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Hi Alizee2007,
In my experience, men aren’t very good at picking up on subtleties.
I think you need to establish whether or not he is in a relationship before you attempt to progress. Have you talked to any other colleagues about this – is there someone you could ask (if you can’t ask him personally)?
You could mention that there is a show that you would really like to see but you have no-one to go with and ask if he’d mind escorting you. I don’t think this would sound pushy or desperate and shouldn’t jeopardize your working relationship. If he rejects your offer (because he’s busy for instance) then see what transpires. You would need to treat this as if you were going together as friends in the first place.
Some people do just “know” when they have met someone who is going to be important to them. Michael Caine saw his future wife on a television advert and went off in search. He claims that he knew he was going to marry her. It worked for him!
There is no other way here but to be brave even if it means stepping outside your comfort zone ever so slightly. The way I see this is that “it is better to have tried and failed than never to have tried at all”. What do you think?
Peggy