You Can't Handle the Truth! Or Can You?

One thing I’ve noticed on my dating exploits is that quite frequently the topic of infidelity comes up.  Generally after some length of conversation the guys realize I’m pretty much an open book and they feel comfortable asking about my marriage to Duckie, which I think is good really.  But inevitably they ask if one of us ever cheated on the other one.

Now I’ve been trying very hard to live my life very openly and to not keep things inside or conceal the truth in any way.  But I always have to stop and think before I answer that question.  It’s scary to tell someone that I did cheat.  People react so differently to the whole topic of cheating.  And the truth is I don’t think I’d ever cheat again if I got remarried but there’s a part of me that wonders “once a cheater, always a cheater.”

So in these situations I find myself evaluating what I know about the person so far and having to make an educated guess to their reaction.  To give you the scoreboard….

Date Boy – I told him the unvarnished truth about Sawyer.  He said it wasn’t an issue but within a day when he was all obsessed with me; suddenly he wanted me to end things with Sawyer and he couldn’t stop talking about the fact that I’d had an affair and it still wasn’t over.

Toe Boy – I told him I had had an affair but left out most of the details.  He didn’t seem to care either way but then again, he was a total freak who wanted to rub my feet and have a threesome with another guy.

Kane – I told him pretty much the entire truth and he wasn’t perturbed by it; though he was pretty much just looking to hook up.  He did want to know if Sawyer would be waiting outside my door to kick his ass if he ever came over – LOL!

Lawyer Boy – Under the influence of too much alcohol, I told him I had had an affair towards the end of my marriage and that it was with my neighbor. I kept the details vague though.  He didn’t seem to care all too much though he did offer me some good legal advice on protecting myself in case I ever got busted.  FYI, he said he’d had a couple indiscretions himself while he and his wife were breaking up.

Motorcycle Man – I told him I’d made a bad decision (true) and had an affair at the end of my marriage.  He revealed that he had had many affairs on his wife.  Obviously no big deal for him but perhaps that’s why he continued to joke that I had a boyfriend due to my “availability issues?”

College Crush/High School Crush – The topic hasn’t come up yet. But it's bound to, especially with my impending date with College Crush (which I'm alternately really excited about and terrified about considering the fact the he may or may not be a total dough boy.)

The Giant – He’s actually been pretty quiet about my marriage and love life. I think he figures it doesn’t affect him so he’s not going to probe about it.  It’s bound to come up sooner or later.  In his short marriage when he was 18, his wife did cheat on him though so it’s definitely a risk to tell him anything about Sawyer.

FJB – This is the big concern.  FJB’s never been married and I get the feeling he’s a pretty straight up guy.  So far the topic hasn’t come up and I’m hoping that it doesn’t anytime soon.  I don’t want to lie to him but you can see that I’ve altered the version of truth I’ve told my various team members.

So my question for you is what and how much do you think is appropriate to tell?  Obviously it’s not really any of their business but this whole “living out loud” attempt would say I should tell the whole truth and nothing but the truth.  My gut says to acknowledge the fact that I had an affair but it was at the end of my marriage and leave it at that.  What do you suggest?

Miranda