How it all Began – The Story of our First Date

Jackson here. This is the story of our first date – from my perspective.

It was mid-March, 2009 when Loretta and I had our first date. I was super nervous. My hands were sweaty, my voice was shaking. I was in trouble.

However, as luck would have it, I was guided by some excellent advice (and even a prop) given to me by Miles, one of my amazing groomsmen. He suggested that if you’re really nervous on a first date, it’s good to have some kind of an activity do so that you can fill in any possible awkward moments with a turn at the activity – and for those who know me well, you know that I have a tendency to be a little awkward at times.

For Loretta and I, this activity was Boggle – Miles actually lent me his personal copy for that night. But even though I had this genius crutch, I don’t think I actually needed it as Loretta and I hit it off tremendously (though, I probably had a little extra confidence having that awkward-saver as a back-up if I needed it!).

Boggle - great first date activity!

Loretta set out some treats for us to munch on – white wine (Riesling, at least a 2) and some pineapple with chocolate dipping sauce (mmmm).

We played a few rounds of Boggle as we munched on pineapple and sipped on Late Autumn Riesling. As I kept winning round after round of boggle (I’m a words-guy!), I could tell that Loretta wasn’t really fond of losing – so I let her win a couple of rounds. Good thing the conversation came so easily, because the Boggle may not have been the perfect fall-back crutch that I had hoped it would be!

Loretta had a great sense of humour and seemed to really take a shining to my goofiness and especially liked my Mike Tyson impersonation – I had been working on it earlier that week. As the night wore on, I noticed that if she got up off the couch to do something, when she came back she would sit down closer and closer to me every time. I thought – she likes me, awesome!

The defining moment must have been when Mr. Deeds unexpectedly came on the TV. Prior to our first date, we had talked about how we loved comedy movies and Adam Sandler’s Mr. Deeds was one of the films at the top of our lists – this couldn’t be just a coincidence!

'The hideousness of that foot will haunt my dreams forever'

When the night was over, Loretta showed me to the door.  This was it – the ‘make-it or break-it’ moment – time to leave a lasting impression. As we both went in for the kiss goodnight, Loretta went for the lips – and I went for the cheek. The kiss ended up being an awkward combination of a half-cheek, half-lip kiss.

I thought to myself – ‘I blew it, best just to get out without any more awkwardness.’ So then I turned to the door and pulled on the handle and it wouldn’t move – it was locked.  Of course it was. Loretta unlocked the door opened it up for me and as my face burned with embarrassment, I thanked her and walked out the door. Way to go, Jackson – way to leave a ‘lasting impression.’

Fortunately for me, Loretta (obviously) overlooked that awkward ending – she actually found my nervousness and awkwardness to be kind of endearing. And look at us now, more than three years later and engaged to be married!

It only took about 15-20 dates for me to stop shaking like a leaf every time I went to knock on her door.

A picture of us during our first summer together