Each year, the Free Press publishes more than 1,000 letters to Miss Lonelyhearts and her responses to the life and relationship questions that come her way.
Please send your questions and comments to email@example.com or Miss Lonelyhearts c/o the Winnipeg Free Press, 1355 Mountain Ave., Winnipeg, MB, R2X 3B6.
Recent articles of Miss Lonelyhearts
Time for sober second thought over reformed ex5 minute read Preview Updated: Yesterday at 7:56 AM CDT
DEAR MISS LONELYHEARTS: I can’t believe it! My love is alive again for my former husband, but I already have a new man.
Jealous, bullying ex has already crossed the line4 minute read Preview Sunday, Mar. 19, 2023
DEAR MISS LONELYHEARTS: My recent ex-husband left a horrible letter in my mailbox. He called me filthy names for starting to date someone he knows right after our divorce.
Stick to your own tune with personal style4 minute read Preview Sunday, Mar. 12, 2023
DEAR MISS LONELYHEARTS: My girlfriend saw the Elvis movie with her girlfriends, and now she wants me to get my long hair cut into a “pompadour” like his. She says lots of guys are doing it now. Oh yeah? I haven’t seen one in Winnipeg yet. I also refuse to wear eye makeup which she has asked me to do when we go out to bars. She has volunteered to put it on for me.
There’s no sneaky subtext to post-cinema candour5 minute read Preview Friday, Mar. 10, 2023
DEAR MISS LONELYHEARTS: My wife asked me if it’d be alright with me if she went to see a movie near her office with somebody from out of town who’s helping with the special project she’s working on.
You walk a dangerous tightrope with button-pusher4 minute read Preview Sunday, Mar. 5, 2023
DEAR MISS LONELYHEARTS: My new girlfriend treats people around her like she’s the Queen doling out her favours. She has a reputation I’m well aware of — treating men like servants. It seems I’m the exception these days. In fact, she treats me like gold, and I’ve never had it so good, in bed or out.
Take things at a natural pace this time around4 minute read Preview Sunday, Feb. 26, 2023
DEAR MISS LONELYHEARTS: I lost my female friend I’d been engaged to for many years. Last spring, I finally gave in to pressure from family and friends and bought her a diamond ring — and I paid a lot for it. I still made no move to marry her, though. I was previously married and divorced, before dating her, so I felt I’d “been there, done that.”
Close ‘hotel’ to defend family from bully in-law5 minute read Preview Tuesday, Feb. 21, 2023
DEAR MISS LONELYHEARTS: My mother-in-law regularly drives to Winnipeg with her gambling buddies to go to the casino. Instead of kicking in her share for the hotel, she insists on staying at our house, and saving her cash for gambling. I hate it! She’s rude, boastful, aggressive and manipulative — especially when she’s been drinking.
If she truly matters to you, park your own judgment5 minute read Preview Monday, Feb. 20, 2023
DEAR MISS LONELYHEARTS: I’ve started hooking up with a girl who’s a bit too scary to be introduced to my parents. I come from a large, well-off, somewhat traditional family. I have siblings who are with their soul mates, and two are already settled down with kids. I’m the middle child, pushing 30 and feeling a ton of pressure any time I bring a woman home to meet my family.
Persistent nocturnal paeans point to buried angst4 minute read Preview Sunday, Feb. 19, 2023
DEAR MISS LONELYHEARTS: My erotic dreams are getting me in trouble with my new husband. Lately, I’ve been dreaming about a Parisian lover from my travelling days. Unfortunately, I’ve been murmuring my sensual pet name for him in my sleep — La Tour Eiffel. My French paramour used to find that name sexy and highly amusing.
Future bond calls for severing some links to past4 minute read Preview Sunday, Feb. 12, 2023
DEAR MISS LONELYHEARTS: I’ve made a big effort to stay friends with all my old boyfriends. I often get phone calls from my exes to see how I’m doing around Valentine’s Day. Two years ago I got a live-in boyfriend, and he really doesn’t appreciate these calls.
Reassuring words may quell discord over musical turn5 minute read Preview Sunday, Jan. 29, 2023
DEAR MISS LONELYHEARTS: I bought myself a bass guitar for Christmas and I’m in love with it. This month I started learning to play, and my wife has started being totally sarcastic. She’s making fun of me, saying things like, “You really think you’re going to be a musician?” or “You’re too old for this. Are you feeling a mid-life crisis coming on?”
Don’t lose any more time with narcissistic user5 minute read Preview Monday, Jan. 23, 2023
DEAR MISS LONELYHEARTS: My boyfriend deserves a kick in the butt. He tricks his family into helping him do things he should hire people for by giving them a big sob story about his lack of money. Then he brags to me about it, saying what suckers they are for falling for his stories.
Wait for empty nest before branching out sexually4 minute read Preview Sunday, Jan. 22, 2023
DEAR MISS LONELYHEARTS: My wife and I are both bisexual, which was working well for us many years ago.
Don’t kiss marriage goodbye over drunken new-year antics5 minute read Preview Sunday, Jan. 15, 2023
DEAR MISS LONELYHEARTS: My husband and I went to our first New Year’s party since the pandemic started, and it was a disaster! At midnight, my guy went missing, so I went looking for him to collect my New Year’s kiss. I caught him in the freezing-cold back porch, and this red-haired witch was kissing his face off! They were both drunk. Unfortunately for her, so was I!
Ex-husband’s flowery missive a manipulative move6 minute read Preview Sunday, Jan. 8, 2023
DEAR MISS LONELYHEARTS: I received an unwelcome note under my front door from my ex-husband, asking me to take him back “in the name of all that’s good and right and honourable, and for the sake of our beautiful young children.”
Enlist grandkids for some spirited holiday cleanup6 minute read Preview Monday, Jan. 2, 2023
DEAR MISS LONELYHEARTS: I’m a grandfather and I love my family, but the holidays this year felt like my wife and I spent a lot of time and effort — only to have family take advantage. We celebrate Hanukkah, and this is a special time for us to be together with our children and their children, but when we host the dinner and do most of the cooking, they up and leave, without even offering to clean up and help with dishes.
Risqué resolutions seem to bode well for new year5 minute read Preview Friday, Dec. 30, 2022
DEAR MISS LONELYHEARTS: I’ve decided to make a New Year’s resolution to have more fun in 2023, starting with eating more indulgent desserts, and researching jokes to be able to tell more of them! l’m a 42-year-old guy with a 38-year-old wife, and I have a tendency to be too serious. We also have two young school-age kids.
Calling Mom before drop-in could warm things up5 minute read Preview Saturday, Dec. 24, 2022
DEAR READERS: Christmas and Hanukkah are here along with drifts of sparkling snow — clogging up all the lanes! But have you noticed this quirky change? Nobody’s seriously complaining about weather anymore. They just shrug their shoulders and say, “It’s only weather!” The pandemic quickly showed us what real trouble can be.
Be careful what you ask for regarding romantic future5 minute read Preview Sunday, Dec. 18, 2022
DEAR MISS LONELYHEARTS: I’m 26, and really want a proposal and an engagement ring for Christmas, but I don’t know if my boyfriend is going to give me that.
Pessimistic view of younger generations misplaced4 minute read Preview Friday, Dec. 16, 2022
DEAR MISS LONELYHEARTS: Too bad “Worried Great-Grandmother” doesn’t get out and to see what’s happening in this city and province. She thinks recent generations are self-centred and addicted to electronics.
Call things even, dispense with the game-playing5 minute read Preview Monday, Dec. 12, 2022
DEAR MISS LONELYHEARTS: I was clearing out the basement storage room and thought I’d accidentally found a Christmas gift for me, from my young husband. It was in a gift box, no wrapping yet. I couldn’t help myself from peeking. It was something I’d never want in a million years — athletic workout clothing. Yuck!
Atone for hair ‘joke’ with sincere show of affection5 minute read Preview Sunday, Dec. 4, 2022
DEAR MISS LONELYHEARTS: My wife is a born-again hippie.
Busted double play makes for very bad hair day4 minute read Preview Tuesday, Nov. 29, 2022
DEAR MISS LONELYHEARTS: I have a hair fetish. But, I recently got “too lucky” if there is such a thing. I started seeing two women with the perfectly coloured, very long hair.
Abetting buddy’s two-timing reveals shady side4 minute read Preview Sunday, Nov. 27, 2022
DEAR MISS LONELYHEARTS: My boyfriend recently helped his best friend cover up an affair, and I am so grossed out after learning of his part in that. My guy doesn’t think it’s a big deal, because, as he says: “I’d never do that to you, and I want you to know that.”