How to send the first message on a dating app

Samantha Rea

There's no doubt about it, making the first move is scary. And if you're not used to taking romance to the virtual world, it can be a tricky thing to navigate

“Don’t bother matching if you’re not going to message!”

As an online dater, I see this rather cross command (or ones very like it) in the bios of men across a range of dating apps. And reading it, I always feel rather rebuked. It’s like your parents sending you to your room for being sullen, saying: “Don’t come downstairs unless you’re going to put a smile on your face!” Or teachers telling you to be quiet, “unless you’ve got something useful to contribute!” 

It’s all a bit stern—which isn’t a great tone to take when you’re trying to woo someone. When Julia Roberts walks into the Notting Hill bookstore, you don’t see Hugh Grant snarling: “Don’t touch the books if you’re not going to buy them!” Just as Patrick Swayze doesn’t spoil the pottery scene in Ghost by snapping at Demi Moore: “Don’t get the clay out if you’re not going to concentrate on what you’re doing!” 

Of course, it’s perfectly reasonable to want a match to lead to messaging—and from there, to frisson-fuelled dating, and a lovely relationship involving lazy Sundays in bed with Bucks Fizz, Eggs Benedict, warm bodies and cool sheets. 

Surely that’s what we all want (or maybe some of that’s just me). But assuming everyone on dating apps is looking for love, lust, and a plus-one for weddings, why would anyone be matching if they have no intention of taking it any further? It doesn’t make sense, right? So, if you’re getting matches, but no response to your messages, could it be that the problem lies in the messages you’re sending? 

For over a decade, I’ve dipped into online dating whenever I’ve been single, and each time I download a dating app, I embrace my husband hunt with the exuberance of Jennifer Grey launching herself at the stage in the last scene of Dirty Dancing. Full of optimism, I swipe right on men with nice forearms in sky-blue shirts, who look like they could carry me across the threshold (and up the stairs). 

And yet, as the messages trickle into my inbox, I start to despair. “Hi” say 70 per cent of them, with all the effort and eloquence of Kevin & Perry mumbling in the direction of their trainers. “Hi Sam,” say a few others, making me wonder whether they’d be quite so cavalier with their abbreviations if they were addressing Joanna Lumley. 

Offering barely any more in the way of conversation are ones that say: “Hi, how are you?” And faced with a dozen or so messages along these lines, my will to live (let alone reply) is on a par with Sylvia Plath sticking her head in an oven. 

At the other end of the spectrum are men who ask me out in the first message, before we’ve interacted. It’s as if rapport is irrelevant, and the (often) copy-and-paste quality of the message suggests a scattergun approach, as if anyone will do. This is like leaving the sommelier to choose your wine without having a chat about which regions you like, or what you’ll be eating. And actually, I’m looking for a man who’s rather more discerning. 

Of course, these messaging blunders aren’t only made by men—and men are often equally disheartened by them. Glen Ocsko, aka Dating Dad despairs at receiving “Hi” as an initial message, declaring: “There’s nothing lazier!” Having sampled numerous apps, he says: “It's even more frustrating when this happens on Bumble, where the woman is in control of starting the conversation on her own terms—such a lacklustre opener utterly negates this feature.” 

So rather than disappointing your match with a damp squib, how can your first message strike like Cupid’s arrow? Here are some hints… 

 

Don’t: 

  • If you’re feeling jaded due to rarely hearing back, it’s tempting to make minimal effort when you reach out to a new match—but if you make the minimum effort, that’s all you’ll get back (if anything) so do go beyond “Hi, how are you?” 
     
  • If you find messaging tedious, you might want to skip it entirely by asking out your match in the first message. But if you develop a rapport, your match is more likely to say yes to a date. Childcare and other commitments mean they can’t meet up with everyone, so if you want them to meet you, establish a connection before asking. 
     
  • Writing one message and sending it to everyone you match with might seem like a time saver, but copy-and-pastes leave the reader feeling something’s amiss. It’s like accidentally opening your neighbour’s post—it doesn’t quite seem like it’s for you (then you notice the address and realise why). So do tailor each message. 

 

Do:

  • Use your match’s bio and photos as a starting off point. Savvy daters will already be doing this, so make your message stand out (and kick-start the conversation) by sharing an anecdote of your own—and always include a question so your match has something to respond to, for example:  
     
  • Instead of saying, “nice hat, it suits you!” say: “I love your hat! Was that Ascot? Last time I went I put £1 each way on Filly O’Fish and went home with enough money to redo my kitchen. Well, enough to buy some bleach to get the kids’ biro off the walls. Do you like a flutter?” 
     
  • Rather than, “I see you like running—I bet that keeps you fit!” say: “Beautiful scenery—was that the Royal Parks Half? I want to do that next year. I had my eye on the Marathon des Sables, but I reassessed my options after a windy day at Camber Sands ;-) Have you done any marathons abroad?” 
     
  • In place of, “Looks like you’re enjoying the sun—I can’t wait to get away!” say: “Stunning harbour—is that Guernsey? I lost my shoes to the tide, wild swimming in Sark. I had to tiptoe through a field full of cowpats, then a waiter lent me some sandals. The seafood there’s amazing. Do you like oysters?” 

Samantha Rea can be found tweeting here


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