Here’s How Ashley Madison is Going for Charles — An Update!

Have a look for yourself!

Photo by Markus Winkler on Unsplash

Behind the scenes, Charles and I have been conversing as we get him close to his goal and fulfill my promise to him. To recap –

  • His goal is to find an affair partner
  • My promise was to stick with him until he has sex with her

This is a report on how it’s going so far using extracts from our email exchanges over the last few weeks, starting with the most recent and going through our chat from there to highlight a few points of interest. There have been many questions, answers, and discoveries, and we’ve shared them all. But today is a special day! No, not “that,” but a step in the right direction.

Today there’s been a slight development! Charles called it a milestone, and I agree with him! Have a look for yourself!

A milestone

(Screencap: Charles)

Charles — With a little luck, I’ll have a nice picture to look at in the morning. I am a little scared if I read her message tonight, I’ll say something dumb, so I’m gonna wait till morning. This is the first time I’ve ever been sent access to more pictures. That’s got to be some kind of milestones 🙂

Cautious congratulations!

Adulterous Fairy Godmother — I’m so happy for you! That is a huge milestone! She sent you a wink too? That’s wonderful, as many women don’t bother with that sort of thing! Because they really don’t need to do that. I’m working on an updated story on how your hunt is going this morning based on this great news.

Oh, and a word of warning. Play this one very cool until you get an understanding for her. Because it’s less likely for a real woman to do this out of the blue, you should always consider that this is a scam.

Don’t reveal any personal info — job — wife — kids — neighborhood/part of the city, or town you live in.

Also, be wary if she gets into a hot sexy chat right away. You can talk about your dead bedroom and why that’s happening in broad details — just say medical condition — but don’t be specific.

And under no circumstances send money. If she asks for money, it is 100% scam, no matter what bullshit story she gives you.

The other thing you need to do, once you see her photos, is to ask yourself:

  • Do they look genuine?
  • Is it normal for a woman who looks like her to be interested in me? IE, has someone with her looks and age ever chatted you up before?

The Nigerian Prince emails work because people fall for them. You’d never send someone $2000 if they just emailed and said — Hey! Send me $2000 for no reason!

But, you might if you think you’d get something for it, like pussy, or $10,000,000, right? And you’d want to help if they were in trouble as well.

If you do start a dialogue with her, keep this in mind as you assess whether or not she has as much to lose as you!

Good luck sweetie, I’m praying for you!


(He calls me 🧚🏻‍♀️, and I think it’s adorbs, so sometimes sign off that way!)

Progress and the ins and outs thereof

Charles — Traction on AM. I’ve been sparing you the blow-by-blow on AM because I don’t want to waste your time.

Adulterous Fairy Godmother — We are due for a status update on Charles’ progress, so don’t worry about wasting my time. I know you are busy too, though. My aim with your story is to point people to the series of articles and say — this is what I can help you with, so call it marketing.

Charles — So as a starting point (baseline). For the last few months, I’ve had zero activity on my AM account. Although I wasn’t actively pursuing either. But there was a couple weekends where I would do 10 or 20 messages and not get any returns. I chalk this up to it being winter and Covid being pretty active. But I think in reality it might have more to do with my lack of experience. Most of my messages contain spelling mistakes and were overly emotionally romantic (not flirty or funny or sexy or laid-back).

Adulterous Fairy Godmother — Makes sense. Laid-back and funny are the way to go. The sexy/romantic stuff can come later.

Charles — Right now, I’m carefully selecting one or two profiles to Target a week. I will increase as time goes on, but I’m still pretty darn busy. I’m spending a fair amount of time crafting the first message. Then sending it to my female account to see what it looks like. I’m using only priority messages and following up when I see any indication of action.

Honesty and vulnerability

Adulterous Fairy Godmother — If you develop a good message, by all means, cut and paste it. Just don’t write a paragraph and expect someone to believe you just tapped it out. I like that you’ve sent it to your female account. It’s good to look at it from that angle. To see how it will appear in her inbox. Those first five or six words are what will cause her to open it, and the priority message will make sure those five or six words are some of the first she reads when she opens her messages. People won’t believe it, but these incremental improvements in your approach will increase your chances of getting a response.

You might not be comfortable doing this, but I would also recommend early that you mention that it’s hard to write spontaneously without making errors because of your condition.

That will do two things –

  • First, it shows honesty and
  • it will help her understand if there are errors in your messages, why they are there.

This will help you get over your worry that there are errors in your messages and will generate sympathy in her at the same time because you are appearing to be vulnerable. Women like vulnerable men. But don’t pretend to be vulnerable — just be vulnerable.

In this game, though, you need to turn everything you possibly can into a strength.

Priority messaging challenge areas

Charles — When I first started using the priority message feature recently and became aware of the message receipt function, I think I was a little too aggressive on my first go. I caught a new user just as she was setting up her profile.

Her profile picture was of a beautiful dog in the background waiting to go out the door. I tried to make a joke that the dog needs to go out as badly as I do. I got no response from her, but the picture was gone the next day. And I got confirmation she opened my message.

So I probably should’ve stopped there. Next, I sent her something laid-back and funny. She opened my message but did not respond or check out my profile. Also, I read her updated profile, which basically said, don’t send me a dick pic or ask her for her pictures, so I kind of knew she was having a hard time.

I also noticed she updated her picture to one that was blurred out, so I sent a message congratulating her for blurring out her picture.

She opened it and then blocked me.

So I clearly creeped her out from the very beginning. The lesson for me here is don’t use priority messages to badger the ladies. Because you’ll get blocked in more ways than one!

A word on marketing

Charles — Silly question, but should I spend the extra cash to highlight my AM profile? To me, this always makes the profile feel a bit desperate, but if it helps, I’m happy to spend the cash.

I will definitely start using priority messages. I already have a Member initial contact Account.

Adulterous Fairy Godmother — As for highlighting your profile? Yes, product placement is important. Just ask Pepsi and Coke!

You are desperate, and it’s fine to show it!

You need to leverage every advantage. The men who cheap out on AM do poorly there and then complain about it.

Editorial note — It is going to cost you money to find someone on AM and date them. If you are counting your pennies too closely, you will probably not get anywhere because there’s always going to be a guy with more cash out there. And just like everything else in life, you always get what you pay for, so if you don’t pay anything, don’t expect anything.

Should I mention my family?

Charles — I know in AM I would want to downplay having children or not mentioned it at all, right?

Adulterous Fairy Godmother — As for kids and AM — leave your kids out of it. If you get chatting with someone, you can mention it, but people don’t like to be reminded of those they might end up hurting.

Things are picking up!

Charles — My response rate on AM, it’s getting significantly better. I still feel like I have a long way to go. But I’m feeling better about my odds all the time.

A point on making women feel secure

Charles — I am actually starting to question the assumption that men have a harder time on AM. Follow my thought processor here

When I message a lady already decided I want to pursue her. I have no fear for my physical safety and don’t have to worry about filtering out undesirables. I’ve already done that work. I guess I could get scammed, but I could probably work my way through that.

For a woman, I’m just not sure they have enough information to make a good judgment about the character of man you meet on AM. So much of it is left to instant. The scariest thing is that most criminals are actually quite sophisticated at conning people (that’s why we called them cons). Anyway, I’ll keep thinking about this and how I can make it easier for the women messaging me to trust me.

Editorial note — What Charles is referring to here are two separate concepts. Men have a more challenging time connecting with women than women do with men, which is one way to contextualize “hard.” The difficulty women have, is connecting with the right sort of man, and as Charles suggests, while there are plenty of men on AM, women have a hard time finding the one best suited for them. So I disagree with Charles that one sex may have it harder than another on AM. I would say they both have it hard, but in different ways, and I’m delighted Charles is picking up on how hard it can be for women — understanding that will work to his benefit.

Adulterous Fairy Godmother — Women’s safety — don’t worry about making them feel safe in your messages. They are already on alert and looking for signs. What you need to do is just be honest and yourself. Men who try too hard to do anything send off the wrong signals.

After all, who tells another person — “I’m safe, don’t worry about me”?

Unsafe people!

Let her feel you out. Just be yourself and let her do the rest. One angle you could take is playing helpless. It’s disarming, and women will be more likely to sympathize.

What I mean by that is tell them you had a lady friend look at your profile and help you out with it a little because you weren’t really sure if you were doing it right.

The other thing to do is avoid all sexy talk until she lets you know it’s ok. It’s these little things that will help her warm up to you. What won’t do that is pictures of your cock, telling her you’re safe or getting sexy early.

And you are right; men never worry, which makes them better targets for shakedowns — because they never believe it will happen to them. I mention that in my book.

Asking for and showing pictures

Charles — Also, when should I give the ladies pictures. Early and often like I seeing the other guys doing, or only she asked, or will she ask? I’m assuming it’s my job to offer. I know asking for hers can be a sensitive topic.

When I do get messages from women on AM, I’m guessing the expectation is that I respond relatively quickly? If not immediately? I’ve always kind of took my time, and I’m not sure that that’s the right model. I’ve always looked at AM as more like email and less like texting.

If I do have to treat it more like texting, I’ll have to develop a system to be a little bit more consistent and faster in my answers while still keeping it genuine.

Be well my 🧚‍♀️, I could not do this without you 😀

Editorial note — See, it’s rather sweet, don’t you think? ❤️

Adulterous Fairy Godmother — As for answering back, I’d say take a little time, but not too much — a few hours up to a day is good. Any quicker than that seems a little desperate, and longer than that could cause her to move on. You said you have the option for members to message you, so you should be ok. If you don’t, sometimes bots and scammers will waste your time. I’d always be skeptical, but a good way to tell she’s real is if she’s mentioned something from your profile.

The first message!

Charles — I thought I’d drop you a line and let you know I managed to get a lady to message me 🙂 She said she liked my profile and my self-deprecating humour. It’s just one nibble, but it feels nice to get some attention. Thanks to my 🧚‍♀️

Adulterous Fairy Godmother — It only takes one nibble.

Getting checked out!

Charles — I just had a lady look at my picture! Well, I got a message receipt from the high priority I sent. I was thinking about sending this back in response:

You see why I work behind the camera! I’m putting this at the beginning of the message, so the 1st couple words catch her attention and then explaining the rest in the body of the message.

“Here’s the list of acceptable responses after viewing the backstage_man’sphoto:

1. I see why you work behind the camera!

2. Clearly, wardrobe was off that day.

3. We’re going to need medical over here, I can tell someone is holding their breath and sucking in their GUT!

4. I was promised a puppy, and there’s no puppy ;(

5. Come on, how am I to know if you have a nice ass at that angle

6. Sure backstage_man I will go on a coffee date with you except, I have…standards and self-worth

Self-deprecating, humorous a side do you like blue eyes?

Adulterous Fairy Godmother — I like it!

Editorial Note — I did suggest a few edits for him, but the premise is sound. If you can make her laugh or at least smile, you’ll have caused a positive emotional reaction, and that’s a great place to start!


So there we are!! Charles is moving along and getting some interest from the ladies while learning along the way — and you can’t ask better than that. For any man looking to find a lady on AM, I would recommend you think about the following –

  • Have a “member-initiated contact” profile — it makes you easy to get in touch with and also says you’re not counting your pennies
  • Pay to have your profile featured on AM — this increases the amount you’re seen, and the more you’re seen, the better chances you have of attracting attention. It also says you’re not counting your pennies
  • Pay for and send priority messages — This puts your message at the top of her list. It doesn’t mean she’ll think more that you did that, but if you were selling Pepsi like you’re selling yourself, where do you want your product, eye-level or the bottom shelf? And again, it shows that you aren’t counting your pennies
  • Make the first five to six words of your message count because that’s all she’ll see.
  • No dick pics or shirtless gym pictures
  • No sexy messages of the start
  • Don’t hit her with a barrage of messages all at once if there’s no response — Definitely do a follow-up, but if she doesn’t message back, even after opening your message or checking out your profile, let her go. And by letting her go that way, the door remains open. If you keep messaging, she’ll never come back
  • Play it cool — be honest, or seem that way where ever possible, be vulnerable, and be funny — but not Bozo the Clown funny.
  • What’s with counting pennies, and why is that a concern? A guy who doesn’t want to spend money on AM to find a lady will probably want to fuck in the car rather than get a hotel, and I have to say, car sex gets old fast if you’re over 40.

This all comes after I reviewed Charles’ Ashley Madison profile for him and offered him some tips on ways he could improve it. The above discussion followed him making the changes to it I suggested—Analyzing Charles’ Ashley Madison Profile
Some men don’t realize how important their adulterous profile

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How to Cheat — Field Notes from an Adulteress

© Teresa J. Conway, 2021

By Teresa J Conway on .

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Exported from Medium on July 29, 2021.

Author of How to Cheat: Field Notes from an Adulteress, several short stories, I'm active on Medium @teresajconway where I sometimes share my blog posts.

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