My Female Friend Joins Ashley Madison: The ‘WTF&$*#& Are You Crazy!?!?’ Interview Tell-All…

When I found out I had a friend that was on Ashley Madison, I was flabbergasted to say the least. I immediately wanted to know every detail of how the operation works and what the heck an attractive, intelligent girl is doing on it!, if you didn’t know, is a dating website with a twist. They promote affairs. AFFAIRS, people! Married folks who want a little bit of tang on the side… not orange-flavored, but poon flavored!!!

Now, I don’t judge my friend, because, let’s face it, first of all, the toilet is my most frequent sleeping partner, but secondly, people very rarely surprise me - and I dig that people can still throw me for a loop. Not the kind of surprise like, “hey, you were amazing last night. Btw, I’m actually a man,” but more along the lines of, “he didn’t die?!? Inconceivable!”

I had heard of Ashley Madison in the press and seen a few billboard advertisements, but I never thought I would get a first-hand account of what goes on. Most of my male friends barely have the ability to read, much less the money to be a Sugar Daddy. As for my girl friends… never would I have imagined. I immediately asked to interview her for SVB. To protect her identity, I’ve named her Blair Witch – interview below:

Me: Holy motherf*&kin sh*t.

Blair: Is that a question?

Me: You’ve got to be sh*ttin me…

Blair: No, I'm on Ashley Madison. I also use sites like and

Me: ……

Blair: Kevin, are you okay?

Me: Why the f*ck would you be on those sites?!?

Blair: That’s professional…

Me: Answer the damn question, you home wrecker!!!

Blair: I like being taken care of.

Me: I like to eat, but I’m not letting Jack in the Box bone me! Well, maybe if he didn’t have that round head… but I’m also not marrying Elizabeth Taylor or Roseanne Barr for money! Okay, okay. I want to hear everything. How the heck did this all start?

Blair: Well, you know that I used to date ****** about 5 years ago [a high-profile Laker's executive]. That was when I first got to experience what it was like have a sugar daddy. He knew that I was struggling to get by, so one day he asked me what my rent was each month. I told him and he sent me the money almost immediately. I wasn’t raised like that, but I can’t say it wasn’t nice to have someone help me out and to have extra money to spend each month.

Me: Can you get me Laker’s tickets?

Blair: Kevin….

Me: What?!! That’s a professional request. I need to do research. Fine. What spurred you to join a website?

Blair: Well, once ****** and I stopped dating, my friend told me about a site called Seeking Arrangement. In the site, you can stipulate how much allowance you want each month, from $1,000 to $3,000, or $3,000 to $5,000, or $10,000 and up.

Me: When I was little I got an allowance of $20 a month from my parents. Now that I’m over 30 years old, I get $25. What I'm trying to get at is, is there a site for Sugar Mama’s?

Blair: Actually, on Ashley Madison you can put that you’re a married female looking for a male.

Me: That’s A-S-H-L-E-Y-M-A-D-I-S-O-N dot com, right?

Blair: Yes.

Me: Okay, so how much money were you making from these sites?

Blair: The first guy I dated on Seeking Arrangement, I told him I wanted $2,000 a month.

Me: And he paid you that!?!

Blair: For about nine months and we saw each other maybe 3 times because he was married and living in Arizona. He also would take me shopping and would pay for anything I wanted, but I didn’t want to be too greedy. We probably spent $4,000 that weekend. I liked him, even though he was kind of nerdy and chubby.

Me: Did you have SEX WITH HIM!?!?

Blair: No, but he would want to cuddle a lot with me naked.

Me: Listen. This isn’t my first rodeo…

Blair: He wanted yummers, which is what I call oral sex. But he would only do it on me. I may have given him a few hand jobs.

Me: Two thousand a month and you didn’t have to have sex with him? Not bad.

Blair: Yeah, looking back, I wish I had stayed with him. He was a really nice guy, a lawyer, and if it wasn’t for him, I wouldn’t have been able to pay for my reel (acting), which was $1300, and a health-related surgery that I had to have done. I’ve gotten a lot of acting jobs with that reel and I’ve also been able to use the money to help my mom, who is on limited income.

Me: I don’t know whether to think that’s sweet or tragic. Anyhow, what happened?

Blair: I asked to raise my allowance to $3,000 a month and he said he didn’t know if he could manage that, so rather than ask him what he meant by that – which I should’ve done – I ended up reposting my profile on the website. He found my profile and texted me that he didn’t want to talk to me again. I called and texted him repeatedly, but he never returned my calls. I was sad because I missed his friendship and I did like him.

Me: And plus, you probably were used to the lifestyle. It must’ve been intoxicating to be able to have whatever you wanted.

Blair: I never was too greedy, but we did spend a lot when he visited. I would buy whatever I wanted at Bebe.

Me: When I am at the buffet line at Fresh Choice, and I’ve already paid, I eat whatever the heck I want. I know exactly how you feel. So, tell me about Ashley Madison. Were your two ex-boyfriends guys you met on that site?

Blair: Yeah, one was married and the other was not.

Me: So you can be single?

Blair: Yes.

Me: I don’t have much to offer, but in my profile, if I put down that I have several varieties of lunchmeat in my refrigerator, would that be appealing?

Blair: Probably not.

Me: You don’t know sh*t. Anyhow, what’s the process like on Ashley Madison?

Blair: I put in my profile that I am looking for people to take care of me. And most of the guys that reach out to me, will ask me how much I’m looking for. I say around $350.

Me: A week?

Blair: No, each time we hang out.

Me: Don’t you feel like a prostitute?!?

Blair: I guess, technically, it is like a prostitute, but I get to choose who I want to go out with. I’m not standing at a street corner. Plus, it’s not like I do it every day with a new guy. These are guys that I see all the time and we get to know each other and actually start to date.

Me: Do you have sex with these guys each time?

Blair: Most of the time.

Me: Wow. Do they treat you like an object or make you do crazy things?

Blair: Oh no, these guys are mostly respected, established people and I won’t do anything I’m not comfortable with. I won’t swallow or do anal.

Me: Swallow what?

Blair: I did meet a doctor who wanted me to do all sorts of weird things and I got the feeling that he wanted to treat me like an object during our meet and greet. This doctor was going to give me a $4,000 allowance, but I said no.

Me: Swallow what?

Blair: Oh, Kevin…

Me: Fine. Do you ever plan on doing any traditional dating?

Blair: I could, but I’ve gotten used to being taken care of. So, it would have to be someone established. I think I could meet someone on Ashley Madison or one of these sites and get married. I have gotten to know and love some of the guys I've met through the site, but it ended up not working out for one reason or another. One of my friends met a married man on the site and he’s getting a divorce for her.

Me: No way!!!

Blair: You’re so professional!

Me: How old is he? Does she really love him?

Blair: He’s like 50 and she really does. She can still hook up with other guys, but he wants to know about it. He likes to talk dirty to her during sex and ask about the other guys.

Me: What a weirdo. Do you see yourself doing this forever?

Blair: No, I see this as a means to the end. I am not lazy like some of the girls who are just in it for easy money. I am still going to auditions every day and working trade shows. I see this money as helping me out as I reach my goals. I think being in LA has really changed my perspective. We all need help. Coco Chanel got help from a guy when she was first getting started. Marilyn Monroe…

Me: Okay, this is good stuff. Now, my readers, well, the ones that can read, they want to know whether you worry about getting caught by the wives or whether you think you're a home wrecker?

Blair: Go tell your readers to go to hell!!! Haha.

Me: That's funny you say that...

Blair: Actually, the answer is no and no. There have been close calls, but these guys are already having problems at home. I provide a moment of happiness for them in their mundane lives of chaos. 

Me: ..... you just used about four words that I'm going to have to look up in a dictionary after this. Well, I should let you get back to home wreck... err, I mean, dating. If by any chance your friend is interested in bologna, salami, turkey, or ham... send her my way. I would be honored if her guy imagined me while plugging away.

Well, there were many things Blair said offline about the pros and cons between the different websites. Leave a comment or email me and I’ll try and answer any questions you have. In the meantime, tell Jack to call me... $350 is a game changer in the world of Sourdough Jacks. 

Kevin L.
The Silicon Valley Bachelor

P.S. On an absolute side note - as a former Public Relations professional, I'm impressed, and as a former journalist, I'm insulted about how Ashley Madison has managed their public facing profile on the web. It seems they have bought several domain names with "Ashley Madison" in the name, followed by "Sucks" or "Scams" or "Reviews." They have even filled the sites with relevant content that points people towards their sister site of The content at first seems negative, but ultimately does little to dissuade someone from joining the website.

Because of that, here is a link of some real comments that are not easy to find, on Dating Site Reviews. The majority of the comments say it's a scam and that there are few real female profiles. How's that for objective journalism? No one's getting a free plug from the SVB! I am a man of integrity... one who only changes his opinion for the right amount of money.

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  1. I felt this story was very entertaining and shocking, but i don't judge you never know what you would do for money, until you really need it.

  2. I agree. I had all these preconceived notions of who and why someone sleeps with married men, but it's not all so clear cut. When it comes down to it - she is a good person and will always be my friend - no matter what other people think of her or what she's doing.

  3. Great interview, however, I feel like she's in some serious denial about her lack of guilt. Marriage is hard and just b/c these guys are at a low point in their relationships, it doesn't make it right for her to sleep with them and take their money (which should be going toward their families.) If she really needs to be "taken care of" can't she try to find rich single men? Also, there are plenty of struggling writers/actors out there that are working real 9-5s to make ends meet, so I can't really sympathize with her money problems. Finally, karma is a bitch, and there's part of me that really wants to see this girl get married and cheated on. She's in for a rude awakening if she really expects a man to take care of her for the rest of her life (or until she becomes a famous movie star of course.) Also, i love that she claims she's not greedy. Finally, Bebe is so 1997. At least get some better style, girlfriend.

    But i swear, i'm not judging her.

  4. PS I love that I had to write two addendum's to my first "finally."

    PPS good info on the URLS that ashley madison has bought, any background on why they call themselves ashley madison in the first place?

  5. @Saaara - "Ashley" and "Madison" were the two most popular female names given to newborns the year they launched (or something like that).

    I love your candor. I do agree with you, but I think the problem starts WAY before she gets involved. It reminds me of people who date and stay in a relationship, just because they can't be alone, and then wait until they have someone else waiting on the wings before they breakup. That kind of thing makes me sick.

    There are a lot of weak, dependent people out there, and I think the main difference is that these guys (and gals), are in the "sanctimony" of marriage - 50% of which, end up in divorce already.

    There is some crazy stuff that goes on amongst the married. People get divorced for other women all the time. And how many people have you run into that have dated someone who is separated, divorced, or "about to get a divorce?" Is what really bothers you the fact that she is getting some money on the side? And is part of a network that promotes philandering?

    Don't get me wrong - I am surprised at her lack of guilt. I also am of the mold to where, if I needed money, I would be working two jobs, flipping burgers at midnight - to avoid ever needing to ask anyone for anything. But people have different mentalities, this just happens to be a very controversial one!

  6. uh. lemme get this straight. struggling actress whores herself out to make ends meet (be vain) until she actually has a career. or, if career flops (statistically favored), until someone 'takes care of her' aka. pays her enough to marry them. all in L.A. yeah. i don't think you could throw a shoe in L.A. without hitting one. she's blond right? no, wait. she's 'different' and 'edgy'. she's brunette.

  7. I love your candor. I do agree with you, but I think the problem starts WAY before she gets involved. It reminds me of people who date and stay in a relationship, just because they can't be alone, and then wait until they have someone else waiting on the wings before they breakup. That kind of thing makes me sick too. In fact We spend a great deal of time reviewing each dating service on the site. Hopefully the questions and chart have helped you narrow down your search for an online dating site to only a few. We suggest at this point reading our complete reviews for each of the sites that seemed interesting for you

    The reviews are very thorough, going over the services from A-Z with details on some of the key features for each, some strong and weaker aspects of the service, and even some special promotions for some of the services you won't find anywhere else

  8. I love the honesty of your friend. She could have taken advantage of the situation but no, she only did it for the money, albeit very professionally but certainly not the home-wrecking type. Sometimes it's hard for most to justify why others would do what she is doing but at the end of the day, who are we really to judge what others do in their life? As long as they show some sense of respect and do not take advantage of others, then the world is also theirs for the taking.

  9. Aha! I dated someone on Ashley who wanted all kinds of money, stuff and told me how he was "struggling". Found out later, turns out the guy was wealthy and just getting his kicks getting all kinds of stuff free from all kinds of women. Whether you're a man or a woman, if you're on that website, you're messed up and you're going to be meeting other people that are crazy too.


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