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The question

My wedding plans are now on hold and I don't know if it is due to my insecurity or my instincts. My man cheated on me with several women a few years ago, and I thought we were finally in a good place. I think he has been faithful. Recently, though, I saw he's still cyberstalking one of them. Why? This week I found flirty e-mails between him and a business contact. Apparently, they met and he wrote it was "really good to see you" and "PS LOVED those shoes." She went on to push for dinner, drinks, golf. I'm not sure if it happened. He became very angry at me when I confronted him, only said she has confided in him after her bitter divorce. I said it was inappropriate and an affair brewing. He told me I am creating problems that aren't there. Advice? I am mid-50s and wanted to start my life again but not with heartache.

The answer

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The problem with infidelity is once you go through that door marked "Adultery," it suddenly becomes easier to go through it again and again.

"The door's open anyway," the once-and-future adulterer/ess thinks. "Maybe I should just check it out. Not go in, of course – just nudge it open and peek in and see if there are any new presents waiting inside."

Infidelity, I've heard, works in increments – at least the first time – a cascading series of minor decisions that add up to a larger one. The adulterer/ess tells him/herself a bunch of smaller lies that ultimately add up to a big one. It tends to go something like this:

First: "I'll flirt with that cute new accountant at work, but that's it."

Then: "I'll go out after work with that accountant I've been flirting with, but only with a bunch of people around."

Next: "I'll go out solo with that accountant but I won't go up to her apartment."

Then: "I'll go up to her apartment, but just for a quick drink and then I'll leave."

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In the apartment: "Just a quick kiss, I'll let it go no further…"

And before the adulterer/ess knows what hit him/her, he/she has his/her ticket punched to "the cheating side of town."

Now, I am the offspring of parents whose marriage contained an infidelity component, so therefore have seen the pain and damage it can cause.

So I'm very careful not even to give out "the single vibe" – i.e., flirt with the hottie at the party, and always make sure to throw in a reference to my wife at the earliest appropriate occasion.

But that's perhaps a tad draconian for some. "Married not dead" people are allowed to flirt. It's pleasant to feel what one friend of mine calls "it" – that feeling that the person you're secretly attracted to is also secretly attracted to you and if you play your cards right you could be having sex with that person that very night or even afternoon. But they don't. They enjoy the frisson, but don't act on it because there's a difference between flirting and "flirting with intent."

Some people need "it." Some people live for "it." When my friend mentions "it" and I forget what "it" is, he explains and I say: "Oh, that it." And he says, like "duh": "Yes, that it. The it. That which makes life worth living!"

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But "it" can be a very dangerous drug indeed. In the case of your fiancé, who has a history of acting on "it," I would say "it" should be off the table.

Listen: I assume in order to be unfaithful, your fiancé filled the air with the blackest of lies, kind of like the way a squid fills the water with ink when it seeks to make its getaway.

And from what I've read the only true antidote to the lies that surround infidelity (like clouds that surround the summit of Kilimanjaro) is scrupulous, possibly even painful, honesty.

You have to sit your fiancé down. Say: "Listen: You lied to me and cheated on me in the past. The only way I'm going to trust you in the future is if you're not only open and honest but in fact transparent to me. I can't be finding any little flirtations on your phone or elsewhere or it's over. I don't want to catch you in stuff. I want you to tell me everything that's going on."

If he agrees to your terms, and for the foreseeable future you feel good about his behaviour, maybe go for it. And if you do decide to go for it, and you believe you can trust him, and he appears to be scrupulously honest, do not give in to the temptation to look through his e-mails and texts

But if I'm to be completely, scrupulously, even painfully honest with you? The prognosis is not good. He sounds like a weasel/snake in the grass who will ultimately cheat on you again. In your shoes I would drop him and find someone who loves you properly and would be faithful.

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Are you in a sticky situation?

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