Be clear that you want to flirt.
Asking them directly is often the way to go. Sure, it may feel awkward to ask “Hey, do you want to flirt?” You probably wouldn’t do that in person, but it makes it easier to be sure that you’re both on the same page about each other’s intentions when interacting online. If they say “yes,” you can be at ease that you both know what’s going on; if they say “no,” you don’t have to waste your time flirting with someone who isn’t interested. If you’re on a dating site or another platform where flirting is assumed, you don’t necessarily have to ask directly. But you still might want to!
Keep things light and fun.
Set just one goal—to enjoy getting to know the person a little. Flirting is supposed to be fun, not stressful! If you set a goal to get a date, hook up, or fall madly in love, you’ll put too much pressure on yourself and end up seeming creepy. Focus on having an enjoyable chat and let the chips fall where they may—maybe something will come of your flirting, and maybe it won’t.
Be yourself.
Yes, be charming, but don’t try to be someone you’re not. Obviously you want to make a good impression when flirting. That said, trying too hard with bragging, self-promotion, swagger, exaggeration, or outright lying is likely to end up seeming annoying or even creepy. Sure, you should focus on your positive qualities and accomplishments and turn up the charm factor a bit, but make sure you’re staying true to yourself if you want to make a genuine connection. Endless self-promotion and exaggeration is always a turn-off. At the same time, though, downplaying yourself too much is also a turn-off. Be confident in who you are and have fun sharing this with the other person.
Share an interesting question or observation.
Give the other person an opening to engage in flirty chat with you. If you start out just by saying “hey,” “what up,” “ur cute,” etc., where is the conversation supposed to go from there? Avoid dead-ends like generic comments, crude jokes, well-worn flirting lines, and yes/no questions. Instead, start out with an interesting observation, question, or comment that encourages the other person to respond. For example: “Were you able to stay awake for that chem lecture today? I was halfway to dreamland. What was the deal with him talking about his shoes?”
Compliment the person, not just their looks.
Pair a thoughtful compliment with a question to spur conversation. A well-considered compliment can open the door to some fun back-and-forth flirting. Pick something to compliment about the person’s personality, sense of style, or interests, then use the compliment as a lead-in to something to chat about. Sending a straightforward compliment like “I like your shirt in that photo” doesn’t do much to inspire back-and-forth flirting. Instead, give more detail and add on a question that requires more than a yes/no answer: “That Reggie’s Pizza Palace T-shirt you have on in that pic is awesome. Isn’t that the one they give out to winners of the Pizza Challenge? You gotta share that story!” Avoid using strictly physical compliments like “ur so hot!” that give off a creepy vibe and don’t help lead to any further conversation. Start with a compliment but don’t keep giving them repeatedly. That can get creepy really quickly!
Focus on your common interests.
You’ll both be more at ease if you’re flirting about something familiar. Now isn’t the time to pretend you’re interested in painting or auto repair because you think that’s what the other person is into. You’ll be out of your element and end up sounding phony and creepy. To make an actual connection with the other person, even just a light, flirty one, talk about something you both genuinely have in common. Based on where you meet the person online, you may already know that you share an interest in the same video game, musician, sports team, craft, etc. In this case, ask a few light questions to get the chat going: “What did you think of that game last night? I can’t believe they made that comeback!” If you’re not so sure what you have in common, ask some probing (but not intrusive) questions to find something you share. Even a few slightly silly questions like “What’s your favorite dessert and why?” can help get you talking about something you have in common.
Take it slow.
Moving too fast is even more creepy online than in person. Because you’re not flirting right there next to each other, the other person’s “creep detector” will already be on a heightened alert level. If it seems like you’re in a really big rush to move things forward with your flirting, their alarm bells will go off! Think of it this way: while flirting in a crowded bar may have to be more like a sprint, flirting online can be like a marathon. Take advantage of the time you have to see if there’s a real connection happening. For example, working your way up to some playful sexual innuendo might be fun—depending on the circumstances—but jumping straight into more crude sexual references is guaranteed creep territory.
Give them the option to keep flirting.
Put the ball in their court at the end of the flirting session. Ideally, you’ll have done such a great job of flirting that you’ll leave the other person wanting more. In this case, try to playfully bring things to a close so it’s up to them to make the next move—hopefully by setting up another flirting session! For example, you might say something like this right after your conversation has hit a real high point: “Aw, looks like I gotta go for now. That essay I have due tomorrow isn’t gonna write itself.” If you’ve read the situation correctly, they’ll want to know when you two can do this again. Alternatively, if your flirting session seems to be running out of steam, see if they want to pick things up again another time: “Hey, would you like to do this again sometime?” Here again, let it be their choice whether to continue.
Don’t flirt on inappropriate sites.
Flirting on an unexpected forum can feel like an ambush. General social media platforms and especially dating sites are definitely fair game for online flirting. At the other end of the spectrum, professional platforms are a no-go, and gaming platforms are iffy. Ask yourself this: could/should this person have anticipated being flirted with when they logged on? Think of it this way: flirting in a bar is definitely okay, while flirting at a business meeting isn’t.
Avoid flirting if it feels creepy at all.
Things like big age differences can make any type of flirting creepy. Some situations are simply going to cause flirting to feel more potentially creepy. For instance, while the “creepy old man” stereotype is often unwarranted, a big age difference will always increase the “creepiness factor” of any kind of flirting. Put yourself in the other person’s shoes and ask yourself (honestly) if you’d be a little creeped out—if your answer is yes, don’t flirt with them. For guys at least, there’s an unofficial but fairly common age standard for avoiding creepiness—don’t flirt with someone unless they’re at least half your age plus 7 years (so, at least 21 if you’re 28). Consider this example: flirting online with someone you met in an online grief support group is creepy if you do it within the group meeting platform, but not necessarily if you save it for another online platform.
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