How to Deepen Relationships Remotely: Lessons From an Extrovert

As a classic extrovert, I’ve always drawn energy from being around people. I organize social gatherings. I love meeting new faces. My social calendar used to be packed with four to eight in-person meetings a day — until quarantine hit.

When lockdown began, I wondered how I would survive. For the first five months, living alone, I didn’t see anyone — not even my family or my boyfriend. To my surprise, while some of my more introverted friends went stir-crazy, I was actually doing okay.

I realized that even though I thrive on connection, I don’t necessarily need to be physically with people to feel connected to them. (My lowest-scoring Love Language is touch — that might explain a lot!)

While the pace of making new connections slowed down, I found that my existing relationships deepened exponentially. Friends I used to see only once or twice a year became people I now talk to monthly or even weekly.

Why Virtual Connections Can Still Feel Meaningful

Before quarantine, I loved big events where I could meet strangers who might become lifelong friends. But my favorite form of connection has always been the one-on-one conversation — the kind that allows for curiosity, listening, and depth.

Now, because I don’t have to factor in commute time, I’m able to have more meaningful one-on-one conversations in a single day than ever before. These virtual connections have been surprisingly energizing and intimate.

Here are the simple practices that helped me strengthen relationships remotely — habits that still serve me today.

1. Text Message Check-Ins

Each week, I text at least five friends or acquaintances to say happy birthday, check in, or simply share, “Thinking of you.”

I use Facebook for reminders about birthdays and life updates, and when I see one, I check if I have the person’s number. Sending a text feels more personal than posting online — it’s a small gesture that says, you matter.

Sometimes, those texts spark longer exchanges or even phone calls. Most of the time, they just brighten someone’s day. The point isn’t depth every time — it’s consistency.

2. Send Personalized Email Updates

Once a year, I send a long email update that’s personalized through mail merge. My rule: if I can’t recall a specific detail about that person’s life or our last interaction, I don’t include them in the list.

To keep the email authentic, I include both the highlights and the hard stuff. I might also add a small invitation — like feedback on an essay, or an invite to a free workshop I’m piloting.

These updates often lead to surprisingly deep replies, with people sharing what’s been happening in their lives. It’s a gentle way to rekindle dormant relationships while also letting others into your journey.

3. Make Phone Calls a Habit

In a video-heavy world, phone calls feel refreshingly personal. I now have regular weekly, monthly, and quarterly calls with friends. Sometimes I’ll stretch or walk while talking.

I’ll often ask, “Want to make this a regular thing?” and many friends say yes. Some calls happen spontaneously — I’ll reach out to four or five friends in a day just to reconnect.

One friend I’d only met a few times before now talks to me every month. Another calls our monthly chats “therapy.” These ongoing conversations have turned acquaintances into close friends.

4. Send Unexpected Cards

Most people send holiday cards in December. I send Valentine’s cards.

Since high school, I’ve made it a tradition to mail Valentine’s Day cards because most adults don’t get any. Each year, I design the card to reflect a theme from the previous year and write 3–5 personal lines in every one.

I use EE Printing to produce about 100 cards annually — the limit is how many personalized notes I can handwrite! These cards have become one of my favorite ways to reconnect with people and express appreciation for their support.

I heard a great interview with Morra Aarons-Mele of Women Online by Guy Raz with more tips. 

This post was based on “Tips on Deepening Relationships Remotely,” which was originally posted on Feb. 21, 2022.