Dear Libby: I’ve Made A Huge Mistake

Dear Libby,

I travel a lot for work, so I’m away from home a good portion of the year. I love my wife and kids, but it gets really lonely on the road. Even though I usually travel with a coworker, I’ve never been that close with any of them. We don’t really hang out outside of work functions, so I’m alone in my room or when I go out to explore whatever city I’m in.

Recently, my boss paired me with a new hire he wants me to train. She’s young, beautiful, and a lot of fun to be around. I think we both realized pretty quickly that we have crazy chemistry together. She’s always down for doing non-work stuff, which has made traveling so much more fun. She’s also in a similar situation to me, so we understand what the other is going through.

Four months ago, we went to Dallas for a conference. After our work obligations were done, we hit the town to check out their nightlife. We saw some really great bands and drank waaaaay too much. The night ended with the two of us in bed together. Even though we’d flirted a lot and make a lot of dirty jokes with each other, this was the first time we really crossed the line.

I’ll spare you the details, but it was an incredible night. She made me feel things I’ve never felt with my wife. She told me she felt the same way. Our connection is like a raging inferno while it’s a BIC lighter with our spouses. We agreed that it’s something we both want to continue, but we don’t want to leave our families to be together. Traveling for work has become something we’re excited for instead of dreading, and it just seems to get better every time we do it.

But I think I’ve made a huge mistake. When my boss asked me to review her performance, I couldn’t stop raving about how incredible she is. He was so impressed with my review that he decided to promote her. That means she won’t be joining me on any work trips, and she’ll have to relocate to work out of a different branch of the company. Basically, it’ll be next to impossible for us to see each other anymore.

Is there any way I can take back what I told my boss without screwing up her career? I thought about telling him that even though she’s showing a lot of promise, she still needs a bit more training until she’s ready for the promotion. I know he hasn’t talked to her about it yet, so she won’t have to know about if I can convince my boss to let her keep traveling with me for a while longer.

I’m just worried he’ll see it as her not being a good fit for the company if he thinks she still hasn’t learned what she needs to after all this time training with me. The last time I trained someone who still wasn’t ready after four months ended with the guy being fired. I really don’t want to get her fired, especially since it’s so hard to find a job in our industry. What should I do to fix my mistake? Is it even possible to fix?

The Traveling Man


Dear “The Traveling Man,”

You really loused this up for yourself, huh? I’m sure you knew going in that your time with this woman wouldn’t last very long. The whole point of training is to prepare the person to move on with their career. If you tell your boss she’s not ready, he might see it as a reflection of your poor mentoring skills and have her go train with someone else instead.

Here’s the thing, though—you travel a lot for work. Unless your wife has some connection to your company, I assume she pretty much takes your word for it when you say you have to go out of town for a conference. The solution to your problem seems deliciously simple: arrange to meet with your sidepiece in some random city and say you’re going there for your job.

Now you can have your cake and eat it, too. It means spending more time on the road, but based on what you said about your relationship with your sidepiece, that won’t be an issue. Of course, even this can’t go on indefinitely. At some point, you’re going to have to decide whether you want to be with your wife or your sidepiece. It’d be nice if you could just have both permanently, but that would require a level of cooperation and understanding from both women that I doubt is possible.

We’ve all had to make a choice like that at some point. You have kids, and it sounds like your sidepiece has kids, too. That complicates things in a way I never had to deal with. If you and your sidepiece decide to ditch your families to be together, they’ll still remain a specter haunting your new relationship. While you could always just ignore them, most people frown upon that sort of thing.

For now, arrange your meetups with your sidepiece and enjoy it while it lasts. Even a raging inferno will eventually burn out. I’ve always found these sorts of things lose their luster after a while. As long as you and your sidepiece have kept your lives completely separate, it should be easy to end it cleanly once it has run its course. Sure, you’ll have to go back to your boring life with your boring family, but that’s what you get for your lack of foresight. Maybe next time don’t marry a BIC lighter.

Lovingly, Libby

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