Don’t settle for so-so time in the sack with new relationship

Hey there, time traveller!
This article was published 22/04/2021 (1951 days ago), so information in it may no longer be current.

Dear Miss Lonelyhearts: I’ve been online dating for the past 10 weeks and it’s been magical.

The single man I met right off the top, in his early 40s, is everything I’ve ever wanted. He has a very successful and fulfilling career, he’s very kind and thoughtful, and he has the best sense of humour.

With both of us working from home, we decided to self-isolate for two weeks, then meet at my place for the weekend. We’ve met for six weekends now. When he arrives he brings dinner, a bottle of wine, a huge bouquet of flowers and a beautiful gift.

These were the most memorable dates ever of my life. The conversation and laughter never ended. You’d think I’d be in heaven! Yet, I’m so conflicted.

He’s such a great catch in all other areas, but not in the lovemaking department. His kissing and lovemaking leave me frustrated. I tried gently showing him what I liked, and nothing has improved.

He always seems to peak after a respectable time, but I never do. I finally have to fake it, even though orgasm has never been a problem for me in past relationships.

He recently said he’d like to make “us” permanent. I don’t know if I could be with someone who doesn’t know how to satisfy me physically.

Is there any way to help him, without humiliating him? Or should I just be happy with all the other areas of my life where he satisfies me, or would I end up regretting that? — Missing that Magical Orgasm, River Park South

Dear Missing That ‘O’: Turn things around. How long would a handsome prince hang around if he could never feel turned on enough with you and had to fake his own orgasms? Not very long.

Men can and do fake orgasms if they’re tired or if things have gone on too long, and they’re worried about the woman being uncomfortable. But, like you, they wouldn’t want a lifetime of it.

“Making do” with a guy’s lacklustre sexual performance after trying to teach him moves you like is not going to work for you in the long run.

Most likely you don’t share the same internal drama. Do you want to be staring deeply into each other’s eyes murmuring words of love or would you prefer naughty chatter? Are you looking for a scene you haven’t had the nerve to confess because it’s so early in the game?

If you just hate to lose him, give it one or two more weekends — where you throw away caution and tell him exactly what you want in a fantasy lover.

If these revelations show you two simply don’t set fire to each other, then set each other free to find better mates.

Why the hurry to do that? Because he’s acting like a man who’s seriously hunting for a wife. Why hinder him — and you? Once he’s gone, you could look for a more natural mate for yourself, too.

 

Dear Miss Lonelyhearts: My girlfriend’s always daring me to do things to prove I love her.

She thinks it’s funny I like to wear flannel pyjamas in the cold weather. So, after we had some “refreshments” last week, she dared me to go out in the cold wearing my PJs and a short jacket, buy her cigarettes at a convenience store on the corner and bring her the bill as proof. And I did!

This weekend I dared her to go outside bare naked underneath her full-length coat and boots, buy me some ice cream and bring me the bill, and she did it… but too easily!

I need to up the ante and don’t know what other daring things there are to do. What now? — Restless, Daring Pair, Fort Rouge

Dear Daring: The old game of Truth or Dare is great dating entertainment, but not for the faint of heart. The rules are easy — players must truthfully answer the question they are asked, or perform the dare they are given instead!

Lucky for you daredevils, the internet is full of lists of Truth or Dare questions.

Note: The “truth” questions run the chance of hurting the other person or making them jealous, as they often delve into past dating experience, so some people skip that option and go straight to dares.

For instance, you can dare each other with harmless but crazy things like, “Grab a marker, run into the bathroom and draw a moustache on yourself and show me!”

If a dare feels wrong or too dangerous, you can opt for a different one, accept a funny punishment activity or just end the game for the night and do something else. It’s only meant to be fun, so just enjoy it!

 

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.