I remember the days when long-term relationships were forged with a snog in the back of a taxi on the way home from a date

Sometime around this point in mid-January, the wheels come off as new year’s resolutions we vowed to keep begin to fall by the wayside. For this precise reason I’ve avoided making any hard-to-keep resolutions. Plus, life has been difficult enough over the past two years to actively choose self-punishment in the form of quick-fix regimes over the long game. No thanks. Resolutions are rarely kept because we are all a work in progress and doing “the work” takes time. Collective eye roll. Bear with me, I didn’t expect to be single in midlife. But as a result, I have spent a couple of years doing “the work” (paging Deepak Chopra) in the form of weekly therapy. Being back on the dating scene in midlife can be ugly and difficult, which surfaced some uncomfortable issues never previously acknowledged, never mind dealt with. Turns out, I needed to master the art of saying “no”.

I met my ex in my early 30s, when my dating skills were as limited as my self-esteem. Back then, long-term relationships were forged with a snog in the back of a taxi on the way home from Soho. You could argue that dating when you’re older is easier or better than it was in your younger years, because we now know what we’re looking for in a partner. And yet it can also be way more complex for the exact same reason. I’m a different person to the one I was all those years ago, which, quite possibly, is one of the best things about growing older. An increased self-confidence results in a tendency to care less about what people think, and caring less is essential when it comes to dating in midlife (boxing gloves at the ready, folks). The same goes for learning to say “no”.

Saying “no” requires firm boundaries and maintaining boundaries requires hard work. This logic applies whether you meet in real life (IRL) or on a dating app. Red flags are red flags, after all. Looking back, there have been so many online dating scenarios that I should have walked away from faster than I did. Now that I’m no longer on “the apps” I’m no longer the recipient of hundreds of digital likes and compliments from men. But I really don’t miss them; compliments sent from behind a screen began to feel meaningless. Although it was way easier to meet people online, I just wasn’t meeting my “type”, and my lack of ability to say “no” meant I allowed conversations to continue too long, even though, ultimately, I knew things would end up going nowhere. Now that I’ve turned my attention to real-life scenarios (imagine!) I’ve had to hone my dating radar and up my game. When I say “up my game”, I’m not exactly walking down the street flicking my hair and batting my eyelashes at every man who walks past, but I have had to work out when someone is flirting with me. Which is weird, unless it’s in-your-face obvious.

I’m not doing dry January, because why punish yourself during one of the harshest months of the year? And I walked into my local pub the other evening to be greeted by a smiling stranger. “We connected on Bumble!” he declared, as I nudged my way to the bar. “Did we?” I asked, somewhat taken aback. “I deleted every single dating app a few weeks ago,” I began telling him, suddenly panicked I hadn’t replied to one of his messages. “Oh, you might not recognise me. I uploaded a picture that was 10 years’ old.” I blinked back at him in disbelief, happy in the knowledge that this was why I left “the apps” in the first place. I didn’t bother asking why he’d uploaded an old pic, nor did I go into the perils of false advertising – he was more than a little tipsy and it would’ve been a pointless exercise. “We should go for a drink,” he said, plonking himself down at my table before insisting I give him my number. A polite but firm “no” took effort, but as he left the pub an hour later hollering, “See ya in The Telegraph – I read your dating column!” I was relieved I’d stood my ground. “Writing a dating column does not make me fair game”, is one of the several and less expletive-ridden things I wished I’d hollered back. Here’s hoping my stunned silence was mistaken for elegance and poise.

This week I also said “no” to a date with an ex (why do they always come out of the woodwork at this time of year?) and also to another man I’d previously met on a dating app. I hadn’t heard from him for a year and it was almost comedic, seeing his name pop up on my phone. I politely declined, saying too much time had passed.

I’m aware how odd this may all sound, if you haven’t so much as looked at a dating app in your life, never mind had a smorgasbord of men to choose from like the wine list at a Michelin-starred restaurant. But believe me when I say, in a digital-first world, turning one’s dating focus back to real-life scenarios takes Herculean effort. Without the fake sense of confidence a screen can provide, we’re more vulnerable and it feels like there’s more at stake. Behind a screen, we can all be an exaggerated version of ourselves, which may explain why men tended to approach me with bravado online. This no longer happens in real life. Well, apart from “pub guy”.

Saying “no” is good dating practice, and not only in a consensual sense. Knowing when something doesn’t feel right, be it a lack of connection or something you can’t quite put a finger on, is important so as not to waste time. If only I’d mastered the art of saying it sooner – all those hours spent scrolling and answering endless messages! After four lovely dates with a man I headlined in this column as “the Environmentalist”, I declined a fifth knowing something was missing. I honestly couldn’t tell you what it was. Everything was there on paper: same age; divorced; two children. And yet there was a “but” hovering in the air like a question mark. Even though in many ways dating him felt comfortable, life is too short for those.


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