dating in your thirties 2

The title of this post is somewhat misleading, as I never actually “dated” in my twenties, so really it should simply be: Dating: some observations. But I am thirty, and I am dating, and so here we are.

I amused / terrified myself recently by counting how many months I spent single in my twenties. Nineteen months. Nineteen (19) months!! Over that entire decade of my young life, this means that less than 16% of that time was spent, as a twenty-something, on my own. It ain’t a lot. To make things more amusing / terrifying, six of those months were spent backpacking and racking up stamps in my passport (*insert sleazy wink*) so that really leaves just over one year of actual singledom.

In hindsight, my “relationship strategy” in my twenties was simple: sleep with someone and then never leave their side for two (or three) years. The closest my darling ex’s and I ever came to “dating” was getting drunk together in the pub, or making homemade tacos before binge-watching Breaking Bad. We’d skip the dating part entirely; move in together right away, merge our lives completely, get a pet, talk about grown up things that neither party were ready for… and then break up. Repeat. etc. etc.

Of course that’s not entirely fair and I’m being a little cheeky. I had some beautiful and very meaningful relationships in my twenties, but the truth is, here I am: 30-years-old, single, and… dating.

And so, here’s some observations I’ve made thus far:

Dating is FUN.

I felt skeptical and nervous as I meandered through Shoreditch. It was dark by 5pm at this late point in the year, but London’s streets were brimming with mulled wine market stalls and the sticky smell of Christmas spice. Suddenly, deep in the chaos of it all, I felt excited. I was on my way to my VERY FIRST EVER TINDER DATE. Let’s call him J, shall we?

J had caught my eye in my Tinder swipe-sesh because he was eating an avocado in his profile photo (lol) and had an amusing bio. Humour for the win. I’d heard the horror Tinder stories of course, so my expectations were admittedly low. Gratefully, I was blessed with what has got to be one of the BEST first Tinder dates ever: J had booked us a table at a busy Italian restaurant, scored tickets to a comedy show around the corner, and because neither of us were drinking at the time (such a relief for me), we sipped on soda waters and hot chocolates in an Irish pub until after midnight. And laughed and laughed and laughed and laughed. 

Since then, my dating adventures have taken me to Harrods for high tea, vintage cinemas, art galleries, park dates, pub dates, dinners, breakfasts (and dinners that turn into breakfasts), I’ve had phone sex, actual sex, no sex at all, and lots and lots of conversations about sex. I’ve played pool and tried virtual reality, had men cook exquisite meals for me, shared writing and books and playlists, and made out whilst watching Londoners stroll along the canal from a gentrified Hackney warehouse flat.

The truth is, I love getting to know new people.

I’m a textbook introvert, and I’ll soon dedicate an entire post to dating as an introvert, but I so adore getting to know people, particularly on a 1:1 basis. For me, this is one of the best things about dating. I’ve got this theory about London see, and it’s that you’ve got to be a certain kind of person to live here. It’s often not an easy city to inhabit; it’s transient, expensive, stifling. But it’s DEEPLY rewarding, and ultimately filled with creative dreamers. London attracts interesting, well-travelled, innovative, intelligent and open people — humans with hunger, passion and vision — and I never tire of hearing how London called to people, and why they’ve made it home. Dating has been a space for so many of these conversations to unfurl. 

I particularly enjoy hearing people speak with passion about their vocation — so far I’ve dated a musician, an architect, a marketing manager, an artificial intelligence analyst, a primary school teacher, a high-end fashion photography retoucher, a start-up software developer, and a few IT dudes — and I’m yet to meet anyone who hasn’t loved their job. (Note to men: this is incredibly attractive).

dating in your thirties

I’ve heard the most wonderful stories from men who’ve lived, worked or studied in Russia, Africa, France, Italy, Ireland, Korea, India, Vietnam, Canada and South America. A guy who once spontaneously cycled from London to Spain with only a backpack, or another who attends monthly group VIP sex parties because, simply, he likes them. I’ve had conversations about dream interpretation, politics, monogamy, romantic compatibility, BDSM, children, meditation, menstrual cycles (of course), Freud, sibling dynamics, divorce, grief and loss, tarot, travel and tattoos, regrets, hopes, art and atheism, and why graveyards are a great place to spend time.

I’ve (mostly) dated men, not boys.

Which is lovely. I’m 1000% not interested in dating boys, as in, male humans who haven’t yet matured through self-introspection, creativity, spiritual development, world exploration, or established any personal convictions. Or, as my (fellow single babe) cousin Gen puts it:


MAN: I’d love to take you out for dinner.


MAN: Don’t worry, I have condoms to hand

BOY: Text message central



The men I’ve dated so far are all in the age range of about 29 — 35, and have a pretty good grasp on who they are and what they want. It’s a real chapter of growth and self-discovery, isn’t it? Which can make for meaningful chats when dating someone, or it can also be a bit of a pain in the arse when they’re deep in the soul-searching and a little off-planet. This happens. And of course, by this age, we’ve all got some emotional scars. Some of us may even have a divorce under the belt or kids in our realm. Ultimately, boys or men, girls or women — we’ve all got healing work to do. 

Which brings me to a few final quick tips (if you’re dating in your thirties too):

— Do not take anything personally. People will flake out, lie, be vague, go cold, become distant, or just completely ignore your text. My skin is thickening… surprisingly fast!

— Embrace online dating. It can be wonderful. My next dating post is going to be just on online dating, so if you have any specific questions on this, throw them in the comments.

— Date multiple people at once. Or more crudely: date like a man. I’ve found three is a good number, and this is particularly potent advice for the fellow monogamists and relationship junkies out there. Break that cycle. Keep it light. Eggs not in same basket, etc. etc. 🙂

— Be intentional. Know why you’re dating, what you want, and what your personal boundaries are, particularly when it comes to time, money, sex, and expectations. The truth is that dating takes up a great deal of energy, and it can be tiring. So be discerning, and take time out when you need it. When I’m on, I’m ON. When I’m off, I’m OFF.

— Be honest. I think it’s so hot when someone knows what they want, and says it straight. Same goes for your current relationship status. I went on a lovely date with a man who completely pursued me. Afterwards, he texted to say that actually, he was in a relationship but (wait for it), “it’s complicated.” It felt icky. Or like one of my London girlfriends who went on a date with a dude who only revealed he was married (and still living with his wife) when she asked if he had housemates. I mean, you know, just be straight up.

— Find the lessons. Trust me to turn dating into an exercise in personal development, right? But it’s true: dating has been a catalyst for establishing new personal boundaries, exploring exciting ideas and philosophies, and shedding outdated and limiting beliefs. Every single man I’ve met has shown me a little more about what I do and don’t want in a partner, and ultimately revealed more about my greatest desires for my life. Surprise surprise, these lessons don’t always come easily, and emotional self-care is P A R A M O U N T in this game.

— Connect with single pals. Most of my women here in London are actually single too, some dating, some not, but it’s been a huge boost of confidence, support and laughter, to journey through this fun and strange terrain together. The laughs are so important! (As are the tears!)

So my loves, there you are, at the very least an introductory glimpse into these past months of dating. I do feel a few more posts on this coming soon: dating as an introvert, online dating, self-dating, dating around your menstrual cycle, emotional self-care when dating, sex when you’re single… what else would you like me to write about?! Let me know in the comments. Are you dating in your thirties? Got a good dating story of your own? Share it with us all!

Sending you love,

Claire x

Ps. Artwork by Maya Land. Listen to, or share this post below, and click here for email updates on fresh content. 🙂

I’d love to send you some love.

Join the tribe!