My 50 year old boss is having a midlife crisis - and I have a crush on him?

by Work Girl
(Georgia)

The Question

Here we go:

I am 30, and my boss is 50. We are both very successful in our company; in fact, my boss recruited me, and I have been working with him for almost two years now. But now that he is my immediate supervisor, I spend even more time with him.

Let me say that I am ostensibly happily married, which is going to make this sound weird. But I am infatuated with my boss. I had a crush on him early on, but now I think about him daily and even fantasize about having an affair with him or starting a relationship. Mind you, I have never cheated before, and everything looks fine in my life on the outside. But I am a little bored with my marriage and a little depressed about my job because it isn't what I thought it would be. Maybe I am the one having a midlife crisis at 30!

Anyway, my boss told me about six months ago in passing that he was having a midlife crisis, but I didn't think much of it.

He has accepted a new job in a suburb of the city we live in, so he will be going through some major changes. But until then, we work together for the next three months.

So here's the thing. I now think my boss is flirting with me. But it sounds to me like he correctly diagnosed himself: he's changing his job, moving out of the house he's lived in for 20 years, and the last of his three children (I'm nine years older than his oldest) are moving out. A lot of changes. And I've met his wife, and she and I are nothing alike.

I am the one who initiated chatting with him online twice the last week, and I'm also the one who ended the conversations. He prolongs them.

What should I do? I fantasize about having an affair with this man or having a proper relationship. Is he doing the same? And can anything proper come out of this? Do these relationships EVER work?

Noel's response

It is entirely possible he is fantasizing about having an affair, or 'proper relationship' with you, as you are with him. That does not mean it would be a good idea, or that it would last, especially if he is in a midlife transition.

Men and women in transitions are not in their normal state emotionally, and are prone to projecting onto others (in this case you would be the mythical 'Helen of Troy' in his psyche), when what they need to do is discover that part within themselves.

The kind of relationship you fantasize about does work occasionally, but more often does not. When the 'honeymoon period' in the new relationship ends, the people involved discover their new 'wonderful partner' is just a normal human being.

My suggestion is that you admit to yourself that you are infatuated with this man, as you seem to be doing, and simply live with the feeling, which will eventually pass. His midlife transition will end, and chances are he will look back at it and wonder what it was all about.

You might also reflect on what it was about your husband that attracted you to him. You may find that if you put your focus back on him, and treat him the way you did in the beginning, he might respond very favourably, and you marriage will no longer be boring.