How to flirt over 50 (and 60, and 70…)

Part 01

What flirting actually is (it’s simpler than you think)

Forget pick-up artistry and rehearsed routines. Flirting is just playful attention: letting someone know you enjoy their company, with a hint that it might lead somewhere. It’s warmth, curiosity and a little bit of cheek, served in whatever proportions feel natural to you. Think of the person at every party whom everyone drifts towards; rarely the best-looking one in the room, nearly always the one who seems most delighted to be there.

In practice that means noticing things about the other person and saying so, teasing them gently, remembering what they told you last time and making them laugh. None of it requires a six-pack or a sports car. Most of it simply requires paying attention, which grown-ups tend to do rather better than twenty-somethings.

Part 02

How to flirt over 50 online, one message at a time

Flirting by message is good news for the shy: you can think before you type, and nobody sees you blush.

• Reply to the profile, not the photoPick up on something they wrote, a place they’ve been or a joke in their bio. It shows interest in the person, which is the most flattering thing you can offer.
• Tease, gentlyA light poke at their questionable football team or their claim to make the best lasagne in Lancashire invites them to tease you back. That back-and-forth is the whole game.
• Ask questions you actually want answered‘What’s the most spontaneous thing you’ve ever done?’ beats ‘how’s your day?’ every single time.
• Use emojis like seasoningOne well-placed wink is flirty. Six in a row reads like a ransom note.
• Leave them wanting moreEnd on a question or a playful cliffhanger rather than an essay. Short, lively messages keep the rhythm going.
• Let it buildSave the saucier innuendo for when you’re clearly both enjoying it, and follow their lead on how far it goes. Naughty is fun when it’s mutual.

Part 03

Mature flirting lines that won’t make anyone wince

These flirty chat up lines were written for grown-ups. Each one is specific, slightly cheeky and easy to answer, which is the secret of any good opener. Tweak them to fit the person, and never send the same one to everybody.

• For the bookworm“Your profile says you’re reading three books at once. I’m impressed and slightly worried. Which one’s winning?”
• For the gardener“I see you grow your own tomatoes. I once killed a cactus. Is there any hope for me?”
• The honest one“I’ve rewritten this four times, so I’ll just say it: that’s a brilliant smile, and I’d love to know what made you laugh in that photo.”
• For the traveller“Of all the places in your photos, which would you go back to tomorrow, and would you want company?”
• The self-deprecating one“I was going to play it cool, but cool left me sometime around 1991. Fancy a chat anyway?”
• For the food lover“Settle something for me: on a scone, is it jam first or cream first? Choose carefully, a lot rides on this.”
• For the dancer“You mention dancing. On a scale from wedding disco to ballroom champion, where would you put yourself?”
• For the dog lover“Your dog looks like excellent company. Does he vet your dates, and how do I get on his good side?”
• In person“I couldn’t help noticing you’ve got the best laugh in the room. What’s the joke, and can I be in on it?”

Part 04

How do older women flirt? Ask ten and you’ll get ten answers

There’s no secret code, and anyone who tells you otherwise is selling something. Some women are wonderfully direct and will tell you exactly what they like. Others prefer a slow build of banter and teasing. Plenty flirt through humour, and you only realise afterwards that the running joke was the flirting all along. The same goes for men, for the record.

If you’re wondering how a woman in her sixties or seventies flirts, the answer is: however she likes, with decades of practice at reading people. Treat her as an individual, not an age, and pay attention to what she’s actually doing rather than what you expect.

Online, the signs that anyone might be flirting with you include quick, longer replies, questions back about your life, picking up on your jokes, the occasional wink and phrases like ‘we should…’. In person, look for lingering eye contact, laughter, leaning in, a light touch on the arm and a reluctance to say goodbye.

Part 05

Confidence, when you feel rusty

Nerves are normal, and they don’t disappear because you’ve reached a certain age. The answer is low-stakes practice: chat to a few people without pressure, compliment someone’s choice of shoes, enjoy a bit of banter in the queue at the post office. Flirting is a muscle, and yours just needs a stretch.

Remember that your age is an asset rather than a handicap. You’ve got stories, perspective and a better sense of humour than you had at twenty-five. And if someone doesn’t flirt back, it isn’t a verdict on you. They might be tired, taken with someone else or simply not your person. Smile, move on and try again tomorrow.

If it helps, set yourself a tiny goal each week: one new conversation, one compliment, one message that’s a shade cheekier than you’d normally send. Small wins add up, and before long you’ll catch yourself flirting without even thinking about it.

Part 06

Cheeky, never creepy

Naughty is the whole point here, but naughty works best when it’s welcome. A few ground rules keep the fun on the right side of the line.

• Compliment choices, not bodiesA great dress, a brilliant laugh, excellent taste in music. Comments about someone’s figure can wait until you know they’d welcome them.
• Read the roomIf replies get shorter and slower, ease off. If they match your energy, carry on.
• Keep photos to yourself until askedUnsolicited pictures rarely go down well. On Naughty Seniors, anything potentially sensitive is blurred and comes with a warning anyway.
• Take no gracefullyA cheerful ‘no worries, lovely chatting’ leaves everyone’s dignity intact. Pushing after a no is never flirting.
• Move to a date when it feels rightWhen the chat is fizzing, suggest a drink somewhere public. Our first date guide is packed with relaxed ideas.