This was a first. This was not a “let’s hang out tomorrow” situation as happens so often when I travel solo. This was a date. A dinner date.

Please allow me to set the scene.

A weekend in Montreal
I took VIA1 to Montreal for a long weekend, arriving Thursday night in the dark and the rain. Have I suggested before not to arrive in a new city in the dark? Well, yes. But this is Montreal, a city I know and know to be safe. But still, I took a cab for the five minute ride  from the station to my hotel – L’Hotel.

The next day was chock-a-block with plans. I took a three hour tour of the city in the morning – something I had never done on previous visits to Montreal – and I learned a lot. At noon, I had lunch with Marie-Jose of Montreal Tourism, my host for this trip, at Plaisirs Coupables on Peel Street. The Mac & Cheese was out of this world. Three cheeses topped with bits of pork and nuts – spectacular.

In the afternoon I went to La Musée des Beaux Arts, The McCord Museum and the Museum of Contemporary Art. At the latter, I met Vickii, a dancer and artist. “Do I know you?” she asked. No, I didn’t think so, though there was something incredibly familiar about her. So we had tea. For over an hour. And, as one tends to do with a new acquaintance who you will not likely meet again, we spilled life secrets.

In the evening, I had dinner at Chez L’Epicerie in Old Montreal and then went to Le Balcon to take in the cabaret.

Solo traveler meet solo traveler
I arrived to a somewhat full house and found that the seats along the wall, preferable when alone, were all taken. So I sat at a table that was quite central. No problem until the dancing started. This was Montreal and Montrealers really enjoy their nightlife. Alma Faye Brooks (you can listen to her on the left as you read this) got everyone up on the dance floor, leaving me sitting alone at my table. I felt somewhat conspicuous.

So at the break I decided to leave. However, on my way out the door I met Brian who is from Massachusetts and a frequent visitor to Montreal. He was at the show alone as well. It was very quick. In a moment he knew why I was leaving and invited me to join him at his table. I did, we danced, and, because it was a loud venue, we left for a quiet drink.

Brian and I had a lot in common. The essentials; we had each had a business, sold it and now we write. There were other interesting life parallels as well.

A mistake and what I learned
I’m not perfect and when I make a mistake as a solo traveler I feel particularly obliged to ‘fess up. When we went for a drink I broke one of my most important rules as a solo traveler: I let Brian know where I was staying.

But here I want to deconstruct the mistake. It was a great learning experience because, essentially, I set myself up. I made the error of asking him where he was staying. He’s a guy. He wouldn’t have the same concerns a woman would have about revealing this, so he told me exactly what hotel he was staying at. When he asked me the same question, which was only natural, I felt it would be rude to be vague or evasive so I answered.

Now, if I had not felt certain that Brian was a safe person I would not have accepted the invitation for a drink and certainly would not have told him where I was staying. All worked out well. He’s a kind, honorable and charming man. But, nevertheless, I consider it a mistake because letting someone know where you’re staying (man or woman) could be an invitation for unwanted attention or even worse. Now that I know how I walked into it, I won’t be doing so again.

The date
At the end of the evening, Brian invited me for dinner the next night. I declined because I had a ticket for Les Grands Ballets Canadiens de Montreal at the Places des Arts. While I wanted to see the ballet, I really wanted to experience the iconic Places des Arts. I like spaces.

But the next morning I awoke thinking that I could see the ballet and experience the building almost any time. It will always be there. A date, on the other hand, is a more unique experience. So I called Brian and accepted.

We had a lovely evening. We had dinner at Laloux on Rue des Pins (the pickerel was fantastic), then we wandered down Rue St. Denis to Casa Galicia for desert and to watch the Flamenco dancers. After that we walked further to the Queen Elizabeth Hotel and had a nightcap at their bar. A big thank you to Brian for a wonderful evening. It was such a pleasure to spend not one, but two, with you.

What do you think?
What would you have done? Do you date when you travel solo or do you keep things more casual? How do you handle the safety issue?

Janice Waugh is the Solo Travel Editor for Wandering Educators