How To Flirt – Flirting Via Texting & Messages

This post addresses how to flirt with someone via texting and messages and to perfect your writing style to win the interest of the object of your affection. In today’s busy world, texting and short messaging is the most common form of communication. Therefore, knowing how to text appropriately, including flirting with others, has become ever more important.

Use appropriate language

There’s nothing worse than someone attempting to use language outside of their age bracket. I’ve seen parents, for example, try to text their children with modern-speak (think LOL, LMAO, and so on) and just look inappropriate and lame. There is a whole group of people out there who think LOL stands for ‘Lots Of Love’. Not only is what you say in your text important, but the language you use tells the recipient a lot about you. Don’t come on too strong or use overly sexual language, which along with sending explicit sexual photos, is a big complaint from many women (see our post on 10 Things Men Want Women To Know & Women Want Men To Know. Your photos can be forwarded onto others at the click of a button, and can embarrass you in front of your friends, family and colleagues. Sexting scandals have ruined relationships, families, careers and reputations.

Check your spelling and grammar

Along with the style of language used in your message, make sure you check your spelling and grammar. Sending messages that are incomprehensible or inarticulate with sloppy grammar or incorrectly spelled words makes you look like a fool and makes the recipient feel like you don’t care about them enough to put in effort for them. Your writing doesn’t need to be perfect prose, but at least give your text a once-over before sending it. Watch out for the auto-correct function on your phone, too – you may end up saying the wrong thing and end up on a website like Autocorrect Fail. And finally, before you press send, always check your text is going to the right person! These quick checks can avoid a potentially embarrassing situation – imagine a flirty message going to a family member by accident.

Choose an appropriate time to text

There are many good times to send a text, but there are also a few times when you should NOT text someone. One such time is inappropriately late at night or early in the morning. Many phones have silent or ‘do not disturb’ functions on them, but be aware of your recipient’s schedule, and when might be appropriate to text them. Another time not to text someone is when you are incredibly drunk – drunken text messages usually end in embarrassment or hilarity (see Texts From Last Night for some examples) – but not very often do they result in a positive impact on your love life. A couple of drinks can give you the courage to message your crush, but any more than a few and you should keep your phone in your pocket. Try not to message someone – particularly someone you like – when in a highly emotional state (angry, sad, annoyed) as you may say something you regret and turn them off seeing you. No-one likes supporting emotional baggage in the early stages of a relationship. Finally, for safety’s sake, don’t text and drive. Texting requires a decent amount of concentration, using both your eyes and hands, which will distract you from driving and put you, your passengers and other road users at risk. Use a hands free kit with a text-to-speech facility or use an app for your phone like Siri, Skyvi (Siri for Android), SMS Reader, and so on. Although, there are studies that show this is still distracting and risky behaviour.

Be casual, be cool, be creative

You should never go too overboard or come on too strong in a text message, so try to be as natural as possible. So many people over-think what they’re going to say that the text or message feels forced and unnatural. Some of the rules of flirting via texting or messaging are not so different to those in real life, and the best flirts come across as easy going and natural. Subtlety and balance are crucial, but also try to be creative. It is a much greater skill to be creative and come across as interesting when using only words as your medium, and they’ll be impressed if you can pull this off. Make them laugh, make a clever or interesting observation, or just be original in the best way that you can be (don’t try to be someone that you’re not). Don’t try too hard, though, and don’t try to be too funny or seem too eager or enthusiastic – it can be a major turn-off.

How to begin your conversation

One of the best ways to start a text conversation is to ask a question. It can keep a conversation going and you can learn more about the other person. Keep the questions simple and open-ended, which gives them more opportunity to answer, but don’t be too open-ended or philosophical in a way that might puzzle them. Ask them their opinion on a new movie, restaurant, band or news item (news that isn’t too controversial). Be thoughtful, too – if you know they were doing something important (a sports competition, a test or exam, or a job interview), ask them about it and show that you care. If they’ve been sick, ask if they’re feeling better. You could also write about an observation or something else that made you think of them. It may have been a place you visited or something you ate or a conversation you had – it informs them that you were thinking of them without being too direct.

Taking flirting to the next level

A little naughtiness or teasing can be a great way to take the flirting to the next level, but it requires subtlety, indirectness and MUCH CARE. As mentioned above, sexting can turn off many women, particularly sending in-your-face sexually explicit photos. Learn to read the nature of their replies to gauge whether or not a particular topic or level of conversation is appropriate at that point of time. Something like ‘TMI’ (= Too Much Information) as a response is good indication you’ve already said enough. Tease your crush lightly and be a little playful, but not too much. Sometimes an overly sensitive recipient, mixed with a lack of forethought, can end up with them being offended – see 7 Deadly Relationship Sins – What Not To Do In Love – Part 2. Keep it light, make it clear that you’re joking, and show that you don’t take yourself too seriously. You could think about a silly nickname for them and use it when you contact them. Don’t forget to complement your crush either – find a subtle way to let them know they looked cute or nice, or that you like their new haircut or outfit.

Do I call or do I text?

Some people really don’t enjoy the cumbersome effort of typing out a message and prefer the relative simplicity of talking on the phone. On the other hand, some people find texting more preferable and hate talking on the phone. With texting, they can answer in their own time and can text more easily in certain situations, like when with others, when on public transport, when in a class or lecture, and so on. Try to gauge your interest’s preference early on and communicate with them in the way they prefer.

Treat texting for what it is – a casual form of communication

Remember texting and messaging for what they are – a casual, short form of communication – and don’t expect to build a meaningful, deep connection. It might be a great way for a little flirting, to learn a little more about each other or to make plans, but you can’t beat the connection that can be made in person. There’s less chance of a miscommunication via texts and messages, too, because you can read their body language and judge the tone of their voice.

With these tips at hand, it’s your turn now to try some of them out yourself. Good luck! And stay tuned for the next post on How To Flirt – Flirting In Person.

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