People like us more than we think and enjoy compliments and outreach far more than we predict, so say the kind thing.
After talking with relative strangers, people consistently rate themselves as less likable and less socially adept than they really are. That's the liking gap. It holds for people we used to be close to, too: the "it's been too long, it would be weird" feeling is super common and probably a mistake. Social media widens the gap, since everyone else looks perfect and popular. Researchers at the University of Chicago found a related pattern with compliments. People underestimate how good the recipient will feel and overestimate how awkward it will be. Same with gratitude letters. And kind words don't get stale: senders expected repeated compliments to wear off, and recipients showed no sign of it.
On a call with someone I've known for years, I realized I'd never told them what I admired about them. So I paused. "Hey, can I say something? You have this rare ability to make people feel like they matter. I've always admired that about you." Silence. Then: "That was really creepy Zvi... go away." Just kidding. Of course they smiled and said they really appreciated it.
"Hey, I was thinking about you and wanted you to know..."