by Vivienne Pratfall’s diary on dating disasters, self-respect, and the peculiar optimism required to keep trying
Monday: The Date Who Talked Exclusively About His Ex
Met a man at a wine bar in Fitzrovia who spent forty-five consecutive minutes discussing his ex-girlfriend with such passionate detail that I began to suspect I was less a date than an unpaid therapist with better lighting and a more expensive glass of Malbec than his usual session rate would provide. Extracted myself with the classic London excuse of an early start, which fooled absolutely nobody, least of all him, given it was barely half past eight on a Monday. Read something on londonish.uk about the general state of modern dating fatigue afterward and felt seen in a way that was frankly a little uncomfortable given how specifically my evening had just illustrated the exact phenomenon being described.
Tuesday: Recovery Wine and Group Chat Debrief
Spent Tuesday evening doing the essential post-disaster ritual of recounting Monday’s date to the group chat in increasingly dramatised detail, because if you can’t get a good story out of a bad date, what exactly was the point of sitting through it. My friends, bless them, responded with appropriate outrage and the kind of solidarity that makes London dating almost bearable, this shared understanding that we’re all navigating the same absurd landscape of apps and awkward wine bars and men who mistake a first date for a confessional booth. Decided, with the confidence that only a second glass of wine provides, that I was taking a brief dating hiatus. This decision lasted approximately eighteen hours.
Wednesday: The Accidental Match
Matched with someone on an app I’d genuinely forgotten I still had installed, a photographer based somewhere around Peckham with a profile that made me laugh out loud on the tube, which is a genuinely rare achievement given how determinedly unamused most tube passengers appear to be by anything, ever. We messaged back and forth all day with the kind of easy, quick wit that either means genuine chemistry or an extremely well-crafted persona designed specifically to lure the emotionally optimistic into yet another Fitzrovia wine bar disappointment. I remained cautiously hopeful, which in London dating terms is roughly equivalent to declaring undying love in any sane context.
Thursday: The Actual Date That Went Surprisingly Well
Met the photographer at a small, genuinely unpretentious bar near London Bridge, and for once, the actual date matched the promise of the messaging beforehand, a genuinely rare and precious occurrence in this city’s dating landscape. Conversation flowed without the usual effort of steering someone away from monologuing about themselves, he asked actual questions and seemed genuinely interested in the answers, and I found myself, somewhat alarmingly, checking the time not to calculate my escape but because I was disappointed how quickly two hours had passed. We’re seeing each other again this weekend, and I’m trying very hard not to overthink this fact while also, obviously, overthinking this fact extensively.
Friday: The Overthinking Continues Unabated
Spent most of Friday analysing Thursday’s date with the group chat, dissecting every text exchange since with the forensic dedication usually reserved for actual crime scene investigation. Is it too soon to suggest a specific weekend activity? Does responding within twenty minutes seem overly eager or perfectly normal? These are the genuinely ridiculous questions occupying meaningful mental real estate that I could theoretically be using for literally anything more productive, yet here we are, because apparently thirty-plus years of life experience does absolutely nothing to eliminate this specific brand of dating anxiety. Read another piece on londonish.uk about navigating early-stage dating uncertainty and found it only moderately reassuring, mostly because I suspect no amount of reasonable external advice actually overrides the particular chaos of your own overthinking brain in these situations.
Saturday: The Second Date and Cautious Optimism
The second date happened, involved considerably less anxiety than my Friday overthinking session might have predicted, and included the genuinely lovely discovery that Thursday’s chemistry wasn’t simply a fluke of good lighting and a well-timed cocktail. We walked along the South Bank for considerably longer than either of us probably intended, deep in the kind of conversation that makes you forget to check your phone, which for me represents a genuinely notable achievement given my usual relationship with notifications. I’m allowing myself, cautiously, tentatively, the smallest sliver of actual optimism about where this might go, while simultaneously bracing for the possibility that London dating will inevitably find some new, creative way to disappoint me regardless.
Sunday: Reflecting on the Emotional Whiplash of a Single Week
Sunday’s typically my day for processing the week’s romantic chaos with tea, questionable reality television, and the specific brand of self-reflection that comes from surviving both a genuinely terrible date and what might, possibly, cautiously, be a genuinely promising one within the same seven-day span. There’s something almost absurd about the emotional whiplash London dating requires you to maintain, the capacity to fully write someone off on Monday and cautiously fall for someone new by Thursday, all while maintaining enough self-respect and humour to survive the whole ridiculous process intact. I don’t have a tidy conclusion to offer, just the honest acknowledgment that this city’s dating landscape remains genuinely exhausting, occasionally magical, and apparently worth continuing to navigate despite every reasonable argument for simply giving up entirely. We’ll see where the photographer situation goes. I’ll keep you updated, obviously, because what else is this diary for if not documenting my own chaotic optimism in real time. You can find my previous entries and ongoing romantic saga on my author page, where London life, love, and everything genuinely absurd in between gets its regular airing. SOURCE: bohiney.com
