Reconnecting With Old Friends: Why It's Harder Than You Think

So last year I decided to reach out to some friends from college that I hadn't talked to in like 5 years. I thought it would be easy - we were super close back then, we'd just pick up where we left off right?

Wrong. It was so weird.

The Initial Awkwardness

I sent my friend Mike a message like "hey man, long time! how have you been?" And he responded but it was all surface level stuff. Then we tried to have a phone call and it was just... awkward.

We'd run out of things to say after like 10 minutes. This was someone I used to talk to EVERY DAY in college.

Why Reconnecting Is Hard

After trying to reconnect with a few different people, I realized a few things:

You're Both Different People Now

5 years is a long time. We'd both changed alot:

We weren't the same 22 year olds who stayed up late playing video games anymore.

You Don't Have Shared Context Anymore

In college we saw each other every day. We had the same classes, same friends, same campus drama to talk about.

Now we live in different cities and our lives don't overlap at all. So there's no shared experiences to reference.

There's Guilt and Weirdness

Both of us felt bad about not staying in touch. And that guilt made it harder to just be natural. Like we both kept apologizing for not reaching out sooner.

What Actually Helped

After some really awkward attempts, I figured out a few things that made reconnecting easier:

1. Acknowledge the Weirdness

Instead of pretending nothing changed, I started being honest:

"This is kinda weird right? Like we used to talk everyday and now its been 5 years."

Just naming it made it less awkward.

2. Ask About Their Life Now (Not Just Reminisce)

At first we just talked about old college stories. Which is fun but it kept us stuck in the past.

Better questions:

These questions helped us get to know the people we are NOW, not just who we were.

3. Start Small

Instead of trying to have deep 2-hour conversations right away, I started with:

Building up slowly felt more natural.

4. Find New Common Ground

We couldn't just rely on our college friendship. We needed to find new things we both cared about:

This gave us stuff to actually talk about.

5. Accept That Some Friendships Have Run Their Course

This is hard but important: not every old friend will become a current friend. Sometimes people grow apart and that's okay.

I tried reconnecting with a few people and realized we just didn't have anything in common anymore. And that's fine! It doesn't mean the friendship wasn't real or important back then.

What Our Friendship Looks Like Now

Mike and I eventually found our rhythm. We're not as close as we were in college but we:

Its different than before but still meaningful.

Tips If You're Trying To Reconnect

If your thinking about reaching out to old friends, here's what I'd reccommend:

1. **Don't wait for the perfect time** - Just send the message

2. **Keep expectations realistic** - It won't be exactly like it was before

3. **Be genuine about why your reaching out** - "I miss you" is a good reason

4. **Give it time** - The first conversation might be awkward, that's okay

5. **Don't force it** - If it doesn't click anymore, that's alright

The Value of Old Friends

Even though reconnecting was harder than I expected, I'm glad I did it. These people knew me during an important time in my life. There's something valuable about maintaning those connections even if they look different now.

Plus its nice to have friends who remember the person you used to be, even as your becoming someone new.

Moving Forward

I've learned that friendships require effort, especially when life pulls you in different directions. But if the friendship was real, you can usually find a way to keep it alive in some form.

It just might take some awkward conversations to get there.

Have you reconnected with old friends? How did it go for you?