New App Considerate Makes Connection a Each day Behavior

Launching today, Thoughtful offers tips for deliberately connecting with friends in bite-sized ways, on a daily basis. Research shows that this kind of regular correspondence and responsiveness³ (rather than grand but infrequent gestures) is the key to good connection. “Relationships are a marathon, not a sprint,” says psychiatrist Samantha Boardman, MD, who advised on the development of Thoughtful. “It’s [by way of] those micro-moments of checking in and showing up for people that friendships are sustained over time.”

“Micro-moments of checking in and showing up for people are how friendships are sustained over time.” —Samantha Boardman, MD, psychiatrist

But the reality is, remembering to touch base with friends is often easier said than done. Even the most attentive person may forget a friend’s birthday or recent surgery or upcoming work presentation if their personal calendar is packed enough. And in the wake of a pandemic that forced us into social isolation, our skills for reaching out and strengthening our connections⁴ may be rustier than ever. Indeed, the U.S. surgeon general recently called rates of loneliness in this country an “epidemic,” noting its prevalence across all age groups.

Where Thoughtful aims to help is by “reducing the friction of reaching out to friends in any way possible,” says Thoughtful co-founder and CEO Elizabeth Shaffer. That means, first, assessing your personality (so that recommendations for connecting with friends feel like, well, things you want to do) and then, offering you personalized daily suggestions for reaching out, remembering important dates, and deepening your connections.

How Thoughtful uses a personality test to help you better connect with others

The bedrock of the Thoughtful app is a three-part personality test called the Connection Style test, developed in partnership with psychiatrists to assess how you behave within, view, and communicate in your relationships. The idea is that different people form and maintain connections with friends and loved ones in different ways, and the best strategies for deepening those connections will take those natural preferences into account.

The test walks you through different scenarios related to friendship—like, “I haven’t called my friend in weeks, but I have recently sent them 200 memes,” and “I like the idea of doing something new, but when the day comes, all I can think is: ‘Why did I agree to do this?'”—and you respond with how much you agree or disagree.

Based on your responses, you’re then sorted into one of five connection archetypes: Seeker, Organizer, Enthusiast, Truth Teller, and Cultivator. (To be clear, no connection style is better or worse than any other; they just reflect different ways of being in relationships.) Here’s a breakdown of all five:

1. Seeker: These people are deeply empathetic and are always searching for meaning and knowledge. However, sometimes their feelings can get the best of them. “They can be vulnerable and get their feelings hurt a little bit, and the ‘why’ can ultimately be unnerving for them,” says Dr. Boardman.
2. Organizer: Detail-oriented problem-solvers, Organizers respond to stress or problems in friendships by plunging into the details and working it all out themselves, says Dr. Boardman.
3. Enthusiast: These people are all about living life to the fullest, embracing new experiences, and having adventures. They bring the party and the fun, but they can also feel stretched thin or not fully present as a result, says Dr. Boardman. “Sometimes, they end up in a position where they’re not able to make time for the people in their lives because they’re busy planning the next thing.”
4. Truth Teller: These people are most concerned with honesty and authenticity. Their candor can be a much-needed breath of fresh air, but “sometimes, it can also feel offensive,” says Dr. Boardman, referencing their bluntness. “Even if they don’t intend to, they often point out flaws in others.”
5. Cultivator: These folks are loyal and dependable—sometimes to a fault. “They like the routines of daily life, and they like to stick to them,” says Dr. Boardman. Thoughtful and conscientious, a Cultivator is always going to be there for you, sometimes even at the expense of their own well-being.

The app tailors its daily suggestions based on your connection style, so you “can capitalize on your strengths and navigate around what may make your relationships complicated,” says Dr. Boardman. If you’re a Seeker, for example, you might be nudged to take a beat to articulate something versus getting caught in your feelings or holding onto a grudge. Whereas, if you’re an Enthusiast, you might get a prompt simply reminding you to say, “Hello” to someone, so you don’t risk ignoring a key connection while overcommitting to other things.

How Thoughtful makes building connection and fighting loneliness a habit

Each time you open the Thoughtful app, you’ll be met with three connection-boosting prompts, personalized based on your Connection Style above: one that suggests a reach-out to a friend, one to help you remember an important date or happening in a friend’s life, and one to help you reflect on a friendship.

While the “reach-out” prompts will offer simple ways to connect with someone, the “remember” prompts will lead you to record specific details and dates gleaned from conversations with friends so that you can receive timely reminders about them. Ideally, you add  “one piece of information every single day about a person in your life, and it could be something as simple as a recent conversation or the holidays that people celebrate,” says Shaffer.

For example, let’s say a coworker recently mentioned an upcoming performance for their theater troupe; you can note that detail in response to a “remember” prompt along with the date, so that you’re reminded to wish them luck beforehand and congratulate them after. Or, if you learn that a friend has scheduled a date for their C-section, you can record that detail, so you can be reminded to send a card or offer your help around that date.

Beyond keeping track of such dates, the Thoughtful app also supplies you with advice on exactly what to say when you do reach out, depending on the event (so, feeling like you don’t know what to say stops being a reason for avoiding connection). Its arsenal of 350-plus articles on connection contains tips from experts about how to support friends and family members through any number of major life events, like infertility or losing a parent.

To keep you plugged into your friendships even outside of the big milestones, the final “reflection” prompt for each day encourages you to log a kind, funny, sweet, or interesting interaction or memory you’ve shared with someone. These prompts might look like, “Who was the last person to give you a compliment?” and “When was the last time you had an amazing time with your friends?”

Having this kind of “repository of wonderful friendship moments,” as Shaffer puts it, can help reinforce the beauty of the friendships you have and remind you why you’re taking the time to invest in them in the first place.