If there’s one rule I try to live by in life, and dating, it’s “always say yes to a boat”. But should the answer still be yes if it’s a first date, you’re not even sure you find the guy attractive, and said boat date is going to be with a bunch of his friends on a national holiday?

In my world, the answer is yes, still say yes to the boat. And so I found myself trying to decide what to wear to a first date on a boat on Canada Day when the (obvious) theme was red. At the time I had one thing in my closet that was red – an all-in-one playsuit. I figured I could dress it down with a pair of converse and it wouldn’t be too dressy, but cute and on theme, albeit not ideal for peeing on a boat… but you can’t have everything.

We weren’t supposed to have such an unconventional first date. We had initially arranged drinks on a Friday night, but when I got carried away having drinks beforehand with a couple of friends, they persuaded me to bail on the date and stay out with them. Which I duly did and, if I’m honest, felt very little remorse about because, well, chicks before dicks. But it definitely moved me one step closer to being the sort of Vancouver flakey dater that I hated, so really not something I wanted to get into the habit of.

He was incredibly gracious about the eleventh hour call off though, and instead he suggested we did something over the long weekend we were embarking on, like maybe watch the Canada Day fireworks. I agreed and when he then got invited onto his friends boat to watch the fireworks, he asked me to join him or said we could still just watch them as planned from land, just the two of us, as we’d already made those plans and he didn’t want to back out. A subtle dig at my Friday night bail? Maybe, but he was more than entitled.

And that’s when the “always say yes to a boat” rule came in. Because you never know how big that boat might be! It’s similar to dating, but in dating it’s not a boat whose size is of interest… it’s his brain. Get your mind out the gutter.

He suggested we meet first for a drink to ensure neither of us were crazy and to make sure I felt comfortable getting onto a boat with a total stranger. When I got to the place he’d suggested and it was closed for the day I was more than a little concerned the whole thing was a set up to get back at me for bailing on him. But when he turned up a few minutes later as I was still texting him to ask for an alternative plan, he quickly found an alternative and we sat down to have our first proper conversation after what had been weeks of texting. In fact it had been so long of back and forth that eventually I’d had to say “let’s go on a date or let’s quit the chitter chatter”. I like a text convo as much as the next basic bitch, but not with guys I haven’t even met yet.

It had given me the feeling that he wasn’t the most authoritative of guys, and in our (many days and weeks of) text conversations he’d come across as a super nice guy… Maybe too nice? I definitely had a feeling that could be the case. But nice guys shouldn’t always finish last so I gave it a chance.

He was a 35 year old Canadian, who worked in business development for a food delivery company and had recently moved to the city from Ontario. I knew from our texts that he was pretty active and had travelled a lot so we had a lot to talk about. Thankfully, Canada Day Boat Guy, as he would be known, was friendly and easy to talk to but even before we’d finished our first drink I knew I wasn’t going to be romantically interested in him.

Had we been partaking in a “normal” first date, I likely would have been ready to go after a couple of drinks, so part of me was relieved when the date moved onto the boat with 6 other people. Though as we walked down to the marina part of me was aware that I was about to essentially be stuck with these people for the next four or five hours, whether I liked it or not, as soon as we set sail.

Thankfully all of his friends were lovely, and amazed that I’d agreed to go on a first date with a guy and his mates on a boat, at night. When they put it like that I realised that, yeah, maybe it was a kind of crazy thing to agree to. But seriously… the boat rule! Unfortunately this boat wasn’t the biggest. It was a little sailboat, maybe 25 feet, but it was cute and had a BBQ on the back for some food later. And as Canada Day Boat Guy had promised, they had all the food and drink bases covered, which was pretty nice. So I just showed up with a bottle of champagne for the start of the fireworks.

The night was great, although I was aware that I spent far more time talking to everyone else than I did Canada Day Boat Guy. A couple of my boat mates were visiting from California, there was a couple from Vancouver, and it turned out that one of the other friends knew Chinese Weightlifting Firefighter, so we weren’t short of conversation. And irrespective of the company, watching the Canada Day fireworks from on the water was quite the memory maker.

Unfortunately it wasn’t the romantic moment it might have been, I guess that’s what happens when your first date includes six other people. It ain’t as cute as it sounds!

By the time the fireworks were finished I was really ready to get off the boat. It had been fun, yes, but things with Canada Day Boat Guy weren’t going anywhere and I was pretty damn tired by that point. Turns out the boat wasn’t really going anywhere either – with a severe lack of wind it took quite some time for us to get back to the marina from the harbour where we’d watched the fireworks.

When we finally made it back to land I realised it wasn’t just a matter of saying goodbye to everyone and heading home. Canadian Boat Guy and I should probably have a chat just ourselves. So we made the walk back along the marina and I felt like there was some similar resignation within him that this wasn’t going anywhere and it hadn’t quite been the first date to spark a million more. At least not with each other.

When we finally reached the gate of the dock and he was going to get on his bike and go one way and I was going to walk home the opposite way, we agreed it had been fun but maybe there wasn’t a second date in our future. It was all very amicable but he then ended it by saying “but if you see me around you can buy me a beer as payback for the boat”.

I laughed it off and agreed but afterwards I felt distinctively like it had been a dig at me, as if I somehow owed him because he’d taken me on a date and it hadn’t gone anywhere. It may not have been how he intended it, but that was entirely the way I took it. And I felt uncomfortable about it every time I thought of it afterwards.

Did he think I’d used him for the boat? Did he think I’d been rude by speaking to his friends so much? Had he expected me to go home with him? I wasn’t sure where that had come from but I decided I really didn’t care to find out. I texted him later that night to thank him for the date – as I always do after a date if he’s paid for anything, as Canada Day Boat Guy had when we first met for a drink – and the next day I deleted his number.

You should always say yes to a boat, but you shouldn’t keep saying yes if there’s nothing but the boat that you’re interested in.

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