Adultery Questions Men Ask

And the answers they seek

Photo by Taras Chernus on Unsplash

When people hire me to review their adulterous profiles on Ashley Madison and draft some opening messages for them, they usually have some questions. That’s normal.

I don’t mind sharing my knowledge, because I know there’s a difference between reading my 250+ adultery stories and asking me about the things they want to know. So when they hire me, they’re paying for access to the research and experience I’ve had that allows me to write those stories.

This client, however, stated he’d hired me to answer questions. I, of course, helped him with his profile and have written some openers for him. But most of our interactions have focused on his questions. After some back and forth, I thought a lot of what he was asking was applicable to many men on a married dating site, so I asked if I could share our discussion, and he obliged me.

I’ll call him Bill, and I’ll be Your Faery Godmother of Adultery🧚🏻‍♀️ (FGM), as always.

Here’s how it went –

Women not replying

Bill — A few times, I chatted with ladies off AM messaging system Kik, Telegram) and the issue was that the ladies were not engaged. They were just replying without being engaged or asking me questions.

FGM — Yes, some are like that. You need to keep working it and exploring different avenues. One client who told a woman he wasn’t interested because she was not communicating. Fair enough, but I never advise shutting a door when there’s no open window.

Bill — Usually, after a session of several back-and-forth messages, they were not responsive enough when we broke off, and soon after that, the connection was terminated. Why is that?

FGM — this is a tough one. Sometimes it could be that you didn’t move to sex fast enough. On the other hand, women like steamy chatting too, so it becomes boring if it’s just endless chat. If you turn up the heat a little, that might keep them engaged. For others, that will turn them off. You really can’t tell, but endless chatting is hard to maintain for most women I know.

Bill — What were they looking for? Why do they behave like that? But, of course, because they were not engaged, I didn’t know which direction to take the conversation.

FGM — See above, lol

Bill — Frankly, I consider myself a good conversationalist, but I was disappointed to see a lack of curiosity in them.

FGM — They could be chatting with five people trying to figure out who the best one is — best for them, though, not you.

What making a “connection” means

Bill — Especially when some ladies say they like connection and sex (and a “one” person relationship).

FGM — Some say this because they aren’t willing to admit to themselves that they’d like to try different men and have different experiences. They usually write that when they first make their profile and never go back to changing it. They don’t want to see themselves as “sluts” and don’t think they are “sluts”. I will say they aren’t, but what happens is when you’ve had a little excitement and sex, it’s hard to stop sometimes.

Bill — To make a connection, two people should know each other, am I right, or am I off-base?

FGM — You’re reading too much into that. As above, it’s again something they say to convince themselves that they aren’t that bad because they’ve insisted on a connection.

Bill — Were they interested in chatting, or did they want someone to entertain them?

FGM — Most aren’t looking for entertainment. They want sex. Chatting is the prelude to that.

Women backing out of meeting

Bill — What can I do next time? In two more successful cases, after chatting for a while when we made an appointment to meet in person, just before the meeting, they changed their mind. Why could that be?

FGM — If they were new to cheating, meeting someone, even for coffee, makes it real. What you can do is ask them if they’ve cheated before. If they say yes, then the chances are better that they will meet. New people, who haven’t cheated, are easily spooked. Most experienced cheaters won’t bother with a new person because they often don’t go through with it and waste time. I’ve had that happen to me several times — it applies to both men and women.

Should we close our accounts if we connect?

Bill — If two folks are texting and communicating, is there “an accepted practice” or a norm on AM world, saying after this many texts or days or… you should close your account?

I mean that I see that I am chatting with a lady, and she has her account on and checks into her AM profile.

FGM — Nope, and don’t ask her too because she’ll walk away. You need to get used to the fact that you are in a footrace with other men. If you end up connecting with someone — in a real way — then they might. I would also recommend that you keep looking. Honestly, to get one date, you will need a 3:1 or even 5:1 ratio of chats to dates, so keep at it. Even then, she might not be the one, so don’t waste time going in sequence — she won’t. And she shouldn’t.

Competing for her heart as she shops around

Bill — That perhaps means she is “shopping around” while chatting with me. So what would be the best way to compete and win her heart (not falling into love…). Is it desperate to tell her, let’s the two of us focus on chatting and knowing each other before having concurrent conversations?

FGM — Yes, and she will not agree in most cases. The way you win her heart is by showing her you are the best of everyone she’s talking to. My lover competed with five other men over six months, and he knew I was meeting them. And not one of them compared to him. It was almost a year before we became exclusive.

Moving to a phone call

Bill — Is there any rough guidance on AM world when a man should ask a woman to talk over the phone or meet in person?

FGM — She might not want to, but you can ask for a call fairly quickly. I wouldn’t wait too long for a meet either. Maybe a few days. She’ll know if she wants to meet. If you spend too much time chatting, she’ll get bored.

Bill — I had a few cases that we chatted, things were OK pretty quick (within a few days), and to me, the next step was to talk on the phone or see each other in person. After that, to go on with dating. It seemed they were scared them off, so I questioned their intention as if they were serious. Because to me, there was nothing else to explore. We had to meet for coffee… to see each other in the flesh. To take the next step. But they brought excuses and disappeared.

FGM — This likely means that they weren’t that interested in you. They were chatting to see where it would go, but when the time came, they decided to withdraw. Perhaps they could read your serious side coming through and didn’t like it, or you might have been “too polite .”That means you didn’t light their fire in a way that made them want to meet you.

Getting to know someone through text

Bill — I think texting is not a good way of getting to know a person. Texting is very one-dimensional, can be interrupted, and you don’t know what condition the other side has or is in. Does she have privacy? Is she shopping and responding to the texts? What type of topic can I bring up at this moment? And most of the time, the woman doesn’t give a clue.

FGM — Give it a shot, and she’ll tell you if it’s a good time or not. Maybe you are beating around the bush too much? Taking too long. I’m not saying get right into sexy talk but get there by being flirty and a little sexy.

Yes, it is a one-dimensional way of getting to know someone, but it’s what you have, so work with it. Don’t forget, many of these women aren’t looking for a boyfriend but someone to have sex with. In some cases, they are doing that because they want to have sex, and in others, they protect their hearts from getting too deep into it.

My recommendation is to focus less on building a “connection” and work towards the first meeting by being sexy, fun, and playful in your texts. Nothing deep!

Bill — That’s why I think minimum a phone call or meeting in person is the best, but this seems not to be the favorite route for most ladies.

You might not be giving them a reason to meet. No spark! No fire in their panties! Women are doing this to be sexually aroused, get horny and have sex. There’s a sure way to go about that — i.e., proving you are a safe and interesting person, but make no mistake — she wants to have sex and get horny.

They don’t always look like their pictures

Bill — Although I’ve seen cases that the ladies asked me to meet in person when I met them, I realized that their physical appearance was awful or they were much older than they wrote on their profile. I genuinely believe one session meeting in person will tell much more about personality and potential match between the two, but this doesn’t happen easily, it seems.

FGM — Yup, one session works for you, but remember, you aren’t trying to go on a date with yourself. There is risk in meeting anyone, so they won’t take that risk if they don’t think you’re the one. As for appearance, most women lie about their weight, and most men lie about their height.

When you asked if they are looking for Brad Pitt, you should ask yourself what you’re looking for? And what you can expect. You are not Brad Pitt, so you’ll likely not get the sort of ladies Brad Pitt would. Earlier, you mentioned that women seemed to have very high standards, but you might also have too high standards. Don’t forget, you are not going to marry these women or take them out on a date. Most likely, you’ll meet in a hotel, and that’s it. Sure, she might lie to present the best side of herself, but you might too. If you want a connection, intimacy, and sex, you might have to overlook some things.

Lying about her age

Bill — BTW, I feel that many ladies on AM lie about their age, from 5–10 years. Am I right? Does this mean that a lady who is, say, 50 and claim that she is 40 is looking for a 40 years old man?

FGM — Nope. It just means she’s claiming she’s forty. Don’t worry about that. Most women will mention it in their write up if they have specific age requirements or interests. If they don’t, then they don’t. If you stay in the 40–60 age range, you’ll be fine.

Messaging Women

Bill — I’ve read the importance of reading ladies’ profiles in your writing. But many don’t have anything except “hi” or “hey .”Amazingly enough, I’ve gotten a response back from several of these. So the general question is, what would be the best first message for these profiles?

FGM — When I write messages for clients and the women they pick have these profiles, I try to leverage their profile name and any other little thing I can. Usually, these messages are shorter because I can’t speak to anything specific, but there’s always something to help you find your way in. So if you pick a few, I can show you what I do.

In general, though, women don’t need to write anything to get hit on. They’ll have a blank profile, and the messages will start rolling in before they finish writing it.

Women who aren’t serious

Bill — Actually, I was not very accurate by writing: “…. I added those after many people, who to me are not seriously on AM contacted me and wasted my time”. I meant they responded to me, by they didn’t appear to be serious.

FGM — You’ll get people who aren’t too serious, or they might like you, but have someone they like better on the string too. Why you don’t put those warnings in your profile is because some women will think you have standards and expectations that are too high, others will see it as a complaint from someone not having a good time on the site, and others will just pick up the negative vibes. These are all downsides. Telling sugar babies to go away is something many can understand, but to more or less dictate what you aren’t looking for will scare potential APs off.

Women are lost and confused

Bill — I feel that many women on AM are lost and confused, or they don’t know what they are looking for. Is my feeling correct?

FGM — Yes. It is. I have one client who was having a great conversation with a lady right now. They were both professionals in a similar field and had already had some sexualized chatting. Then out of the blue, she deleted her account. She not just blocked him but outright deleted her account.

Another had two first-timers on the line, but they broke it off too. They couldn’t handle the stress or were worried about the guilt.

Some women will get up the nerve to open a profile and then just split once the reality of it all sets in.

Do women just play games by saying no?

Bill — I think for some, it’s becoming a habit to come and see who’s out there, who is new, and they enjoy just saying “no.”

FGM — I wouldn’t go that far. There’s no woman on AM who is deliberately out to say no. Men generally give plenty of reasons for that themselves, except me. I have taken some assholes to the wall just to give them a life lesson on how to treat women. Tho 99/100, I’m sweet as pie.

The “spark” they’re looking for

Bill — I wonder, are they really serious? Some are looking for a “spark”? Can you please demystify “spark” or me?

FGM — Some are serious, some aren’t. Just like life. What spark means is — “would I fuck this guy?” You might both get along and have a fun chat, but that doesn’t mean you’ll fire up her level of desire. So not only do you have to be likable, you have to be fuckable too.

Are they looking for supermodels?

Bill — Does this mean they are looking for a supermodel or a Brad Pitt? And when looking at their pictures, these ladies are very ordinary….

FGM — No, they aren’t looking for Brad Pitt on AM. They are looking for a guy who they could see themselves spending time with and who gets them horny. Human sexuality is diverse, and what floats one’s boat will not float another’s. This idea of spark is just that. It could be eyes, a voice, a body shape, a sense of humor, intelligence, height, arm shape and size (I like arms Mmmmm), any number of things. Your job is to cover off as many of the possibilities you can control — kindness, intelligence, humor, and let her decide on the rest.

Singles on Ashley Madison

Bill — Let’s continue on singles. Would you please expand on: “singles are hit and miss”?

FGM — On AM, some singles are looking for other singles. Some are looking for sex but don’t want a relationship so choose the protection a married man brings. In theory, a married man isn’t going to run off with their lover and leave half their assets behind.

The issue with singles is that if they begin liking you too much, they have less to lose than you do, so that they could destroy your marriage.

Bill — When I search, if I include singles, the number of women increases dramatically. Some of them with pictures, some with an assay, like they are looking for the “Mr. Perfect .”I tend to consider these bots, scammers, or a profile written by AM agents.

FGM — You shouldn’t think of them as bots or fake profiles. Ask yourself, why would a dating site focused on married people want to populate itself with single profiles? They’d more likely use married profiles if they were doing this because that’s on-brand.

Ashley Madison’s history with fraudulent profiles

Bill — In the past, I read a lot of news that AM pays people to write fake woman profiles, just for men to spend their money in contacting a person that doesn’t exist. Is that correct? Do you have more recent/accurate intel on this?

FGM — I think AM learned an important lesson from their data breach in 2015, and that’s they can’t game the system and keep the trust of clients. What I see happening now is that they will send system-generated messages to men from real accounts to try and stimulate a conversation. When I look at my sent messages box, I see plenty of these messages from “me” that I never sent.

The other thing I’ve been told and have seen is that when they detect a fake account, they will completely remove it from their system and give anyone who messaged that account their credits back.

There are scammers on AM and prostitutes, but they are more subtle, like the lady who wanted money to show up to your hotel date.

Who pays for the date?

Bill — I got your message about the hotel cost. Frankly, I am fine and a gentleman. I never would ask a lady. Still, another writer in the Medium, MonalisaSmiled, said something about splitting the hotel cost. I wanted to know about the norm in the cheating circle :).

FGM — Mona is a dear friend, and I agree splitting costs is a good idea to show equality in a relationship. That way, the man who always pays doesn’t get the wrong idea by thinking she “owes him something.” And in this day and age, most women wouldn’t think twice.

The other thing I know is that women love being lavished by a man, even if for a few hours, and by paying, you help promote that fantasy of a woman being swept off her feet by a charming prince.

Attitude and approach to the initial conversation

Bill — Yes, I am somewhat serious, but not rigid, maybe because of the Corporate culture that I am used to or some cultural background (I was born and raised in the Middle East) that may come across as serious.

FGM — And that is all fine, but in the opening stages, you need to keep it light when she reads your profile and the initial message. If you meet someone, you’ll get to know each other and then reveal more of yourselves. She won’t mind a serious man if you’re kind and have a sense of humor. The problem with seriousness is that it comes off as too stiff initially, which pushes women away.

Bill — But actually, I have a good sense of humor, once I know a person and I’m comfortable knowing a person’s boundaries and personality. But I love to add humor as much as possible.

FGM — I agree, that’s how it usually works, but you need to be lighthearted at first and appear not to take things too seriously. Remember, she’s in this for fun and excitement, too, so help lighten the mood so she can enjoy the ride.

More on connecting

Bill — Now I know that one issue I had (and perhaps the biggest one) was believing that I had to make a real connection and learning her (and not making things light), as they asked for it in their profile.

FGM — Yes, the connection is more “the spark” you asked about. It’s that emotional, sexual connection. I’ve had sex with people I didn’t have that spark with, and it’s not the same. So what she’s saying, I need to want to get naked with you.

Bill — This was especially difficult as their text soon changed to an “interview” (they wouldn’t ask any question), not a two-way conversation.

FGM — And that’s where you lost them. It happens. I usually know within a few exchanges if it’s going where I want it to go. If not, then there’s no point.

Bill — Your comment these ladies are on AM for sex suddenly cleared my vision and perception.

FGM — The skill you need to develop is knowing this and not treating them or making them feel like sluts or sex perverts. So yes, they’ll get down and dirty in the texts (and in real life), but you first need to show them you’re the guy they want to do that with.

Flirting and Sexts

Bill — This is somewhere I need coaching: how (and when) can I be light and sexual in the communications?

FGM — You should be light the entire time. Casual and friendly, and act like nothing bothers you. Don’t complain about your wife or your life — she’s on AM to get away from that. Be cute and clever. Make her laugh.

Bill — How (and really when) can start to be flirty.

FGM — You can be flirty fairly quickly. Don’t forget, she’s here for fun and excitement. Even if you don’t meet, she’s here to feel something she hasn’t felt in a long time. She wants to feel sexy, wanted, titillated, young.

Writing initial messages

Bill — Can you give examples, opening dialogue, priming ideas…? Are there resources out there for me to read/learn?

FGM — This is a tough one. The opening dialogue is to get her to read your message and respond. It’s best to avoid sex here. Being cute and funny will come off better. The reason is that most men talk about sex and how good they are in the first message because they don’t know what to say.


And that’s where we ended it. In thinking about Bill’s questions again, having gone over them, I think many men might have them when starting out on a cheating site. Things are always as they seem and people don’t always tell you what they want. Sometimes they don’t admit to themselves what they want.

Think of cheating like any other relationship. You have to give and take, overlook things, and recognize people aren’t perfect. And that you aren’t perfect. When you do this, you can see past the extra weight, or the crow’s feet, to see the person there, looking back at you, who, like you, is trying to get some passion back into their lives.

When you do that, you’ll begin to have some meaningful and rewarding dates.

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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