Ashley Madison Messaging — Charles Strikes Out

But he’s finally getting some swings in

Photo by Peter Kasprzyk on Unsplash

Since Charles’ profile tune-up, he’s been getting traction from the ladies. One messaged him and told him his profile was funny, and other women responded to his priority messages. A few weeks ago, Charles decided to focus on a couple of profiles a week, which is a good idea because he has a busy schedule.

When you focus on individual profiles, you can develop a strategy to write that all-important first message concentrating on those first five or six words that will cause her to open it.

What he did

Charles chose two ladies who were near the same age and location. Of these two, age and location, I would say location is more important because if you can’t get to them, you’re wasting your time — even if both of you are into it.

I’ve done the long-distance thing, and even with ten trips a year, it’s wasn’t enough to satisfy me, I needed more, which was a circumstance that nearly ended our relationship.

The two profiles he chose were a new lady and one who appeared to have been on AM for a while. In his own words, Charles wanted to “stick with women who look obtainable.”

That’s reasonable, and the best way to do that is to understand what she’s looking for. On reading her profile, if she’s not looking for you, don’t waste your time or money on her. The other benefit of doing this is if she sees you’ve read her profile and match what she’s looking for, she’ll be more inclined to respond.

The two ladies Charles chose were:

  • Debbie
  • Sky, new to AM

We’ll focus on Debbie because he ended up having an exchange with her.


Here’s her profile:

Debbie’s Ashely Madison profile.
Debbie’s looking for a friend and romantic lover. I don’t think Charles or I paid enough attention to the word “romantic” and that was our mistake. (screencap: Charles).
She’s a professional lady, so one assumes her time is valuable and she wants someone who understands that. Here, she’s looking for passion, romance, and flirty messages. Again, we weren’t paying attention to this and it caused him to get blocked. We’ll need to do a better job here. (screencap: Charles)

Charles then proposed the following first messages:

Too young, Too Tall, Too hot! Yes, you’re a cradle robber, I’m a full 24 months younger than you, how are we ever going to make it work! Strike one. Too tall I get that one a lot! Look up, way up, a full 11 cm up, and yes of course it matters. But much shorter is a bigger problem. Too hot, another fail, turns out you’re the hot one.

With Debbie, after looking at her profile, I told him she wants 45+, and you’re 44. Probably not a showstopper, but if you call her a cradle robber, you’ll remind her that she wants 45+.

I recommended he try this — I’m not quite 45 yet, but I’ve been told I can pass for 47 under the right light.

The height is good because she didn’t specify, so try — I know you like taller men, but if the 11cm difference is too much, maybe you can wear heels when you’re with me?

She also asked for a non-smoker, so try — I’m smoking hot, so it might not work out if you’re looking for a non-smoker, but if you’re willing to meet, I suppose I could wear a turtleneck or something to dial it down a bit.

If you like it, cut and paste it into a message and send it.

Here’s how it went:

(screencap: Charles)
(screencap: Charles)
(screencap: Charles)

And then Charles reached out to me —

Okay, so I manage to jam myself up here. Although even getting to this point is amazing — she open the message, look at my profile, and message back right away.

Do I:

A. Thank her for her time and move on — she’s been pretty oppositional from the beginning

B. Take one last shot at it, maybe something like — being here is about trying things you never try in your regular life, about taking risks and self-discovery — and get Blocked?

I told him it appeared to me as if she missed all of the humor, so there’s a chance English isn’t her first language. I said take another shot but drop the humor and gave him this —

Sorry, I was trying to be funny, but all I really want is to meet someone and see how it goes. I don’t have a type, but I’m bored like you, so thought I would message you.

She never said Charles wasn’t her type, but that she thought she wasn’t his type, so said to go back to her.

Armchair Quarterback

Later, after reflecting on the whole conversation, I told Charles I realized Debbie had been looking at his profile, and that’s why she said she was not his type.

It was the boots and the workout clothes — I didn’t see that at first. She didn’t have or wear the boots or workout clothes he mentioned. That told me his profile needed a tweak to make sure he opened his net wider.

It’s good news that Debbie read Charles’ profile, but women get intimidated by what men are looking for. They will shy away from a man if they don’t feel they aren’t the right fit. While keeping preferences in a profile is good to let people know what you’re looking for, you need to say you’re flexible and that your preferences aren’t fixed.

In Charles’ case, I recommended he add this to the bottom of his profile’s “about you” section –

Jokes and the above aside, I’m looking for someone to get to know and spend some time with. I miss having an intimate partner in my life, and I’ve come here in the hopes I’ll find the right lady who needs intimacy too.

What happened with Debbie

After trying B above, he tried A, which was the “thanks and good luck message.” She wasn’t playing ball at all, and Charles picked up on that. But why wasn’t she playing ball?

He wondered if his going back to her profile a lot was causing her to get emails each time he did and making him look desperate. I’m not sure that’s the case, but whatever it was, it’s done now. To avoid this potential issue, Charles thought taking a screencap of her profile and working off that might be the better way to go. I think having a closer read of it would help too.

I don’t think we looked at her profile close enough — romance, flirty, passion.

What she didn’t say was — let’s go to Yuk Yuks and have a hoot.

Next time I will take a closer look!

As for Debbie? She blocked him and although I’m sure it hurts a little, it’s not a surprise.


Charles is starting to get the hang of AM. His profile is working, and he’s getting bites. Now the focus must be on the profiles he selects and what he writes in his first message.

Looking at this whole exchange, I think she was a little more serious than he was, which showed in her responses. Hitting the right tone is essential, but coming off as casual, fun, intelligent, and charming is tough for anyone in a two or three-line message.

What I’ve learned is that Charles is better to slow his roll going in on the first message and ease up on the humor. In this one, I followed his lead by helping him adjust his message which was a mistake.

I didn’t see how it was the wrong approach, because I assumed Charles had deduced this would be the right message for Debbie. The next time he asks for help, I’ll analyze her profile and tell him to leave the humor for his profile.

I also think it’s important to add warmth to his profile. Telling women that he’s interested in intimacy is vital because many cheaters miss that in their lives. That’s what I was missing when I first went looking.

The sex was good, but I just needed someone to hold me like they loved me.

Here’s a look at Charles’ profile —Analyzing Charles’ Ashley Madison Profile
Some men don’t realize how important their adulterous profile

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© 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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