Like Carrie Bradshaw, I made my career about my love life...

It definitely took its toll on my emotions - now it's one of my many work eras...

October 30th, 2014 - on the front cover of Metro newspaper, next to Taylor Swift, there I was. Posing as if blowing a kiss to the camera, under the headline MISSION TO FIND A MAN BY CHRISTMAS.

It was my latest foray into being a dating and relationships writer - I’d hit the big time. I can remember being beyond excited. I had secured a column with the paper, where I’d just started working, called Boyfriend by Christmas.

The idea was to see if I could find love by going to as many different dating events and on as many dates as possible.

Writing about my love life wasn’t a new thing. I had carefully curated a portfolio of articles about dating. I’d been single a while and I decided that if I couldn’t find a man I’d make a career out of being solo. I lived and worked in London, why not?

As I often told people, I was “Carrie Bradshaw with more comfortable, flatter shoes”.

And so, as And Just Like That comes to a grand finale, I’ve found myself wondering (of course, just like Carrie) why I spent so much of my career writing about my love life. Literally laying my heart bare on the pages of magazines and newspapers, creating a digital legacy about my deepest emotions, and romantic failures.

The funny thing was, the more I wrote about my love life, the more men were wary to date me. “This’ll end up in the newspaper, right?” was often the reply if I asked whether they wanted to swap numbers (yep, it was still number swapping territory, no DM sliding at that time).

I tried it all - and wrote about it all. From Match.com and Plenty of Fish to pizza-making dating, speed dating and even a one-day course on finding love. (That course led me to finding a woman who I ended up working with as a client and I credit having therapy with my now being married. I don’t think without therapy I’d ever have been in a place where I was ready to commit and not look to a man to complete me).

The column didn’t find me love. But it did secure me a book deal. An agent read it, got in touch with Twitter, and secured me a deal with Penguin (Michael Joseph). If you love average chick lit, you can still buy it. It’s also called Boyfriend by Christmas.

The cover was (is) a cracker, pulled apart, on a white background. I ADORED it. My brief had been ‘no cheesy romantic cartoons’. I truly dreamed of writing the next Bridget Jones. I longed to be a real Carrie Bradshaw, making a full living from writing about my relationships.

So, with no bloke and a book deal I carried on writing about it all. My Carrie Bradshaw-meets-Bridget-Jones efforts didn’t end with the column. I went on to write about how I’d never been told I love you, I wrote an article asking friends and family why they thought I was single.

I wrote about weekend loneliness, and I wrote about being single on Valentine’s Day. I wrote about how I wanted men to be more honest in dating and I even went to New York to write about the dating scene (and then Glastonbury, too).

Perhaps channeling AJLT character Che more than Carrie, I decided to add stand up comedy to my repertoire. I took a course in comedy writing, and nurtured a 5-minute stand up routine about my dating life, which I performed at the Edinburgh Fringe. Then I wrote about how I’d turned my love life into a joke…

I had a blast doing it all. But it wasn’t without its downsides.

I think when it came to my career, I was crossing the streams so hard, I forgot where my love life ended and work began. I was trying so hard to be Carrie, I forgot to be Jenny.

As some of you will know, I got married in 2022, after meeting my now husband in 2016. You see, when I wasn’t being all gung-ho around Glasto chatting up blokes, I was crying in a tent, comforted by a lovely friend.

I was deeply lonely. And I knew deep down that exposing my heart on my journalistic sleeve and on stage had made me even lonelier.

I often joke that Mr H has ruined my income stream of writing about my love life, but in reality, I’m beyond grateful to have been able to hang up that hat. To have said ‘no more about the dating scene’.

Writing about your personal life is a tricky tightrope on which to balance. I still do it, these days more about menopause and work than about my love life.

And it feels much better that way. More purposeful, too.

It was, as my cover co-star back in 2014 would say, an Era. Not one to be erased, but one to now leave in the past. It’s one of the reasons I love changing my name so much. That girl was Jenny Stallard, I’m Jenny Holliday.

So perhaps this is the final entry for me, about my love life. A little tribute to Jenny Stallard, the dating journalist, from Jenny Holliday, the coach and careers journalist.

I will never regret any of the over-sharing. I’m proud, and looking back I am also thrilled at how many of my pitches landed and were commissioned.

And I’m also happy - as perhaps Carrie and Sarah Jessica Parker are - to leave someone new to be that writer.

Thanks as always for reading!

If you’re after more content by people exploring single life, I would heartily recommend Nicola Slawson’s The Single Supplement and Help Me! by Marianne Power.

xJenny

Here’s a bit more Carrie-inspired content for you…