By Renato, who builds Kept ·
No, it is not weird, and the awkwardness you expect is mostly in the forecast.
In experiments where people wrote gratitude letters and predicted the reaction, writers underestimated how positive the recipient would feel and overestimated how awkward it would be. The reason is a mismatch in attention: the writer is judging how well it is put, while the person reading it is registering the warmth. The same pessimistic lean shows up when people reach out unprompted and when they start a deeper conversation, so the hesitation you feel is a known bias rather than a reading of your friend.
The short version
- Writers of gratitude letters underestimated how positive recipients would feel, overestimated how awkward recipients would feel and underestimated how surprised they would be.
- The writer grades a performance. The reader registers warmth. That is why the expected cost is inflated and the benefit discounted.
- Recipients appreciated unprompted contact more than senders predicted, and the gap widened the more surprising the contact was.
- What reaches the other person is what they can perceive. A specific thing you noticed says more than a general "you mean a lot to me".
- Keep it from sounding like settling a debt, and write it yourself. Messages known to involve AI were judged less authentic.
Why it feels awkward
The hesitation has been measured directly. In a set of experiments published in 2018, people wrote a letter of gratitude to someone and predicted how that person would react; the recipients then reported how they actually felt. The writers got it wrong in a consistent direction. They underestimated how positive the recipient would feel, overestimated how awkward the recipient would find it, and underestimated how surprised the recipient would be.
The proposed mechanism is a mismatch in what each side is paying attention to. The person writing evaluates themselves on competence: is this well put, does it sound strange, is it too much. The person reading is not assessing the writing at all. They are registering that someone thought of them warmly enough to say so. Because the writer is grading a performance nobody else is watching, the cost they expect is inflated and the benefit is discounted.
The limits matter. These were largely one-off exchanges in study conditions, measured immediately afterwards. Nothing in them says that repeated expressions keep landing the same way, and there is no long-run data on what happens to a friendship afterwards. What they do establish is that the moment before you send it is a poor guide to how it will be received.
The same forecast, everywhere
This is not a quirk of thank-you notes. In a separate series of experiments, people who reached out to someone unprompted predicted how the recipient would feel, and recipients appreciated the contact more than the senders expected. The gap grew the more surprising the contact was. Telling a friend out of nowhere that you value them is about as unprompted as contact gets, which puts it where the underestimate is largest. Those studies looked at single moments, not friendships over time, and nobody has shown that acting on the finding makes a friendship last.
The pattern holds for conversation too. When people were assigned to have either shallow or deep conversations, they predicted the deep ones would be more awkward and less connecting than they turned out to be, and they were most wrong about the most substantive topics. One proposed reason is that people underestimate how interested others are in them. Those conversations were assigned, often between strangers who knew they were in a study, so the stakes were lower than in life, and it does not follow that any given conversation will go well.
Put together, the three findings describe one consistent forecast: that warmth, contact and depth will cost more and land worse than they do. "It would be weird to say that" is what that forecast sounds like from the inside.
What makes it land
The relationship literature gives a working definition of what the other person is listening for. Intimacy, operationally, is feeling understood, validated and cared for, and perceived partner responsiveness, the sense that someone is paying attention to you, predicts the behaviours that keep a relationship going, gratitude among them. The word doing the work is perceived. What moves a relationship is not what you felt but what the other person registered.
A meta-analysis of relationship maintenance found the same thing from another angle: relationship quality tracked a person’s perception of their partner’s upkeep more closely than the partner’s own report of doing it. This is a framework resting on mostly correlational work, and responsiveness and closeness feed each other, so no direction is established. But it explains why appreciation that stays in your head does nothing for the friend it is about.
It also tells you what to say. "You mean a lot to me" is warm, but it could be sent to anyone. "I still think about how you drove over the night my flight was cancelled" could only come from someone who noticed. Referencing something specific is one of the few reliable ways to make attention visible, because it cannot be produced without having paid it.
Two ways to spoil it
The first is turning it into a balance. Research on communal and exchange relationships distinguishes two norms: in exchange relationships, benefits are given to create or repay an obligation; in communal ones, they follow from concern for the other person. Where closeness is wanted, prompt repayment of a benefit reduces attraction rather than increasing it. The studies were mostly short laboratory interactions, and real friendships mix the two norms. Our reading is that appreciation phrased as squaring up ("I owe you one", "I’ll make it up to you") borrows the exchange norm, while appreciation phrased as noticing does not.
The second is handing it to someone, or something, else. Messages known to involve AI were judged less trustworthy and less authentic, with larger penalties for greater involvement. The penalty attaches to what the reader believes produced the words, not to the words themselves. This is a young literature and the norms are shifting quickly, so the size of the penalty may not hold. But a polished message solves the problem the gratitude research says the reader does not have.
Neither of these is about getting the wording right. The reader is not marking it. They are reading it for evidence that it came from you and was about them.
What to actually do
Pick one friend and one specific thing. Not a summary of the friendship, a moment: something they did, said or remembered that mattered to you. Write two or three sentences about it, and resist the urge to redraft until it sounds eloquent, because eloquence is what you are grading and not what they are reading.
Send it without a reason. You do not need a birthday or an occasion, and the research on unprompted contact says the lack of one is part of why it lands. If the forecast says it will be awkward, treat that as the measured bias it is, not as information about your friend.
None of this needs an app. It needs the habit of noticing the moments worth thanking someone for while they are fresh, a note of them somewhere you will see again, and the decision to send the message when your own forecast tells you not to.
Questions people ask
- How do you tell a friend you appreciate them without it being awkward?
- Name one specific thing they did rather than summarising the friendship, and send it without redrafting for polish. In experiments on gratitude letters, the awkwardness writers expected was larger than what recipients reported, because the writer was judging the wording and the reader was registering the warmth.
- Is it strange to send a thank-you message out of nowhere?
- The research suggests the opposite. Recipients appreciated unprompted contact more than senders predicted, and the gap was wider the more surprising the contact was. Writers of gratitude letters also underestimated how surprised, and how pleased, recipients would be.
- Does it matter if the message isn’t well written?
- Much less than it feels like it does. In the gratitude experiments, writers evaluated themselves on how well they had put it, while recipients were not assessing the writing at all. A specific detail matters more than eloquence, and words known to involve AI were judged less authentic.
Where this comes from
Every claim above traces to one of these. Each has its own page with the method and what it doesn’t show.
Senders worry about sounding awkward. Receivers just hear the warmth.
Kumar & Epley (2018) · Psychological Science
People are happier to hear from you than you predict
Liu, Rim, Min & Min (2023) · Journal of Personality and Social Psychology
Deep conversations feel less awkward than people expect
Kardas, Kumar & Epley (2022) · Journal of Personality and Social Psychology
Feeling understood is the working definition of intimacy
Reis, Clark & Holmes (2004) · Perceived partner responsiveness
Keeping score is how exchange relationships work, and it damages close ones
Clark & Mills · Communal and exchange relationships
Messages known to involve AI are judged less authentic
Hancock, Naaman & Levy · Journal of Computer-Mediated Communication, and subsequent AI-penalty research
Read next
Should you let AI write your messages to friends?
Messages people believe involved AI are judged less authentic, and the wording was never what your friend was reading for. Write it yourself, and keep it short.
How to be a better friend, according to the research
Across 38 studies, four things a friend does went with wellbeing: react well to good news, back their choices, keep the effort up, make them feel they matter.
It’s been too long to message them. Send it anyway.
The reluctance you feel is not information about how the message will be received. It is a bias, and it has been measured.
Kept is what we built from this.
Nine seconds of talking after you see someone. Kept files it against the right person and hands it back the day before it matters. No streak or score on anyone in it, and it never writes your messages.
Or see how it compares to the alternatives, including where they beat it.
