She Wants to Be Friends, But Has No Follow-ThroughWhen a promising new friendship has chemistry, interest, and constant cancellations
In this month’s anonymous letter, a reader has found someone she genuinely clicks with. “C” is funny, easy to talk to, and seemingly interested in becoming closer friends. The problem is that when they make plans, “C” cancels, often at the last minute, and rarely initiates anything herself. Because making friends in midlife can be hard, the reader doesn’t want to give up too quickly on a connection that feels promising. But at what point do you stop trying to figure out why someone isn’t showing up and just move on? Dear Nina,I need your help navigating a confusing new potential friendship. I have a friend, “C,” who is an absolute blast to hang out with whenever we happen to run into each other in person. We have great chemistry and make each other laugh. We share things about ourselves comfortably and casually. She has stated being interested in a closer friendship. However, she won’t actually let us develop a deep relationship because she always cancels. So why do I keep trying? I’ve found making friends in midlife incredibly tough, and I don’t want to give up on someone who has lots of great qualities. The one time she reached out to plan a hangout she canceled minutes before we were supposed to meet and hasn’t made any effort to reschedule. I really like her and feel like this friendship is worth pursuing, but I’m also starting to wonder if maybe she doesn’t really like me? We are both ‘people pleasers’ so I have a real fear that she just wants me to like her and is only matching my energy to avoid conflict, rather than forming a genuine connection with who I am. How should I handle this dynamic? Should I say something? Would a ‘people pleaser’ even give me an honest answer? One last thing: she always acts surprised when I say I like her. Is she possibly just insecure? Dear “Always Reaching Out But Never Hanging Out,”Of course you’re frustrated. I was frustrated FOR YOU while reading the scenario! An important aside: longtime readers and listeners know that I do not advocate measuring a friendship from tit-for-tat actions. (I reach out, then you reach out, then I reach out, then you reach out.) That’s not how most relationships work. Often one person is good at reaching out and the other is—not as good. HOWEVER, that consistent advice of mine is with the understanding that the other person is demonstrating effort in some other obvious way. What’s confusing here for you (and for me reading it) is that “C” is using very direct and generous words stating she wants a closer friendship, which actually counts for a lot of effort. Not too many people can be that direct with their desire for a friendship. HOWEVER, as you noted, her actions say the exact opposite. So what should you do? Continue reading this post for free in the Substack app
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Tuesday, 11 August 2026
She Wants to Be Friends, But Has No Follow-Through
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She Wants to Be Friends, But Has No Follow-Through
When a promising new friendship has chemistry, interest, and constant cancellations ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏...
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