You know when you were young and your Mum always told you not to take sweets from strangers and your school used to have sessions about how you shouldn’t get into cars with strange men? When did that change to the point that one random October Sunday I decided it was a good idea to make plans for a strange guy to pick me up and take me to the woods for a walk? It’s funny how things change; at eight I would have been shouting “STRANGER DANGER” to ward him off, but at 32 I was hoping it would be romantic.
On said Sunday, I came out of a morning kickboxing class to a message on Bumble from this guy who I’d exchanged a few messages with a couple of months ago. When he ghosted mid-conversation I never thought anything of it, it happens so frequently when you’re chatting to people on dating apps. Him reappearing was actually more surprising. In fact, it was just nice that the message had been sent at 9am on a Sunday and not middle of the night Saturday, so I didn’t need to try and work out if it was the dating app equivalent of a drunk text, such is the sad state of affairs that we’re dating in.
I replied and we chatted back and forth about what a gorgeous day it was and what we had planned for our Sundays. He said he was going to take his dog out for a walk to this trail round a beautiful cove I’d heard a lot about but never been to. My mindless reply telling him that exact thought, along with “it’s a perfect day for a walk”, resulted in the quickest date arrangement I’ve maybe ever experienced, when he invited me to go with him (and the dog).
By this time, I was home and showered, our chats had moved to text so he had my number and just as I was mulling over in my head whether this hastily arranged date seemed like a good idea, he called me. I was impressed. People are so apprehensive to use the phone nowadays!
He said he would come and pick me up (which also impressed me because it was entirely out of his way) and he’d drop me off again after but he thought maybe I’d want to hear his voice before a strange man came and picked me up. It was a fair point and I appreciated the fact he’d had the foresight to realise that.
In my head I knew that agreeing to a random guy coming to pick me up in his car and taking me to the woods didn’t seem like the most sensible thing I’d ever done but I was trying to listen to my gut, and it was telling me it was ok. Even writing that now, I know it sounds nuts. If a friend had been telling me this story or that they were intending to do this I’d be like “NO! STRANGER DANGER!!!!” My eight year old self, and normally my 32 year old self, was a stickler for the rules.
Instead I decided to text my friend all the information on him that I had – his full name, where he worked, his phone number, screenshots of his Bumble profile – and hoped that if my body was found in the woods, they would at least be able to catch him. Ain’t that a romantic first date thought!
After the sobering experience of having to decide what to wear for my first ever “active first date” (seriously, who am I? I’m that person going on a hiking first date. Ugh. Get out.) and despite the insanity of the situation I was actually feeling pretty good about it.
Until, that is, as I crossed the road to the his car after he’d texted to let me know he’d arrived and he got out to hug me and open the passenger door, I realised I couldn’t see a dog. The dog we were supposed to be walking. The dog he’d said was pretty big. So big that surely I couldn’t miss her in his Audi hatchback. Where was the damn dog?!
I tried not to let the panic rise too quickly, even as I started to slide into the passenger seat, but just as I tried to resist him the closing my door, on the off chance I needed to make a run for it, I saw the sweet relief of a dog ear pop up behind the back seat. Thank god.
She was a gorgeous 5 year old Rottweiler / Rhodesian Ridgeback mix and he was a 38 year old Filipino Canadian who worked in corporate travel and lived in an apartment he owned over on the North Shore. They were both great companions for a Sunday afternoon hike.
The chat in the car was easy, we hadn’t covered much ground in our messaging conversations previously so it gave us a lot to talk about on the 25 or so minute drive out there. And that didn’t stop while we were walking up through the woods to the lookout point over the cove. Or on the way back down as the rain randomly started. And even when we got all the way back downtown for him to drop me off a number of hours after he’d picked me up, he actually drove around the block a couple of times so we could finish our conversation.
Arriving back to my apartment building, all I could think was “I’d really like it if he kissed me” and I was aware that since he’d picked me up earlier that afternoon he’d opened and closed every (car) door for me, so if that continued it would likely present itself as a pretty good opportunity for him to make a move should he want. Well, it would have if it weren’t for my over-eager concierge coming to open my door first.
Why is it that when I’m struggling with shopping bags or luggage, they’re never anywhere to be found, but when I’d like to be left alone to hopefully invoke the perfect end to a date, they come rushing out with a “hi, how are you? Do you have anything in the trunk?” No, fuck off! (Jokes, I’m actually very appreciative of the service they offer. Sigh.) And so a big romantic end of date kiss didn’t happen, but a peck on the cheek and a pretty tight hug wasn’t the worst alternative, albeit that it was done with the concierge only a few feet away.
Closing the door behind me as I got back into my apartment, I remember having an incredibly gleeful moment of “WTF”, which made a nice change from the “WTF I want to kill myself” moments that some previous dates have induced. The whole thing had been such a surprise, both in it’s spontaneity – that morning I’d been planning on a quiet day of chores – and in it’s success – we seemed to really click, he seemed to have his shit together, it seemed like a great first date.
I texted him as I was getting into bed that night and thanked him for including me in their walk (he’d made it very clear, he and the dog came as a pair) and for going out of his way to pick me up and drop me off. He responded by saying they don’t normally let outsiders crash their Sunday walks but they were both incredibly happy they’d made an exception for me and they couldn’t decide which one of them liked me more. Cue falling asleep with a smile on my face.
Four days later we were meeting for our second date. After the outdoorsy nature of the first date, he suggested we go the other direction and do dinner and drinks downtown – much more my natural habitat and far easier to get dressed for. Seriously, trying to decide on an outfit for a first date when you have to take into consideration that you’re going to be doing some exercise, you don’t want to get too sweaty, but it’s kinda cold outside AND you want to look cute? Not easy my friend, not easy.
On the Thursday night we planned a date at a bar not far from my place and about half an hour before we were due to meet he messaged and said “I’m running late so do you mind if I don’t pick you up, I’ll meet you there but I promise I’ll walk you home?” Now, the place we were meeting was literally 4 blocks from my house, which he knew, and he was using transit to get downtown so it wasn’t like he could just swing by in his car. At no point had I imagined he would have been coming to “pick me up”. His manners were a massive turn on, there is something about chivalry that gets me riled up, in the best possible way.
In a similar fashion to our first date, our second followed suit with more to talk about than we had time for. Over multiple drinks (we discovered a mutual love of gin) and some food, we covered multiple topics of conversation. But what was nice was that, whereas on our first date we covered some fairly hefty topics – our parents’ divorces, our past relationships, sibling relationships, how he was open to a relationship but would want to take anything really slowly and the reasons for that -, on our second date we actually talked about a lot more light, random stuff – favourite trips, food and drink loves, friends, home decor.
We also talked about alter egos. A subject I had never thought much about before. Don’t get me wrong there’s a drunk me, but I hardly would call her an alter ego. She’s just an ego. LOL. But he had this whole persona, which in fairness he said did come out when he was drunk but also when he was in any competitive situation. He had a name and everything, his friends would refer to it oftentimes…. Ok, good to know, I guess.
The seeming end of the date brought with it the sense that, again, we didn’t have enough time to say everything we wanted to. So as he walked me home, and made a comment about my apartment, I decided that a nightcap would give us the perfect opportunity for some more time together and for him to see the apartment he was enquiring about.
As we headed up in the elevator I had hopes that he would kiss me at some point, his tactile taking of my arm as we walked home seemed like a good sign. But I was also sure, and happy with the likelihood, that a kiss was as far as it would go. Nothing that I knew of him up to that point gave me the impression he would sleep with someone on a second date and given what he’d said on the first date about wanting to take things really slowly, which again he’d re-iterated over dinner that night, it really wasn’t even a consideration.
Once back in my apartment, I got to making us each another gin of the night. As I did he moved up behind me just close enough that I could feel his clothes just lightly touching mine. Taken by surprise that he didn’t seem to even be waiting for drinks before making a move, I carried on measuring out the gin. As I poured the tonic, he slipped his hand round my waist, turned me to face him and right there, with tonic can in hand, we had our first kiss.
He was sweet and gentle and as far as first kisses go, it was pretty great. It lead to a whole lot of kissing on my couch, interspersed with more chatting and drinking the gins that I’d eventually finished pouring. I had been hopeful for a kiss but this was probably more than I’d been prepared for. It got pretty hot and heavy pretty quickly.
What I definitely wasn’t prepared for was that during the teenage-like make out session, he made a comment along the lines of “I would love to sleep with you”. Now, don’t get me wrong, I wasn’t exactly not having the same thought but, as I mentioned, he had made it so clear, so absolutely crystal clear, that he wanted any new relationship to go slowly that I presumed that would have meant he’d take longer than two dates before he slept with someone.
It turns out, 2 dates was just the right amount of time for him to be ready to sleep with me. I was surprised, but not unpleasantly so. Much like the first date, it took my by surprise but it felt right despite it also kind of seeming a little insane. Initially I did stop and ask him if he was sure. I didn’t want the fun of the night, or the gin, to be clouding anyone’s judgement. He barely let me get the question out before he assured me.
I went with it and I wasn’t disappointed. And neither was he.
He stayed over til morning, and throughout the night there was more great chatting, a lot of incredible sex and an abundance of snuggling. And I’m not going to lie, the snuggling may have been my favourite. Being single there are a lot of things I miss about being in a relationship but snuggles? They might be at the top of that list. And, despite it only being the second date, I was hoping there might be a lot more snuggles to come…