Skinny Dip, Author at Skinny Dip

This is a guest post written by Lisa Watson. Thanks for supporting the content that supports this blog.

Toronto, Canada’s largest city, offers a vibrant and diverse dating scene. With an eclectic mix of cultures, neighborhoods, and attractions, there is no shortage of unique experiences for couples to enjoy. To help you navigate the intricacies of dating in Toronto, we’ve compiled a list of essential dos and don’ts.

Explore Toronto’s Multicultural Charm

Do: Express What You Want

When it comes to dating in Toronto, it’s important to express what you are looking for. Whether you’re seeking a casual date, something more serious, or to find a sugar baby in Toronto, being upfront about your expectations will ensure that everyone is on the same page and can make for an experience.

Don’t: Stick to Your Comfort Zone

Avoid limiting yourself to your usual social circles and preferred hangout spots. Branch out and explore new neighborhoods, events, and social gatherings to meet a diverse range of potential partners. Remember, Toronto’s charm lies in its multicultural atmosphere, so don’t hesitate to step out of your comfort zone.

Plan Memorable Dates

Do: Be Adventurous and Creative

Toronto offers a wealth of unique date ideas, from scenic walks along the waterfront to the city’s thriving arts scene. When planning a date, consider your partner’s interests and try to find activities that you both will enjoy. Some memorable date options include:

Strolling through the Distillery District
Taking a cooking class together
Attending a live performance at a local theater
Exploring an art gallery or museum

Don’t: Rely on Traditional Date Ideas

While dinner and a movie may be the tried-and-true formula for a date, it’s important to think outside the box when dating in Toronto. The city boasts a plethora of creative and unconventional date spots, so don’t be afraid to experiment and try something new.

Mind Your Manners

Do: Be Polite and Respectful

Toronto’s residents are known for their friendly and polite demeanor. Embrace this attitude by being courteous and attentive to your date. Show genuine interest in getting to know them, listen carefully to what they have to say, and be considerate of their feelings.

Don’t: Be Late or Glued to Your Phone

Punctuality is essential when dating in Toronto. Arriving late can give the impression that you don’t value your date’s time. Also, make a conscious effort to avoid checking your phone constantly during the date. This will show your date that you are fully engaged and interested in the conversation.

Navigate the Dating Scene Responsibly

Do: Prioritize Your Safety

While Toronto is considered a safe city, it’s still essential to prioritize your safety when dating. Always meet in a public place for your first few dates, and let a friend or family member know your plans. Trust your instincts and be cautious when sharing personal information with someone new.

Don’t: Overshare on Social Media

While it may be tempting to share every detail of your dating life on social media, it’s crucial to maintain some level of privacy. Avoid posting too much information about your dates or potential partners, as this can make some people uncomfortable and may even jeopardize your safety.

Be Patient and Open-Minded

Do: Take Your Time

Toronto’s dating scene can be fast-paced, but it’s important to take your time and not rush into anything. Allow yourself the opportunity to truly get to know someone before jumping into a serious relationship. This patience will help you build a strong foundation for a lasting connection.

Don’t: Be Discouraged by Rejection

Rejection is an inevitable part of dating, and it’s essential to accept it gracefully. If a date doesn’t go as planned or a potential partner doesn’t share your feelings, remind yourself that there are plenty of other people in Toronto’s vast dating pool. Maintain a positive attitude and keep searching for someone who shares your interests and values.

Communication is Key

Do: Be Honest and Clear

When dating in Toronto, it’s essential to maintain open and honest communication with your potential partner. If you have certain expectations or desires, make sure to express them clearly. This will help you and your date to understand each other better and avoid misunderstandings.

Don’t: Ghost or Ignore Your Date

Ghosting or ignoring someone is never a good idea, regardless of where you’re dating. If you’re not interested in pursuing a relationship with someone, be upfront and let them know. It’s better to be honest and respectful than to leave them wondering and waiting for a response that will never come.

At the beginning of 2018, I decided my motto would be “catch flights, not feelings.” I was ready to travel and experience as much as possible, without tying myself down to any one person. I got half of the equation right (I hopped on 20+ flights over the course of last year), but as far as not catching feelings, I kind of failed miserably (if you consider allowing yourself to be vulnerable a failure, which I don’t).

One thing that’s become very apparent over the past year or two, is that I’m very all or nothing when it comes to sex and romance. I don’t meet that many people that I connect with, so if I’m into you, I’m into you. Even if I know a situation is destined to be casual or fleeting (for example, a fling while travelling), I still feel all the feelings. I don’t think this is necessarily a bad thing (it’s nice to have good feels towards the people you sleep with), it just is what it is.

In May 2018, I was on a press trip to an adult’s summer camp in Pennsylvania (more on that later) and I met a guy. He was the marketing director for the company sponsoring the camp. We flirted a bit over the weekend, which lead to us making plans to meet up once we were back in New York City (I was in town staying with a friend for the week). This lead to dinner at Miss Lily’s in the East Village, a post dinner kiss at Death & Co, backseat Uber make-outs, a couple of dates & me rushing from his bed on my last morning in NYC to grab my suitcase and head to the airport.

Oh god, did I like this man. He was smart and beautiful and creative. The sex was passionate and connected. I was smitten.

I asked him if he’d like to see me if I came back to visit. He said yes, but in the fall. His son would be staying with him during the summer.

We stayed in touch over the next few months. We sent sexy toe-curling messages back in forth. Sometimes we didn’t speak for a few days. I continued to travel a lot. I went to the Bahamas and Mexico twice. This didn’t feel like other recent flings (there was a guy in Mexico and another in Jamaica). I didn’t date anyone else. I didn’t want to. I kept thinking about our bodies wrapped around each other; his eyes staring into mine the entire time we made love.

It felt special. He felt special.

Fall rolled around and I booked a ticket to New York City. The plan was to stay with the same friend I’d stayed with after camp (we’d become really close the last time I was in town — another piece of my heart I left in New York City).

I was looking forward to hanging with my friend (co-working! drinking wine! vintage shopping!) and spending time with NYC bae, exploring the city hand-in-hand. I was planning on staying a couple of weeks and seeing what happened.

Almost nothing went according to plan.

Here’s something you should know about me: I don’t cry very often or very easily anymore (thanks, anti-anxiety meds!) but few days into my New York trip, I found myself having a full out emotional meltdown while walking through Times Square. I never thought I’d be the kind of person who’d burst into tears in front of the M&Ms store, but here we were.

(Note: if you’re going to cry in public, do it in Times Square. It’s already kind of awful and it’s so busy that literally no one will care/notice.)

The source of my tears was a culmination of several factors.

Right before I was set to depart, my friend texted me to let me know that she was going to be out of town when I arrived and wouldn’t be able to let me into her apartment (she was abroad visiting family and an elderly relative had passed; prolonging her stay).

There was no way for me to get her keys. I had to find somewhere else to stay at the last minute. I felt weird asking NYC bae if I could stay with him, so the night before I booked an Airbnb (my booking got confirmed a few hours before my flight).

When I got to New York, I learned that NYC bae was also going through some tough family issues. We still had a connection — he held my hand and kissed me on the street and told me it felt like time hadn’t passed at all — but he seemed sadder, quieter and more reserved than he had before. Distracted. Distant.

The dreamy eye-contact was still there. But lying in his bed as he snored next to me, I couldn’t sleep. My mind raced. Was this going anywhere? Had I made a mistake coming here?

My airbnb situation proved to be bad news (turns out sharing a bathroom with strangers isn’t much fun!); my friend still wasn’t back in the city & didn’t have a timeline for when she would be back, and NYC Bae was busy with work and social commitments. Making plans with him felt like pulling teeth.

After a few nights I ditched my sketchy Airbnb and booked myself a room at the Pod 39 Hotel, which turned out to be perfect (I loved this little hotel!) but NYC prices are no joke and it felt like my bank account was bleeding money.

According to scientists, AI can now predict how long your relationship will last, but I’ve always felt the end of love/lust deep in my gut. It’s like a nagging ache that doesn’t go away. It feels like butterflies — the bad kind.

The bad news butterflies were coming in loud and clear. Yet, I was caught in this weird emotional limbo; part of me hoping that the tide would change, while also mourning the likelihood that it wouldn’t.

Throw in the fact that Fall just isn’t my season AT ALL (my seasonal depression is very real) and all felt unexpectedly lonely; like the city of New York was rejecting me; chewing me and spitting me out (which, according to New York transplants, is a very authentic NYC experience).

Since getting treatment for my anxiety, my moods have been really stable. So, to feel this sad in one of the most amazing cities of the world, was kind of scary.

It’s taken me a year to write about this experience, partly because I wasn’t sure how to frame it. I could have glossed over the whole thing and only mentioned the sexy details, but that wouldn’t have been the truth.

The truth is that part of me still feels embarrassed. I wanted so badly for things to work out with NYC bae and for us to build on that little bit of magic we’d had together in the Spring, that I never even considered that it wouldn’t happen. I mean, that’s pretty naive. Especially for someone like me who writes about relationships for a living. I know better than to plan a trip around someone else (without being 100% crystal clear on their intentions) but I did it anyway.

After about 10 days in NYC solo, I was scheduled to go on a press trip to Puerto Vallarta. My friend still hadn’t come back and I was seriously considering changing my flight so I could fly back to Canada directly from Mexico. But, then at the last minute I decided to keep my original ticket and finish out my time in NYC on my own terms.

I’m so glad I did.

When I got back from Mexico, things got better. My friend Gary offered to let me stay at his apartment on the Upper East Side. I stopped waiting around for NYC bae and instead went to a ton of museums. I crossed a few items off my bucket list. I spent time with another girlfriend in town. I also hung out with Gary a bunch and ate lots of good food. Eventually, my friend came back from abroad and we got to hang out, drink wine and dance around her living room to RuPaul.

If you want to find out exactly how I spent my time, make sure to check to check out my post about how to travel to NYC solo in my new travel blog (yes, you read that right!) Love, Peace & Tacos.

(In the end, NYC bae went out of town while I was in Mexico. We stayed in touch while he was gone, but he didn’t make it back in time before I had to leave the city. At the end of my time in NYC, I flew to St. Lucia for another press trip and then went back to Canada from there.)

I don’t regret going to New York. I also don’t regret any of the feelings I had (even the uncomfortable ones). However, in hindsight I wish I’d been more upfront and asked NYC bae more questions (like, how do you envision our time together in NYC? What will your schedule be like? Do you see this as a fling or something more?) to get a clearer picture of his intentions — before I hopped on a plane.

With that said, life is short. Sometimes you have to take chances to answer questions about the people in your life. I got answers. They weren’t the ones I expected or hoped for, but they were answers nonetheless.

Even though it was uncomfortable, I’m happy I had this experience. It clarified a few things for me — like, I am not destined to be a New Yorker. The city is amazing, but it’s a lot. A wonderful place to visit, but not somewhere I could live longterm. When I got back to the West Coast, I breathed an audible sigh of relief.

Instead of making me bitter, it softened me. It made me realize that I do want to have a partner and to fall in love again. Most importantly, that I can have feelings for someone, they can go away and I’ll get through it. I’ll come out the other side just fine.

One of the things people have asked me most often over the years is: how do I get the confidence to start dating again? Let’s be real, breakups not only can leave your heart battered, they can also be a blow to your confidence and self-esteem. If you’ve been reading this blog for a while, it may seem like I fearlessly go from one relationship or situationship to the next, but that’s far from reality. I rarely blog in real time, so often there’s months between a breakup and when I get the nerve to get back on the proverbial horse.

Getting your dating mojo back doesn’t happen overnight. It’s a journey. Here’s a few things that have helped me over the years.

Heal what needs healing.

Even if it’s been a while since your last relationship ended, there’s always emotional stuff that comes up. In my experience, taking the time to reflect, process and heal these sore spots before you start dating again is never a bad idea. This could involve journalling, making art, taking a personal development course, working with a life coach, talking to a licensed therapist (something I’m a huge proponent of!) or working with another kind of healing professional.

Do things that make you feel good in your body.

I have the tendency to get stuck in my head a lot, so taking time to reconnect with my body is something I try and prioritize (whether I’m dating or not). Confidence is all about how you feel. When I move my body, the endorphins flow and I focus less on how my body looks and more on the cool stuff it can do. Whether it’s running, doing a barre class, yoga, using your favourite sex toys or having an epic bedroom dancing session, find what kind of movement feels good to you & go for it.

Pamper yourself.

I’m also a big fan of getting a beauty treatment (or something done) after a breakup and before re-entering the dating scene. Note: you don’t need to change how you look to be a confident dater, but I find sometimes doing the smallest things (getting a haircut, a pedicure or heck, even a new tattoo or piercing) can give you an extra pep in your step.

For example, I recently had a couple of skin tags removed from the base of my neck. I’ve had them for a while and they’ve always bothered me. But it wasn’t until I was on a date recently and the guy actually tried to pull one off (“hey, you have some fluff on your neck. Let me get that!”) and I had to tell him that “uh, that’s actually attached to my body,” that I decided to have them removed for good. Not only does my neck feel ridiculously smooth now, I also (hope) I’ve helped prevent future awkward moments. Skin tugging = not sexy.

(Sidebar: I used to be very anti cosmetic surgery + treatments, but as I get closer to 40 I’ve become a lot less judgemental. I have several friends who’ve had facial surgeries and cosmetic treatments to reduce the signs of aging & they’re happy, bad-ass women who still very much look like themselves. Next time I’m in LA, I may even swing by Dr. Binder to get an anti-aging treatment of my own. At the end of the day, it’s your body. Do whatever you want for you, not for anyone else).

Update your wardrobe.

When you look good, you feel good. Go through your wardrobe. If it doesn’t fit or you don’t feel good in it, donate it. You don’t need a whole new wardrobe to re-enter the dating scene, but it helps if you have a few pieces that you feel comfortable in. Instead of always scrambling before a date, I like to have one or two go-to date outfits preplanned. For example, my go-to fall/winter look is a black dress, tights, ankle boots and a leather jacket. Done.

Take your time.

When I first re-entered the dating scene after ending a long term relationship (which involved venturing into the world of dating apps for the first time ever), I mistook “not terrible” for “good.” Figure out how you want to feel in your next relationship (for example, safe, supported, respected). If you don’t feel that way with someone, give yourself permission to walk away.

Be kind to yourself.

RuPaul always says, “If you can’t love yourself, how in the hell are you gonna love somebody else!” And while I do think this is true to a certain extent, I think it fails to acknowledge that self-love is a process. Just because you’re still working on it, doesn’t mean that you’re not deserving of love & respect from the people you date. (I used to think that people treated me poorly because I didn’t love myself enough, but the reality is that some people are just crappy. That’s their problem, not yours. End of story.) You’re worthy of being treated with respect, just the way you are. When you remind yourself of this on a regular basis and cultivate a strong sense of self (regardless of where you are on your self-love journey), rejection doesn’t feel so bad.

When I first started this blog in 2009, I was 29. I knew I eventually wanted to write professionally and publish a book. I also had lot of emotional baggage I needed to write my way through. This blog served me well and provided a place for me to write about breakups I’d kinda-sorta-not-quite-healed-from, share bizarro dating stories, talk about sex and (hopefully) make you guys laugh as I journeyed into the world of comically strange products. I wrote openly about my mental health and experiences with heartbreak. I rode the wave of balls-to-the-wall personal blogging, until, well, things changed.

The internet landscape changed (with Instagram taking the place of deeply personal blogging), but I changed too. I always tell people that I chose the blog name Skinny Dip because it’s good metaphor for sharing your life on line. When I started blogging, I wanted to strip away outer layers of myself; shed my figurative skin if you will, in hopes that I would eventually arrive at the most “me” version of myself. Ten years ago, I felt so full of angst and feelings that I couldn’t envision a time in the future when I wouldn’t have things to get off my chest in a very public way. But then I arrived at that point.

The stuff I needed to let go of got let go of. Sex blogging stopped feeling fun and I started to save my time, energy and juicy stories for my book. But then, even book writing became challenging.

The problem with shedding your skin is that eventually you reach a point where you hit actual flesh and bone. It’s raw. It’s tender. It’s uncomfortable. Self-preservation kicks in and you instinctually tell yourself to pull back.

This is basically the point I reached sometime in 2018. After nearly ten years of personal blogging and several years of working on a book project (and watching it shift & transform) I hit a wall. I was suffering from a vulnerability hangover that I had no cure for. So, I switched my focus to travel writing and went on a bazillion work trips. Okay, it was more like seventeen — nearly half of which were to Mexico — but still, it was a lot. I needed a break and travelling provided that.

While I’m super grateful to have travelled so much over the past two years and have no plan to abandon travel writing (or blogging) any time soon, eventually my “break” started to feel like I was running away. In my gut I know its time to slow down and get to work.

The idea of “time” is something that’s been on my mind obsessively for the past few months. How should I spend my time? Is it better to go with the flow? Am I better served by sitting still and doing the work? These are questions that have been on my mind obsessively since I turned 39 in September.

Looking ahead at 40 is such a weird feeling. On one hand, I’m much happier and in a better place mentally than I was at 29. I’ve also accomplished some major goals and had some amazing opportunities. On the other hand, there’s still so much that feels…in progress. Things that (society tells me) I should have checked off by now just aren’t. While my friends are closing on houses and renting out a gender reveal smoke cannon to honour their third kid (yes, that’s a thing), I’m here — still single, still living at the same spot, still working on a book that isn’t quite finished yet. I’m happy and healthy but all the external stuff that I just assumed I would have taken care of by now — the fat bank account, the home, the committed relationship with plenty of hot sex –are still works in progress.

It’s so easy to let my thoughts spiral into an anxiety-driven maelstrom start thinking of the what-ifs. What if things never work out? What if I fail? I’m neutral on children, but what if I never even get the chance to veto a gender reveal cannon because I end up ALONE, BROKE AND LIVING IN MY MOM’S BASEMENT FOREVER. While there’s literally no evidence that any of the above will happen, the FEAR takes me to some really dark places (literally. Hello, Mom’s basement?)

(I have a friend/colleague who’s in a similar situation and I was joking with her that maybe because we’ve spent our thirties sorting out our internal selves & living our lives on our own terms (with plenty of freedom), that we’ve preempted a 40-something mid-life crisis where we go out and randomly buy a speed boat to fill some kind of deep emotional void. Here’s to hoping!)

I know my writing has the greatest impact — both for myself and others — when I allow myself to be vulnerable. But guys, I’m kind of fucking scared to dig into that tender flesh. Every day I have moments where I think of just escaping (saying yes to a press trip, running off to visit a friend, etc) just so that I don’t have to sit down and feel the things I need to feel so I can write the things I know I have to write.

So, while I work my way through to the other side of this vulnerability hangover, I’m reclaiming this space for my writing. While I can’t promise a return to the no-holds-barred blogging days of yore (in fact, it likely won’t look anything like 2009 or even 2013), I do plan writing things that feel honest, true and (ahhh) vulnerable, while I work through all these feels.

Maybe people will read. Maybe they won’t. But if you’re interested in following this journey, you know exactly where to find me.

Although I’ve been known to rail against the (ahem) “aesthetic choices” of single men in Victoria and have questioned whether my hometown really is one of the best cities for dating, when it comes to actual date night spots, it’s actually pretty great thanks to an abundance of gorgeous scenery and a thriving indie food & beverage scene.

If you’re looking to impress your date and/or want somewhere cool to hang out that isn’t a coffee shop or the beach (please, stop asking me if I’d like to “grab a coffee and go for a walk on the beach” for the 500th time) here are some date night spots in Victoria, BC that have been tried and tested by yours truly.

1. Little Jumbo.

If you visit Victoria, there’s a 95% chance I will take you to Little Jumbo — a small tucked away bar and restaurant that has a locals-only vibe. There’s a couple of reasons for this. For starters, it’s cozy and romantic (but still casual enough for a spur of the moment drink or laid back night out with friends), the ever-rotating cocktail menu is phenomenal and the food is delicious. Come for a cocktail or beer, stay for the truffle fries and leg of lamb (incredible).

2. Stage Wine Bar.

This is another of my go-to date spots. Whether its the first date or the 50th, you can’t go wrong with Stage Wine Bar. The high ceilings, exposed brick and candlelit tables give the place an urban, casually romantic feel. Naturally, they have a huge selection of wines, with glasses starting at around $6 (something thats becoming a rarity in Victoria, unfortunately). Plus — acoustics wise, it’s a lot quieter than the Fernwood Inn (the pub located across the street).

3. Clive’s Classic Lounge.

At first glance, this place looks like your stereotypical, slightly old-school hotel bar. However, inside you’ll find a selection of world-class, award winning cocktails. A local favourite, this is the perfect spot for a cozy drink with a date or a small group of friends. Oh, and they have a happy hour.

4. Ferris’ Oyster Bar.

A local Victorian institution, Ferris’ has a great menu (OYSTERS!) and a cute garden patio that’s perfect for casual (but nice) date night. If you want to get a bit more fancy, upstairs they have their “Upstairs” seafood & oyster bar (which is one of my favourite places to go for a special occasion) and their sister restaurant Pero Negro, which serves delicious tapas.

5. Bodega & Poco

Both of these bars/tapas joints are small, stylish and located in Trounce Alley — separated by another Victoria institution The Tapas Bar. While the Tapas Bar is great, it can get a bit noisy inside if you’re not able to secure a place on the patio. From what I understand, they’re all owned by the same company but each menu offers something slightly unique. Try one or hop between all three.

6. The Drake.

Looking for somewhere a bit more casual? Love craft beer? Head to the Drake. This lively spot features West coast craft beers and casual eats in historic Market Square. Also, compared to some of the other options on this list, it’s super affordable — making it a perfect first date spot, for when you want something nicer than a dive bar but still want to keep things fun and casual. FYI, they also serve cider and a handful of gluten free food options.

7. Chorizo and Co.

This is what happens when two guys who used to manage your favourite bar decide to open their own bar; completely revamping the previous iteration of Chorizo and Co. I love this little spot on Fort street. The cocktails and wine list are awesome, as is the small plates menu (perfect for impromptu date-night nosh). It’s also located a few blocks off the usual beaten path, giving the place a sense of intimacy. Like Stage, it’s stylish and low-key romantic. However, because C & C is still relatively new, you’re less likely to run into everyone you know there.

At some point I’ll put together a full post of my favourite “romantic restaurants” in the city (because people are always asking me for recs!), but in the meantime here are a few that are sure to be hits:

Where are some of your favourite date night spots in your city?

The Dos and Don’ts of Dating in Toronto