15 Ways to Take Yourself on a Date During COVID Times

Pictured drinking a martini on the roadside patio at the Queen & Beaver.

I’m a long-standing proponent of the self-date, but a pandemic is not exactly the best time to go on one, to say the least. Just because you’re by yourself doesn’t automatically mean you’re self-isolating to a medically appropriate degree, y’know?

We all have our own unique lifestyles, financial situations, and risk tolerance levels in these scary times, so I know not all of these suggestions will work for you, whether due to geographic limitations, immunosuppression, anxiety, money, or any other factors. But here are some ideas for self-dates in pandemic times. Take what works for you (and what doesn’t terrify you) and leave the rest.

For the purposes of this post, let’s assume that ALL of the following activities will be performed while wearing a mask (if applicable – there are a few where it wouldn’t make sense, like those involving eating or drinking), staying several feet away from anyone you encounter, avoiding touching things as much as possible, washing your hands whenever you can, and using hand sanitizer as needed. Okay? Okay.

Go on a really long walk. This has become one of my sanity-saving measures in COVID times. It gets you outside, it gets your body moving, but it doesn’t necessarily require you to interact with anyone or endanger anyone, including yourself. Load up your phone with podcasts that make you laugh or music that makes you smile, slather yourself in sunscreen, try not to get too frustrated when the warm air emerging from your mask fogs up your sunglasses, and enjoy the day as best you can.

Read a book somewhere pretty. I’m fortunate to live within walking distance of Toronto’s harborfront; I’m sure there’s somewhere idyllic near you, even if it’s just the tiny dog park across the street. Bring a blanket so you don’t have to worry about sitting on mud, etc.

Talk on the phone from an unfamiliar location. Okay, this is more of a friend-date (or date-date) than a self-date, but you’re still physically by yourself so it kinda counts! If there’s someone you miss and are dying to talk to, you may as well do it in a locale more exciting than the house/apartment/room you’ve been trapped in for months. Take your phone (and maybe a hands-free headset situation) to a park, or a lake, or a quiet alley.

Do a selfie photoshoot in public. I can already hear you yelling that this would be embarrassing and strange. I know. That’s kind of the point of this one. We live in an era when social norms are breaking down because the world is kinda breaking down. You might as well tote a selfie stick to a place with a good backdrop and take some goofy shots of yourself in your mask et al. You can think of it as a historical document you’re creating so future sociologists will see what these times were like – or it can just be something you look back on in a couple years and (hopefully) think, “Thank god that’s over.” Bonus points if you do your makeup for the occasion (albeit only on the parts of your face that’ll be visible!).

Pick up a to-go meal from your favorite restaurant, if it’s still in operation (womp womp). This is a good excuse to go on a journey, and is also fancier and more self-care-y than just heating up another frozen burrito in your microwave. (No? Just me?)

Deliver food or gifts to someone you love. You don’t have to get anywhere near them to do this; you can just leave it on their stoop or in their mailbox, and text or call to let them know. Probably your isolated elderly great-aunt could use some toilet paper or your best friend would appreciate some basil from your herb garden.

Assign yourself a scavenger hunt. Go for a walk and… take a photo of every pink thing you see? Try to walk along 5 streets you’ve never set foot on before? Bird-watch? People-watch (from afar)? There’s always something to see, if you’re looking.

Arrange a movie night for yourself. Go all out: pick two films that work well as a double feature, plan your menu (even if it’s just popcorn and a beer), ask your friends to watch along with you if you feel like it, and settle in for a nice night of entertainment.

Be near water. If there are no oceans or lakes or rivers or streams or ponds within walking distance of you, maybe there’s an outdoor fountain or a mostly-closed wading pool or somesuch. Clementine Morrigan says being near water is good for calming your nervous system and I am inclined to agree.

Visit a significant (outdoor) place from your past, like a neighborhood you used to live in or a park where you had your first kiss. Take your journal, if you’re that way inclined, and write about how the place makes you feel and what memories it brings up.

Learn to make a new meal/drink/treat. Have you ever tried to do this with a partner? It can be wonderfully silly and fun, and there’s no reason you can’t have that same type of experience solo. The internet is full of recipes for delicious delicacies, beautiful baked goods, and top-notch tipples. Best of all, you’ll have something yummy to show for your travails when you’re done.

Take a decadent bath. Who says dates have to involve leaving your house? You can jazz up a bath (or even a languorous shower) with all sorts of goodies: beautifully-scented body wash, Epsom salts, candles, hot oil hair treatments… or just bring a waterproof sex toy in with you and call it a day!

Buy a new sex toy. A lot of sex shops are offering curbside pickup now, and they need your financial support more than ever – so if you have the means, why not buy yourself a pleasurable treat? Then take it home and seduce yourself…!

Go geocaching. I’ve never done this but it seems like a relatively low-risk thing to do these days as long as you stick to little-trafficked areas and thoroughly sanitize anything you take home with you. Here’s a video where Justin McElroy explains how to geocache.

Eat/drink on a patio. Many people still have very mixed feelings about doing this, which is very reasonable, and I wouldn’t blame you for wanting to skip this one. Where I am, in Toronto, patio tables have to be properly distanced from each other, waitstaff have to get your info on file for contact-tracing, and masks and hand sanitizer are everywhere – so I feel pretty safe sitting down for a drink or a small meal at local places I hope don’t go under. Bring a book or other diversion, be polite as hell to the staff (they have it rough right now), and tip generously.

 

How have you been romancing yourself and going on self-dates in these difficult times? Or what would you like to be doing?

How to Take Yourself on a Date

I’m an introvert in a long-distance relationship, and I work from home. This all means that I spend a lot of time alone. For me, that doesn’t just mean sitting around at home: sometimes it means taking myself out. For as long as I can remember, I’ve enjoyed solo outings – though, as I’m occasionally reminded when someone gives me a weird look, not everyone is as comfortable with the notion of the self-date.

However, if you’re introverted or single or otherwise relegated to frequent solitude, I think it’s imperative to make your alone time not only as frequent as you want but also as special as you want! So here are some of my best tips for taking yourself on a date…

Psych yourself up. It can be hard to drag yourself to a traditional date activity, like dinner or a movie, on your own if you think people are going to judge you for it. So just remind yourself that no one really pays that much attention to strangers in public, and people do this kind of thing all the time. Get hyped for your outing: put it in your calendar, plan it out, make it something you look forward to, just as you might with a “regular” date.

Pick an activity you love, even if other people might not. Some of my favorite solo dates are dinner, going to see a movie, or attending a comedy show. Sometimes the restaurants, movies, or shows I pick are ones I like but that other people might find strange (oysters and a documentary about an obscure queer icon, anyone?). That’s the beauty of a date with yourself: your input on the activity is the only input that matters! So pick something you adore, and if potential companions might turn up their nose at it, well, so much the better.

Make getting ready a ritual. I often think of getting dressed for dates as a sort of magic spell. I’m adorning myself in totems and trappings that make me feel confident and beautiful: a cute dress, kickass boots, pretty lipstick. This process builds excitement about the date for me in an almost Pavlovian way, so I don’t skip it even if no one else is going on the date with me! This little bit of extra effort could help you elevate a sad, perfunctory night alone into a celebratory occasion.

Bring a diversion of some kind. I always have a book (or my Kindle) with me when I go on a solo date. I also usually bring my journal and a pen, and my phone with some podcasts loaded onto it. While it would absolutely be a power move to eat dinner alone while simply looking around and enjoying the atmosphere of the restaurant, that’s not something I’m interested in doing – it makes me feel awkward, and I get bored. A book can entertain and captivate me in the same way that another person would, if they were sitting across from me at dinner.

Spoil yourself. I know I’m guilty of often thinking I don’t “deserve” nice things, especially if I’m by myself on a mundane Tuesday night or somesuch. But you deserve that extra mile. Sometimes this can be a pricey thing, like a trip to your local fancy cocktail bar or a decadent multi-course meal, but it doesn’t have to be – it could be as simple as adding an extra apple pie to your McDonald’s order, springing for extra butter on your popcorn, or bringing a plush blanket to the park so you don’t have to sit on the damp grass. You’re worth it, baby!

Take photos. We live in an age when it often seems that something only really happened if there are pictures of it on the internet. While this has its pros and cons, the benefit of photographing and sharing aspects of your solo date is that it may help legitimize it in your mind. When you put your meal on Instagram or text a patio selfie to your best friend, you’re saying, “This is nice and deserves to be remembered.” And hell, sometimes those moments can be perfectly Instagrammable!

Stay open to adventure. Many times while on solo dates, I’ve gotten into an interesting conversation with the stranger next to me, or discovered a new hangout I didn’t know about, or tried a new-to-me food and loved it. A beautiful thing about being alone is that you can follow your own impulses; you don’t have to check with someone else first to see if they’re on board. So if you find yourself wandering into a shop with an eyecatching window display, or considering a weird-sounding cocktail on the menu, go with that gut feeling – it could lead you somewhere lovely.

End on a high note. If I skip this step, I often end up wallowing in loneliness, so it’s important to deliberately plan an uplifting ending for your solo date. Mine often involves listening to a comedy podcast on my walk home, or watching something funny on Netflix once I get there. If I’m really absorbed in my book while I’m out, I might continue reading it once I get into bed. Ah, bliss.

Do you ever take yourself on dates? What do you like to do/where do you like to go?

Date Diaries: Montreal

Montreal is a beautiful city that I love. I’ve only been there a handful of times, but each time, I’ve fallen in love all over again with the bilingualism, the cultural flair, the low rents compared to Toronto (!), the beautiful restaurants and cafés. It’s a city I would love to live in, if my French were a little sharper.

My partner and I spent a week in Montreal recently, and he’s the type to seek out the absolute best places on Foursquare whenever we go anywhere new, so I got to experience a lot of MTL highlights. Here are some spots I think you should check out if you and your beloved(s) ever set foot in this city…

Toqué!

If you’re looking for fine food and great wine, this spot is a must-do. Their foie gras is absolutely divine, and I loved their duck. Their dishes are plated meticulously and artfully – “tweezified,” as my partner says. We were also charmed by how they brought over a portable hook to our table for me to hang my bag from!

Onoir

This was a recommendation from Rae and Piph, whose tastes I trust, so we knew we had to check it out. It’s a restaurant where you eat in COMPLETE DARKNESS. The waitstaff are all blind, and once you’ve been briefed on the protocol of the place and chosen your menu selections, they lead you into a pitch-black room as you cling to their shoulder with one hand. Then they bring you food and drink, bumping each dish or glass into your shoulder so you can take it and place it on the table in front of you, hoping against hope that you won’t lose it once you’ve set it down.

It was an absolutely wild experience having dinner across from someone I’ve had many dinners with but being unable to see him, or my food. It completely changed the way I experienced the meal, and the date. Certainly it gave me more empathy for the blind (though, notably, not all blind people think the restaurant is a great idea), and it also amped up my appreciation for the taste and texture of my food. However, by the end of the meal, my partner and I were starting to panic a little; we wanted to get back to our lit-up, visible world! I’ll always remember shouting our waiter’s name – “MAURICE!” – as we sat together in the dark, frozen in fear but also giggling in glee…

La Finca

This sweet little café was less than a block away from the hotel we stayed at, so we went here several times, and it was great every time. Great coffee, great baked goods, great vibe.

Boho

The classy and tropical vibe of this cocktail bar makes it feel like someplace Don Draper might go while vacationing in Hawaii. And my drink was served in a plastic pineapple, so I don’t know what else you could want from an establishment, really.

Le Cartet

Hard to go past this place for fancy breakfast/brunch! I ordered a big skillet full of eggs, bacon, sausage, ham, and toast – pretty much everything I could want from a breakfast – and a big ol’ maple latte. (When in Québec, consume as much maple stuff as possible. You gotta.)

Le Mal Nécessaire

While my boyfriend tells me this isn’t technically a tiki bar because we didn’t see any tikis, they do have a tiki-ish vibe and you can order a cocktail served in a full-size pineapple, so there’s that. I loved the atmosphere in this cute little underground bar.

Bagel, Etc.

Leonard Cohen supposedly hung out here a lot when he lived in Montreal. It’s an eclectically-decorated restaurant known for its breakfast and brunch offerings. I love to get a big breakfast special here – eggs, bacon, the works – with an obligatory locally-made bagel. Divine.

La Grande Roue de Montreal

If you think Ferris wheels are at all romantic or exciting, this one’s worth a visit. You get a fantastic view of the city, plus you get to walk along the lovely waterfront to get there. You’ll be placed in groups of 8 for the ride, so it’s not the most intimate experience, but it’s still nice nonetheless.

Moishes

This steakhouse obviously does steak quite well; their shrimp cocktail is also great and our meal came with GIANT PICKLES that delighted me to no end. Also, can confirm that Moishes leftovers hold up: the day after our dinner here, I shoveled cold steak and potatoes into my face while sitting in our hotel bed and they were honestly still delightful.

Olive et Gourmando

I’m still daydreaming about the sweet ricotta dish at this sweet brunch spot in historic Old Montreal. They also had fantastic fresh-squeezed orange juice, and staff who were attentive and (frankly) attractive as hell. We will definitely go back here next time we’re in MTL.

Dominion Square Tavern

This unassuming gastropub ranks among the best cocktail spots in Montreal, which I felt doubtful about until I actually tried one of their drinks. Their “Gin & Mint” – actually just a Southside, my fave, with lemon juice – was blissful, and they do a super-boozy “Canadian Old Fashioned” that led to some good sloshed conversations at their cozy bar. I bet their food is great too, but we didn’t try any.

Divine Chocolatier

If artisanal chocolate is your jam (so to speak), you gotta check out this little chocolate shop. Their truffles are adorable little bites of perfection, and their “secret bar” is intriguingly delicious. (I asked “What makes it a ‘secret’ bar?” and the owner smiled mysteriously and told me, “It’s a secret.”)

Belon

This oyster bar was a block from our hotel, and boy, were we glad. It’s spacious and sophisticated, with a fully-stocked bar and – of course – amazing oysters, with all the fixins. We were feeling indulgent and had two dozen – whoops.

Au Pied de Cochon

This very, very French spot has some weird-yet-delicious items on their menu. I got a squid ink risotto – definitely one of the strangest things I’ve ever eaten or even seen at a restaurant – and my partner got this odd “duck in a can” dish. The portions were big and the atmosphere was jovial. I mean, how can you not love a place that’ll serve you champagne and a jet-black risotto that “tastes like the sea”?

Café Olimpico

This Mile End spot is known for its excellent coffee. It’s also the spot where author Sean Michaels (my cousin) wrote his Giller Prize-winning novel Us Conductors, which I love, so I’m biased. Get an allongé and a biscotti and soak up the atmosphere.

Montreal Improv

Montreal has a robust improv comedy scene, and this theatre offers shows in both English and French. If you can see anything featuring their director, Marc Rowland, absolutely do – I’m a total improv snob and have rarely laughed so hard at a show as I did watching him do a longform set at Sunday Sunday.

The Coldroom

You have to ring a bell at a mysteriously blank door and wait to be let into this secretive underground cocktail bar, but it’s worth the rigamarole. They can make you any classic cocktail, as well as several drinks from their in-house menu. I’ve ordered a Southside at nearly every bar I’ve visited in Canada and the U.S. over the past year and a half, and the one a bartender made me here was one of my all-time faves.

Atwater Cocktail Club

Another must-visit if you love cocktails, especially classics. The bartenders here are skilled and personable – ours took the time to learn our names, and chatted with us in between bringing us stellar drinks (the margarita I had here was one of my fave drinks of the whole trip). It’s a bit tricky to find the entrance of this place, hidden away between two buildings, but it’s worth sleuthing out.

L’Express

This place is just a good old-fashioned classy French restaurant, complete with charmingly cordial waiters, an epic wine menu, and a killer cacio e pepe that rivals the ones I had in Italy. Their desserts are particularly magnificent.

 

Do you have favorite date spots in Montreal?

Date Diaries: Towers, Oysters, & Amorous Nights

Hi! Welcome to something new I’m trying, Date Diaries, a feature where I’ll write about dates I go on. I’m revisiting a week I spent with my partner in Toronto back in December, for our first anniversary…

On Matt’s first night back in town, I went to meet him at the airport, which has become a tradition for us. We have a protocol whereby I have to ask him, prior to his takeoff, what he’d like me to bring him at the airport – food, gum, coffee, whatever – and then meet him in the arrivals area. It’s exciting, getting to see him at the earliest possible moment, rather than waiting for him to Uber to my apartment like I used to.

On this day – December 12th – I subwayed across town to Pearson Airport in the west end from a psychiatrist appointment in the east end, trying to read my Kindle on the train but failing because I was too excited to concentrate. Once we found each other in arrivals, we took a car back to my place, ~reconnected~ with some sex-‘n’-kink, and then were faced with the question of where to go for dinner.

This always happens. Usually he gets in late, because air travel is a chaotic nightmare, and by the time we’re settled and ready to eat, many restaurants have closed their kitchens. So it’s become a tradition of sorts for us to go to Bar Isabel on those first Toronto nights, because their kitchen is open until at least midnight (bless them, bless them all). It’s one of the best-reviewed restaurants in the city, and for good reason: the ambiance is chill and romantic, the tapas-style menu is impeccable, the cocktails are swell, and the servers are top-notch.

As the clock ticked over to 12:00AM of the next day – December 13th, our anniversary – I tweeted about how happy I was to have spent a year with such a wonderful person, and we toasted to our relationship, our love, and our future. Aww.

What I wore: I was feeling romantic so I put on the dress I was wearing the day that we met, one year previous. It’s a black and red floral-print fit-and-flare dress I got at H&M god knows how many years ago. I also wore my collar, of course.

What we ordered: We usually get the punch when we go to Bar Isabel; I think this time we got the “fancy punch,” which contains liquors, citruses, teas, herbs, and bubbly wine (they change up the specific ingredients on a night-to-night basis), because we were celebrating! We ate oysters, bread, manchego cheese, shishito peppers, and grilled octopus. Divine.


My boyf is an over-the-top romantic, making him a good match for someone like me who is sentimental as fuck and also likes to write about dates she goes on (hiii). For our anniversary, he surprised me by taking me to one of the fanciest and most tourist-y places you can go for dinner in Toronto: the 360 Restaurant at the top of the CN Tower. As we were walking to the elevator that would take us up to the restaurant, we were bustled into a photography area where they snapped some cheesy pictures of us in front of a green screen – hence the adorable watermarked monstrosity you see above.

The whole conceit of the 360 Restaurant is that you get the best possible view of Toronto, and the entire restaurant rotates slowly, so you get to see all the way around over the course of your meal. I hadn’t been up there since my mom took me to an opening-night party for The Lion King back when she was working as an entertainment reporter more than a decade ago, so it was cool to go back, especially with someone I love so much.

After dinner, we checked out the famous glass floor and then cabbed to Civil Liberties for a nightcap before heading home. Ideal date night!

What I wore: Sir told me weeks beforehand that if I planned on buying a new dress for our anniversary, he wanted it to be blue and shiny/sparkly in some way – which, honestly, knowing me, it would’ve been anyway. I trawled the local mall all day, trying on several unsatisfactory contenders, before finally landing on this $17 pale blue velvet spaghetti-strap dress from Forever 21. I wore it with black tights, my collar, a black cashmere cardigan, and the gorgeous blue Coach bag Matt had just given me as an anniversary gift. The suit he’s wearing, by the way, is the same one he wore on our second date; aww.

What we ordered: We split a dozen oysters and I thiiink I had roasted salmon with risotto on the side. And, as per usual, we drank excellent cocktails, though I can’t remember what they were. I was pretty focused on the cute boy across the table from me!


Sir introduced me to La Banane and it’s become one of our favorite Toronto dinner spots. The food and service are both absolutely incredible. I feel like a queen every time we go here.

After dinner, we rounded out our evening by going to see Hook-Up at the Bad Dog Theatre (their hilarious and often quite romantic runaway hit) and stopping by Civil Liberties again for more cocktails. Three of our very favorite things in one night – amazing!

What I wore: This dress is one of Sir’s faves in my wardrobe so he chose it for our fancy night out; it’s a form-fitting, low-cut, navy velvet dress with an asymmetric hem. I bought it at Forever 21 when I briefly had a sugar daddy, envisioning wearing it on elegant dates with him, though that plan never came to pass! This time I paired it with black tights, a black cashmere cardigan, my collar, and my new Coach bag again.

What we ordered: Our appetizers were oysters again (we’re so predictable) and seared foie gras with hazelnuts and a little cup of wine on the side. I had their duck breast entrée (soooo tender and good) and Sir had the Eurobass. My fave cocktail here is the Penicillin; I don’t normally like smoky Scotch but this drink blends it with lemon, ginger, and honey, making it much more palatable. Toward the end of the meal, the restaurant staff had to re-seat us to make room for a big group that was coming in, and they sent over two glasses of amaro on the house for our trouble (my first time ever trying amaro!). Sooo fuckin’ classy.

Been on any date you’ve especially loved lately?

5 Ways to Play with D/s on a Dinner Date

Doing kink stuff in public is a hotly debated practice. Some say it ropes strangers into your activities without their consent; others say it’s harmless and fine. I fall somewhere in the middle: I think it’s okay as long as it’s subtle enough that it’s likely to go unnoticed by those who don’t know what to look for.

If you’re in a relationship that involves dominance and submission, there are few better situations for playing with those kinks publicly than a dinner date. Like any romantic date, dinner out together can help build anticipation and excitement for sex that might come later. Dinner dates also feature some interaction with other people (e.g. hosts, servers) but not a ton, so you can remain in your little two-person bubble for most of the night even though you’re out in public. Low-lit restaurants make a great backdrop for subtle, blink-and-you-might-miss-it kink games.

As a submissive whose boyfriend is a fine-food fan and a fellow pervert, I’ve been on many kink-tinged dinner dates as of late. Here are 5 of my favorite ways to play with D/s while out to dinner with a dominant!

The dominant chooses the submissive’s outfit. Get the kinky fun started before you even leave the house! Letting someone else choose your ensemble is vulnerable, because you’re trusting them with your self-presentation, and you’ll be wearing that outfit all night. Giving the dominant this degree of control also works well if they prefer the date location to be a surprise; the submissive won’t know the appropriate way to dress but the dominant will. If you want, you can play with clothing as bondage: for example, as Siren Vandoll points out, tight clothing or high heels can restrict the submissive’s movement in a way both partners might appreciate. Getting dressed before the date is also a good time to put a collar or other symbol of ownership on the submissive, so both partners can enjoy the sight of it all night.

The dominant holds onto the submissive’s wallet, phone, keys, or another important object. I discovered the joys of this power-play last summer, when my then-dominant would sometimes keep my phone and debit card in his pocket while we grocery-shopped together if I didn’t feel like schlepping my whole big purse to the store. We initially did this purely for practicality’s sake, but I immediately noticed how it deepened our power differential: I had to ask him every time I wanted to look my phone or buy anything, so he had a ton of real-world control over me. Taking a submissive’s phone away for the evening could also be a fun way to “punish” them for being too distractible on dates, if they consent to that type of discipline.

The dominant defines and enforces “table protocol” at the restaurant. This is a fantastic way to reinforce your dynamic within the structure of a meal out. Some examples of potential table protocols you could instate: the submissive pulls out the dominant’s chair for them; the submissive doesn’t sit until the dominant does (and stands up every time they do); the dominant orders the submissive’s food and drinks; the dominant gets the first taste of the submissive’s food and/or drinks; the submissive must eat without ruining their lipstick; the submissive keeps the dominant’s water glass topped up… or whatever else your pervy little minds dream up! Keep in mind that this stuff should be pre-negotiated (as should everything in this post, really), because one or both partners might have a history of disordered eating or another past trauma that could make some of these protocols difficult or inadvisable.

The dominant sends the submissive to the bathroom with instructions. Maybe their task is to take a series of dirty photos and text them to the dominant; maybe it’s to remove their underwear and surreptitiously give them to the dominant upon their return; maybe it’s to touch themselves until they’re super turned on and then come back without finishing the job. (Wash your hands, please.) It’s probably best to avoid anything that could get you arrested or will result in a long lineup of other patrons waiting to use the bathroom, but hey, what happens in the bathroom stall stays in the bathroom stall.

The dominant and submissive use a remote-controlled sex toy together. This one’s a little riskier, depending on how good the submissive is at maintaining a “poker face”… Remotely controllable sex toys like the We-Vibe Sync are ideal for discreet public play if you’re into that. The dominant can enable and control the toy from their phone, or with a remote. It’s best to save this one for interludes when other people aren’t interacting with you, so you’re not involving them, such as after your food has arrived or in the taxi home after dinner. If you play your cards right, the outing will end with both of you totally turned on and ready for more explicit private play.

What’s your favorite way to infuse a little kink into a dinner date?

 

Heads up: this post was sponsored. As always, all writing and opinions are my own.