Michael Bailey


Michael Bailey is a rough and tumble sort of bloke with absolutely no sense of romance. In three days, he intends to propose marriage to the woman of his dreams but his lack of self confidence and questionable manners are a huge roadblock.

Mike has a heart of gold but his first attempt at proposing marriage was in front of the TV! And it didn’t go over very well.

Mike now has one more chance to pop the question only this time he’s got to get it right. That means a romantic dinner for two at a high end restaurant. But is he up to the task?

On the agenda for Mike’s transition…


First there’s Mike’s wardrobe: if he’s going to win Anne’s heart, he’s going to have to propose in something more elegant than ball caps and wrinkled t-shirts.

Mike’s also got to work at expanding his food repertoire which now consists mainly of junk food and everything deep fried.

Mike’s teeth are his biggest physical drawback, he’s so self-conscious about them that he rarely smiles.

Mike may need help on the outside, but on the inside, he’s got the makings of true gentleman. He’s a great boyfriend, he takes care of his granny, and he’s a great father to his son Dustin. But while he’s been taking care of everyone else in his life, there’s one person he’s forgotten – himself.


My job is to boost Mike’s self-image up to a point where he’s confident enough to pull off the romantic proposal of his life and we’ve only got 72 hours to make it all happen so he’s coming with me to the gentlemen’s academy where Asha and I will need to turn our working class dud into a well dressed man of manners for the big night.

Mike’s job here is to work on his fine dining skills, expressing his romantic feelings, and his appearance – particularly that smile…

One of the basics of true gentleman-hood is to take a lot of pride in one’s appearance, starting with clean, pressed shirts.


I’m an expert with a steam iron so it should be no trouble giving Mike a lesson in starching and pressing…or is that speaking too soon? Well, if nothing else, at least he’s an enthusiastic student.


Mike, despite his good intentions, needs a total makeover in the romance department. So I’ve called in my associate in matters of the heart Asha Daniere, to speak to Mike’s girlfriend Anne and give us the inside track on their relationship.

Anne’s verdict is the same as ours, Mike’s low self esteem is the root of most of their problems. Anne insists that she thinks Mike is great the way he is, she just has a hard time convincing him of the same. She mentions that his biggest insecurity is his smile.

Sounds like I’ve got a bigger problem to sink my teeth into. Time to call in my expert in matters of the mouth…

And so the first in a series of dental visits…to make Mike’s teeth gleam in time for his big proposal. While I read three year old magazines, Asha is still getting the goods on Mike from Anne…

Anne seems overall happy with her relationship with Mike except when it comes to the romance department. She writes him love letters a lot and reports that she has yet to receive one in return…

Oh Mike! So Asha’s putting him to the test. His tools: a pencil and some sheets of paper. The task: write Anne a love letter that will knock her off her feet.


Tomorrow we’ll find out how that goes over – but for now there’s still an awful lot of work to be done.

Looking good is one thing, but Mike must learn to behave like a gentleman in order to gain confidence in himself. Mike’s next challenge will take him well out of his culinary comfort zone. Today we’re encouraging Mike to try something different.

Mike’s resistance to change is definitely frustrating to Anne so his attempt at trying something new to impress her is really sweet, even if he’s a little hesitant to start.

When it comes to fine dining, first things first Mike…no ball caps at the dinner table. He is a trooper though. Caviar, oysters and brie and, to his surprise, he made it out in one piece.

Now that Mike’s palate is up to par it’s time to do something about his dreadful wardrobe! But before that, he has a little shopping to do with Asha.

A beautiful invitation to dinner is what they’re on the hunt for and Mike passing with flying colours when he finds a simple yet elegant that ties in one of Anne’s favourite things, angels.


Next stop, a rendez-vous between Mike and fashion expert Melissa to turn Mike’s look from rags to riches. Mike’s a handsome guy, he just lacks the confidence to pull off super style. I have no doubt that Melissa will be able to bring him out of his shell.

Well, the wardrobe challenge may be out of the way, but Mike’s got a long way to go before he gets his thoughts down on paper for Anne.

Mike’s frustration about writing the letter has affected all his lessons here at the gentleman’s academy – bringing him almost to a boiling point…

Before it gets to that point, it’s time to give Mike a little reward for all of his hard work so far. He needs a boost to his manly confidence, so I’ve brought him to meet a friend of mine: Joe Smith, formerly of the Boston Red Sox…

Alright Mike, enough fun & games, it’s time to get back to work. Now the big moment where we really get Mike ‘straightened’ out. Not his attitude, but his teeth...

Mike’s time at the gentleman’s academy is almost at an end. His dedication to this program has really proved his loyalty to Anne. Will Mike’s love letter be the key that opens Anne’s heart – for marriage?

Drum roll please…Anne receives the love letter and tears of joy stream down her face. Well done Mike!!!

We’ve had three days at the gentleman’s academy to reconfigure Michael Bailey’s wardrobe, manners and attitude… and tonight’s the night when we see if all the hard work of being groomed pays off.

Michael Bailey used to be a strictly sweat pants and ball cap sort of bloke. But today he graduates from Gentleman’s Academy appropriately groomed…

And it’s time for dinner and the big moment!!!

Mike looks amazing and he’s actually following through with all of the dining rules I shared with him. Anne is glowing and her reaction to his new smile has made the entire experience worthwhile.

Mike still has one big challenge – asking the woman he loves to marry him – and this time – it’s for real!

All right Mike, let that wine give you courage for the big question. Mike’s a man of few words but he gets straight to the heart of the matter.

And the verdict is…yes!!!! Yes!!!!

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