How to Flirt via Instant Messaging

Looking to flirt with someone on MSN, AIM, Facebook Chat, or any other instant messaging platform? If you're worried about coming off as awkward, congratulations – by seeking advice, you've already proven you have more self-respect than most online flirts. Check out Step 1 to learn how to flirt in a smart and respectful way.

Start the conversation casually. Just like in real life, the first step in flirting is to overcome your own nervousness and take the plunge! Send a short message asking about their day, their work or school, or simply say 'Hello!' The hardest part of flirting is getting past that initial hesitation, so if you're struggling with it, remind yourself that, no matter how awkward it gets, it will still be less stressful than talking face-to-face.

• There’s no reason to be anxious about flirting over IM – if the person you want to talk to doesn’t want to chat with you, they have the right not to reply to your messages, and you’ll probably never know if that’s the case, since they could simply not be online.
• This also means that if you don’t know the person well, you can always find an excuse to start a conversation to avoid the awkwardness. Asking for help with something academic is always a great way to begin, or asking about something interesting they seem to be into. For example, if their username is related to a band, you might say, 'Hey, cool name. Did you catch their last concert?'

Chat. After exchanging greetings and talking about light-hearted topics, you might want to learn more about the person (just like in real life). You could ask about their work, studies, hobbies, or recent trips. Instead of just asking questions, you can also share your own thoughts on these subjects. When they respond, add your own comments or ask follow-up questions to keep the conversation going! Avoid getting too personal – keep the tone casual, fun, and focused on light topics.

Make them laugh. Everyone loves a good sense of humor. Marilyn Monroe once said, "If you can make a woman laugh, you can make her do anything" (don’t worry, ladies – this applies to men as well!). Be playful and even a little sarcastic in your responses.

• For example, if they ask what you’re up to, instead of saying 'flirting on Facebook,' you could respond with something cheeky like 'writing a novel' or 'drowning my sorrows.' This could naturally lead to a conversation about your hobbies, such as your writing or the amazing bourbon you had yesterday.
• Take our conversation as an example – you can add a joke or two while chatting about music. For example, you might say, 'I don’t know why, but every song on the radio lately has a bit of a Texas Flynn vibe. Did he record something while in rehab?'

Playfully tease. Once you’ve established a good rapport with the person you're chatting with, teasing a little can help elevate the conversation. Keep it light-hearted so the exchange remains fun and easy-going. The general rule is, the better you know someone, the more you can tease them in a light-hearted way.

• Tease in a fun way. Of course, you’ll want to avoid sensitive topics related to their personal life, career, ambitions, etc.
• The line between being flirtatious and being rude is thin, so be cautious when in doubt. It's easy to find another excuse in the future, but harder to fix things once you’ve hurt someone's feelings. For example, you could ruin a conversation about a band they like by saying, 'Oh no, not them! Hahaha.' However, if you say, 'They’re just posers and their fans are the worst,' it’s less threatening.

Use bold emoticons. One of the benefits of using emoticons in instant messaging compared to text-based services like email is that you can convey your intentions more clearly through your words. When flirting, you’ll want to include lots of winking faces (;) and 'tongue out' emoticons (:p) that almost every IM service provides. These will make your flirting clearer and more playful.

• A word of caution – don’t overdo it with emoticons. Sprinkle them sparingly throughout the conversation to sweeten your flirting and make your intentions a bit clearer. Using them too often will make you seem childish or annoying.

If you’re getting good responses, you can turn up the heat! If the person seems receptive to your jokes and playful teasing, you might want to take things a step further and make the conversation more intimate. But be gentle with it – don’t escalate too quickly. Instead, use subtle hints. Be suggestive rather than blunt. This is a form of 'grace' and a skill that many people, both in the virtual and real world, seek to master.

• Make humorous comments. Every form of flirting or seduction carries a certain level of innocence. Understanding this innocence can help you stay grounded and avoid coming off as too eccentric.
• Take the band example above – if the person mentions that they find a certain song sexy, you could jokingly raise the stakes by saying something like, 'Play it cool!' or respond with an exaggerated 'Oh, really? ;)'.

If the person responds negatively, stop. Flirting with anyone, anywhere, means you’ll have to deal with the risk of rejection. In the virtual world, where communication can often feel cheap and indifferent, this risk is very real. If the person you're flirting with shows signs of discomfort, gracefully end the conversation. For example, you could say you need to do something (homework or work tasks are good excuses) or that it’s time for bed. The reason for ending the conversation doesn’t matter – what’s truly important is respecting the other person’s wishes and avoiding an awkward situation.

• Using the band example again, if you mention a song and the person says it's their significant other’s favorite, it might be time to politely end the flirting. You could say something simple like, 'I’ve got to go now. Talk to you later!'

Be the one to end the conversation. A good rule for online flirting – and real life – is to end the interaction in a way that makes the other person want more. In the world of IM flirting, this means you should wrap things up before the conversation starts to drag. By doing this, the person will remember only the fun, positive parts of your conversation – not the awkward moments when you’re scrambling for a new topic to discuss.

• If the person responds positively to your flirting, create a fun sign-off so they’ll always think of you. You can even use an emoticon. For example, saying 'Good night' might feel a bit dull and lackluster, but 'Good night ;)‘ carries a subtle message that you’ll be thinking about them (and vice versa).

Don’t be too self-deprecating. Simply put, confidence is attractive. This is especially true in real-life situations, but it also holds up in the world of IM flirting. For example, don’t make too many jokes at your own expense. Once is enough – it shouldn’t become a recurring theme throughout the conversation. Constantly doing this can quickly turn your flirting into a conversation where you come off as self-loathing and pitiful.

• In other words, this doesn’t mean you should mock others, because that’ll make you seem petty and mean. Any negative comments about yourself or others won’t help your flirting efforts.

Avoid coming off as too silly. People generally prefer flirting to be lighthearted. For most, receiving compliments is enjoyable to an extent – too many can make them feel awkward or embarrassed. It may even make the other person question your intentions, suspecting you might want something in return. Additionally, overly effusive praise loses its impact, especially when presented in a small box under the screen next to smiley face icons.

• Rather than bombarding them with compliments, focus on engaging in a fun, genuine conversation. Think about the saying "Show, don’t tell too much." In other words, you can demonstrate your attraction by offering them an exciting conversation instead of bluntly declaring it.

Don't be too clingy. Flirting with someone via instant messaging on the first interaction can show how ordinary your relationship is. For this reason, you'll want to keep the conversation casual and natural. Avoid diving into topics like love, long-term commitment, or anything similarly serious – these are taboo subjects early on and can ruin any chances of securing a date.

Don’t be crude. Different people have different attitudes towards using vulgar language, crude humor, and sexual matters. Respect these differences. In the digital world, where profanity, violence, crude jokes, and sexual content are just a click away, it’s easy to forget that many people are uncomfortable with such content. Therefore, keep your chats PG (appropriate for all audiences) until you get to know the other person better. At the very least, try to consider whether they would enjoy this kind of conversation.

• The rule to remember is: try to avoid vulgarity until the other person initiates it. In other words, if you're flirting with someone, avoid crude language, inappropriate jokes, or unhealthy comments unless they start it first.

• Quickly review what you’ve just typed to avoid spelling or typing mistakes. You wouldn't want someone to misunderstand.
• Don’t rush if the other person is busy or hasn’t responded to your message. You can’t know what’s going on in their life.
• Don’t reply immediately – doing so will make you seem desperate! Wait a minute or two before replying. This gives you time to think about what you want to say.
• When flirting on MSN or similar messaging apps, use soft expressions like "ha ha". It helps keep the conversation light and shows that you’re enjoying chatting with them.
• Be sincere, but not overly pitiful.
• Make sure the conversation isn’t just about you or one specific person.
• If the other person types slowly, try to slow down too, so you can see their reactions. Are they shy or introverted? If they’re extroverted, you should offer subtle hints. Do you know them? Flirting online can be tricky if you’re worried about potential consequences. If you met them on a site like MySpace, ask questions carefully to figure out if things are real.
• Being too eccentric on sensitive topics isn’t the best way to flirt. You can drop a few "hot" hints, but being overly eccentric could become annoying and awkward, especially if the other person isn’t interested.
• A hug is a more intimate and gentle gesture, much like a kiss but less provocative, and it fits well with flirting.
• Try not to be too obvious with your flirting. It can make the other person nervous.

• Avoid mentioning other people too much, as it may make the person you're chatting with feel uncomfortable.
• Flirting online, like anything else, can be risky. Never give out your phone number, home address, or any personal information to someone you don't trust!
• Just like any other type of flirting, don’t get too comfortable and start complaining about life. You may feel desperate, but don’t make it too obvious.
• Don’t whine about your day – stay positive.
• Avoid steering the conversation into a dead-end. It’s just bad form. Don’t flirt just for fun. Only do it if you truly like the person and want to send them signals.
• Don’t send too many offline messages, as it will make you seem desperate. You can occasionally send them if you need to let the other person know you won’t be online that day or if you have something important to say that can’t wait until tomorrow.