Miss Lonelyhearts
Miss Lonelyhearts
Your patience could pay off in the long run
5 minute read 2:00 AM CDTDEAR MISS LONELYHEARTS: My former girlfriend moved to Toronto at the start of April and then in mid-August married some idiot she met there — all in just under four months! It was a ridiculous move if you ask me.
I wished them luck in a sarcastic congratulatory email. She caught the dig, and wrote back, “What’s your problem? You never asked me to marry you when I was in Manitoba!”
I guess she has a point, but I’m not one to rush into things. That’s how my parents did it as well— they probably got married way too soon and didn’t get along very well afterwards, which ended up in divorce.
Also, a wedding is a big expense these days — too much for me, unless I was to take out a bank loan. The sad thing is I still love this woman and really miss her. I’d marry her if she ever came free again, no matter what it cost!
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Miss Lonelyhearts
Have dance ‘maestro’ step up before referring
4 minute read Yesterday at 2:00 AM CDTDEAR MISS LONELYHEARTS: A big handsome man recently moved in next door. He’s been chatting up both me and my girlfriend (she lives on either side of him).
His wife just arrived from B.C., and she’s delightful and fun. She says, “Don’t mind my husband, he ‘s a bit of a flirt. He knows I’ll hire someone to break his legs if I catch him actually doing anything!”
She’s already working full-time in finance downtown. He tells us he’s an experienced dance teacher and he plans to offer lessons or dance-related workouts for women in his big basement space. I told him I know a lot of women who might be interested, and now he’s asked me to put him in contact with those people.
Whoops! I feel awkward doing this — giving an almost-stranger my blessing and helping him launch his biz. I don’t really know what he’s like as a teacher. Should I help out or not?
Miss Lonelyhearts
Don’t deny kids a bedtime bond with Gran
5 minute read Monday, Sep. 14, 2026DEAR MISS LONELYHEARTS: My mother is coming to visit and our little kids want her to sleep in their bedroom, where there’s a double bed and a single. My husband thinks this idea is ridiculous and says grandma needs her sleep, but I disagree.
I remember sleeping with my grandma — who’s now with the angels — and she told us grandkids (two girls) some wonderful bedtime stories she made up herself. She even put our names into them, making us the stars of the stories.
The best part was getting into our pyjamas with our grandmother, who showed us the magic cord from the little thing that ran from her near-deaf ear down to the secret battery pocket hidden in the bra of her slip. It made her hear us better in the daytime. We thought, “Wow!”
Not surprisingly my own mother has inherited her mom’s fantastic storytelling talent and who knows what else she has to teach the kids when she’s alone with them? I want them to be close.
Miss Lonelyhearts
Nifty neighbours also jonesing for geniality
4 minute read Saturday, Sep. 12, 2026DEAR MISS LONELYHEARTS: Recently, a new couple with no children moved onto our cul de sac, and everybody is taking notice! This attractive pair with no kids both drive amazing cars, work from home and leave their garage doors up a lot. Everybody on the street walks by to sneak a peek into the big garage at just about any time of day.
Lately, the man’s been out on his front lawn in a muscle shirt in the late afternoon, planting shrubs and putting up stylish fall-themed ornaments. At night they often leave the living-room curtains open. That makes for convenient viewing for curious neighbours like us!
A few days ago, my wife invited the new couple over for a barbecue and swim in our pool. They are really nice people, but mentioned that other people nearby have been pretty stand-offish. They wonder why. Should I tell them it’s probably just jealousy over their beautiful vehicles and enviable lifestyle, or should I just shut up?
—Wanting to Help, Sage Creek
Miss Lonelyhearts
Don’t let bitterness isolate and dispirit you
4 minute read Friday, Sep. 11, 2026DEAR MISS LONELYHEARTS: I just got out of a relationship a few months ago, and I’m still so hurt that life seems unreal.
The woman I thought I was going to marry cheated on me with an old boyfriend — a real jerk, but very good-looking. I’m still feeling totally crushed.
I worry I won’t be able to trust any woman now. I know that sounds unfair, but I’ve been cheated on twice before, in just five years! I realize it might just be the type of person I’m attracted to — a bit on the wild side — but my most-recent girlfriend wasn’t like that and seemed to have her life together and knew what she wanted. But she was also secretly playing around on me — Mr. Clueless.
I can feel resentment building inside me toward all women. I really don’t want to become one of those bitter guys who ends up single for the rest of his life because they don’t trust anyone. But how do I get over this? Is it even possible or am I going to be a loser who is forever cheated on?
Miss Lonelyhearts
Scrounging bestie overdue for reality check
5 minute read Thursday, Sep. 10, 2026DEAR MISS LONELYHEARTS: I’m almost 40, and one of my closest friends who was jobless for three years is once again earning decent money again — but she’s still acting like she’s broke!
I don’t care how people spend their money, but she still expects me to pay for her. For instance, if we go out for lunch, she’ll ask if we can do a 75-25 split, with her paying the lower amount. She also comes to potlucks with nothing to share, and then has the nerve to ask to take food home. She will also ask me to cover something and promise to pay me back, but then I have to hound her for weeks to get the money!
But it really took the cake recently when we went to a concert and she asked me to cover her ticket. Then she bought two T-shirts at the merch table! It feels underhanded to me — and insulting to my intelligence. It also feels weird to have to bring it up to her. We’ve been besties since high school —many, many years ago. Please help.
— Taking Advantage, Riverbend
Miss Lonelyhearts
Forgo faceoff and augment wife’s self-esteem
4 minute read Wednesday, Sep. 9, 2026DEAR MISS LONELYHEARTS: I’m married to a woman who’s older than I am, and it’s the second marriages for both of us. She’s beautiful, even after having what she calls “a few nips and tucks.”
Seriously, it was more than a few.
Her former husband insisted she had to appear a lot younger than him — so ridiculous!
I’ve never seen even one picture of her when she was not wrinkle-free.
Miss Lonelyhearts
Time to ditch role as ex’s emotional crutch
4 minute read Tuesday, Sep. 8, 2026DEAR MISS LONELYHEARTS: I mourn the end of summer every fall, but this year it’s far worse. My partner (a man, like me) broke up with me and my menagerie of animals.
The hardest part is that he still calls me before he goes to sleep at night — to see if I’m OK, and to tell me essentially, to buck up! Nothing like losing somebody and being told to be happy about it by the exact person you’ve lost.
He goes on about his new life and the people he’s meeting, and sometimes I just have to hang up on him.
Why does he bother calling? It seems like he maybe doesn’t know if he’s completely through with me yet, so he’s using me as a crutch. (Do I sound bitter?) What can I do?
Miss Lonelyhearts
Career, domestic shake-up could bode well
4 minute read Saturday, Sep. 5, 2026DEAR MISS LONELYHEARTS: I gave a big “present” to my husband this summer and it backfired royally.
My gift? He was free to work overtime without family concerns for the whole summer, to give the big boost to his business, which he needed badly. My newly-retired parents were happy to keep us at their cottage for the summer, and have the grandkids close to them. My dad stood in as the active on-site father figure, and he loved it! This was a break I know my husband never thought he was going to get, after marrying me and having kids right away.
I thought his work dream these days was to go from a medium to a major competitor in his building field! Summer is the biggest money-making time for him, so I really wanted to support him in that.
But a major shock was waiting for me at summer’s end! My husband wants to go back to university, first part-time and later full-time. And he needs me to go back to my career! Another shock? He’s already spoken to my parents behind my back!
Miss Lonelyhearts
Don’t settle for being ‘reasonable facsimile’
4 minute read Friday, Sep. 4, 2026DEAR MISS LONELYHEARTS: I always fall in love when the leaves start turning to fall colours. But, this year I have a big problem that could get me in terrible trouble. My heart is burning for a guy I can’t have — because he used to be married to my older sister. My sister is “possessive for life” and would divorce me as a family member if I took up with him.
Still, he’s been calling me at night to talk about her and I have been giving him advice during the long calls. You know what that means — a lot of things are being said in conversation after midnight, especially when both of us have been drinking wine!
The trouble is I know deep down I’m only a substitute for my older sister. I even look like her! He was crazy about her, but he wasn’t true to her, and she can’t forgive him for that!
I understand him. It isn’t in him to be “true blue” to anyone, just like it isn’t for me, either. He can be talking about missing her and then start talking about how much I am like her — “in all the good ways, minus her bad habits.” Nothing would hurt my sister more than me messing with her ex-husband seriously. How do I get myself out of this mess? He calls me almost every night.
Miss Lonelyhearts
Reach out after communication breakdown
5 minute read Thursday, Sep. 3, 2026DEAR MISS LONELYHEARTS: I recently heard the love of my life, who got sent off to her aunt’s place in B.C. after she got pregnant, came back to Winnipeg. She lost the pregnancy early on, but her parents wanted to keep us far apart, so she had to stay on with her aunt and uncle and wasn’t allowed phone calls from guys.
Now that she’s finally back in Winnipeg again, I got her new cell number and I called her right away. She said, “You never called me after I was sent away, and I waited for your call every day. How dare you call me now?”
I said, “I didn’t have your new number, and I was scared to call your family here, for it.” She said, “You could have gotten my new number from my sister or any one of my friends if you tried! They kept asking me if you’d called yet. They said it showed you didn’t really care.”
I didn’t know what to say. I was too chicken to stand up to her family. Don’t you think she should stop being cruel to me? What can I say to her?
Miss Lonelyhearts
Jockey wisecrack a hurtful low blow
4 minute read Wednesday, Sep. 2, 2026DEAR MISS LONELYHEARTS: I ran into my boyfriend from Grade 9 at the horse races recently. He’s still really short. I said, “You’re so small you could be a great jockey!” He said, ”And you still talk before you think!”
Ouch! I was just stating what was true. If he doesn’t like being compared to a jockey, he should stay away from the racetrack, where people will mistake him for one, don’t you think?
— Hurt Feelings, St. James
Dear Hurt Feelings: It’s important not to make cracks about personal traits people are sensitive about.
Miss Lonelyhearts
Autumn need not be melancholy forever
4 minute read Tuesday, Sep. 1, 2026DEAR MISS LONELYHEARTS: Autumn is almost here (the most beautiful time of the year) but it always puts me in mind of my dearest love — a young man from my university days who died tragically in the fall, a couple decades ago. I lost him forever!
How can I get through this time, when it feels like I’ve been punched in the gut every September, and I have to stay home in bed pretending to have flu for a week or more?
— Numbing Out Again, Headingley
Dear Numb: See your physician and confess that you haven’t been able to heal this serious emotional wound. You should really book a visit to a psychiatrist, sooner rather than later, as this tragic loss from the past incapacitates you every fall. A professional therapist can help you to carefully undo these painful “knots,” and a psychiatrist would also be able to prescribe medication that could help you with the process of getting into an improved state of mind. That way, you won’t fall back into a serious state of mourning every autumn.
Miss Lonelyhearts
Times of transition can be tough to traverse
4 minute read Monday, Aug. 31, 2026DEAR MISS LONELYHEARTS: My wife has really enjoyed staying home with the kids all summer, as she is a teacher and has the two months off. Last night she was tearful at bedtime because she has to go back to the classroom and “this perfect summer together is all over.”
I told her I could afford to look after us financially if she ever wanted to quit teaching and stay home, and she blew up and said, “I love to teach and our kids won’t at be home. They’ll all be at school.” Then the tears really came. Sometimes I just can’t win. What’s up with her? Please advise.
— Willing to Help, Winnipeg
Dear Willing: The same thing that’s happened to your wife, you often see with kids at this time of year — over-excitement. It’s hard on everybody when there’s too much new stuff going on and the daily schedule is totally changing from summertime.
Miss Lonelyhearts
No kidding with comment on son’s resemblance
5 minute read Saturday, Aug. 29, 2026DEAR MISS LONELYHEARTS: I saw someone on the beach I used to love. She was with her husband, who had just gone into the water. She had several children with her, playing in the sand.
Her oldest kid looked right up at me and I said to my ex in a shocked whisper, “He looks like me!”
She replied in a whisper, “And my husband looks a lot like you, too, you idiot. My son was born two years after we broke up. He’s not yours, and you and I mean nothing to each other anymore.”
Interesting! That child had my colour of eyes and my colour of curly hair. Now what?
Miss Lonelyhearts
Size up ex interest for what it is: trouble
4 minute read Friday, Aug. 28, 2026DEAR MISS LONELYHEARTS: I spotted a familiar male figure at the beach, seeing him from behind. It had to be my old love from Grade 12. I’d know that big body anywhere. He was a football player and weightlifter — a real find in my graduation year. Why? I was five-foot-11 in heels. We were together for a few months, through graduation, but broke up shortly after. Mutual height can only get you so far.
I followed the big guy into the water at the lake, and tapped him on the shoulder. My high school ex turned around, holding a small child in his big arms. Within two minutes, his wife was suddenly at his side! I saw her wedding ring.
So much for that, or so I thought. But a few days later I got a phone call at my work, and my old love said he wanted to talk, now that there’d be no one listening in.
He went on to say how great it was to see me again, and he wanted to apologize for what an “awkward guy” he was in high school. He said he stopped calling me back then because he didn’t feel he was up to keeping someone like me interested.
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