Colin Bailey

**Colin Bailey** is a possible match in Winked and the counterpart of Joshua Whitaker.

## Profile

**Profile picture Caption:**

Yes, I'm one of \*those\* Baileys, but... Give me a chance anyway? 😉

**Profile bio:**

My full name is Colin Rutherford Bailey VI and I'm looking to piss my family off... Want to help? 😉

## Appearance

Colin has short brown hair, grey eyes, stubble and light skin.

## Biography

Colin's family owns the largest media conglomerate in town and his family expects him to become the next CEO.

## Story

**SPOILER WARNING! ->**

**The following is a summary of the story where the premium option was chosen every time.**

It's revealed in the first chat that Colin and MC know each other: Colin's family owns the largest media conglomerate, MC's family owns the second largest one. They both quarrel and tease each other for a bit. MC eventually brings up the time they hooked up once at a fundraiser event and admits that it was the best sex she ever had. Colin reveals that he is currently very upset with his family. He happens to be texting from another fundraiser event and invites MC to join him. She agrees and heads to the fundraiser.

Colin impresses MC by remembering her favourite drink from the last fundraiser. They start playing "Never have I ever" while hinting at how much they enjoyed their previous hookup. They eventually head to the bathroom together and start getting intimate, but Colin stops and says that there will be a better time and place for it. They return to the gala.

The following day, both talk about how they are tired of always having to do what their family wants them to do. Colin invites MC to his penthouse to give her a massage. She heads over to his place in the evening. After a glass of champagne, they start kissing on the couch and Colin reveals that he is into role-play. Eventually, they head to his bedroom. Colin ties MC up and blindfold her. After he teases her for a bit with a feather, he removes the silk rope from her wrists and they have sex.

In the following chats, both talk about how they need to look out for themselves and Colin explains how he has been burnt before in a previous relationship.

Eventually, Colin invites MC to dinner. They take Colin's limo and head to a new upscale restaurant. Over dinner, he tells MC that he is planning on leaving his dad's company.
Unsure what to think, MC heads to the bathroom to think. Her family is aware of Colin's Winked profile and tried to get MC to reconnect with him, so she could get confidential information out of him. She has to make a decision on whether to betray Colin or not.
She eventually heads back to the table and they finish dinner. In his limo, Colin reveals to MC that he genuinely likes her.

After she gets back home, Colin texts her saying that he wasn't serious about leaving his father's company. He was just testing MC.

**Bonus scene 1:**

This scene is a flashback to when MC and Colin hooked up at a fundraiser two months before they started chatting on Winked. They start talking, then head to the bar. It ends with them leaving the bar after some small talk.

## Gallery

### Date pics

First dateSecond dateThird dateFourth date (bar)Fifth date (restaurant)Sixth date (Colin's apartment)Seventh date (Limo/Restaurant)Eighth date (private plane)Extra Scene 1Ninth date (Barcelona restaurant)Bonus scene (flashback)Tenth date (business investor meeting)Eleventh date (meeting Colin's brother)
### Additional (NPCs)

Anselm Hughes, business investor and Colin's friend from universitySimon Bailey, Colin's brother
### Other

Promo artDream Date December '23 promo art
## Voice Messages

**Colin's thoughts**

Look, I'm not gonna lie, I like this hot'n'cold thing we've got going on as much as the next guy. But I also like you, like, genuinely. Might sound a little bit soppy, but... That night we shared... It was one of the best nights of my life. And if I had to choose a favorite amongst all the enemies my family has accumulated over time, well, you have absolutely no competition.

Yeah, so, you say you can't stand me, but... some of the greatest love stories started like that, right? And our story could be pretty great... Since we're definitely not the boring sort.

**Colin's speech**

First of all, thank you all for joining me in this joyous celebration of this momentous occasion! Similar to the way even the most stubborn of snows thaw when the sun rises, so has a certain individual warmed up after coming into contact with... Well, the human version of sunshine, if I may say so. For the sake of preserving their privacy, I shall not reveal any names, but let it be known that both of these individuals are among the hottest representatives of the human race. No contest there.

**Colin's experience**

I know I should've known better, given where I come from, but, well, I was way more gullible in the past. I'd fallen in love with this young reporter... You can probably guess how that went.

Everyone tried to warn me, but I didn't want to listen. Or I wanted to prove them all wrong, I don't know. Anyway, I ended up a fool and I swore I'd never let that happen again. That's probably why I've never let my guard down since.

**Colin's seduction**

Well, believe it or not, I'd be a perfect gentleman. I'd take care of your every need, no matter how small. I'd treat you with the utmost respect, but I'd also show you just how attractive I think you are. I'm human, after all. But I can promise you one thing... When I really want something, I know how to turn on the charm. And you are more than welcome to test that out. In fact, I encourage you to do that.

**Colin's clues**

I'm not going to let the cat out of the bag just yet, but I'll say there is one word that sums up what I wanted to tell you. It starts with the letter 'p' and has seven letter... No, wait, eight letters. Yes, eight letters. I think that's a pretty solid hint, right? Now all you need to do is guess. And if you can't figure it out, well, you'll just have to sit tight for a little longer. But then it will be just that much sweeter when you finally find out.

## Aspirations

**Fantasies**

**Favorites**

**Impressions**

**Secrets**