Knowing When to Say “When”

by Penelope Smallbone

I think a really tough part about the pursuit of relationships is knowing when to call it quits in an unsuccessful relationship. It’s so easy to stay put, and much easier to stay settled than it is to stand up and freely move on. I’ve had to learn this lesson the hard way, but nonetheless it is a lesson I’m grateful to have learned.

Scenario One: The Facts of Life
I dated my high school boyfriend for five and a half years, beginning midway through my junior year of high school. We stayed together because were in love, and at the time I thought that love was a magical, once in a lifetime thing that wouldn’t happen again if you passed on “the one.” (I was wrong, I hope.) We probably should have ended things about a year before we actually did. We had both grown up over the duration of our time together, and it was slowly becoming clear to me that we wanted different things. The tragic end to the tale is that I didn’t know how to recognize the point at which things are over. I eventually cheated on him. A lot. At the end of a three-month breakup, there were a lot of people who were involved and got hurt that probably could have been saved by my knowing when to say It’s Over.

Scenario Two: Repeat
For a time I dated my kickboxing instructor. It was only about four months after the Big Breakup, so I didn’t really expect to find anything significant so soon. But I did. We got really serious really fast, and it was wonderful at first because we fit together so well. The tipping point came when Thanksgiving was approaching. I was already feeling a little stifled in the relationship, and after only three months of dating we were already talking about spending a holiday with each others’ families. I flipped out. This was going to be my first time in FIVE YEARS where I didn’t have to go to anyone else’s family. I could just see my own family and spend time with them. I realized that if I was freaking out over this small issue, there would be bigger issues to deal with down the road. I broke it off with the instructor before we got even more attached and would be more hurt by a breakup. Although I knew it was the right thing to do, it sucked. It was the worst I’ve felt in a long time and it took us about nine months to actually get over each other. In retrospect, maybe it would have been better to drag it out a bit so that there was some aspect of hate involved, which would make getting over each other a lot easier. All things considered, I am happy that I was able to identify and act upon my feelings. Knowing your gut and going with it is a hard thing.

Scenario Three: Recent History
This year I went on a blind date. When I first saw him I didn’t think he was all that great. Kinda short, older, rotund. Not exactly the big, burly, manly type that I usually go for, but I gave it a shot. He ended up being really interesting, funny and considerate — a rare find in Manhattan. We went on a second date and also had a good time. The turning point happened when I visited my family this weekend. I remembered that all the men in my life are 6’0 and over, and that they are big guys. And that I am used to that, and naturally find that to be attractive. I pictured myself bringing home a short dude to a family event, and couldn’t see it working. The real kicker came in the form of a text message on Saturday. It was a “just thinking of you, so I thought I’d send you something to make you smile” type of message from the blind date guy. (gag me! …but I can see how some girls would appreciate the gesture…) I realized that my reaction meant that I just wasn’t that into him, and after being out of town for the weekend, and out of my normal life, I remembered that I don’t need to be with somebody just for the sake of not being alone. So I came home tonight and broke off the third date. Even though it may hurt him now, I’m proud for having done the right thing, and for knowing when to say When.