I’m Done Entertaining My Friends In Relationships With My Dating Stories

Photographed by Renell Medrano.
I had barely set foot into my friend’s house party a few months back, when a woman asked: “So, tell me! Been on any fun dates recently?” She’s someone I vaguely know — a friend of a friend — and she asked me this in front of a group of strangers. This often happens as soon as a wine cap twists open, usually by people I don’t have much of a relationship with. I said I wasn’t focusing on that and needed a break from how rough the dating scene can be. This was a mistake, because that opened up more questions which I awkwardly gave non-answers to until the topic changed. I can already predict the onslaught of similar questions that will come my way over the next few weeks, thanks to the holiday season. It’s in equal parts bleak, annoying and monotonous. 
I used to share stories from my dating life freely for the sake of comedy. The older I get, the more personal this information feels. I don’t want to rehash why it didn’t work out with the most recent person at a party, when I’m supposed to be enjoying myself, or be made to feel like I’m failing at something when I’m genuinely happy being single
Culturally, single people aren’t granted the same boundaries as couples — we don’t ask “Are you still having date night? Is the sex stale?”, but they do ask “How did it go with that guy? Are you getting back out there?” and even “How big was his dick?” A societal shift is needed: the romantic ups and downs of single people are not a source of entertainment. Of course, couples get asked when they’re going to marry or have children, which is also problematic and invasive. However, the sense of entitlement to the nitty-gritty details of a person’s romantic life seems to be levelled at single people in a uniquely casual, offhand way.
Charlotte Greaves, 34, who works in TV production in London, calls this phenomenon a “free-for-all”, and is tired of being prodded and probed — and she too knows the arrival of the holiday party season will bring on a fresh slew of interrogation. Having been single for two years, she says: “People ask me how dating is going, and I feel that societal push towards being in a relationship. It tends to come from the people I’m not close to, as my closest family and friends who’ve seen me a lot happier since being single and moving to London 18 months ago don’t ask me so much.”
Greaves feels there is an element of performance, in that people are hoping she’ll have outrageous stories to share — meanwhile, these people are less interested in her wellbeing while dating. “People are usually looking for horror stories to be told. Having to explain to people that the most recent guy I dated ghosted me, or the time I got stuck in a storm on the way to a date and arrived completely soaked through, is exhausting.” Sharing can sometimes help her feel less alone in the bad experiences if others can relate, but there’s a time and a place for these conversations.
“Bringing it up yourself and being in charge of the narrative saves the inevitable conversation of ‘How are things going with so and so…’ and then having to explain what had happened,” she adds. “It’s no one’s business if someone is happy being single, and they may not even be focused on that part of their life.” 
A study published this year found that 50% of unpartnered adults in the US aren’t interested in finding a relationship. Another study from 2022 found single people loved having more time for themselves and their goals. A further study found young women overall were less interested in dating than young men, and that more women are opting to be single than ever before. It also concluded that for 38% of women, the “major” reason they aren’t dating is because they haven’t met someone who meets their expectations. Perhaps, with this in mind, as the benefits of a life lived single are slowly becoming better documented, there’s a subconscious undercurrent of couples looking to their single friends to validate their decisions — that is to say, if they settled down in a partnership, their single friends should want to as well.
Caroline Plumer, psychologist and founder of CPPC London, says this could be driving much of the questioning single people face when it’s coming from couples. She explains: “If we don’t have conviction in what we have chosen for ourselves, or it isn’t going as planned, we may feel threatened by someone who is in a different situation. This can be highly destructive when we discredit other people’s choices in order to make ourselves feel better about our own.” 
When I’ve entered into “situationships”, some friends have struggled with the idea that I can be happy in these and not desire anything more — the expectation is that I should want a solid commitment, and that as a woman a “situationship” is likely leaving me disempowered in favour of the man involved. In actuality, to quote Cher, “I pick them because I like them”. 
Most people don’t have ill intent, but we should question why it’s become such an automatic talking point. Plumer adds: “These can be very sensitive topics for some people. Social media exacerbates this sense that we’re entitled to know the ins and outs of someone’s personal life. There is also the assumption from some that a single person must be lonely or feel they are somehow lacking something.” 
Hannah Thompson, 25, who works as a beauty journalist in London, has been single for three years. “I’d be lying if I said that I didn’t love hearing a dating story, but I don’t think I’ve been at a dinner party or gathering where the dating lives of me and my single friends haven’t been a topic of conversation,” she says. “I don’t mind talking about it with my close friends at all. It’s therapeutic to share dating stories with other people going through the trenches of the London dating scene — at least I can get a good story out of a bad date. 
“What I find jarring and exhausting is when you get a tirade of questions from people that you don’t know well, most often those in couples. It always ends with something along the lines of ‘The right person will come along when you least expect it,’ and I’m like, why is it expected though? I’m 25, I’m not on the lookout for something serious, I enjoy being single and dating, but there still seems to be this assumption that if you’re single it’s not by choice. I think I can then go to the other extreme and end up becoming an oversharer in these situations to avoid the whole pitying thing.”
Kate Moyle, sex and relationship therapist for LELO, says this is all the result of us living in a “very couple-centric society”. She says most questions come without much thought and are a habit of people “living vicariously through your single life”. 
“All of these types of questions are about finding something to talk about in a context where you don't really know people — people are searching for common ground. We often see this echoed in films and TV shows where we see these types of questions being shown, which unhelpfully normalises them and reinforces the idea that being single is something to be fixed.” Personally, I see this play out when I’m conventionally dating: no one is ever as happy for me as they are when I tell them I’m seeing someone.
For Thompson, there’s a lack of empathy at play. She says: “I don’t think people that have been in long-term relationships for much of their 20s realise the emotional toll dating takes on you, so sometimes if the conversation is bought up and I’m not in the right headspace I’ll just shut it down straight away. If I don’t want to talk about it, you’re not hearing it. There can be a lack of understanding around how much emotional pain can stem from shorter relationships or ‘situationships’ if people have never been in one.”
Sometimes, going through the motions of a repeated conversation — because I can guarantee your single friends will have cycled through the same stories time and time again for people — is draining, and like Thompson, you might want to shut it down. If you’re struggling with how to do that without appearing rude, Plumer says it’s always worth throwing the questions back at the asker. One, people love talking about themselves, and two, it might help the asker realise how the question sounds when reversed. 
“If this doesn’t work, kindly but firmly say you’d rather not talk about the topic and suggest something else to converse about,” she adds. Moyle agrees, and recommends reminding yourself — perhaps before going to social events — that you don’t have to disclose anything you aren’t comfortable with. “You don’t have to cross your boundaries to satisfy someone else’s curiosity. The chances are nobody has challenged them on this before and they may not even be aware that what they were asking felt intrusive.”
Let’s all pledge to do better by our single friends. The topic doesn’t need to be boycotted altogether, but no one should feel like their dating life is “rolled out as spectator sport for coupled-up friends or family members to live vicariously through,” as Lucie Kerley, 38, from Lymm, tells us she experiences. “It’s the ‘We just want you to meet someone nice’ or ‘I don’t understand how you’re still single’ curious but pity-laden comments after sharing hit me hardest. Christmas can be extra tough,” she adds.
That single person at the next party you go to has more to offer than their dating mishaps, wins and bafflements. So when the wine cap twists open, ask: “How have you been?”, “How’s that promotion going?”, or “Your holiday looked awesome! Where’s next?” Anything else, because our lives are so rich.

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