sex diaries

The Montreal Guy Sleeping With Two Girls From His Book Club

Photo-Illustration: James Gallagher

This week, a man pines for this therapist while wondering if his French lover is about to leave him: 29, single, Montreal.


6 a.m. Rolling in and out of sleep while cuddling with A. Mornings are my favorite time with her. Everything seems less harsh in the morning light. She starts rubbing my chest, and I start to breathe heavily. This is usually all it takes to initiate morning sex. I love when she gets on top and curses at me in French.

8:30 a.m. We’re still lying in bed cuddling and drifting in and out of sleep when A gets a message from her boyfriend back in Nice. They’ve been together eight years and known each other for 16. She tried breaking up with him two years ago, when she moved here, but as she puts it, he’s part of her “architecture.” I didn’t know she had a boyfriend until the morning after our first night together, when she started bawling her eyes out. In the four months since, I still don’t know (or want to know) his name. He does not know about me.

9 a.m. A has just returned from the washroom and is super-pissed that I’ve left a hickey on her neck. Not even the side of her neck, either. She has a right to be upset … What are we, in high school again? I don’t even remember giving it to her. I make moves to leave; I can tell she needs to be alone, but my anxiety is through the roof. Thankfully, I’m getting on my bicycle, which is my ultimate stress reliever.

11 a.m. I stop off at Le Main — Montreal’s best smoked-meat joint. I’m about to indulge in my other stress reliever: eating. The guilt I’m about to feel over this will be immense as I haven’t eaten meat since March. I’ve been in a terrible head space over the situation with A, and I have a feeling it’s coming to an end. I love her, though I know I’m not in love. She’s brilliant and beautiful in many ways, but the status quo simply isn’t sustainable. And I’m not about to let her shatter her architecture. Not that she wants to anyway.

8 p.m. My day has been nothing but sheer gluttony. A pound of smoked meat is not meant to be inhaled that quickly. I’m going to destroy my body and distract my mind tomorrow with cardio. Is it weird that I haven’t showered yet and love that lingering smell of sex?


8:03 a.m. I’ve hit the snooze button every nine minutes since 7 a.m.

9 p.m. Finished up a five-mile run along the Lachine Canal. Heading to the rooftop pool at my bougie condo for some laps.

11 a.m. Sign in to work in my kitchen. My job is super–laid back and essentially involves account management for high-priority assholes. When it rains it pours; mainly I do nothing but skim sub-Reddits and listen to podcasts.

Noon Sign off and decide to do an hour bike ride up Olmsted Trail on Mont-Royal. Unfortunately, I’m absolutely one of the asshole bikers detested by pedestrians and cars alike. I’m not stupid on my bike; just reckless. It’s residue left over from my yearish as a bike courier, though the hard-core couriers here would scoff at me as a papillon (butterfly) considering I never made it through a full winter. Fuck that — if you think New York winters are bad, try trekking up here in February.

1 p.m. Survived another adventure weaving in and out of traffic. Had my sunglasses on and my headphones in as usual so I can ignore the world. Trying not to think about the fact that I haven’t heard from A. We’ve been seeing each other for four months and haven’t really gone much longer than a day without talking. This doesn’t bode well.

10 p.m. I fall asleep listening to the most recent premium podcast from Chapo Trap House. Best $5 a month I spend.


8 a.m. Wake up to texts from A and J. We all met in a reading group I started back in March. Two goals before I hit the big 3-0: finally stop being that guy who keeps classics on his bookshelf only as pretentious, dusty ornaments and see if I can go a year without eating meat. I’m failing at both.
Texting back and forth with both girls at the same time. Feeling vaguely sociopathic considering that neither one of them knows about the other, even though they’ve met before. At least J doesn’t have a boyfriend — this situation seems complicated enough as it is. Fairly certain that this whole charade is going to fall apart sooner rather than later. Plan to meet up with J tonight.

5 p.m. Insane day at work but managed to sneak in a bike ride. I get it, I bike like an asshole, but if I make a mistake, I’m the one who’s dead. When drivers do, it’s someone else. That’s the difference.

10 p.m. Great night with J. She’s relatively vanilla (it’s hard to top the French), but she’s sweet and innocent and a total science nerd. She’s getting her master’s in civil engineering but doesn’t flaunt it. She gives surprisingly excellent head for such a wholesome Albertan blonde. We don’t take it farther than that tonight.


11 a.m. I sleep past ten for the first time in months but it’s going to be a long Sunday Fun Day. My friends from Toronto and San Francisco are in for a music festival, our first in two years!

1 p.m. I’m feeling like an absolute degenerate. My friends are railing lines of coke and molly off my glass table, and I just washed down a handful of shrooms with some dépanneur wine. I’m kind of over all the harder drugs. I’m old, I’m washed up, I’m over the hill. Really I just can’t take the comedowns anymore.

8:45 p.m. Festival is the usual debauchery. My anxiety feels off the charts at times, but I love my Cali friends, so that helped a lot. Plus the people watching is great, like the two girls making out while dancing on top of a water fountain — or was it all just some seriously good shrooms and an overactive imagination?

11 p.m. Singing old Blink-182 songs a cappella with strangers and friends alike in the over-crowded Metro. “What’s my age again?”


7 a.m. My friends and I stumble in from the after-hours, which is actually relatively early, considering. I don’t know how I made it that long with no stimulants. Someone grab a shovel and bury me right here.

7:30 a.m. Thank God I scheduled a therapy session for today.

Noon Scratch that. Thank you, Montreal, for bottomless mimosa brunches.

3 p.m. Can’t say this is the first therapy session I won’t be sober at.

4 p.m. Before you judge, yes, I’m a walking cliché. My therapist is beautiful in that girl-next-door sort of way. I’m aware it’s all transference. But today seemed different. I had thought I’d seen her while biking through Parc Lafontaine one day but didn’t acknowledge it. Today, on my way out after the session, she blurted out, “I saw you.” It seemed kind of flirty to me, but I’m definitely reading too much into it.

9:15 p.m. Pass out after masturbating to fantasies of fucking my therapist on her couch.


11 a.m. Catch up on some sleep. Try not to think about A, whom I’ve barely heard from.

1 p.m. My friends from Cali had their flight overbooked, so good ol’ Air Canada paid for their flight, hotel, and gave them $1,600 to stay an extra day. What to do with free money and excess drugs?

3 p.m. We take our shrooms and money and decide to spend the day on a spa boat in the Vieux Port. When we first arrived, I thought our drug use was a mistake until I realized the majority of people were messed up on some sort of substance.

10 p.m. Today was perhaps the most bougie, amazingly relaxing day I’ve had in years. Nothing but thongs, laughter, and steamy sauna serenity.


10 a.m. I wake up fully relaxed until I realize that tomorrow all my selfish decisions will likely come back to bite me in the ass. I’m hosting a potluck for the reading group, and I have a bad feeling that having both women in proximity to my bed will not end up like one of my fantasies …
I’ve only had one threesome before with my male roommate and our favorite bartender (female), and I’m not looking to get back on that horse, though I imagine (have imagined) a FMF threesome would be better.

5 p.m. Spent the entire day dealing with pain-in-the-ass clients and worrying about the potluck.

7 p.m. I dropped $150 on that Headspace app and have barely touched it. My therapist highly recommends meditation, and A keeps dragging me to yoga, back when I was hanging out with her. I really don’t know what’s happening there.

Everyone keeps preaching the power of now, but all I do is worry about tomorrow. The only time I seem to be able to live in the moment is when I’m inside someone. Speaking of which, I think I just heard my phone ping.

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The Montreal Guy Sleeping With Two Girls From His Book Club