He Went On a Date and Didn’t Tell Me. Why Didn’t He Want Me to Know?

Dr. Wendy Walsh
Dr. Wendy Walsh Updated:
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Reader Question:

There is a man, Scott, at my work. He recently had his divorce finalized. We talked about the possibility of letting things happen, but I realized since we work together we aren’t allowed to date.

I also encouraged him to be single since he has been in a relationship since he was 18. He is in his late 20s and I am in my earlier 30s.

I figured out he went on a date. I made a comment about who he is smitten with. He commented he didn’t want a certain person to know. I said me and he said yes. He seems to like this girl.

Why didn’t he want me to know he went out on a date?

-Marie (Illinois)

Dr. Wendy Walsh’s Answer:

Dear Marie,

Let me get this straight: You have a crush on a co-worker who is newly divorced.

You have stopped yourself from really letting him know you are interested in him because of a workplace rule against personal relationships between employees and because you worry he will abandon you if he doesn’t sow some wild oats before settling down again.

Add to this the fact you are older and have a fertility window to consider if you plan to become a mother. (The height of female fertility is the age of 20.)

And now that you’ve gotten wind he is dating, you are a little jealous and don’t know what to do at this point.

Do you really want to know why he didn’t want you to know about his date? That’s simple.

It’s because he didn’t want to hurt your feelings. And he wouldn’t be concerned with your feelings if he didn’t care about you.

But the bigger question is how do you flirt with him and invite an advance from him if the whole thing is illegal at work?

My suggestion is to talk to him about it. Of course, men like to do the chasing and really hate to hunt in a zoo, so you’ve got to be coy.

Use lots of eye contact instead of words. Or maybe say something like, “I wonder if we’d like each other if we didn’t work together.” Then smile and walk off.

Of course, if he does pursue you, you two have to address how to deal with the workplace rule. One of you may have to go job hunting if you decide to take your relationship to the next level.

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