Dating app advice for novices

Samantha Rea 6 August 2020

It's not easy to automatically know what to say in the language of digitally enhanced love, so here's some great starting advice

“Up to anything fun this weekend?” From Thursday onwards, my dating app inbox becomes congested with this question—until about 5pm on Sunday, when it switches to the past tense: “Get up to much this weekend?” This one will keep on coming until Tuesday.  

While there’s nothing inherently wrong with asking about the weekend, receiving the same messages, week in, week out, from every man I’ve matched with, means my inbox holds all the appeal of a turgid toilet with rapidly rising water levels.  

This dating chat déjà vu puts the prospect of replying to messages on par with filling out my tax return. The only difference is that HMRC are far more forgiving of tardiness. The £100 penalty for missing the deadline seems like an absolute bargain compared to being pelted with passive-aggressive messages from men who’ve decided I’m too slow to reply. 

“Oh, I suppose that’s it then?!” they’ll gurn. “Clearly I’ve offended you?!” Sometimes they’ll simply send a series of question marks or a heavily punctuated: “Hello???” As nudges go, this is the equivalent of seeing I’ve left my parsnips, and slopping on some runny pigeon poo, to encourage me to eat up. 

One guy messaged me out of the blue, a month after our last interaction, to say: "In London today... let's meet!" Presumably, he sent this to every match in his inbox, but the chance of anyone jumping at a careless proposition from a random man in the approximate vicinity is about as likely as a flasher being besieged by lust-struck women: “Oh, I fancy some penis! How marvellous! Shall we...?” 
Then there are the man-babies with an aversion to structured sentences. Discussing where you’re both at (raring to start a family or kids ticked off the to-do list already?) with a guy who’s using “text speak” is the online equivalent of screaming for an epidural while your partner poses in clown shoes and a red nose while making a TikTok video involving a whoopee cushion. 

Of course, men aren’t the only ones to send messages that miss the mark—and they’re often equally frustrated by humdrum exchanges. Glen Ocsko, aka Dating Dad despairs of women who respond with “the barest minimum effort.” He’s even coined his own term for it: MVC (Minimum Viable Conversation). “It's single word responses,” says Glen, “or a simple answer to a question, with no effort to turn it into a conversation.” Exasperated, he quips: “I'm not interviewing a suspect in custody!” 

It’s easy to become disheartened, but there will be someone on the app who’ll make you light up like the northern lights when you meet them. So get matching, send a fabulous first message, and then keep up the momentum until a date is the natural next step. Here’s how… 



1. Do make your messages unique.

Instead of just asking about their weekend, share something about yours, eg, “I’ve just taken the kids swimming. There was an incident with an unidentified olive and the entire pool was evacuated. How’s your triathlon training? I told the kids that Olympians eat kale but they’re insisting on sausage and chips. Have you read about the triathlete who broke world records while he was in Belmarsh?” So send a message they'll want to reply to.

2. Do include a question.

A stand-alone statement (“Hope you’re having a good day!”) is difficult to reply to and it can leave your match wondering if you even want to hear back. A question gives them something to respond to, eg, “Boots have just barred me for stockpiling sun cream—the struggle is real when you’re strawberry blonde! Are you still working or have you sloped off to a beer garden? I’m having a G&T by the river as soon as I’ve sourced some Factor 50 off the dark web. Do you like Yuzu gin?” 


3. Do send properly punctuated messages.

Slinging across a few words, with no start or finish to the sentence, gives the impression that you’re sulky teenager who doesn’t want to come down for their dinner. You don’t need to send the equivalent of War and Peace. One or two sentences is fine—but an off-hand manner isn’t attractive. 



1. Don’t assume the worst if it’s a while before you hear back.

People are busy with jobs, kids, cleaning and trying to keep up with the friends and family who were already in their lives before they matched with you! It is OK to nudge, but send a message they’ll want to reply to, eg, tell them what you’ve been up to and ask for the latest on something you’ve been chatting about. 


2. Don’t delve too deep via messaging.

You may want to know exactly why their previous relationships ended, or why they haven’t had children—and it is OK to ask. However, the answers may be very personal and even painful, so have some empathy and patience, and remember that you’re not Andrew Neil grilling a politician. 


3. Don’t wait too long to arrange a date.

If you’ve established a rapport, and you want the same things, suggest a date to see if you click in person, eg, “I’m roasting potatoes with garlic I’ve grown in the garden. Do you like Sunday roast? I’m a glutton for gravy! I know a gastropub with a wine list that would dazzle Dionysus and gravy boats the size of the QE2! Would you like to go next Sunday?” 

Samantha Rea is a freelance journalist living in London. She can be found tweeting at @Samantha_J_Rea 

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