Read between lines of ex’s flirty missive

Hey there, time traveller!
This article was published 20/08/2022 (1501 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: I got a love letter on my birthday from an old girlfriend and I don’t know where to go with it. It was a card dropped in my mailbox with a big bear on the outside. I’m big and hairy, and she used to call me her Bear.

I’m a single guy in my early 40s. She left her new phone number, saying “Please call me!” I don’t know what to do now. It was a nasty breakup. She said I committed the worst of sins in her book — that I was “terminally boring.” That really hurt, and still does.

She must have gotten pretty bored with her own life lately to come back over to rattle my cage. It makes me kind of mad — but curious, too. What am I supposed to do?

— Still the Same Boring Guy, Fort Garry

Dear Still the Same: She probably got a kick out of imagining your surprised face when you opened her card. You’ll note there was no apology in her card — because she really isn’t sorry for hurting you.

Look, you don’t owe this ex a response! You certainly don’t need her toying with your emotions, because she has some time on her hands.

Dear Miss Lonelyhearts: I thought I was ironing my husband’s shirt when I realized it was the same azure blue he loves, but it was a woman’s blouse!

I asked him why we had a woman’s shirt in his laundry that wasn’t mine. He looked startled, but didn’t reply.

Then it dawned on me he must be cheating. I yelled, “What is going on? Are you having affair with another woman?” He said, “No, there’s just you.” I heaved a sigh of relief.

Then he said, very quietly so I almost didn’t hear, “But sometimes I wear women’s clothes.”

I looked at his closely shaven face and his beautiful eyes and the careful, layered haircut he always gets, and suddenly I could envision it. I remembered when we were first dating, I used to think: “He’s so beautiful, he should have been a girl!”

Maybe I sensed it at some level over the years, but I couldn’t consider that possibility, or my whole world would crash and burn.

Then he said, “Please don’t leave me for this! I love you and our kids so much.” It was a cry from his heart! Now what do I do?

— Totally Lost and Scared, Winnipeg

Dear Lost and Scared: You know he loves you and doesn’t want to lose you, though he has a feminine side and “dresses up.” Maybe that’s just happening at home when you’re not around, or possibly it’s with other friends who cross-dress.

What needs to happen now is a lot of truth-telling, starting with the beginning of his cross-dressing up to the present.

You love his soul and he loves yours, so you may be able to stay together, depending on what you both want and need in the end.

Ask him to share with you what he knows about himself. Perhaps he already has a private life with a circle of cross-dressing friends — maybe some you’re already acquainted with.

It’s likely he already knows about Masquerade — a local cross-dressing group with social events for themselves and partners. It is not a hook-up group. To protect folks’ privacy, they don’t publicize the location of meetings, but those interested can connect with the group through its website at masquerade.ca.

There is also the Rainbow Resource Centre, if your husband “identifies anywhere under the Rainbow umbrella or is questioning,” and you both are also welcome to access Parents, Family and Friends of Transgender Individuals (PFFoTI), as they welcome family members and partners of gender-variant people (rainbowresourcecentre.org/support/groups/pffoti).

Rainbow’s full counselling program is always an option. Your husband may already have other contacts and sources of education he can share with you.

The more information you have, the less helpless you will feel.

Dear Miss Lonelyhearts: Walking down the beach at sunset, I saw a tall man coming toward me who looked strangely familiar. We both started walking faster. In the end we laughed and had a hug. Wow! It was my old boss, from a job I once had in the music world.

Then we sat down on the beach and talked about all the musicians we knew in common, and what they were doing. The one thing I didn’t ask him was if he had a girlfriend, wife or anything!

I noticed his hands were bare of any rings. We had a great time, and stayed to watch the sunset together. Then it got kind of awkward, and we parted ways. Neither one of us talked about our love lives. I want to see him again. Help!

— Old Crush Revived, St. Boniface

Dear Crush Revived: First, you must find out his relationship status. You’d skip that move at your own peril. You may not have said anything about your own love life, or lack of it, to him either, so he may be wondering too.

Be aware that people who are someone’s former bosses may have other considerations, as there is a history of being in a position of authority. If this man is free, and you are too, it’s up to you to make that clear and make the first move.

Please send your questions and comments to lovecoach@hotmail.com or Miss Lonelyhearts c/o the Winnipeg Free Press, 1355 Mountain Ave., Winnipeg, MB, R2X 3B6.