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How to subtly ask an older man if he wants to spend some time together


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Posted

Can I be that direct or is there a subtler way that's better?!

Posted

This person is in your office right?

Why don't you talk to him over IM and see how it goes?

Posted

Your repetitive posts sound very much like the woman who was asking about the married man at work a few weeks ago.

 

And even if you're not her, why are you posting the same thing over and over? How are we supposed to know if he could like you? Clearly in your mind he does but he's shy.

Even the shyest man will ask a woman out if he likes her. You don't sound very subtle so he knows you like him.

Posted

Do NOT ask over your work IM unless you want the IT department & your boss to know. They read your IMs you know.

 

 

Have lunch with him.

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Posted

Why do you need to be subtle? You're 32 and he's in his 40's. You're not going to know until you ask.

 

You've been overthinking this for too long and it's going to drive you nuts! I've forgotten, did you determine his marital status? We've all told you workplace relationships are rarely a good idea, but you seem determined, so go for it. Would it be easy for you to find another job if you had to?

Posted

Missy - Another post about the guy in your office?

 

You want our approval - Okay, here it is.

 

Just ask him. Go for it - you know you want to and are willing to throw caution to the wind.

 

Hey Frank, Tom, Bill, etc - I was going to try that new (Whatever Food) restaurant, you should join me.

 

Then wait for his answer. He'll either tell you that will be great or tell you he's married, seeing someone, or I don't think so. Then you know, he's not interested.

 

If he says I can't today or not today but how about tomorrow , Wednesday, Friday or some other day. He's interested and you have your answer.

 

We all look forward to your next post which will either be I asked him and he said yes or I asked him and he said no and now things in the office are awkward.

 

Either way Good Luck!!

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