Was it worth it?
03: Kid-free date nights and some ideas for what to wear.
After my husband read my last Was it worth it, he lightheartedly joked that he’s been getting more insight into my shopping habits. For the sake of changing it up, I’m devoting this edition to some recent date night experiences.
We don’t do many outings together without the kids—partly because we don’t have babysitters close by but also because we (mostly me) often feel guilty about leaving them. On the rare occasion we have a kid-free night, we try to take advantage and plan something special. Mind you, our last two date nights involved celebrating our anniversary and my birthday, so we planned a little more than usual.
I know I should feel less guilty about spending on experiences than, say, a pair of new shoes but I always hesitate at first, wondering if the money could go to better use. Usually, it’s not until the next day that I realize how much we needed those nights out. They give us something to look forward to that’s just for us and break up the monotony of parenting and working.
Fine dining
I don’t take for granted that I have a husband who loves food as much as I do. Many of our date nights revolve around what we’re going to eat and trying restaurants we wouldn’t be able to take our kids to.
We went to Osteria Giulia for our anniversary and Alobar Yorkville for my birthday—two restaurants in Toronto we’ve been wanting to check out. We were impressed by both for different reasons but agreed that if we had to pick one to go back to, it’d be Osteria Giulia. It’s one of those restaurants that doesn’t seem to be trying too hard and lets the food speak for itself. The menu is Italian with lots of seafood, and we loved everything we ordered. The service was also so attentive and personable. Throughout dinner, we chatted with a friendly bartender who shared stories about the Toronto food scene and what it’s like working in the industry (very much like The Bear, he confirmed.)
Alobar, on the other hand, was more of a lounge-y cocktail bar. Being the more accessible (meaning you can actually get resos) counterpart to Alo, the food was good, especially the wedge salad and confit duck pappardelle. Service was fine, although nothing special. What stood out to me the most was the vibey ambiance and good music, which made for a fun night out.
All this to say—any chance to get dressed up, eat a nice meal and have uninterrupted conversations is always going to be worth it for me.
A memorable concert
Concerts can be one of the best date night experiences, in my opinion, although I have to say the price of tickets nowadays is wild to me. Combining it with a special occasion, like celebrating an anniversary or birthday, helps us justify the cost a bit (is that crazy?) We’ve spent past anniversaries watching John Legend and Leon Bridges live and had no regrets.
I always told my husband if Sam Smith comes to town I’d want to go, and it just so happened their Toronto tour date coincided with our 9-year anniversary. I wasn’t as familiar with their newer music, so I didn’t know what to expect, but they put on a great show. It was soulful, theatrical and uninhibited—quite the spectacle. Overall, a memorable date night.
Hotel accommodations
When you’re a parent, any time you get to sleep in feels indulgent. When my husband first suggested we get a hotel in the city for my birthday, I hesitated. We hadn’t done something like that since we were dating and financially carefree. But I was also coming off the busiest month of work, burnt out and sleep deprived, longing for a night out without having to wake up early the next day to kids jumping into our bed.
He ended up getting us a room at the new-ish W Hotel in Yorkville, which was the perfect spot for our dinner plans (Alobar). The hotel was stunning, the rooms were spacious and modern, and the whole experience felt like a mini getaway. We didn’t have to drive to dinner, could have more than two drinks and, of course, sleep in the next day. I felt very spoiled—the hotel even surprised us with wine and treats to celebrate. It was a 10/10 experience.
Date-night looks
There was a thread on another Substack about what to wear on date night, so I thought I’d share some looks I found and saved, in case you’re looking for inspiration.
Can you tell I have a thing for satin slip dresses? This Doen Obelia dress in black, seen on @sarahkimharned, has contrasting lace detail, which adds a little drama and romance to the look—something I’d definitely wear on date night.
If we’re going someplace a little more casual but I still want to get dressed up, I might do a satin skirt with an oversized sweater. Similar to this look but with a pair of boots for the cold weather.
Not ideal if you’re eating a big meal but I like the option of leather pants for a date night. This look in brown with an off-the-shoulder knit feels in season and simple enough. I’d also keep it more casual on top with just a sweater or cardigan.
Lastly, here’s a quick reminder to check your closet first for pieces you already have and can put together for an easy going out look. Jeans, a black top, blazer and boots is what I’d wear going out for drinks, accessorized with big earrings and a red lip.
If you’ve got your own noteworthy date night experiences and/or looks, I’d love to hear about them. Reply or share in the comments below.