Start the conversation with something interesting. If you want someone to talk to you, you need to have something to talk about. Start with an interesting question or an observation, or a comment. There's no way I can't ask you about your new profile picture. Is that a waterfall? 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 the waterfall profile picture was in Cancun last summer, ask about the trip. What was the most ridiculous thing you saw there? Worst thing you ate? I'd be scared to try sky-diving. 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. If someone doesn't think that's funny, they're better off with someone else. Plus those plants are wack. 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. If you want to chat online, be there to chat. If you want to ignore people's messages, go do something else. 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. Gotta feed the dog, though. He's about to eat me. If you can't start a conversation with someone, you can't start a conversation. Have lots of conversations, and keep them light. 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. It'll come off as fake and awkward. It's good to talk about yourself in positive ways. 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. Just chat like you would with a new friend. Just read a funny article or saw a funny. Something to share and talk about. 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. 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. Just focus on having a few laughs and seeing if you like someone. Some innuendo can be flirty with the right person, but only once you've gotten to know someone. If if feels pornographic, it's not flirting. 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. 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. 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. Talking about your whole history and backstory is a good way to make someone think you're self-obsessed. 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. If you've been striking out a lot lately, it won't sound flirtatious to say so. 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. I say hiking, I'm not lazy I swear. Go on, I'm sorry. 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. What happened that day? 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. 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. 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. Be honest and find something interesting to say. Pull out the most distinctive, interesting and true things about yourself to put out there for all to read. If you haven't been on a date in 20 years, it's not necessary to broadcast it for attention. 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. 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. Not a good idea. 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. Anyone you're flirting with will start to think that you're vain. Seriously, every idiot is sending the other person these - don't be one of them. If he or she is that hot, guess what? They already know it! So who cares if you message them that, now they know that you're not worth taking seriously. Steve Santagati, a self-styled dating expert, suggests that women should seek as much personal information as possible about the man while keeping back too much personal information about themselves, as a safety precaution. Whatever your gender, this is sensible advice, you don't want to hook up with a bot, fraud or serial killer. Use instant messaging as a way to get information you need to know. Search the identity online, to see what else you can find out. It is also good to know this person through a friend or someone else to make sure that this person actually exists.