Goodbye is a word that can either trigger no emotional response, make your heart twist up, or do something in between. Last week, I got to feel that something in between, as it was the day when one of my roommates moved out. He wasn’t here for long, maybe half a year, but we got along well. He helped me out with a few things during my reno and always had great stories about his day at work. When we gave our final handshake, I noticed that I was a little sad. Was it because of the 6 months together, or was it because the stories ended? I don’t know.

We said we’d keep in touch. I told him I was quite interested in how he navigated his current career goal of being a financial planner and he wanted to see the finished basement. We promised each other that we’ll keep each other in the loop, and I know we were both sincere with those words. But I’ve probably made dozens of similar requests over the years and now I don’t even talk to of them.

It’s kind of difficult, keeping in contact with old friends. Life happens on both ends and unless there’s some sort of trigger, you can completely forget about their existence. When you finally remember, it might’ve been months, years, or decades later. For example, as I wrote that, my memory flashed back to my best friend in elementary school. I went through 10 years of life with him but haven’t kept in contact since we both went to different high schools. Now that he’s on the top of my mind, I’m thinking whether I should reach out. Will we have any similar interests or goals? Is it going to be weird if I randomly sent a message and said “hey, just remembered old times and wanted to see how you were doing”? What’s the worse that can happen?

I actually did the latter recently to a previous girlfriend. I met someone who was facebook friends with her. It reminded me of her existence, I was genuinely curious of how she’s doing, and so I shot her a message asking just that. The conversation was pretty short – she didn’t seem to want to reconnect. Granted, after a few lines back and forth, I asked if she would be interested in grabbing coffee to catch up. Maybe she saw that as some sort of advancement, or maybe she understood the value of her time and didn’t see a catch up to be of value. Regardless, it was unfortunate as we did spend about 2.5 years together. Cie la vie. I guess that’s the worst thing that can happen.

Then there are people you want to stay connected with, but, once again, life happens. For example, I have had a few mentors throughout life that I just want to keep them in the loop on where I’m at and see how they’re doing. I also have a few friends whom I want to make the effort to stay connected with but currently fail to do so. I’ve asked myself a few dozen times: how do I schedule connecting with these people in my life. I mean it doesn’t have to be a specific time on a specific day, but schedule as in I get more reminders of their existence so I can reach out and say hi. Or do I use this blog as a platform for reminding them of my existence and hope that they reach out?

In other words, I’m currently looking for a system of reconnecting. A few years back, I scraped my facebook and linkedin for all the contacts that I wanted to keep in touch with. I just pulled up that list and there are 67 people. But even as I scrolled down, I’m wondering why many of those people are on that list – I guess the emotions from the experiences I’ve shared with them are now gone. Once again, unfortunate.

I’m going to reach out to them all before the end of the month and get a feel of how many people are interested in staying connected. But I’m still looking for a way to systematize this whole thing so if you have any ideas – I’d love it if you could share.