It Happened To Me: my father taught me how to be the perfect mistress

There is so much more to being a good mistress than discretion. Philosophy and tips on executing the perfect extramarital fling.

The day Jesse James’ affair with Michelle McGee hit the news, I got a phone call from my father, who was uncharacteristically beside himself about the news. He adores Sandra Bullock, but his beef wasn’t with James’ audacity to cheat on the award-winning actress with perfect girl-next-door charm – it was with James’ complete lack of judgment in choosing a proper mistress and executing a clean extramarital affair.

Should you choose to take one, a mistress – or perhaps I should say a lover, as this applies both to men and women – must be chosen with even more care than a spouse.

“A mistress must be discreet,” he told me. She must be able to abide by what she has agreed the relationship to be, able to manage her emotions, and equally committed to keeping the affair in the vault.

I’ve never had occasion to discuss this sort of thing with my father, so I decided to take the opportunity.

“How do you ensure someone can be a ‘proper mistress’?” I asked him.

“She must have as much to lose as you,” he said.

It reminded me of something my friend Edith had once told me about her own affairs. Edith, a mother of two, has been married for eighteen years. Her marriage is “fine” and she has no interest in leaving it, though she does long for a level of passion that no longer exists at home. To meet her needs, she occasionally allows herself to take on a lover – so long as he is married and also unwilling to leave his wife.

“There are three questions you have to ask,” she told me when I called her to ask. “The first, obviously, is: do you understand what it means to have a mistress? Most men don’t and I think that’s why men tend to get caught. They get excited and forget everything. Having a mistress is not like having a girlfriend and going buck wild at a candy store. It’s having a mistress, which is a lot like becoming a CIA operative. You need a clear head and an understanding of how to compartmentalize.”

“What’s question two?”

“Two and three run along the same vein,” she said. “Two is: do you love your wife? You need an unequivocal yes. If they hesitate, you can’t do it, no matter how attracted you are. They’re on the way out if they don’t love their wife. They don’t have to be in love, but they have to love her. Love her and understand she has needs, too, that they can’t forget.”

“Because a mistress who’s an exit is no mistress at all.”

“She’s an escape chute,” Edith said. “And she’ll be burnt for it. It’s not worth it. The third question is: would you leave your wife? The more reasons they have to stay, the better.”

According to Edith, it’s easy to think that an affair is a perfect relationship – it happens inside a vacuum, after all, free of all external factors that tend to put pressure on relationships in the real world.

“Very few affairs survive the transition from secret to established relationship,” she said. “It’s because of this. People are always surprised somehow – things were so good, what happened? What happened? Reality happened. Don’t do it. The temptation will be there. Your lover will know you in a different way – maybe even a deeper way. But that’s a luxury afforded to you by the bubble you’ve made for yourselves, not an actual characteristic of the relationship.”

My father agreed.

“Whatever you’re looking for,” he said, referring to emotional connection or sexual fulfillment, “she has to understand she’s a supplement, not a replacement.”

That night, on a late run to the grocery store for snacks, I saw Maxim‘s March issue: “SEX,” read the cover. “CHEAT & DON’T GET CAUGHT. Women Tell You How.”

Timely. The piece opened with the appropriate references to Tiger Woods, Mark Sanford, and John Gosselin. “But famous men aren’t the only cheaters,” writes Gillian Telling. “According to a recent MSNBC poll, one in five people in a monogamous relationship has a side piece – and that figure includes women. Yet you never hear about female betrayal in newspapers and tabloids. Why? Because we’re better at hiding it.”

The article lists seven tips for avoiding exposure:

  1. Switch the gender
  2. Hackproof your life
  3. Be available
  4. Take it to the grave
  5. Choose wisely
  6. Don’t date your fling
  7. Don’t overcompensate

I don’t know how feasible item six is on that list, knowing how many people cheat because they’re lacking emotional connection and passion, but I am in agreement in that emotional involvement does cloud one’s judgment and complicates matters.

“You might fall in love,” Edith said. “You can’t help it. You can’t stop it. What you have to understand is that you have to let it be just that. That’s why choosing someone who knows how to manage his emotions and can compartmentalize is so important. They have to be ready to love without possessing. And so do you. I told you what you need to ask someone to see if they’re a good match as a lover, but the most important question you have to ask is of yourself: do you have what it takes to satisfy your cravings in a precise and measured way so you don’t bring your home and everything in it crashing down? Tread with care.”