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.

‘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?”

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!”

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.