I generally feel like it’s worth it. Even if that worth is only validating why you stopped chatting to that person in the first place.

Especially because I have no irl-linked social media, Im often initiating contact… But I like checking in on random people every few years or so, you never know, you might brighten someone’s day; develop connections you might not have with acquaintances because you’ve both changed; or at the very least, reminding yourself that there’s no loss if you don’t talk to that person ever again!

I’d rather be regretting my interaction than to regret not interacting at all.

I keep trying this, usually when I come across someone in my contacts who I haven’t seen in a decade or something. Particularly after deleting Facebook a few years ago, I want to keep up with people.

It’s always the same pattern though. We hang out, have a great time, sometimes do it one or two more times, and then it just never happens again. The problem is that it’s always me doing the lifting. I have to remember to call, set up some plan, make the thing happen. If I don’t do the work, it doesn’t work.

I generally end up deciding that it’s not worth my time to fight so hard to see someone who obviously isn’t interested in prioritizing time with me.

One or two have maintained touch, but there’s probably a dozen more who fell back off the map. Forever the optimist though, I’ve got another one on the calendar in a couple weeks.

I’ve had a few experience with this and each was drastically different.

On one end, I reconnected with a friend I hadn’t seen since high school and invited her out for dinner. We met and just picked up right where we left off. Every time I see her now, it’s the same. I invite her to all my parties by default because she’s a great person to hang out with. We’re very much similar people and really enjoy each other’s company.

On the other, I reconnected with an online friend I hadn’t spoken to in a few years. It was nice to chat with him again but the more we talked, the more it was clear to me why we stopped talking in the first place. He was sort of controlling and jumped to a lot of weird conclusions and never communicated what he wanted clearly. We stopped talking regularly and while we’ll say hi if we’re online at the same time, we don’t seek each other out for long chats.

I once did that, after unexpectedly stumbling upon an old college friend of mine. We had a nice lunch, planned to have another one but didn’t really scheduled it. Life did its trick, and we lost touch again.

Yes - I am in the process of doing that right now. The results are mixed but mostly positive. Without going into too much detail, we were very good friends for 3 years at my first job out of uni but when my contract ended we lost touch. It’s about 20 years later now and although I still enjoy their company the friendship is very different. It’s helped me reflect on how I’ve changed since then. Definitely worth it, but not without challenge.

I’m marrying his ex-wife.