Chatting Flirtatiously
Start the conversation with something interesting. If you want someone to talk to you, you need to have something to talk about. Whether you know the person in "real" life or just from a dating profile page, it's impossible to find a connection if all you've got to say is "hey" or "ur cute." Don't start conversations with, "hey" or "what up." It doesn't give you anywhere to go. Start with an interesting question or an observation, or a comment. Even if it's small, start with, "Whoa, whoa-whoa. There's no way I can't ask you about your new profile picture. Is that a waterfall? Please dish." Don't start with a line. Innuendo or crude jokes aren't the way to get someone interested. Read the next section for more specific advice for picking conversation topics.
Get the other person talking. People like talking when it's easy. If you want to have a fun, flirty conversation, make it easy for the other person to have it by asking them questions and being a good "listener" to their responses. Ask lots of follow-up questions. If the waterfall profile picture was in Cancun last summer, ask about the trip. How was it? What was the most ridiculous thing you saw there? Worst thing you ate? Don't pry. Asking questions like, "That sounds so fun! I'd be scared to try sky-diving. How was it?" is one thing. But the answer to "How can you afford to sky-dive when you work in the service industry?" isn't any of your business.
Be playful. It's hard to define flirting exactly. Lots of people just want to look for a connection, some kind of electricity. Often, this has to do with your sense of humor and your playfulness. Let your sense of humor come through. If you think it's funny to reference obscure Wu-Tang Clan songs, or random facts while you're talking, then do it. Be yourself. If someone doesn't think that's funny, they're better off with someone else. Sometimes, gentle teasing can be flirty and electric, or it can make you come off like a jerk. It might be funny to one person to say, "Whoa nice waterfall picture. That looks cold. Plus those plants are wack. Nice try though." To others, not so much.
Respond in a timely way. Flirting needs someone to be at the other end of the line or it won't spark. Respond to as many messages as you can when you see them, and show the other person that you enjoy the exchange between the two of you. "Leaving them waiting" is the rallying cry of people with no dates. If you want to chat online, be there to chat. If you want to ignore people's messages, go do something else. If someone else isn't talking to you, leave them alone. There's no sense in peppering them with a million interesting and well-formed questions that they're going to respond "lol" to.
Be the one who ends the conversation. The best flirtatious conversations end with the other person wanting more. You want to leave them thinking about you, and wishing that you'd log back on for more chatting. Before the conversation runs out of steam, it's a good idea to cut it short and leave them thinking about you. Look for a high note that might be difficult to top. If you get someone really laughing, but can't think of anywhere to go beyond that, just end the conversation: "Good talking to you. Gotta feed the dog, though. He's about to eat me."
Be persistent. Invest some effort into flirting, but don't expect a lot of return initially until you "click" with the right person. If you can't start a conversation with someone, you can't start a conversation. Flirt around. Have fun. Have lots of conversations, and keep them light. On the other hand, don't give up too easily. Online chats can take some time to get to know someone. As mentioned earlier, keep it lighthearted and stay approachable.
Stop trying to make yourself look good, and just be yourself. If you want to flirt and find a genuine connection with someone, it's important to be yourself, not the self-promoting Facebook version of yourself. It's all too easy to come off as conceited online, the more you talk about yourself and your accomplishments. So don't. Just be you. Write the same way you talk. You don't need to make yourself "sound smart" or try to use words you wouldn't normally use to flirt. It'll come off as fake and awkward. On the other hand, self-deprecating humor can sometimes be funny, but it can also sometimes come off as desperate or annoying. It's good to talk about yourself in positive ways.
Knowing What to Say
Keep it light. Flirting is just like having a regular conversation, but more fun. Go into expecting that you're going to laugh and you're going to have a good time, not like you're going to get a date with someone, or make them fall in love with you. That's too weird. Just chat like you would with a new friend. Take advantage of the Internet as a resource. Just read a funny article or saw a funny .gif or a cute video? Pass it on. Something to share and talk about. Different people like to talk about different things. To one person, it might be flirty to tell long stories and talk about serious subjects, while to another it might be dull. To one person, it might be flirty to talk about partying, while to others it could be a turn-off. Read each person and adjust.
Take it slow. Online flirting is a marathon, not a sprint. There's no reason to rush right into talking about what you want, or planning a date, or figuring out where you're going to move in with all the children you're going to have. Whoa there. Just focus on having a few laughs and seeing if you like someone. Don't go right for the crude sexual references. Some innuendo can be flirty with the right person, but only once you've gotten to know someone. If it feels pornographic, it's not flirting. Avoid blurting out "I love you" on the basis of five minutes of chat and one profile photo. That will be an immediate relationship killer. It's okay to tell the other person that you think they're lovely, fascinating and gorgeous, but leave out love language until you both seem to know each other quite a lot better. If you wouldn't say it flirting in real life, don't say it online.
Talk about common ground. If you're in class with someone you're chatting with, talk about class. If you're in the same town, talk about what neighborhoods you like. Talk about the best hang-outs. Talk about something that you have in common with each other to help make a connection. If you don't have anything in common, or can't figure out what you've got in common, ask questions until you find something. Even if the questions are silly, like, "What's the best month and why?" or "What's your sign?" you'll be able to start talking about something.
Talk about something funny that happened to you today. Everybody you talk to online has been fed the same lines at some point, and been asked the same dull questions. "What do you like to do for fun?" and "What are your hobbies?" are sort of dull flirtation questions. But, if you tell a story about how your neighbors are fighting about how the one's dog peed on the other's stoop, you'll have something funny to jump off from. "What do you think of dogs? And ridiculous neighbors?" Don't ramble about your own life too much. Talking about your whole history and backstory is a good way to make someone think you're self-obsessed. Share smart details.
Don't overshare. Someone doesn't need all the intimate details of your entire life story, your problems, and your innermost thoughts and desires. Save it for later. That's not flirting, it's blurting. Don't be a sad-sack if you're trying to flirt. If you've been striking out a lot lately, it won't sound flirtatious to say so. It'll sound desperate. Be very, very careful about talking about serious things like marriage, monogamy and having children, especially if you don't know the person. These are all flirt-killing words. Wait until you're in person to talk about these things.
Play a silly associative game. If you really can't think of anything to talk about, but really want to be flirtatious, you can always just start playing the random question game and talking about silly things. Talk about your best meals, your favorite animals, whether or not Katy Perry's a genius or more boring than white toast. Good silly questions or prompts to show your funny side: "Tell me the story of the best sandwich you ever ate." "Which member of the Wu-Tang Clan or One Direction or the Beatles best represents you as a person?" "If you could go to any country, what would it be?" "What's better, naps or hot-tubs? Or Netflix? Or...hiking? I say hiking, I'm not lazy I swear. Go on, I'm sorry."
Compliment the other person, sometimes. Good compliments can be a way to get the door open and have more to talk about. Pick something that you like about the person, or have noticed, and use it as a compliment, then turn that compliment into something you can talk about. Compliments are nice, but they're also hard to respond to. Try to turn it into a conversation: "That picture of you at the waterfall is so pretty! You look great. What happened that day?" One compliment per conversation is appropriate. If you start to seem overly complimentary, it can seem obsessive or creepy. If you think someone is attractive, that's nice to hear, but it's not necessary to say five times every minute.
Getting Dates Online
Sign up for an online dating service. Online dating is increasingly common and almost necessary, especially in bigger cities. It's just the way people meet nowadays. If you want to flirt online and meet exciting people, start a profile on a dating service and start reaching out. It's a good way to get in touch and flirt online. The most popular and common dating sites are: Match OkCupid Tinder MeetUp Plenty of Fish eHarmony
Make your dating profile honest. If you want to connect with someone, fill out your profile information honestly and in a flattering way. Make yourself sound like the kind of person you are, to attract like-minded people. Don't be basic and boring. Every other profile has the phrases, "Living life to the fullest" and "I just like to travel" on it. Be honest and find something interesting to say. Think carefully about how you summarize yourself in the profile. Pull out the most distinctive, interesting and true things about yourself to put out there for all to read. Honest doesn't mean desperate. If you haven't been on a date in 20 years, it's not necessary to broadcast it for attention. Share the interests you're most passionate about. Someone else may just have the same ones! Reader Poll: We asked 183 wikiHow readers who’ve dated online, and 59% of them agreed that they look for a common interest to bond over before messaging someone. [Take Poll]
Use a flattering profile picture. A connection is more important than looks, it's true. But when you're flirting with someone online, good looking photos of your face and clothed body are still important. If you can't take lovely shots of yourself, have a friend or professional take a few that capture you in your best light. Be yourself. Don't try to be the tough, scantily clad, or bizarre version of yourself in your photo. Show yourself as a genuine, regular and likable human being with a photo that shows you at your best. No nudes and no drunk pics. Not a good idea.
Keep some mystery. There's no reason to over-sell yourself. Keep some privacy, even though you're dating online. Spend a lot of time getting to know someone before giving out intimate details and even then, make the first meetings very public ones. Once you stick to this rule, the rest of your online flirting is about having fun. Having someone who seemed nice at first but turns really weird holding your phone number or address is plain creepy, if not downright frightening. Avoid any temptation to post hundreds of photos of yourself for people to check out. Anyone you're flirting with will start to think that you're vain.
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