Despite daters wanting to meet in person, online dating isn’t going anywhere. That means that you might meet your future partner in cyberspace — and you won’t keep their attention if you don’t know how to talk to them. Or, more specifically, how to flirt with them.
Much has been written on the art of seduction because flirting is intimidating. This was the case before dating apps and the onset of the pandemic, but now in 2025, the concept of chatting up a stranger can be more intimidating than ever before. We fear being cringe, being judged, and getting rejected.
There’s no way around that: those are possibilities. But to ease the anxiety of showing your peacock feathers online, we asked the experts for advice on how to do it.
How to flirt over text
First, we need an understanding of what flirting actually is, said Laurie Mintz, Ph.D., author of Becoming Cliterate and sexpert for sex toy brand LELO. Citing Psychology Today, Mintz said that flirting is a time-honored way of signaling interest and attraction to another person. Someone can do so in small increments, so both people can gauge how interested the other is.
Historically, flirting was all about body language (like whether someone smiles or leans into you) or verbal cues (like playful banter). The internet can strip those factors away, but that doesn’t mean that it’s completely changed the way we signal interest in someone.
Flirting has and continues to occur both live and in person, and asynchronously, former sociologist for Tinder and Bumble, Dr. Jess Carbino, told Mashable.
“Letter writing was historically a dominant mode of asynchronous communication that served as a mechanism to flirt until the early part of the 21st century,” she pointed out. “Asynchronous” means not happening at the same time. In the days of old, someone would write a letter and might only get a response weeks or months later.
Now, when flirting is staggered like that, it’s usually over text or an app — which means it’s instantaneous.
“While individuals could and certainly do take time to respond, historic forms of interpersonal communication that was asynchronous [lent] themselves more to strategy and consideration,” Carbino said.
So, how can we flirt both out of sync and in real time?
The key is using words to give compliments, playful banter, and references to being available, Mintz said.
She recommends starting out with an open-ended question about something on their profile, or pointing out something you noticed on it. For example: “I notice a lot of your pics are with your dog!” Establish that you want to get to know them, and take note of any common interests. You can also share your own interests, too.
Mintz suggested keeping the tone light and fun and saving the deep talk for in-person. Use emoji and photos to show that you’re interested.
Relationship coach for politicized people and Ph.D. in human sexuality studies, Melissa Fabello, also told Mashable that well-placed punctuation and emoji can go a long way.
“Flirting can be hard to do digitally because by its very definition, flirtation is about implication and suggestion. Without body language, that can be hard to pull off,” she said. Use punctuation, emoji, and gifs to get your tone across.
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Also: the eggplant and water drop emoji aren’t suggestive, Fabello said, they’re direct.
Watch out for mismatched live and online flirting styles, Carbino said. For example, someone who’s a more polite flirt in person might be emboldened by an online medium to engage differently. When they’re flirting IRL, their politeness could potentially lead to mixed signals.
Should I use ChatGPT to flirt?
For years now, some people have relied on large language models like ChatGPT to flirt for them by generating messages to matches. But both Mintz and Fabello told Mashable that being authentic and truly yourself when flirting is important.
“You want the other person to be interested in you, not a false persona,” Mintz said.
Fabello advised having a strong sense of who you are and what you want to explore — or at least as strong as possible. “Being performative or faking it sets up an unhelpful dynamic for if and when you two are actually naked,” she said.
Ask yourself: “What are your sexual desires and boundaries? What is your comfort [level] with IRL dirty talk?”
ChatGPT won’t have those answers for you. As Fabello put it, sexting starts with your relationship with yourself.
Fabello also advises against forcing digital flirting if it’s not your thing. If you can’t be your true self over text, that’s OK. Some people feel more comfortable expressing themselves in person.
What about flirting with nudes?
Nudes are an art form, said Fabello. Think of them as such and get creative.
“I promise that every woman in the world has received a photo of a penis from that exact angle in that same lighting with that same setting,” she said.
You don’t have to send standard dick pics (and, it should go without saying, but you should never send them unsolicited). Ask yourself how audio and visuals can entice someone, rather than leave nothing to the imagination.
If you need more tips, Mashable has a guide on taking nudes and how to store your nudes safely.
More digital flirting tips
Don’t be afraid to take a risk, Fabello said. As long as you’re not pushing or crossing boundaries — and you’re open to your flirting partner saying you have — step outside your comfort zone.
“Say the sweet or sexy thing that you want to express. You might be surprised at how they respond,” Fabello said.
And know this will get easier over time. Especially if you meet in person (more on that below), you’ll get to know this person and know what they respond to over text. And if you move on to someone else, you’ll have more flirting practice under your belt.
And if someone you’re talking to seems dull, it could just be that they’re not comfortable flirting online. It might still be worth giving a date a shot, Fabello said.
How to flirt in person
Unless you want an online-only relationship (power to you!), the time will come when you meet IRL.
“Don’t keep talking online forever — eventually make it clear that you’d like to meet in person,” said Mintz.
When the COVID vaccine became widely available, Mashable wrote about how to flirt in person again, and the top tips weren’t much different than online flirting:
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Don’t worry about being interesting (aka, be yourself)
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Acknowledge that dating comes with risk — and that’s OK
Flirting is ultimately about sending that signal of interest, whether from a feather-tip pen or your fingertips. It can be nerve-racking, but don’t let that stop you.
