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Janitor shouldn't mess up sticky situation at school

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Dear Miss Lonleyhearts: I'm madly in love with the most unsuitable woman in the world. She is the principal at our school. I'm a caretaker there and it isn't even possible that she's going to look my way. You would laugh if you saw me getting ready for school every day. I get cleaned up, dressed up and wear cologne. She seems to like me but she doesn't make flirty eyes at me. She is divorced and I am free, too. I am about eight years younger than she is.

Should I make a move, and if so, what kind of a move? She is a sophisticated, well-educated, fun woman. I just adore her from afar. I am a creative person who works at the school to support my musical and artistic activities. I could call myself a fancy name but I am really... -- Just the Caretaker, Winnipeg


Dear Caretaker: Worship her from afar for now as there is still a lot left of this school year to be uncomfortable, especially if she doesn't appreciate your making a move towards her romantically. You can compliment her if she's wearing a new outfit, or ask her advice on things as an excuse to talk, but your best bet is to become friends and see what happens, making no moves towards her. Just see what happens. She may like you and come after you, or totally ignore your friendship attempts. That's the chance you have to take -- unless you change schools.


Dear Miss Lonelyhearts: This is for Unsure, Fort Garry, who suspects an affair "across the way" in the neighbourhood. Coincidentally, I saw the same mysterious woman (reported by Unsure as coming out of a house with wet hair). I was taking the garbage to the street that night and came to the same conclusion that there may be an affair going on.

I do know the family, and have met their siblings and good friends over the years. I am also familiar with the cars that they drive. The mystery woman is not one of them. It's no secret that the husband and wife's relationship has been rocky, so it's easy to make assumptions that satisfy a bored mind. I agree with Miss Lonelyhearts: let it go and stop snooping on the neighbours (all of us). -- Sure, Fort Richmond


Dear Sure: It's not up to a casual neighbour who is not an intimate friend to make a report to a spouse who may be betrayed -- not even a note in the mailbox. Added to the embarrassment would be the feeling that the whole neighbourhood is gossiping. So I say, let this couple sort it out themselves. You never know if the "poor wife" is having her own affair at work or somewhere else.

When I used to do face-to-face counselling it was amazing how many of the couples who were no longer sleeping together both had something going on outside the marriage, but only one got caught and the other one looked like the innocent victim to the end.


Please send your questions or comments c/o or mail letters to Miss Lonelyhearts c/o Winnipeg Free Press, 1355 Mountain Ave.,

Winnipeg, MB, R2X 3B6

Republished from the Winnipeg Free Press print edition February 21, 2014 D4

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