By now, most dating sites have added instant messaging (IM) features. They’re a fun way to flirt in real time with people you’re interested in. IM can also be an easy way to gauge chemistry. After all, if you can’t hold a conversation over IM, it’s doubtful that you’ll be able to do so in person.

However, you should exercise care with the feature. Because of the on-the-spot nature of IMs, it becomes especially vital to stay on your toes to ensure that the interest level of the person you’re chatting with remains high. If you inadvertently bore or offend them, the IM session is not going to end with the flirtatious exchange of phone numbers.

However, using IM the right way is a great way to impress someone with your confidence and your skills as a conversationalist. Here’s how:

1. Don’t Start With “Hi”

While “hi” is a perfectly nice thing to say, it’s not incredibly interesting. Almost anyone who receives their fair share of attention on a dating site with IM features routinely gets so many “hi”s that they become easy to ignore. Your opener should make it obvious that you read their profile and were so interested that you simply had to IM them.

For example, asking someone their opinion of the book that they just read cries out for a response much more urgently than a generic greeting. Think of something memorable and unique to them. The effort you put forth will put a smile on their face.

2. Ditch the Small Talk

Chit-chat about the weather or what you both did last weekend won’t do much to increase their interest level. Flex your conversational muscle. Be funny, witty, and always interesting. They’ll love the way your IMs keep them on their toes. Don’t be afraid to be confident and respectfully flirtatious. It’s a much bigger risk to be boring and safe, especially during a conversation that can end immediately. Don’t have them close your window with a yawn — keep it lively.

3. Keep the Conversation Short

Don’t overstay your welcome. Once it’s clear that they’re interested, bring the conversation to a gentle close. Leaving them wanting more is infinitely preferable to a long IM session that exhausts all conversation and has them ending it with a bored “Anyway…” Unless the interest level is through the roof for both of you, you probably shouldn’t ask for a date immediately.

But you should advance the idea of a face-to-face meeting in the near future. Tell them about a cafe you love or a new restaurant you’re dying to try. Make it obvious that you’re interested in their company and that you intend to raise the stakes sooner rather than later. A little forwardness can work in your favor. Even during a first conversation.

4. Be Interesting — But Be Interested, Too

In your conversation, make it very clear that you read their profile. Ask them questions about themselves, about their careers and extracurricular passions. A genuine interest will be much more attractive to them than any line. Listening skills can be apparent even over IM. And, yes, they’re very attractive.

5. Use IM to Quickly Move Past IM

Even the most fascinating IM sessions will soon lose their thrill. After two or three (at most), ask for a face-to-face meeting and a number. Too many IMs will make them wonder if you’re looking for a chat buddy instead of a romantic partner. Once you rapidly escalate the interest level via IM, you should strike while your text banter still makes them smile. If you wait too long, they’ll undoubtedly move on to someone with more initiative.

taraDating EssentialsConversation Topics,Flirting,Instant MessagingBy now, most dating sites have added instant messaging (IM) features. They're a fun way to flirt in real time with people you're interested in. IM can also be an easy way to gauge chemistry. After all, if you can't hold a conversation over IM, it's doubtful that...Advice and Tips for Online Dating