How to ask people out irl without it being awful

Dating apps allow us to know we can pop the question, but what happens outside of them anymore?

Hero image in post
photo: 500 Days Of Summer / Fox Searchlight Pictures
Hero image in post
photo: 500 Days Of Summer / Fox Searchlight Pictures

Dating apps allow us to know we can pop the question, but what happens outside of them anymore?

By Rhys Thomas09 Jun 2023
7 mins read time
7 mins read time

Tired of the ghosting, endless swiping, and boring boring boring prompts you have to read all day on dating apps? It seems, some of us are. Surely, even if you’re coupled up, you’ve seen plenty of Hinge horror stories and Tinder turn offs, on socials. A Google of “why are dating apps” prompts autofill phrases such as: so expensive, so bad, so depressing, so addictive, so bad for guys, and so hard.

But you’re not tired of dating, really, are you? Perhaps many of us are more done with the annoying, frustrating, futile labour of online dating, than we are actually done spending time with new people. Of course, an app makes that initial connection easier, which isn’t always simple IRL. Most of the time, you’re on the app to date, right? Whereas you aren’t always in a smoking area or following someone online, to potentially date them.

So, say you’re sort of into that person you follow on Instagram, or your friend’s friend who is going to be at that party next week, or just love the vibe of someone at the gym, or the club, but are completely clueless on how to ask them out without fear of rejection or restraining orders? How do you play it?

There’s the basics, right, you want to appear friendly. Make sure they can see you approaching them (i.e. don’t approach from behind), make eye contact because that’s a nice and intent-filled thing to do, and if you can at all tolerate it, smile. It takes a tenth of a second to form a first impression, so you know not a lot of time but definitely worth a little smile. Of course they’re only first impressions, so don’t stress too much.

“It is also important to consider body language, ensuring you appear welcoming and not closed off,” says Charlotte Johnson, sex and relationships expert at Mega Pleasure. Johnson goes on to explain that crossed or closed arms can be perceived as unwelcoming and detached. Other physical considerations include respecting personal space – you don’t want to stand too close to the person you’re trying to chat up. Also, if you’ve literally never met this person before, there’s no need to go in with a hug or anything like that. And even if you have met them before once or twice, allow them to make the first physical move. In general, it’s good to respond to their signals. If their hello seems a little like they don’t want to be saying hello to you, be aware of that. Pippa Murphy, sex and relationship expert at calls this “non-verbal communication flirting: eye contact, smiling, and sending positive body language are positive ways to flirt without feeling too vulnerable.”

Assuming all is good and comfortable after you’ve struck up a hello, Johnson would suggest “creating a little small talk before approaching a topic of discussion.” Bethan says “A bit of chit chat first will allow me to be more open to the idea, because I’ll have a sense of the vibe, it’s more comfortable, even if they’re obviously going to ask me out.” But don’t be ridiculous with it. You are there to ask them out, not to end up in a 20 minute chat about the weather, or interest rates, or what you’re doing this week, or the very specific things about your job that annoy you sometimes. Stay on track.

You could ask about their evening, maybe what they do and do a bit of chitter chat on that if it’s interesting.And then, when you have a bit of a conversation going and have maybe even exchanged little laughs or noises that suggest it’s an okay and pleasant conversation, cut to the chase on why you initially said hello.. “If you are going to go in with a compliment, focus on something specific like their outfit, makeup, or hairstyle” adds Dr Becky Spelman, Registered Psychologist and Founder of The Private Therapy Clinic. This is important because you’re highlighting something they’ve actually chosen for themselves, they’re less likely to have insecurities about these things. Johnson implies that it might be best to keep the compliments to a minimum until an actual date is happening. This might be a nice way to get into a conversation on the date about why you approached them, perhaps you can even ask why they said yes.

Back to the moment of possibly popping the question: There are a few signals to look out for when gauging the vibe. Assess the length of the conversation you’ve had, if it isn’t boring or forced, and they genuinely do seem to want to speak to you. These are all good things, and Johnson points out. “If someone’s not interested in the conversation or the person, they’ll often find ways to remove themselves from the situation, such as going to the toilet or taking a phone call.”

Body language will also help you assess the vibe. Some people are just lovely and don’t know how to not speak to others if spoken to, so if they’re speaking nicely to you but looking a little restless, or looking over your (or their own!) shoulder a lot, or being stand-offish, perhaps this is a cue to pay closer attention to whether they’re genuinely interested or not.

But ultimately, if the vibe is good, then there’s really no harm in asking. So how do you ask? As in, what on earth do you actually say?

Asking someone out is down to complete preference; yours but also theirs. “Some people find being asked on a date outright really attractive, other people can find this quite intimidating and would prefer a slower approach, such as introducing and communicating via social media.” Johnson says.

Thing is, ultimately, as with dating apps, the end goal is to try and spend time together. So you could find you have success by saying something like: “would like to go out sometime or perhaps exchange numbers” Spelman says. Of course, you could ask for their social handle instead.

If they’re with a friend, or friends, it can be a little awkward. You don’t want to make the friend stand on their own for ages. However, it shouldn’t stop you (what if you never see this person again !!)

“Address the friend first, saying something like, "I hope you don't mind, I would love to talk to them for a second," Johnson says. You could also look to include both in the conversation. If you’re planning to date this person, you’re going to want their friend to like you. Or whatever it was the Spice Girls said.

When speaking, “focus on being yourself. Express your genuine interest and personality. Never pretend to be someone you’re not, as it’s counterproductive, will be easy to spot and may make the conversation awkward” says Murphy. Even if they don’t realise you’re lying, and you’re good at lying on the spot, it isn’t going to be sustainable to do that. Just be yourself.

All three of the experts say a version of: if you’re rejected, know that it’s completely normal. We don’t see lots of rejection in real life because a lot of rejection is done and felt in private. We can hide it behind and within the cosy screen that is dating apps. Still, rejection happens a lot, while it can feel a lot more vulnerable in person, both because we can’t hide away from a response, but also because it requires more confidence to deal with in the here and now. But rejection happens all the time and it’s okay. “If they say no, it's important to respect their decision and not push the issue. It's okay to continue the conversation if it's respectful and enjoyable, but be mindful of their time and boundaries.” Says Spelman.

“Of course, it is important to remember that these indicators are not foolproof, and everyone is different. It's crucial to trust your intuition and take into account the specific dynamics of your interactions.” Murphy says. Again daunting, but it’s very much just part of the process. Lock that phone and give the IRL approach a go, it might be the way back into dating you’ve been looking for.