and avoid discovery. But perhaps a short-term fling is exactly what she needs to remind her to live.But what if Violet is right to push them together? Can Mia trust Connor enough to let him see the real person behind the facade she's built? Or is Violet's little scheme about to put both their lives in danger?

208 pages, Kindle Edition

Published November 1, 2020

216 people are currently reading
76 people want to read

About the author

Alyssa J. Montgomery

20 books85 followers
USA TODAY Bestselling author, Alyssa enjoys writing pacy, passionate contemporary romance novels and her favourites involve some plot twists. She also writes medieval romance under the pen name Alyssa James.
Alyssa still has a busy private practice where she works as a Speech-Language Pathologist - mainly with children with developmental disorders, literacy difficulties and autism. She has also been a professional pianist and worked for Qantas Airways as an International Flight Attendant.
Alyssa lives with her husband and three children in New South Wales, Australia on a five acre property. They have a menagerie of animals and also enjoy occasional visits from deer, wallabies, echidna and the daily morning singing of numerous varieties of native birds.
Spare time is fairly limited with three children, however dinner parties with friends, gardening and playing tennis or saddling up the horses and going for a trail ride, are favourite activities.

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5 stars
192 (47%)
4 stars
122 (29%)
3 stars
64 (15%)
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20 (4%)
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9 (2%)
Displaying 1 - 30 of 46 reviews
Profile Image for Wendy'sThoughts.
2,670 reviews3,282 followers
November 4, 2020
3.5 Coming Out Of Hiding Stars
* * * 1/2 Spoiler Free-A Quick Review
Alyssa J. Montgomery takes the reader's love of anything Billionaire, a secret reason for a woman to hide who she is, and puts a pushy grandmother forcing her grandson into dating her. This has all the usual stuff but also has a little more to add to the mix.

The grandmother needs surgery but has not wanted to do it.
The grandson is concerned and needs her to do buckle up and do it. He loves her, has felt close, and needs her in his life. Making it very clear, no surgery unless he dates this woman. The deal is made, he will do the dates, only five.

What makes this more than usual is the hidden suspense and reasons as to why our young woman has been trying to live in the shadows. We are there as she emerges in his eyes to more of who she really is in body and soul and how all of these revealing factors play out.

A gifted copy was provided by author/publisher via NetGalley for an honest review.

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Profile Image for Lee at ReadWriteWish.
834 reviews92 followers
March 12, 2021
I was pretty excited with this book at first. It showed great promise for the first couple of chapters. But…

Connor’s grandmother, Violet, is great friends with Mia and, after she has a heart turn, refuses to have corrective surgery until Connor and Mia go on five dates together. Violet is certain Connor and Mia are a perfect match and they’ll realise as soon as they start dating.

Sounded okay. But… It all went downhill rather quickly.

Mia is, of course, a 26 year old virgin. *eye roll* And even if I could get past that point we get cliche/trope number 2, which is that they agree on a brief affair so that she can lose her virginity to Connor, an expert at loving and leaving them. *eye roll*

Then there is cliche number 3. Mia works for Connor and, up until this point, he hadn’t looked at her twice because of her dowdy appearance. Suddenly, after a makeover from Violet, apparently Connor ‘sees’ the real Mia. Yeah, really? There's too much botox and false eyelashes in the world now, so do we really have to perpetuate the idea that the only way a woman can still get noticed by a man in 2021 is from her appearance (and I mean noticed in a ‘you're great at your job’ way as well as in a 'let's date' way). Oh, Montgomery tries to explain away some of this plot point but it still comes down to the idea that a rich intelligent billionaire could only find worth in a hot woman, regardless of her intelligence or competence in her chosen career or sparkling personality. Blah.

There is a mystery plot thrown in too. Overall though, it's completely unbelievable. The most interesting aspect of it was Violet and her old friend's spy life but this wasn’t explored. Instead, we got just more about how Mia wearing dowdy clothes and unflattering glasses should never be an option for her again… (Do you sense how mad this storyline made me at all?)

There’s also the ‘other woman/ex wife is such a conniving bitch’ cliche, the ‘must kiss to avoid the baddie’ cliche, and the ‘you must be trying to get my grandmother’s money’ cliche. They are all tolerable but I don’t really understand why Montgomery didn’t just go with the original premise. If we had the book without the virgin and ugly duckling idiocy at least, it might have worked. Such a shame.

2 out of 5
Profile Image for 🦉Maggie Whitworth.
3,254 reviews112 followers
October 30, 2020
❤️❤️❤️❤️
💋💋

Good story and has characters that keep your attention beautifully.
A really good plot that is tense and exciting, of Mafia and witness protection.
It’s a good length and is so romantic it gives you some real ‘sigh’ moments.

My only problem was I found a couple of instances where it felt a little rushed , or disjointed, and wasn’t quite as smooth flowing.

On the whole it’s a good read and one I would happily recommend.
I’ve enjoyed others I’ve read from this author, and would read more.

I received an Arc copy of this book and chose to post this review
Profile Image for CB.
402 reviews13 followers
February 6, 2025
REVIEW
Score: 3/5
POV: Dual
Heat Level: 1/5
Tropes: Boss/Employee; Suspense; Virgin FMC; Meddling grandmother; insta-love

Likes:

Dislikes:
* I didn’t like the insta-love part. It definitely could’ve been written without that. It would’ve changed probably how some things would’ve gone down but the insta love just did not work for me


This was a quick sweet story. I personally don’t like “sweet” lol so I was pretty bored but I could see others liking this type of story and the pacing. The pacing was quick which was good but it was also insta-love. I didn’t like that. It was kind of fun having the meddling grandmother like what we see in HR sometimes.

3/5
Profile Image for Helen.
2,836 reviews39 followers
January 8, 2021
I loved this one, a beautiful romance with danger and suspense added to the mix makes this one a page turner, when billionaire Connor Stewart is blackmailed into taking a staff member Mia Simms on five dates by his grandmother of all people, he is not happy and for Mia to be miss mouse quiet and dowdy nothing like the woman he normally dates, but for his Grandmother he will do it.

Connor loves his grandmother who has been there for him always but she always gets her way and the surgery she needs will be done after the dates, at least he will not want to break his short term rule with the likes of Mia, but he is astounded when Mia stands up to him like no other woman has before and he is sure she is hiding something and thinks the worst of her.

Mia has led a very quiet life for the last ten years and there is a reason for that, she likes to stay in the shadows and be safe, but when her friend Violet, Connor’s grandmother who has been a dear friend for all of those years decides it is time for Mia to live and that means spending time with Connor, Mia is in panic mode she is scared of what will happen.

Connor and Mia get closer on their dates, closer than either of them thought they would but Connor is still very suspicious of Mia and when in Venice a gentleman causes Mia to retreat into herself Connor starts to investigate and he opens up a world of danger, will their love be strong enough to get them through and will Mia be safe ever again?

This is a fast paced story filled with romance and danger, I loved Mia and the strength she shows with everything she has been through and Connor the ever caring hero who falls head over heels for Mia when it was the last thing he thought he wanted. There is lots of emotion running throughout this one. This is a fabulous story that I highly recommend.

Thank you Escape and Netgalley for my digital copy to read and review.
Profile Image for Lauren.
2,509 reviews159 followers
October 6, 2020
Five Dates with the Billionaire
3 Stars

***An ARC of the book was provided by the publisher and NetGalley in exchange for an honest review***

Billionaire CEO Connor Stewart is manipulated by his grandmother into dating Mia Sims, the woman he calls the "Mouse in marketing" due to her dowdy looks and bland personality. However, beneath her boring facade lies a gorgeous and intelligent woman hiding a devastating secret. Will Connor be able to see beneath the surface appearances? Will Mia's secret doom the potential for a future together?

The book has tremendous potential and contains many of my favorite tropes, i.e, office romance and witness protection. The suspense plot is surprising and engaging, but the romance is a bit lackluster.

The story begins like any other category romance with a mix of one cliché after another - sexy billionaire hero betrayed by his ex and dead set against marriage; ugly duckling heroine who wows said hero after a makeover; suspicion and animosity that turns into sexual attraction and love. While these themes are common in contemporary romance, they can be quite entertaining. However, in this particular case, they are too prosaic. Connor and Mia's chemistry is subdued and their eventual "I love you's" feel forced and contrived.

In contrast, the suspense plot is very well-written and interwoven with the romance. The threat from Mia's past is believable, and there are excellent twists and turns as well as some intense and satisfying moments. The only minor issue here is that the government agency responsible for the Witness Protection Program is the US Marshalls and not the FBI.

Overall, worth the read for the solid suspense rather than the predictable romance.
Profile Image for Stella Thompson.
487 reviews3 followers
November 13, 2020
Five Dates with the Billionaire

This book is a romantic suspense and a billionaire/virgin romance. It was a quick read. Connor and Mia were set up by Connor’s grandmother to go on five dates. She needed surgery, and refused to have it until they’d gone on the dates. Connor and Mia did not have any affinity for each other, mainly due to their own assumptions and lack of communication. I’m not usually happy with virgin books. This one did not seem too focussed on the sex, but I did hope it had focussed more on the mystery aspect. This was a good book, but will not be one that stayed with me, nor will I pick it up to reread it.
Profile Image for Vicky.
457 reviews5 followers
October 2, 2020
When you see titles like these you are expecting sappy Harlequin Romances which I enjoy for a quick lighthearted read, but this book is truly not that way at all!,

This book has an exceptional in depth plot and twists with a insight into the characters which made this a superb read! I found the storyline to be plausible and believable and the pages seemed to flow and turn quickly because I truly was immersed into the book.

Connor who is a CEO of a company has a arrogance and is extremely attractive. He is a love Em and leave Em short timer attitude when it comes to women so it’s a revolving door!

Mia , a Marketing employee is a friend as well to his grandmother is a plain Jane and stays under the radar.

The grandmother devises a scheme where she uses her recent illness to get the two of them together!

Will fireworks go off on this situation and is this going to backfire because Mia is hiding a secret!

Connor & Mia are excellent characters that the author has weaved together and actually you can see the growth in the plot of the book! The author has a wonderful flow of writing style and I was intrigued throughout the book.

I would recommend this book to anyone!

I received an advanced copy from NetGalley and these are my willingly given thoughts and opinions.
93 reviews
September 26, 2020
I received this book in exchange for an honest review.

The book starts with Connor being blackmailed by his grandmother, who seems like she would be a hoot to be friends with. She is making him go on 5 dates with her young friend before she will get her heart surgery. After much resistance he agrees. Connor's character evolves from being a jerk at the beginning of the book (because he was forced into this situation), to being a decent guy.

Mia plays Mahjong with his grandmother on Saturday nights and doesn't like being forced into this situation by her elderly friend anymore than Connor does, but because of her love of Violet, she agrees. She is resistant, because dating a billionaire would put her in the spotlight. Mia's past comes back to haunt her during their dates. Due to her past, she hides behind baggy clothes and glasses so she is not recognized. Once Connor sees behind this shield, he is intrigued.

This book was a quick, fun read. It had a little action and romance and kept me hooked so I could see what happened in Mia's past. With the timeline of the book, I did feel like the characters fell in love a little too quickly and that there could have been a little more background between the two main characters.
Profile Image for TLynn.
1,467 reviews16 followers
September 26, 2020
Five Dates with the Billionaire is the first book I’d read by this author. The storyline was original, and the characters were realistic. Connor Stewart was emotionally blackmailed by Violet, his grandmother into going on five dates with Mia Simms, an employee at their company. Violet needed a cardiac procedure but refused to have it done until Connor completed the five dates. Mia’s past made it necessary for her to stay hidden in the background. She tried to explain to Violet that the dates put her at risk since Violet was one of the few people who knew her past. Connor and Mia were worried about Violet’s health and reluctantly gave in. The had one dinner date and then took a trip to Venice and Paris. While in Venice Mia was recognized and the danger in her past put her life at risk. Can Connor and Mia overcome the danger and have a future together? The book was fast-paced and kept my attention from the beginning. I really enjoyed getting to know the characters and it was so easy to connect with them. I look forward to reading more from this author.
*I received a complimentary copy of this book from the publisher and author through NetGalley. I am voluntarily leaving a review and all thoughts and opinions are my own. *
402 reviews
October 16, 2020
Mia Simms has been living her life as someone else. For once in her life, she wants to let go, be herself and enjoy life. This is when her dear friend and mother figure, Violet, comes up with a crazy scheme. Go out with her grandson for five dates, and then she’ll agree to life saving surgery that she needs. The main problem here is that Connor Stewart, is the billionaire CEO of the company she works for.

When Connor hears the scheme that his grandmother propositioned to him, he almost loses it. Violet needs surgery soon and she won’t have it till he goes out with his dowdy marketing assistant for five dates. For his grandmother he will do anything, including this crazy plan. When Connor sees Mia for their first date, his jaw hits the floor! Why has she been hiding all these curves all this time! Come to find out, she is totally different than he imagined, but he feels she’s hiding something. Their chemistry is off the charts. Color him shocked when Mia suggests they have a fling until the end of their five dates.

Sometimes flings turn into love. Can these two keep working together after their arrangement ends.
This is my first book by this author and I loved the story and the characters.
Profile Image for Shelagh.
1,743 reviews25 followers
November 27, 2020
Set in London and Venice, this sexy contemporary romance also incorporates a hint of suspense. Heroine Mia Sims is not who she seems and her reasons for hiding herself behind heavy glasses and frumpy clothes has hero Connor Stewart completely baffled.
Connor’s grandmother Violet, who is also close friends with Mia, is a lovely character who owns the page when she appears. I loved her no negotiations attitude. I also liked Mia, who refuses to back down when challenged by Connor. While her obvious fear of being exposed to the public eye impacts on her behaviour she is still a strong woman. The sex scenes between Mia and Connor were packed with tension.
For me this romance happened far too quickly. I couldn’t quite imagine these two falling in love in a matter of days. I also found the sub-plot involving the Mafia a little bit too neatly tied up. Given this is fiction I’m prepared to suspend belief and just go with the flow of what has been an enjoyable story to read.
345 reviews4 followers
September 25, 2020
Five Dates with the Billionaire is a lovely romance with a touch of mystery and suspense.
Connor Stewart is told by his grandmother she will not have life saving heart surgery unless he goes on five dates with Mia an employee in his company’s marketing division. Having met Mia at a previous meeting he found her drab and uninteresting so is resistant but knowing how stubborn his Grandmother is he agrees.
Suddenly Connor finds himself very taken by Mia after she has undergone a make over at his Grandmothers insistence and gives as good as she gets with Connor. But Mia is holding on to a big secret and if discovered could put all their lives in danger, so begins an exciting story.
A great entertaining read which I found most enjoyable.
My thanks to net galley and publisher for the opportunity to review this book honestly.
Profile Image for Adrienne Bird.
589 reviews13 followers
October 3, 2020
Less than 48 hours needed!

Five Dates with the Billionaire is amazing! I may have spent two nights reading way later than I should have, just so I could find out what happened! Connor Stewart is the billionaire every woman wants to have fall in love with them. He’s philanthropic, gorgeous and did I mention rich?! Mia Simms is just a dull, plain woman that tries to hide away in the shadows. Despite Mia working for Connor, his grandmother manipulates them into five dates together. The following story leaves you cheering for them but at the same time leaves you wondering....this books is amazing! You have mystery, romance and such a longing for everything to have a happily ever after that you end up reading all the way through! This was the first book I have ever read by Alyssa Montgomery and let me tell you....I will be happily reading many more of her books in the near future!
Profile Image for Lisa.
564 reviews21 followers
November 9, 2020
This is a Netgalley ARC review. All opinions are solely my own.

Five Dates with the Billionaire by Alyssa J. Montgomery is a quick romantic suspense read. This is a CEO/virgin romance.

Mia and Connor are set up by his grandmother to go on five dates. These two don't see eye to eye but mostly that's due to misconceptions. Grandma knows best.

Initially this book did not hold my attention. I can't say it's because of the story. Big real world changes happening. Once I was able to give the book my full attention I really enjoyed it. I wish there would have been more focus on the suspense and intrigue. I also liked that with this virgin romance it wasn't a bunch of crazy bed shenanigans. That never seems plausible to me.

Overall I enjoyed this book. I will read more from Alyssa J. Montgomery.
218 reviews
March 16, 2021
Mia finally is out of Witness Protection and Connor is waiting!

A beautiful and lovely story of Mia and Connor. His grandmother Violet needs an urgent heart operation but she refuses until Connor agrees to go on 5 dates with Mia. He is outraged but they agree, and go to Venice.
Mia is in witness protection and wants no media attention and they begin to fall for each other, unfortunately the mafia people she has been hiding from are also in Venice! Drama follows them to Paris and then London. Mia retained her mother’s chain which held a distinctive Georgian pendant. This gives her away and a mob hit is set up but the FBI and MI5 set up a sting which snares the hit man. more to the story and I do recommend the book for an afternoon of light reading.
Good story and developed characters which makes the book enjoyable.e
Profile Image for Cindy.
1,852 reviews13 followers
July 10, 2023
This was a freebie from Amazon. I thought I've read this author before, but apparently not.
Placed on my Harlequin shelf because it reads like one. I'm not really sure if it is or not.

No spoilers!

So, this wasn't too bad. Young woman on the run, hiding from a bad situation. Handsome, buff billionaire who's blackmailed by his grandma to have 5 dates with her. It starts off like a typical Harlequin billionaire story. It gets serious by the middle of the book.

I liked it, but it was a little too much. Drama is neatly wrapped up by the end & a HEA.
This author has a bad habit of one character saying something & the other character answering in the same paragraph. It's a chore then figuring out who's talking to whom.

I would still read another book by this author if there was a deal involved.
811 reviews8 followers
April 26, 2021
This didn't work for me. I think partially the author had too much going on. We have the woman who dresses so she's not attractive who catches the Prince/Billionaire/rock stars eye. We have the couple trying to deny the attraction between them and then having to fake date. We've got the businessman dating someone that works for him. We have the woman who is in danger from her secret past and needs to be saved so she can truly live. And probably a few more.

As a result, no one theme was really focused on and it kind of bounced all over the place without catching my emotional interest. I didn't care about either of the characters honestly. But I didn't dislike them and while I skimmed a lot, I did make it all the way to the end. So that's something I guess.
1,606 reviews15 followers
October 29, 2020
Such a good story. I loved Violet as a secondary character. Connor and Mia did not have a great beginning. He was angry at his grandmother's condition of her having some surgery and took it out on Mia. Once she had a makeover (again the grandmother insisted), Connor start looking at her differently. It wasn't just how she looked but how they interacted. Connor had lots of dates, but there was no substance. Just when he thought he found what he was looking for, the world fell apart for him. The story had some great romance, some drama, a very narrow escape and a very good ending. Very enjoyable read.
I got this book from NetGalley for an honest review
Profile Image for Pamela Devereux.
1,032 reviews2 followers
February 14, 2021
Connor Stewart has met his match with his grandmother Violet. She is bound and determined to set him up with Mia Simms and blackmail is in her bag of tricks. Connor is a cynic. He sees females as conniving to get at his wealth or be seen with him to enhance their careers. Mia craves the shadows. She dresses and acts likes she is invisible. From the moment Violet sets the terms of 5 dates, she has them planned out. She has her reasons. Mia's past has kept her from living her life and now that past has reared its ugly head. She is not alone. Connor would do anything to keep her safe and he does. I am so glad they get their HEA.
Profile Image for Thuy Taylor.
1,390 reviews18 followers
November 11, 2020
Connor's grandmother needs surgery but she's making a stipulation before her surgery that Connor needs to go on 5 dates with the boring, dowdy Mia. At first he is annoyed and angry but once he interacts with her with this chip on his shoulder, the real fiesty Mia comes out. Total opposite of who he thought she was. He is definitely intrigued. These two have hate/lust chemistry and it shows throughout the book. I enjoyed their story. I liked the grandmother alot, she was funny. There was some suspense in the book that kept the story exciting.
Profile Image for Rachel.
Author 9 books34 followers
November 2, 2021
A fantastic read! I loved Connor and Mia as they were forced to date by Connor's well-meaning grandmother. Neither of them were impressed by the arrangement, but they both begin to soften when they arrive in Venice, where their second and third date is supposed to occur. Sparks fly and Connor and Mia surrender to their chemistry...only for Connor to discover that Mia isn't all she seems. Mia's been running for ten years, part of a witness protection program which quickly turns this book from a hot romance to a suspense. Mia and Connor both fight to achieve their happily ever after
Profile Image for Cindy Beasley.
163 reviews
March 13, 2025
Mysterious emerging love affair

Violet's plan to bring Connor and Mia together was very calculating. She wanted the 2 people she loved to experience what she had with her husband. She knew Five Dates would be enough to start the fireworks between them. The mystery of Mia's background would not stop what was going to happen between them. This book I could not put down, it had me with the first few lines and I wanted to read it without stopping.
1,919 reviews6 followers
October 11, 2020
A big thank you to NetGalley and Escape Publishing for the ARC. I am voluntarily reviewing this book. This is a cute book. It has very fast love so maybe not very believable, but its fun and quirky. A determined grandmother and a handsome billionaire and Mia in witness protection! It's got a few laughs, suspense and romance. 4 stars
208 reviews
June 27, 2021
Title doesn’t give it away

This was more than just a rom-com, in a surprise way. I will say the characters attitudes were, at times, off putting. Plus Brit slang was confusing in a couple places. But, 5e story was very readable and great read while lounging by the pool. I would read it again.
Profile Image for Brandi.
1,490 reviews9 followers
February 9, 2022
Five dates to make his grandmother happy was something that would uncover the secrets he knew Mia possessed. He wasn’t actually thrilled with the woman who wasn’t his type but made his body become alive. Did his matchmaking grandmother know something? A positively delightful story and Alyssa always makes you fall in love with her characters.
Profile Image for Clare Miles.
Author 9 books10 followers
September 13, 2022
This is the first time I've read this author and I immensely enjoyed this highly emotive story. It had well developed characters with heart wrenching back stories making the stakes even higher as they worked their way to a hard fought HEA. I also loved the superb settings. I will definitely be reading this author again.
Profile Image for Kristen Dalrymple.
631 reviews5 followers
July 14, 2023
This book was so funny and cute. Mia was sassy and strong. Her backstory was crazy. I liked how connected she was to his grandmother and Stanley. I thinks funny how Connor reacted to her when she argued and called him names, then again to her makeover. Overall this was a cute book that had a plot twist!
1,475 reviews
October 2, 2020
The storyline took to long to build. Its a predictable romance with interlude thrown in. She’s hiding from her past. He’s suspicious if her. They’re being forced together...


********I received an ARC from NetGalley for my honest opinion. *************
1,396 reviews11 followers
October 25, 2020
I loved this book so much. Mia is so strong and doesn't let Connor walk all over her. He might be a billionaire but he can still be put into his place. When Mia needs someone to be strong for her, Connor steps up perfectly.
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