Use this search feature to quickly find the information you're looking for.

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

by Work Girl

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.

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

Click here to add your own comments

Mar 02, 2012
by: Anonymous

I'm going through something very similar. I'm almost 30, he is in his 50's and my former boss until he was laid off. He was my hiring manager and he was very successful and well respected. I wanted to make him proud always and somehow it turned to an infatuation. It's been 3 years since he left the company and I think he is struggling to get back into the job market, but we'd keep in touch via email once every couple months or so and I always accept when he wants to catch up over lunch. Our email and lunch conversations are always safe topics but my mind totally gets consumed by him whenever I hear from him. When I see him I always ask myself why the fantasies since he is going through a prolong depression. Part of me wants to see him like he was at the company and seeing him like this breaks my heart... So perhaps I'm justifying my interaction by being a friend to a someone who is in pain. The fantasies are great but I know so obviously that it won't work. I love what I have with my boyfriend and he is married too. I'm sure if I was his wife, I'd hate that he'd write and have lunches with another woman. I think I respect our friendship more and like the person above, i'd like to see him as a good friend 20 years from now. I don't won't to ruin anyone's lives so I'm anxiously hoping that these feelings will pass...

Feb 05, 2011
You are just bored
by: Anonymous

Something similar happened to me, although I was happy in my job. An older colleague, of the age of my Dad, seemed to be IT. He was wonderful, witty, intellectual and courteous. To me. Probably less so at home.

Guess what? I looked at my Dad, who was a great man but we at home saw him as he was, "warts and all". I never admitted my crush to my colleague and we remained great friends for over 30 years. I did not ruin my marriage. My husband was just slightly older than me and certainly didn't have my friend's maturity.

Now, with a hindsight, I know it was the best thing to do. Not just for the other people involved, for me too. I am now 50 something and my friend has very sadly passed away.

A girlfriend of mine, who has many male friends, says that a friendship lasts longer than a .... .
Consider this man a friend, don't chat him up, just be nice. Your reward will be greater that way! Trust me.

After all, you said it yourself. You are bored. That is not a reason to play with another person's life. You said he is going through lots of changes, he doesn't need another one. If/when he hits MLC, that's going to be big enough!

Again, trust me. I am being the "standing partner" in one right now with someone of about your age pulling at my husband's strings! Back off! I beg you.

Click here to add your own comments

Join in and write your own page! It's easy to do. How? Simply click here to return to Ask Noel.