When Milly Goldsmith uploaded a TikTok describing herself as “chronically single”, she thought a handful of people might relate. Instead, millions watched, and thousands of women flooded the comments to admit they'd never had a boyfriend either, confessing feelings they'd not shared out loud: that they felt left behind, embarrassed or convinced something must be wrong with them.
For Goldsmith, the response was a revelation. For years, she'd believed she was the only woman approaching 30 who'd never experienced romantic love. Instead, she’s since been called the voice of a generation and “the Gen Z Bridget Jones”.
Here, she reflects on shame, loneliness, people-pleasing and grieving the life she thought she'd have by now, and explains why she's finally stopped seeing being single as her greatest failure.
What It Feels Like To Have Never Had A Boyfriend
As told to Mischa Smith
I always thought getting a boyfriend was something that would just happen. It seemed like one of those milestones everyone reached without really thinking about it, like learning to drive or moving out. Everyone around me just seemed to find someone naturally, so I assumed the same thing would happen to me.
It wasn't until I was about 18 that I realised maybe it wasn't going to be that straightforward. By the end of school, I'd never had a boyfriend. I'd barely spoken to many boys, and all of my friends were starting relationships. At first, it was just something I noticed in the back of my mind, but over the years, that feeling slowly turned into fear.
@millygoldsmith 📔Chapter 31: the deadline for love It’s weird I’m fine one day and then not the next Like today I’m fine. I’m loving life. I’m loving my singeHOOODD But 2 days ago, I wasn’t. My mood was interrupted by this overwhelming sense of fear and panic Like SHIT I’m 28 and I’m still saying later ha haha but I’m fine with it??? Like I’m happy and if I’m like this for the rest of my life it won’t phase me because it’s all I know But the fear comes when i actually sit and think…huh…I haven’t experienced that thing everyone raves about and “can’t live without” Like that thing called love. The thing people say is the best feeling in the world?? Almost so goood that it feels like a drug Crazy Crazy how I’ve never come close to that feeling So then I’m like f*ck I WANT THAT but yeah I’m not doing anything about it because I’m so comfortable so I just tell myself I’ll experience that later (That ‘later’ is now and also 4 years ago) Sooooo…I had a little wobble in therapy because I realised ah shit time is no longer making me feel comfortable, if anything it’s making me feel panicked Idk if I’m making sense But just another brain dump as always
♬ original sound - millygoldsmith
I got to university and still hadn't had a boyfriend. I hadn't even had a situationship, and the longer I stayed single, the more it became my normal. Being independent became my comfort zone, so the idea of letting somebody into my life started to feel unfamiliar, and because it felt unfamiliar, it also felt frightening.
Even now, relationships are still this huge unknown to me because I've never experienced anything different. Love is such a huge shared human emotion, and I haven't really experienced that side of it. For something that's such a fundamental part of so many people's lives, it can feel quite isolating. There's definitely a sense of fear, but there's also a huge amount of FOMO.
I felt like I'd been left behind.
I think the turning point came after Christmas in 2024. I come from a family of four siblings, and Christmas has always been loud. There are loads of people in the house, presents everywhere, food everywhere, games, and conversations. I absolutely love Christmas. But that year, all of my siblings were with their partners and for the first time ever, it was just my parents and me.
If I'd had a partner, I would've been doing exactly the same thing as everyone else. Instead, I felt like I'd been left behind. Not just within my family, but somehow in life itself. I remember sitting there thinking: why? Why does this seem so easy for everybody else? Why can't I experience something that everyone else seems to experience naturally?
I'd been going to therapy already, but I'd never really spoken about being single. I think part of that was because I hadn't fully acknowledged how much it affected me, and the moment I said it out loud, it would become real. It would stop being something I could blame on bad luck or bad dates or bad men.
Deep down, I think I knew there was something about me that I needed to understand, but I wasn't ready to face it yet. Then I started journaling. I'd never really journaled before, but suddenly I had all these emotions that needed somewhere to go. There was a lot of crying, a lot of confusion, and a lot of anger.
I kept thinking: why me? As I wrote, I slowly started connecting the dots. One of the biggest revelations was learning about attachment styles. I'm an anxious avoidant, which is probably one of the worst combinations if you're trying to build relationships. I need enough space to realise I actually want somebody, but by the time I've taken that space, I've usually pushed them away.
To someone else, it looks like I'm not interested; to me, it feels like I finally feel safe enough to let them in, but by then, they're already gone. That cycle suddenly explained so much about my life.
Being single wasn't the hardest part. The stories I'd told myself about being single were.
One of the strangest parts of all this has been talking about it publicly. When I first made a TikTok about being "chronically single", I genuinely thought people would think I was weird. I honestly didn't know anybody else who'd reached 28 without ever having a proper relationship.
I uploaded the video without overthinking it, which is unusual for me because I'm a perfectionist. I just wrote honestly about how I felt. Then it exploded. Suddenly, thousands of women were commenting, saying they felt exactly the same way, which completely changed my perspective because I'd spent years believing I was the odd one out.
Saying "I love you" to my parents honestly feels like saying a swear word.
The more I started understanding myself, the more I realised this wasn't just about dating, it was about the way I'd learnt to protect myself. One thing therapy made me think about was how difficult I find vulnerability.
Saying "I love you" to my parents honestly feels like saying a swear word. Everything in my body just tenses up.
It feels like I'm stripping away every layer I've built around myself. Every wall I've spent years putting up suddenly comes crashing down. They're only three words, but they carry so much weight. I just haven't had enough practice saying them to make them feel normal.
Even now, after my parents have read the chapter in my book where I write about this, my whole body tenses up knowing they know how I feel. There's still a small version of me that's trying to protect herself.
Growing up, love wasn't really expressed through words in our family; it was always through actions. My mum would cook dinner, and she'd give me a hug. My dad would give me £10 after a dance exam and tell me he'd been proud of me, that was our version of saying, I love you.
I know my parents love me; I've never doubted that for a second. It was just something that went unsaid. Now that I'm older, I can see how growing up in an environment where we didn't verbalise those feelings has shaped me. It makes sense why opening up to people doesn't always come naturally. It's something I'm still trying to unlearn.
With some people, saying "I love you" feels completely natural. One of my best friends says it to me all the time, so I say it back really easily because I know there isn't any risk. I know it'll be received in exactly the way I intend it.
The same is true with my nieces; I'm always telling them how loved they are because I want them to grow up hearing those words. Maybe there's a part of me that's trying to give them something I would've found easier to hear growing up.
If I'm changing myself depending on who's in the room... who actually am I?
I don't think I'm broken; I just think some relationships require me to unlearn habits that have been there for a very long time. The same thing happened with people-pleasing; for years, I thought I was simply being kind. I thought changing my plans to suit somebody else or making myself endlessly available was just what nice people did. I didn't even know what boundaries were. Therapy taught me that being a kind person and being a people pleaser aren't the same thing.
When it came to dating, I'd let people move dates three or four times because I didn't want them to think I was difficult. I'd convince myself it was absolutely fine. Now I realise I could've said, "No, this day works, or it doesn't." That isn't rude; that's self-respect. I think there were lots of moments where I could've respected myself more.
For a long time, I worried more about whether someone else was annoyed with me than whether I was happy. I was constantly moulding myself to fit other people. Eventually, I had to ask myself a really uncomfortable question: If I'm changing myself depending on who's in the room… Who am I?
For years, I believed being single meant I'd failed somehow, that there must be something wrong with me. Now I see being single completely differently.
It's actually the default; it's where we all begin. It's given me an incredible amount of independence: I can travel on my own, spend weekends on my own, enjoy my own company, and I know myself incredibly well. Some people joke that maybe I know myself too well now.
Of course, there are moments where I think it would be lovely to have someone to book holidays with, cook dinner with or go to the cinema with. I'm still human, I still want love. But I don't see being single as something that's wrong with me anymore.
That's probably been the biggest shift of all.
Things I Told My Notes App by Milly Goldsmith, published by Bantam, is out now.
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