I think I’m falling in love with a younger woman at work

Tell Me About It: If I were to ask her out I would likely be perceived as a pervert


I am a man in my early 50s, I have been more or less single all my life, I have had several casual relationships over the years. But I have never really wished to be in a long-term partnership.

In the past five years, I have not had any relationships whatsoever. I have had a great life; I own my own home, am in a position where I can take months off work at a time to travel extensively.  I don’t see myself as lonely and greatly enjoy my own company. I think I am quite popular among my peers who have long accepted me as a lifelong singleton. About six months ago a beautiful young lady has joined the team that I lead at work. She is 30 years of age, we have spent a lot of time in each other’s company and her energy and sense of humour is infectious.

I so look forward to seeing her that I recently cancelled a trip abroad. I think I may be falling in love. This is not a feeling that I have really had in several decades. We did share a kiss about a month ago and I feel that she may be attracted to me. But if I were to ask her out and perhaps start a relationship, I would feel like a dirty old man, and am likely to be perceived as a pervert.

It may risk my position of authority at work. I also feel that I risk having my heart broken.


I am interested in the language that you use: pervert and dirty old man. You are in your early 50s and are hardly old or lecherous. You sound like someone who is happy in their own skin and who has a rich and enjoyable life.

The woman in your workplace is 30 and no doubt is capable of making her own choices in terms of who she dates or chooses to be her life partner. It seems that there is already an acknowledgement of attraction in that you two have kissed but the next move is one that you will have to make.

  The difficulty here is vulnerability. If you declare yourself, the people at work or your peers might judge you; they might be jealous of you or they might support you.

All relationships require risk and this is perhaps how desire works: it gets us to reach out to another and be brave enough to risk rejection. Without desire, we would no doubt stay safe in our lives and the world would be a poorer place for it.

  It seems that you have created a life that you love and being in a relationship would challenge this comfort. This is one of the functions of a relationship: to make us generous, less selfish and to sacrifice our own desires for that of another; in other words it is a developmental stage for us as human beings.

There is also no guarantee that the other person will continue to choose us but we know that to willingly engage in this risk will stretch us too, and maybe beyond our limits.

Relationships at work are challenging, yet this is where many people fall in love. We can discover that we are in love rather than have our list of attributes ticked off before we actually meet someone. What younger people tend to do is ask someone else to intervene to check out if their advances might be welcome as a way of staving off potential embarrassment or awkwardness.

The braver and perhaps more adult action is to be upfront, ask the person for coffee and declare yourself. Allow the other person the right to say no; to take their time considering or to say yes. These are not the actions of a pervert but of someone who is able to speak honestly and who respects another person’s right to their own response.

If there is awkwardness following a disclosure, behave in a way that matches your principles: be respectful, be honest about your hurt and know that exercising courage will contribute to your life.

But rejection is a tough burden on us and we might need support from friends and some healing time for ourselves. I wonder if the fact that you have not had a relationship for five years means that this fear of rejection plays a big role in your life and if so it might now deny you an opportunity for something special.

The question is whether to stay with the security of a good and pleasing life or to take the risk of an uncertain but possibly fabulous relationship. It seems that the choice is in front of you right now and making a decision is required and if possible to follow it wholeheartedly.