The Challenge of Saying the Thing: Why Is It Hard to Tell Friends We Want to Connect?

Many of us want to feel connected, but sometimes, expressing that desire feels complicated and risky.

In conversations lately—both inside the therapy room and outside it—I’m listening to a common thread: sometimes, we can struggle to say the simplest, truest thing.

When we want to connect with someone, instead of saying, “I want to spend time with you, are you up for making that happen together?” we can dance around it, asking if someone is free, seeing if they have plans, or vaguely suggesting something to do together if they’re not busy.

There’s an accepted rhythm to these interactions, and I wonder if we get there because the alternative seems too exposing. For example, if we approach someone by asking, “What are you up to this weekend?” we’re framing it as a casual inquiry rather than a direct invitation. If they say they’re busy, it can feel easier to accept because they’re saying “no” to the activity, not to us. But in doing this, I wonder if we are losing an opportunity to make our intentions known?

Likewise, when we are the person on the receiving end of the request, we can also play along in this dance. If we do have plans, we may stick with them even if we might prefer to spend time with the person asking. It’s socially easier to defer to existing commitments rather than confront the possibility of change. To not have to deal with the consequences of choosing the thing that we want most. In many ways, this approach protects both people from the vulnerability of directly expressing a desire for connection—and the possible discomfort of rejection.

An example that comes to mind for me is from a friendship I value deeply. For a while we had fallen into a kind of diary ping-pong. Instead of simply expressing that we want to see each other, we spend time suggesting activities, juggling dates, and coming up with ideas that ultimately don’t matter to the goal. It’s a way of doing things that, for me, just felt really unsatisfying and pushed me further from feeling the connection that I was looking for in the first place.

In my case, I think I started to lose sight of the fact that the activity was never the point. The real point was the time we wanted to share. And yet, in this indirect way of inviting each other, we may have been trying to protect ourselves from the vulnerability of directly expressing the desire for connection. It’s as if we both needed to believe that our company alone was enough without the need for an impressive plan. Imagine doing that, and not just saying “Ugh my heart is sore from not having you around”, after decades of friendship.

I have been thinking a lot about why it can be so challenging to make that simple statement: “I want to spend time with you”. In friendships, especially adult friendships, I wonder if there is an assumption that closeness doesn’t require explicit statements. However if we’re not turning up at each other’s doors at 4.30pm, asking “Is X in? Do they want to come out and play?” like we did after school, we’re also not necessarily choosing and being chosen in a very clear and deliberate way.

I’ve heard and experienced that without these affirmations, relationships can drift. I think the difficulty often lies in the fear of exposure—saying, “I miss you” or “I want to see you” can feel risky. It puts our desire out in the open, where it could be unreciprocated.

I think that deferring to activities or conflicting schedules also has a hidden cost.

When we constantly play the game of scheduling and rescheduling, we may avoid directly facing the reality that our friendship isn’t working as it once did. If we let a year go by, filled with nearly-meet-ups that never actually materialise, we’re not just unsuccessfully juggling diaries—we are allowing the friendship to drift without confronting why. Over time, I think that this dance around "scheduling" can let us avoid the truth that what once brought us together is now slipping away - that we might have grown and changed while our relationship has not.

I wonder if it is possible that by softening our language, and by focusing on the “what” and “when” instead of the why, we are safeguarding ourselves from the sting of feeling unimportant to people we love. Or from the difficult truth that someone has become less important to us.

I think that one of the most powerful (and scary) things we can do in friendships is to simply say what we feel: “I miss you,” “I’m thinking about you,” or “I’d love to see you.” If we’re able to put this into words, we can create a direct line of connection that helps us avoid getting lost in elaborate plans or mixed messages. When we lean into simplicity, we make our intentions clear—giving both ourselves and the other person space to respond honestly.

Saying the simplest thing is a way of honouring our own intentions. Rather than masking our desire for connection in casual invitations or veiled suggestions, we can affirm that we want time together. It might feel vulnerable, even a little awkward, but this kind of honesty can build the foundation for a deeper connection.

There’s no “right” or “wrong” way to invite someone to spend time together. I think it’s worth reflecting on how our communication habits can shape our relationships. What might happen if we took a chance on vulnerability, letting people know we enjoy their company without the social scaffolding of “are you free?” and “if you’re not doing anything, do you want to…?” It might be uncomfortable at first, but it could be a powerful way to affirm the value of our friendships.

In another close friendship of mine, we’ve experienced some really difficult life events together. Like, THE WORST stuff. Over time, the friendship has evolved into one focused on deep, meaningful conversations that helped us both process and support each other through those challenges.

Lately, I’ve been thinking that in doing so, I have somehow deprioritised—maybe even forgotten—how much we enjoy each other’s company in simple, lighthearted ways too. It’s something I’m actively working on now: remembering that, in addition to sharing the heavy stuff, I also love those easy times we spend together, like roaming through the shops, spending half an hour at the candles in TK Maxx just holding them up to each other’s faces going “This one?” Those moments are just as meaningful and help me stay connected in a way that feels lighter and full of ease. Saying and doing the simplest thing is how we can honour the full range of the relationship.

Being direct can feel risky; it can also feel freeing. By naming our desires clearly—without wrapping them in disclaimers—we could find more meaningful connection and remind ourselves that it’s okay to want someone’s company simply because we enjoy them.

Ultimately, being honest about what we want is a practice. And when we can do this in friendship, we invite a kind of closeness that comes from mutual openness. If you’re feeling uncertain about a particular friendship, or hesitant about what to say - you could get curious about how those relationships might change if you take the lead and say the simple thing.