Mr. Right... Now. Or So I Thought. - Uncover Ostomy
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Mr. Right… Now. Or So I Thought.

I am an extremely lucky girl to be able to say that I’ve been on a tropical vacation at least once, every year.

99% of the time, it has been with my family.

Usually, after dark, on these vacations, my mother would go to bed early and my brother and I would find some friends. Eventually, my brother would go off with the kids close to his age, and I would go off with some friends closer to my own.

Ok, well… usually with a boy.

In the past, going on vacation was a chance for me to live outside of my normal, strange life. In high school, I was picked on by boys, instead of picked by these boys. I was that awkward girl who could never get a date, all thanks to the 2 years I spent isolated in the hospital, battling Crohn’s.

Eventually, I came to realize that on vacation, these people who I would meet didn’t know about my past and didn’t jump to tease me or to shun me for being so strange. On vacation, I had confidence. On vacation, I was the girl that the guys wanted to talk to. It was weird. It was also really fun.

So, I started collecting vacation boyfriends.

Ignoring the fact that it sounds really bad…. as the years went on, I found that every vacation there would be some boy that would be interested in me and vice versa. Even though I had moved on to university and had overcome my boy repellant curse, vacations were a time for me to just enjoy someone’s company. For the week of the vacation, I’d usually find a boy to hang out with around the pool/beach, to hang out with in a larger crowd, and then to stay up really late talking with/maybealittlebitofkissing. It was just a way to add an extra element of fun to the trip, you know? (don’t judge me……….)

Every vacation, however, the same rules would always apply. We’d have a fun week, we’d maybe add each other to Facebook, and then we’d never really talk again.

And it was awesome.

Unfortunately, as things got a little crazy for me last year, the last tropical vacation I went on was last February in Jamaica, and it was the first tropical vacation I was taking without my family. It was actually a destination wedding for one of my utmost favourite couples, to which the bride also happens to be one of my sorority sisters. And yes, other sorority sisters were coming too. I thought it would be nothing but partying. I booked the trip as soon as I could, and was dying for that week to come.

Long story short (since I already wrote a bit about it here), I met Matt on this trip. He was on the same resort trip that I was on, for a different friend’s wedding. Wanting to maintain my vacation boyfriend streak, and despite my friends calling me ridiculous, I set out to get him to notice me and join me for a week of fun.

My (super secret) tactics worked, and we ended up hanging out all week and having an amazing time. It also didn’t hurt that my sorority friends ended up going to bed early every night, leaving me with no other option than to hang out with Matt. We partied with his friends, we stayed up late sitting under the stars talking about everything we possibly could, and…etc.

Matt had become my vacation boyfriend and had made that week even better than I had ever imagined it could be (and I had already imagined it being pretty great).

When the vacation came to an end, I knew there would be rules to follow. Matt was only in my life for that week. No matter how good looking he was, no matter how nice he had been, and no matter how happy I had been that week – our vacation relationship was over. And I kept repeating that to myself even in the boarding area of the airport on the way home. After all, in real life, he lived 2 hours away from me.

I was never going to see him again, and I was actually really bothered by that thought. But I shook it off.

GET IT TOGETHER – I told myself.

Then, something happened: In the airport baggage claim, back in Toronto, Matt called me over and asked for my number.

Ummm, what?

This isn’t how it’s supposed to happen! I thought we had both agreed to these unspoken rules of awkwardly adding each other on Facebook and never seeing each other again. No one keeps talking to their vacation boyfriend/girlfriend after the vacation is over! It’s the RULE.

I still don’t know why I did it (and I almost didn’t), but I walked over to him and gave him my number.

1 year later, I have never been happier at this very moment than I have been in my entire life. 

This past weekend, Matt and I celebrated our “official” 1 year anniversary. Though we met last February, we continued to see each other every weekend, until he eventually asked to be my “real” boyfriend, last April.  Since late October, he’s been living in Toronto, and next month, he’s moving in.

I’m usually one to follow rules, and I’m also usually one to cut emotions from a situation – it’s how I’ve been able to just “have my fun” on vacation. But there was something about Matt that I couldn’t forget. Whether it was the way he made me think, the way he made me laugh, the way he looked into my eyes, or the way he held me – there was just something.

And there still is.


Jessica Grossman
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