How to hit on someone in real life – without being a creep

If you’re single, chances are you’ve been trying to get off “the apps” for a while. These days, dating app fatigue is a well-worn and much-discussed phenomenon; perhaps it’s only a matter of time until it becomes a recognised psychiatric disorder – again, if you’re single, you’ll understand.

But what happens after you triumphantly delete Hinge, Bumble and Tinder from your phone and you’re suddenly slung back into the real world? It’s not exactly easy to meet people out and about – or “in the wild”, as is common parlance today, which in itself perhaps indicates how feral modern dating has become. If it was easy, the apps wouldn’t be popular in the first place. But now we’ve grown so accustomed to them that trying to meet people the old-fashioned way can feel like totally foreign territory.

It’s something all of us should be trying, though, regardless of whether or not we still have the apps on our phones. Being more open to having meaningful interactions with strangers can widen more than our dating pool; even if you don’t end up in a relationship with the person, they might be able to introduce you to a whole new network of singletons. Plus, it’s worth remembering that only around 10 per cent of people in committed relationships or marriages met their partner on a dating site or app, according to data from the Pew Research Center in 2023.

As for how to go about it, well, that’s where things get a little more complicated. One wrong look or remark and your approach can easily be misconstrued, which could ruin your chances entirely and risk you being written off as creepy depending on how much the other person fancies you – and also how badly you messed it up. Get it right, however, and you could wind up finding the love of your life. In short: the stakes are high.

This brings me to the first tip for hitting on someone: read the room. “You can tell if someone is open to conversation or just lost in their own world and preoccupied, in a rush or even grumpy by paying attention to their body language,” says dating coach, Sophie Personne. “The easiest thing to do if you’re unsure is to make eye contact and smile. There is no harm in that and you will know from their response if they’re interested in having a conversation or would rather be left alone.”

In an ideal world, the object of your affection will smile back and a “meet cute” will ensue that you can retell to relatives and friends ad nauseam at the wedding. But if that doesn’t happen, and you get even the slightest instinct that the other person is not interested, walk away. “This isn’t rejection, this is just bad timing,” adds Personne. “But don’t force an interaction.”

Context is also key: what is the person you want to approach doing? Do they look like they’re in a position where they have time and space to talk to someone they don’t know? “If they look as if they might be rushing to work or late for an appointment, they aren’t going to be approachable,” says dating coach James Preece. “Do it at a time when they are likely to be most receptive, such as browsing in the supermarket, waiting in line or reading a book in the park. Weekends are best for this as single people are more likely to be chilling on their own than those with a partner.”

Once you’ve successfully approached, your next dilemma is working out what to say. Again, high stakes: say something too boring and you’ll have to fight harder for their attention, which could work against you. Then again, say something they’re not in the right mood to hear and, well, you’ve become a pithy anecdote they’ll regale on their next good date. It goes without saying but leave cheesy chat-up lines at the door; sure, sometimes they’re cute but other times they are a symptom of a problematic pick-up culture you need to stay very far away from when trying to flirt with a stranger. With this in mind, it’s probably best to avoid them completely.

“The easiest way to start a conversation with a stranger is simply to ask a question,” advises Preece. “Something like asking for directions or asking what they think about something going on nearby will work wonders. Don’t overthink it: just act as if they are someone you already know well.” Open-ended questions work best, like asking what someone likes about the place you’re finding them in or what brought them there.

James Preece, dating coach

In some cases, depending on where you are, it can also be helpful to use your surroundings. “This is particularly easy if there is something obviously going wrong around you,” adds Personne. “For example, I was in Waterloo a few years ago and a lot of trains had been cancelled. I fancied McDonald’s but the queue was so long I didn’t want to risk missing the one train going out so I just grabbed a boring sandwich. A guy walked into the carriage with a McDonald’s bag and I just said, ‘You have no idea how jealous I am right now…’. Not only did he give me a cheeseburger but we carried on chatting through the journey.”

If there’s something to be careful about, though, it’s giving out compliments, particularly those that focus on appearances. “I recommend you make it meaningful and specific,” suggests clinical psychologist Barbara Santini. “Instead of the usual, ‘You’re beautiful,’ you might say something like, ‘I couldn’t help but notice your energy, it’s really refreshing.’ This shows you are noticing more than just their appearance and value their vibe.”

Once you’ve established a rapport with someone, try to find out their name. “Then you can be sure to use it naturally to establish a more personal connection and demonstrate you care about what they have to say,” adds Preece. Mirroring their body language can help, too, and draw someone closer to you. Then you can work on solidifying the interaction by either asking for their phone number, or suggesting meeting for a coffee another time.

The most important thing, though, before you even attempt any of this, is to check in with how you’re feeling about yourself. “You won’t get anywhere if you don’t approach someone with confidence,” says Annabelle Knight, relationships coach and resident sex expert at Lovehoney. “By no means does this mean you should come across as arrogant or aloof. There’s no point in putting on an act or a front that isn’t who you really are, as it will quickly fall apart if things do progress. By being yourself you can talk more confidently about your own likes and interests if they ask, and they can gauge their own interest.”

Of course, you might feel apprehensive the first time you try any of this. But the more you do it, the more you’ll feel comfortable putting yourself out there, and handling rejection if and when it comes.

Ultimately, though, being able to do this successfully boils down to self-esteem, which is why snappy chat-up lines generally don’t work and serve only as WhatsApp group fodder. “After all, if we feel like our ‘killer line’ has snared a new partner, then what happens when we don’t have this kind of toolbox available?” says counsellor Georgina Sturmer. “When we feel comfortable with ourselves inside and out, we are far more likely to be able to be authentic and comfortable when we are dating.”

Bear all this in mind next time you find yourself in the wild and hopefully you’ll have some success. Or at least enough to stop you from asking anyone if they “come here often”.