Save the chattiness for when you finally meet in person.
Remember, when you send a woman a message on Match.com, you don’t always know why she doesn’t respond. But, if you visit her profile and see an “IM Her Now” button – BOOM, you’ve got yourself a paid subscriber.
The answer is: There ISN’T a good way to use this feature. Or, if you do, do so as an experiment, knowing that it will very likely backfire on you.
Here’s why: If you do this, make the conversation really short, and get on your way.
One of the reasons could be that she isn’t a paid subscriber. She should be able to read and respond to messages you send her. Remember, don’t open with an IM unless you really just don’t care!