'Chatted With A Guy Online. The Shock? He's My Boss'

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Last updated on: July 25, 2025 12:12 IST

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rediffGURU Kanchan Rai explains how to deal with an awkward situation and the emotional mess when your secret online relationship unexpectedly collides with your real life.

I fell for a stranger. He's my boss in real life

Illustration: Dominic Xavier/Rediff

A fake identity. A real relationship.

A life-altering revelation.

What do you do when you realise you have built your deepest connection on a lie?

rediffGURU Kanchan Rai, therapist and founder of Let Us Talk Foundation, explains how to deal with an awkward situation when your secret online relationship unexpectedly collides with your real life.

  • You can post your relationship questions to rediffGURU Kanchan Rai HERE.

Anonymous: I am in an awkward position. I am 34, single. I have been chatting under a false identity with a guy who is cute and charming.
In the last two years, we got really close where he told me a lot of things about his personal life, how he was coping with an ugly divorce and politics at work.
Without realising we helped each other get better in our lives.
In fact, he has been my greatest cheerleader, pushing me to do better at work, even get a promotion.
While he has been honest about his intentions, I have never shared my real name.
I got the shock of my life, when he sent me his recent picture.
This guy turned out to be my current boss!
It can't be a coincidence, right?
I feel so wrong to have led him on. Now I can't even send him a picture! Or should I just send it?
He is in his early 50s and I am pretty junior to him at work.
Will he think I manipulated him?
Ever since I have known that I am dating my boss, I have been avoiding him.
I have also noticed that he is distant and stressed at work.
I feel guilty. What should I do?
It's been two weeks and I have kind of ghosted him, he is worried sick and wants to know if I am alright.
He texts me almost every day and night.
He thinks I don't like him because of how he looks. But I don't have the courage to tell him that I was talking to him pretending to be someone else while we worked in the same office.
How do I explain this without hurting both of us?

The longer you avoid the situation, the more painful it will become for both of you.

Ghosting him may feel like self-protection but, to him, it's abandonment, especially after the emotional bond you both have developed.

More than anything, that silence feeds his worst fear: that he is unlovable.

So, what can you do?

You begin with honesty, not by confessing everything at once, but by taking responsibility gently.

You can say something like: 'There's something very difficult I need to share because I value the connection we've had and the kindness you've shown me.

'When we first started talking, I didn't expect it to mean so much. I used a different name and didn't realise who you really were until recently.

'That discovery shocked me, and I've been scared -- of your reaction, of mine, of the consequences. But I also feel immense guilt, because the connection was real for me. You've been someone I admire deeply and I didn't want to disrespect or mislead you.'

This is not about asking him to forgive you or continue anything. This is about closing the gap between who you were and who you are now -- with courage, clarity and care.

He may feel betrayed.

He may take time to process it.

He may even need space.

But you will have done the right thing by coming clean.

And regardless of what happens next -- whether the connection continues or not -- you will walk away knowing that you chose truth over fear.

Also, give yourself grace. You're human.

We all make decisions that seem easier in the moment but become difficult to carry later.

What matters now is how you handle the truth -- not just for him, but for your own growth and peace.

  • You can post your relationship questions to rediffGURU Kanchan Rai HERE.

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