How to Reach Out to an Old Friend Without Making it Awkward

If you are or have formerly been friends with a male, you probably know that the process involves taking something simple and making it inexplicably, stupidly hard. It’s something akin to picking up a baseball, drinking with it for 10 years, never actually telling it how important its friendship has been, then waking up one morning to find you haven’t heard from the baseball in 10 years. This may be an imperfect metaphor, but we’re sticking with it, because it has a baseball.

Whether uniformly fair or not, men are renowned for their friendship troubles, for a long and colorful list of potential reasons that you can basically X out and replace with “inability to forge meaningful emotional connections based on anything other than going online and pretending you can coach an football team.” This is doubly true if you have kids, which are usually not allowed into something like 85 percent of the activities you and your buddy previously enjoyed. Before anyone realizes it, the years have vanished. Nothing feels faster than realizing how little time it takes for people to drift away.

Yet as we age, these old bonds can be the most crucial — if you can get them back. The good news: There are endless ways to reach back out to old friends. The bad news: Some of them will feel weird. Here’s how to do it and not make it so.

1. Figure out the level of this friendship.

Let’s just start with some ice-cold practicality: When you get to a certain age you acknowledge and accept that friendships have importance levels, like the emails in your inbox. Some people warrant the sporadic check-in, the swapping of a dozen pleasant but sort of cursory texts. Zero of us have the bandwidth to maintain connections with the whole of our history. So for the purposes of this, we’ll assume you’re re-connecting with someone pretty important. And if that’s the case…

2. Use a grown-man form of communication

Preferably one that doesn’t routinely send your information to Russian deep-state spy networks. Facebook is fine for occasionally glimpsing spring breaks or birthday milestones, but its baseline ability to facilitate meaningful connections started low and can’t seem to stop dwindling. If you’re moved to get back in touch with someone important, do it with an Actual Message, something written via electronic mail or Facebook Messenger, if you’re a a millennial (an aspiring one). Just make it an actual message.

3. Or use a phone, we guess?

Phone communication takes time, energy, and a certain degree of emotional integrity, and it may frankly be too much for this initial hello. But, if you’re a chatty sort who works best when playing off others and employing social cues, go for it. If it’s a super out-of-the-blue message, or someone you haven’t seen for too long, a little advance warning might be wise, and give all parties time to prep for the actual talk.

4. Try to write like a non-creepy stalker.

If you do go the written route, you have two ways to begin. The first is opening with a joke or reference, some sort of hilarious deflective means to attempt to jump back into your old style of conversation and forget that it’s been eight years since you acknowledged this guy’s birthday. The second is to write like a normal person. “Hey, this is random, but I ran across some old photos/videos/memories and thought it a good time to check in a say hi. I know it’s been a while / Hope all is well / Glad to see your family looking great,” etc. We advocate Option 2. If it’s been a way long time since you chatted, cop to it, be open about it. Your buddy wasn’t in touch with you either, so the communication gap goes both ways.

5. Start with the family.

No human alive objects to talking about their families/kids/dogs. If you’re totally stuck for an opening line, start by referencing a recent vacation, kid sport/activity or simple adorable picture, something that shows you’ve been paying attention to your buddy’s comings and goings, even if you haven’t told him so. “I also have a son in Little League/auto racing/theater/aspiring samurai competitions,” or “I saw you went to Tanzania, we’re thinking about hitting up Slovakia later this summer,” whatever. Find something both of you can talk about it, so you’re neither interviewing him nor delivering a 3,000-word monologue about yourself.

6. Keep in mind: He will be glad to hear from you.

We guys are, for the most part, large and obnoxious children who have to do things like read Internet lists to complete basic friendship tasks. It’s not great. But we can be assured of one thing: Your buddy is probably in a different part the same boat you’re in, one that limits the amount of time he can reboot old connections, revisit his sea of memories, or spend a little bit of time being himself instead of a dad or a husband. Seeing your name pop up in his inbox or call list will, unless you, like, got him caught up in a Ponzi scheme, be a positive joy, something that’ll briefly shake him out of his probably dug-in daily routine.

All of this is to say that any way you do this is good. Most of us have this all backwards, telling ourselves we don’t have time to communicate because of commutes or coaching or deadlines or sleep deprivation. This is exactly backwards. One day, you’ll want to look back and realize that you prioritized these bonds, these people, these memories, over the daily routine that appears to be of paramount importance today, but will be faded and forgotten one day. Start now.