💬💬💬 COMMUNITY CHAT: This week, in the spirit of today’s newsletter: Where in your life are you practicing being a little less accommodating and a little more honest? CLICK JUST BELOW TO JOIN! 💬💬💬
And now, on to this week’s newsletter!
Likes being active, loves my dog, makes great guacamole.
A client we’ll call Annie, who is working on social anxiety and people pleasing, was getting back on the dating apps after a breather. She’s in her mid-thirties and is serious about dating effectively in order to meet a life partner and start a family. “I don’t have time to waste a year or two on a relationship I know isn’t going to last,” she said.
Annie had recently asked a friend to audit her profile, and the friend (lovingly) called it generic. “‘There’s not really any Annie here’ was how she put it,” said Annie. “She told me, ‘Active could mean anything, of course you love your dog, and who doesn’t like guacamole?’”
Without blaming the victim, Annie’s friend had illuminated a symptom of the problem Annie was having: people pleasing.
More broadly, Annie was in a cycle where three things always seemed to happen:
First, her generic profile attracted, well, everyone. She went on a lot of first dates with a huge variety of people. When she was in her twenties, this was fun—she met cool people with interests she had never considered. But now, her broadly appealing profile wasn’t filtering like it was supposed to. Her matches were based not on attraction to Annie and her goals, values, and interests, but on the absence of objection.
Second, once she met her matches, her instinct to be broadly appealing meant most people liked her. On one hand, this was great. It felt good to get along, but she was starting to suspect she was unconsciously people-pleasing. After dating one guy for a month, she realized she had started following his favorite hockey team and had become a regular at his favorite restaurant, but they had barely delved into her interests at all.
Finally, Annie’s relationships always lasted looong past the time her gut told her it was time to end them, mostly due to conflict avoidance. Her last relationships had lasted a year (“We should have broken up after 6 months,”) three months (“I should have figured that one out instantly,”) and three years (“That entire last year was procrastination.”) She knew she could handle both rejection and being the rejector—she had done both before—but she had to spend an inordinate amount of energy summoning the will to do so, and it took her weeks to recover.
In short, in an unconscious drive to be liked by everyone, Annie was attracting false positives, overriding herself to maintain connection, and staying long after the relationship had run its course in order to avoid conflict.
On reflection, it made sense. Annie had grown up in a critical family where making oneself unobjectionable was a way to avoid being criticized. No wonder Annie was presenting herself as universally acceptable.
Therefore, Annie has begun to question the assumptions that make her want what she thinks others want. Here are three new thoughts she is test-driving as she consciously shifts the goal from being unobjectionable to finding the right match:
“It is my ethical obligation to show up as myself.”
For folks familiar with people-pleasing, exhortations like “put your needs first” or “you deserve it” feel rude at best, illegal at worst. Better to read the room and want what everyone else wants in order to keep the peace and stay socially safe.
It might sound weird to frame “being yourself” as an ethical responsibility, but for a highly-conscientious people-pleaser, it’s the needed permission to opt out of “I just want what they want” without guilt.
Therefore, in an effort to fulfill her duty to be herself, Annie made her profile more specific (“I check a bald eagle webcam daily; I’m teaching myself to identify trees”) and selective, toggling on “life partner” and “wants kids.” She made a conscious effort to introduce her own interests early and kept an eye on whether or not her dates took them into account.
The duty to be herself also helped Annie at the end of the relationship. Seeing breaking up on time as an ethical responsibility to be met—rather than a failure to be avoided—made it easier to override her anxiety and stop dragging it out. Either way, framing authenticity as a duty took out the guesswork and guilt and made dating easier to navigate.
“It’s more respectful to speak up than to avoid conflict.”
Like many people familiar with social anxiety and people pleasing, Annie’s tendency to avoid conflict led to an all-or-nothing pattern where she would keep the peace, keep the peace, keep the peace, and then suddenly lash out in a way that felt unsettling and out of character: “We always do what you want!” Her outbursts were objectively pretty mild: increased intensity, a slightly raised voice; regardless, when they happened, they took everyone aback.
Annie’s lifelong habit of avoiding conflict didn’t actually prevent friction, she observed. It just delayed and internalized it. When her frustration eventually surfaced, it was harder on both her and her partner.
Annie started floating kind yet clarifying statements like: “Can we alternate restaurants? I’m missing some of my favorites,” and “I’m happy to watch hockey sometimes, but I don’t want that to be our main thing,” as well as kind discussion openers like, “We’re both being totally reasonable, but some things aren’t working for me,” and “Can we check in about something small before it gets bigger?”
To encourage herself to speak up before she got frustrated, Annie tried to think of it not as complaining or criticizing, but as communication that was more mature and respectful of both of them than continual accommodation. After all, she wasn’t a kid trying to avoid her parents’ unavoidable criticism anymore—she was part of a couple trying to make things work.
“I can be a good person AND reject someone”
It’s easy to buy into the idea that rejection inflicts harm. And that inflicting harm makes us bad or cruel.
When it came time to say “no” to a second date or end an established relationship, Annie realized that she was conflating “be a good person” with “minimize discomfort.”
By procrastinating an eventual end, Annie was prioritizing comfort, but it wasn’t honest or respectful to keep someone in a relationship after her gut told her it had run its course.
Instead, being a good person actually meant communicating kindly but clearly, like “I keep hoping I’ll feel differently, and I don’t think that’s fair to either of us. You deserve someone who’s all in.” Or “Nothing is ‘wrong,’ but this doesn’t feel right enough for me to continue. I don’t want to keep going out of momentum.” Ultimately, being clear matched her value of being a good person better than procrastination and avoidance.
All in all, in her quest to extract people-pleasing from her dating life, Annie is trying to approach authenticity, speaking up, and on-time endings as ethical responsibilities rather than danger zones for criticism and conflict. Some moments are hard, but they’re no longer misspent, and Annie is relishing shifting from overriding her gut to following it.
**As always, all HIPAA identifiers and story details have been changed or combined while keeping the essence intact. My goal is to honor the confidentiality of therapy while sharing relatable, based-on-a-true-story examples.
Be good to others and yourself!
