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‘Debrief’ of hot first date will help, one way or the other

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DEAR MISS LONELYHEARTS: I’m 27. I couldn’t abide my usual rule of three dates before having sex, as I’d been single and alone all through the worst years of COVID. It was the best experience! I was thrilled about seeing my new guy again. Then he said, as he went out the door, the words of doom: “I’ll call you.” Of course, he didn’t! It’s been two weeks. Should I call him? If so, what do I say?

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Opinion

DEAR MISS LONELYHEARTS: I’m 27. I couldn’t abide my usual rule of three dates before having sex, as I’d been single and alone all through the worst years of COVID. It was the best experience! I was thrilled about seeing my new guy again. Then he said, as he went out the door, the words of doom: “I’ll call you.” Of course, he didn’t! It’s been two weeks. Should I call him? If so, what do I say?

— Embarrassed, But Wanting Him, Downtown

Dear Embarrassed: Men aren’t sole masters of the who-calls-whom game anymore. So, call and ask him out on a date — doing something outside of the house. If he refuses, say something like, “I thought we had a great time when we first met each other. Was I mistaken?”

You might be surprised what you find out. The reason he didn’t call probably wasn’t about the sex, since it was great. In fact, it might have been too good, and he can’t afford to see you again — because maybe he’s involved with somebody else. Or, you just may not be his type, beyond the physical. That certainly does not mean there’s anything wrong with you. Still, it will feel better to know your perception wasn’t off about the one date you had.

Dear Miss Lonelyhearts: I’m a mostly-shy gay man, but made a new year’s promise to myself that I’d come out further and follow my desires to “dress up” for drag nights. That includes wearing my cocktail dresses, a fur stole I own and high heels. I gave a beautiful pair to myself as a Christmas present — but my live-in man barely commented. On New Year’s Eve, I told him of my desire to explore that side of my sexuality and he said, “Really? And you expect me to escort you to events, going as a couple?”

I said, “Well, yes. That’s how it works.” He said nothing more. How do I deal with cold reticence on his part, when I need him along as my support and protection?

— Going it Alone? Wolseley

Dear Going it Alone: People have to develop at their own pace, and in their own direction. Your partner may not be ready to play the role of escort when you’re dressed up — now, or ever. You may have to find a different friend, who will be very happy to escort you.

If you feel vulnerable going out of the house dressed up and on your own, you might need to get dressed in your finery when you get to the venue. Don’t hold it against your partner that he’s not up to playing a complementary role. He can’t help how he feels any more than you can.

Dear Miss Lonelyhearts: I’m a female graduate student with an immature younger sister of 19 who lives with me while she attends the University of Winnipeg. Our folks, who live in a smaller city in the province, pay her expenses.

She hates university, is quite lonely and has not made friends. This month she announced to me she felt sick, and “might“ be pregnant by her boyfriend. She seemed kind of happy — not at all worried. Then the light came on! My sister may have found a way out.

I sense she will do anything to offload her lonely school responsibilities, and she’s always been big on having kids. I contacted her boyfriend — a nice, innocent guy — and took him out for lunch. I told him what I thought was going on. He said she’d told him of the pregnancy scare, but when he freaked out about it, she said the scare “was over already.” What should I do?

— Worried Sick, St. Boniface

Dear Worried Sick: Having a baby is definitely not the answer to her problems. You’ve warned the boyfriend, but that may not be enough. Perhaps your sister needs to go home to your parents. Call them up for a heart-to-heart talk, when your sister’s not within hearing range. Not everybody is ready for university in their late teens, and the city can be a very lonely place. She should not be shamed by anyone for dropping out.

She might be much happier living back at home with a job and old friends and relatives nearby. College classes may be offered remotely, or she could get a job through friends. As for the Winnipeg boyfriend, who seems too young to be a daddy, he may want to distance himself, at least for now.

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.

Maureen Scurfield

Maureen Scurfield
Advice columnist

Maureen Scurfield writes the Miss Lonelyhearts advice column.

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Updated on Friday, January 20, 2023 8:39 AM CST: Fixes byline

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