August 19, 2017


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Cross-dressing lady pushing his buttons in public

Hey there, time traveller!
This article was published 6/6/2014 (1169 days ago), so information in it may no longer be current.

Dear Miss Lonelyhearts: My girlfriend is 46, tall, has big feet and gets a kick out of wearing my shoes and boots. If she stays over for the weekend, she annoys me by pointing it out to people who wouldn't have noticed otherwise.

She tells me not to be such a big baby and that I'm over-reacting. If I wore her high heels to a big event she would have a lot to say about it, yet she recently wore a tux and men's rental shoes to a formal dinner where she arrived on her own (on purpose) dressed in clothes identical to mine with her hair combed back like a guy. No, it was not a feminized woman's tux. What's up? She says nothing's up and I'm the one with the problem. -- Dating My Double? St. James

Dear Dating: Your girlfriend is pushing the envelope with you. There's something more to this than wearing your shoes once in a while for comfort or for a laugh. As shrinks are wont to say, "Show me a man who dresses in a fireman's suit and I'll show you someone who wants to be a fireman."

Surprising you at a event with a tux and hair combed back was forcing the issue with you in a public place. She's saying: "Accept me when I dress up like a guy in public with you, or else. Here I am, the way I want to look. Love me or leave me."

There are a certain percentage of heterosexual women who like to cross-dress, some for occasions, and some all the time. In our society, a woman can wear jeans and work boots and it's part of a full wardrobe of normal clothing for women, but your lady is making a point. It's time to have a heart-to-heart talk about it. There is also another percentage of women who are interested in playing/living a different sexual role. You have a lot to talk about.


Dear Miss Lonelyhearts: We have an anger problem where we live. My neighbour is always angry at us: he hates our cats, our friends parking on the street to visit us, our garbage bins, the state of our yard and how close we park to his truck. I also hear him shouting at his wife and kids and know he has an anger problem that stretches all over the map.

We have a chance to move because our friends are leaving for Ontario and want to sell their house. They are only two blocks away, so our kids wouldn't even have to change schools. We are thinking of moving to get away from this guy, but I hate to give in to him. What do you think? -- Stubborn Neighbour, River Heights

Dear Stubborn: Where you live and your comfort there has a bearing on your health. You can end up with high blood pressure living with a loose cannon next door. Why not move and relax into this other house nearby? But first make sure your friends who want to sell this house to you have good people on either side of them, plus nice folks in front and back. You don't want to move next to a new person whose volatile actions you cannot control.

Dear Miss Lonelyhearts: My weird ex-husband just sent a photo of us together when we were very much in love sitting on the pier at our cabin. All he sent was the photo in a brown envelope. It felt creepy. What should I do? -- Feeling Uneasy, Winnipeg

Dear Feeling Uneasy: In this case your best defence is a good offence. Instead of remaining silent and uncomfortable over the photo, get on the phone and tell him off. "I don't know what your point was by sending this photo, but it is just creepy behaviour. If you ever do anything like this again, I will call my lawyer."


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

Read more by Miss Lonelyhearts.


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