Shoot your shot: how to flirt online in the age of internet dating - according to the experts

Recently, superstar singer Lizzo revealed that after a night of drinking, she attempted to slide into the DMs of none other than Captain America himself, Chris Evans.

The Grammy Award-winning singer took to TikTok to warn her followers “don’t drink and DM” and said she had messaged Evans after a few drinks.

She sent the actor three emojis: a wind blowing emoji, a woman playing basketball, and a basketball - basically, Lizzo was “shooting her shot”, which is a phrase that means pursuing someone you’re interested in.

A few days later, Lizzo hopped back on to TikTok to update her followers about the ongoing saga, revealing that Evans had responded to her message, and even followed her back on Instagram.

While Lizzo is a world-famous recording artist and Evans a Hollywood star, the question here is one that we can all relate to - how to grab the attention of a person you have a crush on via the internet, without scaring them off.

While many of us had already dabbled in internet dating thanks to the boom in popularity of apps such as Tinder, Bumble and Hinge, 2020 was the year that all forms of flirting and dating turned digital.

So what do the experts think of Lizzo’s bold approach - and how exactly are we supposed to flirt online? This is what they have to say.

Be fun and playful

Hayley Quinn, a dating coach for men and women, says: “I have respect for Lizzo’s DM slide. She sent a playful emoticon based message to Chris Evans which depicted that he should hurry up and take his shot.

“For women who want to make the first move, she did a lot of smart things: the message was short, light, playful and left plenty of room for him to take the next move forward.”

When it comes to flirting online, it can sometimes be intimidating to take that first step.

If you’ve matched with someone on an app like Tinder or Bumble and have finally worked up the nerve to send that first message, it can be discouraging if they don’t message you back - but Quinn says to avoid the temptation to reach out elsewhere.

She says: “If you’ve matched on a dating app, message them on that platform.

“If you find their linked Instagram account, don’t make the effort to follow and message them there, or show that you’ve creeped on their profile too much.”

If you are looking to do a bit of flirting over a social media platform like Instagram, instead of a dating app, then Quinn recommends engaging in some lighter communication to begin with just to get on their radar.

“You can do this by replying with an emoji to their story or writing a short, witty comment on a picture,” she says.

Having a well maintained Instagram account yourself, or whatever social media you’re trying to flirt over, is also something to keep in mind.

However, Quinn warns against delving deep into someone else's account and liking old pictures as this will likely come across as a bit strange.

Keep it short but snappy

Quinn advises that when you’re just getting the conversation started with online paramour, it’s best to keep it short, but that doesn’t mean compromising on the quality of the message.

She says: “Long messages immediately communicate you’re more invested in the outcome than they are, so keep your messages half as long and twice as strong.”

Kezia Noble, celebrity dating coach for men, adds: “People who find it awkward to flirt in real life tend to do better when flirting online.

“However, although you get to bypass those uncomfortable silences and awkward moments, you will still have another set of challenges to face.”

Noble explains that one common obstacle people face when it comes to finding love online, is the inability to stand out.

She says: “Most women are inundated with messages from guys, and most of those guys are saying the exact same things as the guys before them.

“The advice I give to my students is to avoid generic messages that have that ‘copy and paste’ feel to them, and instead, go for a message that will catch her attention but not in a sleazy or strange way.”

Don’t over-do the compliments

So how exactly does one stand out? Well instead of going for just a simple “Hello”, Noble suggests mentioning something specific about the person you’re trying to woo - perhaps something from one of their pictures, or their profile.

“Make an observation about her recent photo or something she mentioned in her bio that probably didn’t get much attention,” she explains.

If they are matching your energy and you think it’s the right time to drop a compliment in the mix, Quinn suggests going for something other than the obvious.

“Go for unique compliments: they may have been told they have a nice smile a thousand times, so try to pick up on a more unusual characteristic they exhibit,” she says.

However, Noble warns, don’t overdo it: “A very common mistake men make when messaging women, is that they over kill the compliments and as a result they lower their own value.

“Messages that start with “I bet you get thousands of guys like me messaging you” will be immediately deleted, as will “I bet you hear this all the time.”

Noble says that once you’ve made that initial connection online with someone, then you can begin the flirting.

She says: “I always advise my students to keep it cheeky and playful rather than x-rated.

“The aim is to make the other person feel comfortable enough, intrigued enough and excited enough to meet up with you, and when you do eventually meet up, that’s where things can and should start heating up.”

If someone isn’t reciprocating - move on

Quinn says that the number one more important factor you need for successful flirting is reciprocity - after all, it takes two to flirt.

She says: “If someone isn’t responsive, or is doing the bare minimum to keep the conversation alive, move on.”

So, for example, if you’re getting one word replies to your messages, or they aren’t asking any questions about you, it might be time to let the conversation go.