Love your column, appreciate your straight up advice and am seeking it here:

I am 50-year old healthy, established linens importer and a divorced heterosexual male who for five years has been dating and loving a 32-year old beautiful, smart and sexy, successful businesswoman who likes to be pampered, appreciated and supported in her burgeoning career, which I deliver on all counts. I am very domestic and happy in my role as “wife.” Dinner is always ready when she is home, I keep up with the laundry and am always game to run errands when needed. We are great travel buddies, love each other’s company and have an amazing sex life. We role play in the bedroom and put on costumes and make videos together. In life she likes to be the boss and always in control but in the bedroom she likes to be told she has been a bad girl and told what to do.

When we met she was juggling an affair with an older married man and an old high school flame while getting her business of the ground. I was immediately attracted and we started dating. After a few months I made it clear that I wanted a monogamous relationship and she concurred. After an incredible 18 months together I broke it off when I found out she was seeing someone else on the side and hiding it from me. Over the next three months she begged me to take her back and I was consistent in saying no. At first she tried convincing me that if guys my age want to date hot girls her age then we have to put up with generational differences: sleepovers at guys houses as “friends” for example. I reminded her and myself that I wanted monogamy and eventually she said what she wants that too, that she was done spending nights out partying with the guys, and that she wants me and only me. We got back together.

Our second, equally wonderful, 18-month run end when I came home from a family reunion at Thanksgiving and found out that she had been sleeping with an employee—a friend and former lover with whom she had a secret relationship prior to meeting me and had only recently hired. It sickened me knowing that they had been sleeping together. I frequently interacted with him and they both they acted like nothing was going on. Shadow affairs are frightening to me and I vowed to stay away.

The rest of this epic question—and my response—after the jump.

Four months later, after dating two other women, neither of whom got me as excited as her, we got back together. It was an amazing reunion. I had been spending my time working out for a marathon and she had been getting in touch with her spiritual side, had stopped drinking, and was working on designing and opening a second location for her business in another city. I stood by her side as her emotional and domestic support as she expanded her growing empire. She got a small apartment in the second city near and hired her old employee—the one with whom she had an affair—to run it day-to-day. He was butt-hurt, she said, that I had won and "got the girl" over him and she convinced me that I had nothing to worry about. I was at first leery but just got over it as we continued to elevate the parts of our relationship that worked so well—sex, companionship, travel.

It’s been almost two years back together and just yesterday I found out she had been sleeping on the side with the same employee for the past six months. I broke it off and we had an adult conversation about it.
She says this is who she is, that I know this, and that everyone is a package deal and that I need to learn to love her for all her aspects. She said this is who we are, that we break up every 18 months and come back together stronger than ever. And that’s okay she said. She says she has the ability to love more than one person at a time but in different ways and that what we have is the most meaningful relationship she has ever had and she does not want to give me up. She was adamant in saying that there is nothing wrong with deceit and that I must have known what was going on anyhow and that I should read Dan Savage.

I said I do read Dan Savage and that those couples that choose to have additional partners do so based on mutual consent, which is quite different than one partner doing so in deceit. She argues that it is no different and that I knew what she was doing anyhow. I said whether I lied to myself, or she deceived me, it’s the same thing and I made it clear that I cannot do it, that I cannot maintain the role as the primary love and most meaningful relationship while she continues to have other lovers on the side, secret or not. Is that what you want, I asked her? She said she is about to expand her empire and that all she knows is that she wants me by her side.

She put her arms around me, and asked me to hold her, saying we still need to love one another. I took her arms off me and said I can’t, that I will try to be her friend but cannot be physical with her. She cried and before leaving said that the most special and most appreciated she has ever felt was when I took her back last time and that she wants to feel that way all the time. I said she needs to find someone else for that role and that I am done. She said sorry she is a flirt and sorry that I am attracted to it and left.

She has since emailed that the relationship with the employee was ending on its own because it wasn’t worth it, that she is sorry for her deceit, she knows we cannot have a relationship built on it and that even though we may not be together we still need to love each other. She wrote she is sorry she is not the person I need and deserve, that she loves me and misses me.

I know it’s her open invitation to have it whenever I want it, or to sign on for more of the same. But the thought of being with her right now knowing she is with her employee is physically revolting to me. Though I admit I am not above watching videos we made and masturbating.

I am more convinced then ever that I won’t go back this time, though I know she expects I will. In fact, I want nothing to do with this woman ever again. She is not good to me and not good for me. My quesitons:

1. Deception is wrong; it’s a form of abuse, right?

2. While I am physically sickened and angry by the thought of her with this other man, I am equally mad at myself. Did I know? Did I look the other way?

3. Are there generational or age differences here? Do people grow up and out of having multiple partners? Or do some people, regardless of gender or age, simply have the ability and desire for keeping shadow relationships while others, myself included, don’t?

4. Why am I attracted to this addictive cycle and will I stay away from repeating it? Were the videos all I really wanted?

Cuckolded Three Times And No One To Blame But Myself

I recall reading something at the start of your letter about how this woman was fucking two other men when you met her. And she continued to fuck those other two guys over the first few months that you were dating her, right? She fucked those other two guys until you insisted on a exclusive relationship? And wasn't one of those other two guys married or something?

Forgive me if my memory is a little fuzzy, CTTANOTBBM, but I started reading your letter back in October of last year and only just finished it and I don't have the time or the inclination to go back and re-read the whole thing. But this woman was fucking two men when you met her and has cheated on you twice (three times?) over the course of your relationship. (And not to pour poison in your ear, but... those are just the times you know about.) Seems to me that if you're not willing to be this woman's "primary love and most meaningful relationship" while she fucks other guys on the side, front, and back, then you cannot be with this woman. The end. Fin. Roll credits. Lights up. Please exit the theater now. Check under your seat for any belongings you may have dropped. Get the fuck out.

But in answer to your questions...

1. Deception is wrong. Usually. A relationship is not a deposition... by which I mean to say: You're not under oath and you don't have to answer to every question truthfully. No relationship would last longer than a week if every question was answered truthfully. But while honesty gets all the praise—it's the best policy, right?—there are times when a lie is the kindest and most loving option. But there's a difference between, say, deceiving someone about whether or not they look fat in those jeans* and deceiving someone about whether or not you're capable of being monogamous. Lying about a brief, ill-advised, much-regretted affair can also be the loving thing to do. But carrying on multiple affairs behind the back of a partner to whom you've made an exclusive sexual commitment is not permissible, excusable, forgivable, etceterable deception. It is CPOS territory. (Please tell your ex not to hide behind me. While I do sometimes give people permission to cheat, CTTANOTBBM, it's a relatively rare occurrence. You can tell your ex that I view her as a CPOS ("cheating piece of shit"), not a disciple.)

2. Pick one, CTTANOTBBM: You knew and looked the other way or you're a fucking idiot. She started a new business in another city, got an apartment in that city, and re-hired the person she cheated on you with in the city where you both live and moved him to that new city. Hello?

3. Some people want monogamous relationships, some people don't. Some people are honest, some people aren't. Some people date idiots, some people are idiots. Age has nothing to do with any of it.

4. Will you stay away from her? I dunno. She's being honest with you—she is now—and she's made it clear that she wants to be with you but that she's always going to have other lovers. If that's a price you're willing to pay in order to make some new videos, CTTANOTBBM, pay it without complaint. If it's not a price you're willing to pay, walk the fuck away. Yes, yes: you ruled out getting back together, CTTANOTBBM, but you wouldn't be writing to me (or wanking to those old videos) if you weren't at least tempted. But don't take her back on the condition that she be faithful. Because she won't be. Ever. She's incapable of it. You know that now, you should've known it then, and I'm warning you: a monogamous commitment made to you under duress, i.e. as a condition of getting back together, will be violated in less time than it would take this woman to read your letter to me aloud.

* A cliché example, yes, but a non-gendered one! I'm always asking Terry if I look fat in these jeans! And he deceives me! And I love him for it!