I’m Helping My Friend Have an Affair
She doesn’t know why I give such good advice.
The two most hip ways to make passive income right now that “anyone can do from their home” are dropshipping on Amazon and creating online courses.
I considered the latter, except you have to be good at something. I could teach technical writing but since I do that as my real job, I don’t want to put anything out there that could discredit me in some way or get judged by the masses. I’m a master of nothing.
Except…affairs. I’m fucking great at giving advice about affairs.
With a marriage of almost 20 years finally ending, it’s crazy to look back and think of how many affairs I’ve had. That includes both one-night-stand types and more serious relationships too.
Before anyone flips their shit on me, my disclaimer is that my husband was addicted to porn, got happy endings at massage parlors, and rejected me the instant we got married due to his Madonna-Whore Syndrome. I’m not proud of my affairs. I’m just good at them.
During this pandemic, I reconnected on a deeper level with my friend Ellie, who lives a few states away. We chat occasionally on the phone and have divulged almost all of our secrets. The one thing I haven’t told her is that I’ve had dozens of affairs. I’m not ready to open that can of worms; there’s plenty of open cans already.
Ellie is married to a fantastic guy and has three small children. On paper, her life is perfect. She has no complaints about her husband, other than wanting him to put in more effort with his appearance.
We yell at each other to stop being so hard on ourselves. Ellie keeps repeating that I’m hot and I keep repeating that she’s a gorgeous mermaid with luscious hair. We’re the emotional support squad we need during this pandemic.
She confessed months ago that she reconnected with her college boyfriend. They never formally broke up; he got sucked into his own world of his friends and things fizzled out. To Ellie, he was The One; thoughts of him invaded her brain constantly for 20 years.
Ellie tells me this as I’m still grieving my breakup with Jon. Maybe I wanted to live vicariously through their romance. My heart was shattered and I ached to be with someone who wasn’t mine to have. If anyone understands what it’s like to love a married man, it’s me.
Initially, she was hesitant to tell me things in case I would judge her. Ellie immediately realized I wouldn’t give her morality lessons. “Holy shit,” she said. “Only you and my friend Beth know. And Beth keeps telling me that I’m a horrible person for this. I can’t believe you’re don’t think I’m a piece of shit for this.”
I told her that I understood. Especially with the pandemic, we’re losing our minds. And the same routine, day in and day out, it feels like your job is motherhood and nothing else.
Having someone that you find sexy to talk to gives you something to look forward to. Jon was my favorite notification. Like Pavlov’s dog, I jumped each time my phone buzzed. Never knowing when I’d hear from him, my phone became a slot machine; sometimes I’d win big with a message from him but usually, they were from other people.
Ellie didn’t understand why she couldn’t stop contacting him, despite the emotional rollercoaster. Not being able to message normally or communicate on-demand drove her bonkers. I explained that this has become a psychological drug. Every time he messages her, she gets a hit. And while she’s euphoric initially, it’ll have awful lows that will have her shaking in withdrawal.
Tom lives in another state. The same state Ellie’s sister lives in. Guess who is visiting her sister next week for the first time in months courtesy of Covid?
Right now, Ellie is in panic mode. She doesn’t understand what they’re doing. She doesn’t understand what he’s thinking. Why would he say this or that, what did all those things mean?
I tell her that he’s just as clueless as she is. They’re both in a runaway car with no one steering. That leaves them both at the mercy of the present and nothing else.
That’s the thing with affairs: there’s no future guarantee. Not even tomorrow. It’s the perfect exercise in living in the present because you want to savor every precious moment, never knowing when it will be your last.
Ellie bemoans his gorgeous wife and trillions of kids. “Why would he want anything to do with me, look at her, she’s stunning,” she says as she sends me a link. Yup. Been there, done that with self-comparing to the wife. Even worse is when you go down the rabbit hole of comparing yourself to his rebound girlfriend but I managed to wrangle that under control with Jon.
“First off, you’re gorgeous. Secondly, it doesn’t matter how hot she is. New Hot always trumps Old Hot. Think of all the married celebrities where the guy cheats despite having a beautiful model wife,” I tell her.
Last night, we talked about the logistics of her trip. “I don’t want to sleep with him. I think if I do that, then I’ll really hate myself.”
I replied, “Yes, you will hate yourself. Because you can never undo that and then you’re opening a whole new Pandora’s Box. But you know how to prevent that, right?”
She knows she can’t let him into her hotel room. “But what if we just watch each other masturbate?” Ellie pleads with me.
I flashed back to my pre-op session with Jon, where I had to get half-naked for him to mark up my new tummy tuck incision. You know…the location right next to a girl’s vajayjay. With him so close, I got wet. He told me that he knew that I was, which is what led his fingers in me and a porn-like scene between a doctor and his patient.
“There is no chance you can be naked, turned on, in a room with him while he’s naked and turned on, and expect him to sit in his seat.” My wisdom comes from experience. If a guy has to choose his hand or a chance at some turned-on vag, he’s going to choose the latter. “If you get in a hotel room, just know that it guaranteed will lead to sex.”
I think about it some more. “Come to think of it, regardless of how this plays out, his dick will end up in some hole on your body. It may be your ear canal, but I’m just sayin’, Tom will do everything in his power to make sure it ends up somewhere in you. If you don’t want that to happen, then you need to plan accordingly.”
Ellie sighs. We then plan out her outfits. She’s much more girly-girl than I am. I know a form-fitting top and skirt are more than plenty when you want to turn the guy on. She texts me pictures of potential outfits.
Good lord, woman. Do you need me to shop for you? These thoughts I did not repeat out loud.
I tell her that those are all good dresses when hanging out with friends, but not something that will turn him on. Since they’re just walking in the park and she’s not sure what she wants to have happen, she needs to wear a tight, low-cut top (she has fake boobs) with super tight skinny jeans. Add some knee-high boots. I then add a picture of J Lo wearing the same thing to get the idea.
“You have a waist. Stop dressing like you’re a bigger girl when you run and are in shape.”
Poor Ellie. She’s stressing about jackets. She says how everyone has long cardigan sweaters, should she buy one? “Girl, I have three. They’re what you wear when you’re cold at work. Those long cardigan jackets are the ultimate boner-killer.” I should write a How-To book at this rate.
Going through a list of jackets, she mentions a crazy cropped furry one. “THAT,” I tell her. “That’s the one you wear. If you can’t wear a crazy furry coat when seeing your hot ex-boyfriend, when else will you wear it?”
Ellie texts me this morning, still panicking over her outfits. I remembered that I made her buy the same Free People top I wore with Sean earlier this week. “I wore it with skinny jeans and no bra. Sean seemed turned on by it. That’s a solid bet. It shows a lot of skin but still is loose around the stomach area. Effortless sexy.”
I don’t know if this makes me an awful friend or a great friend. I just know how lonely it felt when I was devastated over Jon to not have anyone walk me off the ledge. This will only end badly for Ellie; she knows that, and I want to make sure I’m there for her every step of the way.
In the end, it’s her decision. I’m trying to show her both sides of all options as best as I can, based on too many years of experience.
“In the end, Ellie” I tell her, “this won’t end well. Your heart will get broken. It just depends how much more broken it will get and how long before you want that to happen.”
