‘My Boundaries Are Killing My Love Life’

Dear Allison and Amy Rose,

I’m single and, by many traditional measures, thriving. My calendar is color-coded. My mornings are optimized. My weekends are full of all the self-actualizing stuff you’re supposed to do: the run club, the pottery class, the solo museum date with dinner and a book, the Sunday reset and time with the girls. I’ve built a life I’m genuinely proud of, and I protect it fiercely.

But lately I’m worried that, maybe, I protect it too much. I say “No” to the after-work drink or random invite to go out because it’s not on the calendar. I’m in bed at a certain time every night to ensure I get enough hours of sleep, and I monitor those hours with my Oura ring like there’s some sort of test I’m trying to pass. I get up at a certain time every morning for my workout, which means the night before has a hard stop no matter what. That, of course, means the spontaneous third drink at the bar — where I could maybe, finally meet someone — is off the table before it’s even on the table. I have healthy boundaries with my family and work, and while I keep meticulous track of everything, somewhere in all that optimizing I think I’m missing the actual point of interacting with people as well as enjoying myself.

Last week a guy struck up a conversation with me when I was running errands. Instead of leaning into it, I realized I was thinking, Oh, he’s going to make me late to the farmers’ market, which is a nice-to-attend thing but definitely not some urgent task. I’ve now replayed this encounter in my head more times than I’d like to admit. Why was I in a rush to get cherries? I’m not sure. I have a window for everything and somehow no window for the one thing I say I want.

My entire friend group is like this, too. We’re a group of accomplished women who all say we want to date, yet none of us are actually dating. We get dinner (booked three weeks out, naturally) and it’s the same conversation every time: Nobody’s meeting anyone; nobody has the time. We’ve read the same advice about protecting our peace and holding our boundaries, and we’ve all followed it by the book. We’ve turned our lives into these beautiful, airtight fortresses.

These boundaries were supposed to shield us from being confused and strung along (or from the guy who doesn’t text you back for days each time). And it’s true I think boundaries have saved us from many heartbreaks and wasted efforts. But I worry now that we’re almost too protected to fall in love, or at the very least to have an unexpected meet-cute and flirt. I don’t want us to look back on this time in our lives and not have stories to tell because we were so focused on being productive and safe.

The mood board and TikToks are all preaching for women to be whimsical and spontaneous, but I don’t know how to do it! What do you do when you’ve boundaried yourself out of dating?

Sincerely,
Not Carrie Bradshaw

Dear Not Carrie,

While I was reading your letter, I envisioned you as a rom-com heroine — particularly, as Jennifer Lopez’s Mary in the first act of The Wedding Planner. She, too, hasa perfectly organized, color-coded planner. Her little Blackberry stylus goes tap tap tap with ultimate efficiency. She’s dressed perfectly, not a hair out of place, her manicure never chipped. She excels at her job, at being a friend, at being a daughter. Given how neat her bun is, you just know that by the third act, some man is going to introduce some shenanigans that will mess up her hair and her life for the better.

Because rom-coms of yore love to gently punish career women, we’re supposed to feel bad for Mary. We’re supposed to realize that her color-coded planner is really just a cover-up for her lonely life of Lean Cuisine or whatever. But nothing about your life makes me feel bad for you, Not Carrie. Actually, I’m quite envious. (Healthy boundaries? Tell me how!)And yet — I’m excited for your feral-hair third act to come.

While I commend your schedule, your boundaries, and your commitment to a regulated nervous system, it sounds like you haven’t just boundaried yourself out of dating; you’ve boundaried yourself out of living! Out of pleasure! Out of the friction of life that’s uncomfortable but worth it! I don’t think the answer here is to throw your Oura ring into the sea. (Actually, perhaps you should — for surveillance-related reasons — but my tin-hat self digresses.) And I don’t think you need to lean into some prescriptive TikTok version of a “whimsical life” either. Neither extreme — Über-optimized or Über-chaotic — is necessary all the time; both have their season. One season begs for you to go full Bryan Johnson, and the other asks you to prioritize your most hedonistic side.

My best memory of 2026 was right at the start: On New Year’s Eve, I went to a Robyn concert with a group of friends I don’t usually go out with. To put it mildly, they are fucking pros at parties/raves/concerts/festivals and anything that falls under that category. They planned everything: when and where we met for dinner; where we went for drinks and drugs between dinner and the concert; exactly what drugs and what time to take them so we peaked at the right time. They had a hand signal (the Goose!) to find each other in the crowd. It was partying with military precision. But right as the concert started, a fire alarm went off, the security team rushed Robyn off the stage, and I started panicking. This could have derailed the night, but my friend noticed, led me out of the crowd, got me water, sat me on a bench, and asked me if I wanted company or to breathe it out alone. When I said “alone,” he told me to text him when I was ready for him. When I was, he came back and led me back into the crowd to meet the rest of our group, and I danced my face off. It’s a little earnest (as MDMA-fueled “Aha!” moments tend to be), but it gave me a new mantra: Build a safe container for chaos.

There have been many times in my life — post-heartbreak, mid-burnout, whatever — when I had to rely on a regimen to keep myself grounded, when a Sunday-night scheduling session was the key to my mental health and basic survival. The structure seemed really necessary to protect whatever internal work I was doing at the moment. Then there have been times when I needed to release my grip and invite some unpredictability. Even if that unpredictability ended in disaster, I still had a set point in my structured life that I could return to: I could withstand the chaos because the “container” was sturdy. Now, my rally cry is, There is a container for the chaos, LFG! I lend this to you.

It seems there might have been a season when this maximum-optimization approach really served you and served you well. But it sounds as though it’s now an obstacle to the life you’ve acknowledged wanting. I’m not saying anything revelatory here, but dating (especially in 2026) will be messy. Somewhere along the way, someone isn’t going to text you back; someone is going to confuse you; someone might even hurt you. It might seem absurd to say “Let all that chaos in, for a date!” That’s why my advice is to think about loosening the reins in all areas of your life, not just when it comes to dating. Let your days, in general, get a little wilder.

Start small. Take baby steps toward full-on ferality: Put it in the calendar that you’ll have a chaos night with a particularly spontaneous friend — agree to start in one location and go wherever the night might take you. (Optimization + whimsy!) Say yes to a last-minute invitation and risk being tired for your gym class. Make some decisions that might knock you off your axis; you can be confident you know how to set yourself right again.

Yours in chaos,
APD

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