swAIpe right? We asked a dating expert to judge a chatbot’s chat-up lines
Dating apps are not my strong point.
Loathing the prospect of spending another Valentine’s Day stuck for things to say on Hinge, Bumble and the like, I wondered if the internet’s new favourite assistant – ChatGPT – could help secure a date.
After all, it’s already written complex computer code, crafted successful job applications, composed songs, and aced an 11-year-old’s homework.
Before daring to take its suggestions into the dating trenches, I enlisted an expert to assess the chatbot’s ability to strike up conversation.
For dating coach Hayley Quinn, this was undoubtedly one of her strangest assignments. For me, it was a chance to finally find a better conversation starter than a GIF of Obi-Wan Kenobi saying “hello there”.
‘Avoid physical compliments’
We started by assessing ChatGPT’s top three chat-up lines.
“Do you have a map? I keep getting lost in your eyes.”
Alarm bells are ringing immediately here, says Coach Quinn.
“In a post #MeToo era, physical compliments are dodgy territory. Instead of focusing on someone’s looks, try complimenting them on an aspect of their personality.”
“If you were a vegetable, you’d be a cutecumber.”
Even I think this one’s bad, but Coach Quinn is more forgiving.
“In the age of dating apps, funny first messages can go a long way. Just make sure yours is original, and not one a thousand people (or AIs) have used before.”
“Do you believe in love at first swipe, or do I need to unmatch and match with you again?”
It’s the lack of originality that’s done ChatGPT in here again, says Coach Quinn.
That highlights the chatbot’s established limitations. It’s a so-called large language model trained on a massive amount of data, but that means it draws on things that have already been written.
Dating expert Hayley Quinn
‘Presumptuous and creepy’
Some dating apps have tried to pivot away from a pure focus on matching based on photos.
But they no doubt remain the key feature – and so we asked ChatGPT for some catch-all compliments.
“Your smile is so warm and inviting!”
Coach Quinn is not very impressed: “Can we ban the use of the word ‘inviting’? This message comes across as presumptive to the point of creepy.”
“This photo really captures your adventurous and fun-loving spirit.”
A bit like the “cutecumber” line, ChatGPT might be on to something here.
Coach Quinn suggests a tweak: “Edit this to make it shorter and sharper – saying ‘adventurous’ and ‘fun-loving’ is borderline tautology. Keep it to a snappier: ‘This photo captures your spirit.'”
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Conversation starters
If a match is secured, ChatGPT has some conversation ideas.
“What’s the most spontaneous thing you’ve done recently?”
Coach Quinn says: “A good online dating rule of thumb is to never ask ‘how are you?’.
“By creating a more specific question to answer, ChatGPT’s suggestion is more likely to gain a response.”
“If you could be any superhero, who would you be and why?”
Coach Quinn reckons this would work as an opening gambit on a dating app, although “overly random” if you attempted it in real life.
“Do you have any travel plans coming up?”
Not quite so good from ChatGPT here, but it’s done the groundwork for a better question.
Coach Quinn suggests: “You have a plane ticket to somewhere tomorrow… what’s the destination and why?”
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Taking things further… or not
So you’ve talked about spontaneous things, shared your superhero preferences, and talked travel.
If you don’t see things going further, ChatGPT offered ways of bringing the conversation to an end.
“It was great chatting with you, but I think it’s time for us to move on.”
“Ouch,” says Coach Quinn.
“Try just saying, ‘it was great chatting to you’, shake hands, smile, leave.”
“I appreciate the conversation, but I don’t think we have a strong connection. Best of luck in your search.”
Much better! As Coach Quinn says, it’s “simple, clear and does the trick”.
But what if things have been going well, and it’s time to ask your match on a date?
“Would you prefer a picnic in the park, a hike, or checking out a museum this weekend?”
“Giving options is wise, but try to phrase this in a way that shows greater leadership,” says Coach Quinn.
And don’t pester with specific dates and locations until you know they’re excited about seeing you.
“I’ve really enjoyed our conversations so far, and I can’t wait to meet you in person.”
“Expressing enthusiasm several dates in, when you know they’re on the same page is great,” says Coach Quinn
“Just don’t go overboard and scare them off before date one. Play it cool, ChatGPT!”
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So, can AI help you date?
If all you want is some general advice to get you started, the answer may be yes.
ChatGPT signed off our dating advice session by suggesting we “keep the tone light and friendly”, not coming across as “pushy and too eager”.
“A nice, if a little generic, pearl of wisdom,” says Quinn.
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But don’t go relying on ChatGPT as some sort of digital Cyrano de Bergerac. While it may give better dating advice than plenty of your friends, you’ll want to do a sense check before taking its suggestions on board.
Is it inappropriate? Does it sound inauthentic? Do I sound like a robot?
If the answer’s yes, it’s probably time to swipe left on this particular love guru.
Sir Keir Starmer has joined other European leaders in Kyiv to press Russia to agree an unconditional 30-day ceasefire.
The prime minister is attending the summit alongside French President Emmanuel Macron, recently-elected German Chancellor Friedrich Merz and Polish Prime Minister Donald Tusk.
It is the first time the leaders of the four countries have travelled to Ukraine at the same time – arriving in the capital by train – with their meeting hosted by President Volodymyr Zelenskyy.
Sir Keir Starmer, Emmanuel Macron and Friedrich Merz travelling in the saloon car of a special train to Kyiv. Pic: Reuters
Leaders arrive in Kyiv by train. Pic: PA
It comes after Donald Trump called for “ideally” a 30-day ceasefire between Kyiv and Moscow, and warned that if any pause in the fighting is not respected “the US and its partners will impose further sanctions”.
Security and defence analyst Michael Clarke told Sky News presenter Samantha Washington the European leaders are “rowing in behind” the US president, who referred to his “European allies” for the first time in this context in a post on his Truth Social platform.
“So this meeting is all about heaping pressure on the Russians to go along with the American proposal,” he said.
“It’s the closest the Europeans and the US have been for about three months on this issue.”
Sir Keir Starmer, Volodymyr Zelenskyy and Emmanuel Macron among world leaders in Kyiv. Pic: AP
Trump calls for ceasefire. Pic: Truth Social
Ukraine’s foreign minister Andrii Sybiha said Ukraine and its allies are ready for a “full, unconditional ceasefire” for at least 30 days starting on Monday.
Ahead of the meeting on Saturday, Sir Keir, Mr Macron, Mr Tusk and Mr Merz released a joint statement.
European leaders show solidarity – but await Trump’s backing
The hope is Russia’s unilateral ceasefire, such as it’s worth, can be extended for a month to give peace a chance.
But ahead of the meeting, Ukrainian sources told Sky News they are still waiting for President Donald Trump to put his full weight behind the idea.
The US leader has said a 30-day ceasefire would be ideal, but has shown no willingness yet for putting pressure on Russian president Vladimir Putin to agree.
The Russians say a ceasefire can only come after a peace deal can be reached.
European allies are still putting their hopes in a negotiated end to the war despite Moscow’s intransigence and President Trump’s apparent one-sided approach favouring Russia.
Ukrainians would prefer to be given enough economic and military support to secure victory.
But in over three years, despite its massive economic superiority to Russia and its access to more advanced military technology, Europe has not found the political will to give Kyiv the means to win.
Until they do, Vladimir Putin may decide it is still worth pursuing this war despite its massive cost in men and materiel on both sides.
“We reiterate our backing for President Trump’s calls for a peace deal and call on Russia to stop obstructing efforts to secure an enduring peace,” they said.
“Alongside the US, we call on Russia to agree a full and unconditional 30-day ceasefire to create the space for talks on a just and lasting peace.”
Sir Keir and Volodymyr Zelenskyy during a meeting in March. Pic: AP
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The leaders said they were “ready to support peace talks as soon as possible”.
But they warned that they would continue to “ratchet up pressure on Russia’s war machine” until Moscow agrees to a lasting ceasefire.
“We are clear the bloodshed must end, Russia must stop its illegal invasion, and Ukraine must be able to prosper as a safe, secure and sovereign nation within its internationally recognised borders for generations to come,” their statement added.
“We will continue to increase our support for Ukraine.”
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The European leaders are set to visit the Maidan, a central square in Ukraine’s capital where flags represent those who died in the war.
They are also expected to host a virtual meeting for other leaders in the “coalition of the willing” to update them on progress towards a peacekeeping force.
Military officers from around 30 countries have been involved in drawing up plans for a coalition, which would provide a peacekeeping force in the event of a ceasefire being agreed between Russia and Ukraine.
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This force “would help regenerate Ukraine’s armed forces after any peace deal and strengthen confidence in any future peace”, according to Number 10.
A special constable has been jailed after taking pictures on his phone from bodycam footage showing a dying man.
Former police volunteer William Heggs, 23, was sentenced to 12 months’ imprisonment at Leicester Crown Court on Friday after showing the photos of victim William Harty, 28, to a female colleague and storing them on his Snapchat account.
Mr Harty was found seriously injured in a residential street in Leicester on 25 October 2021 and Heggs had attended the scene, helping with CPR before paramedics arrived.
Mr Harty died in hospital a day later and the man responsible for his injuries, his brother-in-law Martin Casey, was subsequently convicted of his manslaughter.
Heggs showed the pictures he had taken of bodycam footage of Mr Harty’s body to a Leicestershire Police constable, who reported Heggs and said she did not like seeing blood.
His phone was seized and officers discovered other photographs and video clips of bodyworn footage of incidents Heggs had attended on duty, including of a knife seizure, use of baton and pepper spray, and a man with an injured hand receiving first aid.
He also took pictures of a police computer screen, showing details of crimes and suspects, without consent.
Heggs stored the materials in a Snapchat folder and disclosed graphic details – most of which were not in the public domain – about the injuries to a woman who was killed in a road traffic collision he had attended, to a friend on the social media platform.
Heggs was suspended from the force in November 2021 and resigned in October 2024 before pleading guilty to 11 computer misuse and data protection offences this March.
William Harty’s widow Mandy Casey. Pic: PA
‘He has traumatised me’
Mr Harty’s widow, Mandy Casey, said in a victim impact statement read to the court that Heggs “took (her) husband’s dignity when he was most vulnerable”.
“You don’t take someone’s dignity and pride from them on their deathbed.”
She continued: “When I found out special constable Heggs had done this, I just wanted to ask why. He has traumatised me. I feel I will never know if he showed them to others.”
Ms Casey said she was still scared that photos of her husband’s body might appear on social media.
She added that she had lost trust in the police.
Public trust in police ‘significantly undermined’
Judge Timothy Spencer told Heggs, who has autism and ADHD, that he was “probably too immature to be working as a police officer” as he handed down the sentence.
He said Heggs had received “extensive training”, including on the importance of data protection, and knew he should only share materials for “a genuine policing purpose”.
Heggs’s actions had “significantly undermined” public trust and confidence in police, according to the judge.
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Malcolm McHaffie, from the Crown Prosecution Service, added: “William Heggs abused the public’s trust in the office he held as a special police constable.
“He violated the dignity of the deceased victims for no apparent reason other than what could be considered personal fascination and to gain credibility among his peers.”
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