Your juiciest love and sex questions answered

Threesomes, open relationships, polyamory...readers take a bite out of our burning questions on love and sex

When it comes to love and sex, experience often yields the best advice, so we asked readers to take a stab at answering all of your burning questions from whether threesomes can happen without someone feeling jealous, to the best way to introduce a fantasy or new sex position to a partner. Here are our top 10 love and sex questions answered.

Is it considered cheating on a partner if you talk to strangers online in chat rooms and social media apps?

It depends on what topics you talk about, the purpose of the communication and if your partner knows of these communications.

If it’s sexual, yes.

Yes, it’s emotional cheating, and if you’re talking to others online, your partner is just an “option.”

Probably, but either way, if you feel you need to [talk to others] you should probably reassess your current relationship.

It is considered cheating if you start to form an emotional connection, but sometimes it’s nice to flirt and feel wanted in a way that you don’t always get from a long-term partner.

It completely depends on the nature of your agreement with your partner. If you are in a strictly monogamous relationship and develop attachments to folks online, then yes. It could be considered cheating on an emotional level.

It depends. It could be as innocuous as watching porn, if you don’t plan on meeting anyone in person.

How do you bring up a fantasy you want to try or introduce a new move or sex toy with a partner?

I tell my partner I want to talk to them about our sex life and then openly and honestly bring it up and ask if it’s something they’d enjoy. I also ask them what fantasies they’d be interested in.

I introduce new moves organically in the moment. 

Find it in porn and watch it together. 

After a couple of drinks.

I’m just open about it. I find it easiest to talk about sex during or after sex.

I would do it spontaneously. Bring in the toy, try the move or suggest the fantasy in the middle of hooking up. 

How do open relationships actually work? 

I’m not sure they actually work. If you want to introduce it, just get it over with and rip the Band-Aid off, but be prepared for a number of reactions. Do your best not to be a dick about it if the reaction is not what you want to hear. Chances are, it won’t be.

Open relationships are based on responsible consent and having clear communication about feelings and what you’re looking for.

It takes very specific sorts of people. Otherwise, it generally goes poorly – for at least one of the people involved. The best way to broach the subject is calmly and honestly. Ask questions and listen. There needs to be ground rules. It can’t be a free-for-all unless that’s what you want it to be, and in that case, maybe it’s best to just break up. Be prepared [for the possibility] that your partner might feel hurt just from the mere suggestion. 

Open relationships mean different things to different people. Some view them as no commitment, while others would say there’s definitely commitment but [also] open sexual relations with others. 

Is it possible to have a threesome and not feel jealous or hurt by your partner? 

It’s possible but rare.

Every story I’ve heard of people describing their threesomes ended badly, sometimes with the relationship ending because of issues that came up.

Absolutely, if your partner hooks up with someone else in a threesome, it’s not because they’re not interested in you any more. They are simply exploring this new and exciting sexual encounter. Watching your partner pleasuring someone else can be an exhilarating and empowering experience. 

It is if the third person is a complete stranger to both you and your partner. 

What is the strangest sex you’ve ever had? 

I had sex with someone outside a furry convention.

I had sex at a sex club, and it was pretty hot having people watch us and seeing other guys masturbate to me eating my girlfriend out.

Rubbing his penis on the soles of my feet thinking it would turn me on.

I tied up my cousin when we were both 47 and did a striptease for him. He’s hated me ever since and I regret it.

The person wasn’t looking at me at all but at a candle above my head. It was strange to be completely disconnected.

I don’t consider any sex strange.

In a mud puddle behind a shack in the rain with a dude I hated. My David Bowie T-shirt was ruined because of dirt. I felt like a pig in the mud.

He talked the entire time – THE ENTIRE TIME.

I had sex with a guy who kept talking to his Amazon Alexa during foreplay, like turn on the air conditioning or dim the lights. It was the closest I’ve ever had to a threesome.


When do you know a relationship is truly over? 

When you dread seeing them or getting calls from them.

When you’re happier without them than you are with them, and their presence no longer excites you.

When the smell of them makes you sick.

When you don’t feel like you’ll ever be on the same page with goals.

When one partner cheats.

When sex stops.

When you start breaking your own rules in a relationship.

How can long-term and married couples keep sex fresh after so long together?

Shake things up by role-playing, watching porn if you’re both open to it and arriving separately on dates.

Going to sex workshops and talking about your fantasies.

If you’re truly emotionally compatible, you won’t need to “keep sex fresh.” The panties of someone in love are always wet.

Making time for dates and sex.

Butt stuff.

How many dates should you wait before having a sex? 

It can be three dates or 10. It’s when you feel comfortable. 

However many dates it takes to build up chemistry and trust.

At least three.

There’s no magic number. I’ve had sex on the first date and I’ve waited until it was an established relationship. Do what feels right in the moment.

Is it important to know how many sexual partners a significant other has had, and what’s an appropriate number? 

I don’t think it’s important but I do think it’s something every partner wants to know. There’s no appropriate number. It’s all very subjective.

It’s not something you need to know right away, but eventually. Under 20 would be nice.

It’s not important but I’d say an appropriate number is more than 10 and less than 100.

It’s more important to know about a partner’s STI and STD history.

What are some good places to meet people offline? 

Parties, bars, museums, classes, cafés, pet stores, grocery stores, social groups, coffee shops, the Queen West sidewalk, the gym, church, sporting events, libraries, the TTC, weddings, dog parks, running groups, brunch lineups, a Drake-related pop-up shop, volunteering, literally anywhere.

NOW’s interactive Love & Sex survey was brought to you by:


For more on Love & Sex check out:

More to love: how polyamorous relationships work

My first threesome: a Toronto millennial shares all the details


Brand Voices

Leave a Reply

Your email address will not be published. Required fields are marked *