Online Dating Conversations: Don't Let it Be Awkward!
Simple Tips to Get Things Going

"Do you really like (X)?"

Interests are always a good thing to ask about. It will also pique the interest of the person you're tallking too. As an example: "Do you really like playing cricket?" "Did you really take a holiday to Azerbaijan? That's one of my favourite destinations!". Immediately, you're showing that you have an interest in your potential date's life and what he or she does. This also helps to get them to try and impress you!

"Not really sure if we're gonna get along, but I thought I'd throw you a message since you seem to love (X)."

Men often feel safer and are more willing to be open when the lady they're speaking with has an interest in and/or shares their passion. This can be a cereal, a book, making fruit friends or a band. "Don't really know if we're going to get along..." is a good way to begin because you're making it a subtle challenge. It's definitely a good way of putting the ball in their court!

"So, (Elliot), will be chatting or are you just into staring at profile pics?"

Utter silence can be broken by statements like this, but it is also an excellent way of doing it lightheartedly. Most guys want an excuse to talk to a woman on a dating site, and being invited makes them feel a bit more relaxed about it. It also allows you to let them take the lead. Using their name, naturally, is going to a much more personal dimension to it (which is what you're going for anyway!).

"(That shirt/those shoes/that apron) in your pic…"

This kind of cliffhanger is certainly going to build intrigue. They'll be absolutely dying to know what you think about it. As an example: if he’s wearing a costume from Halloween, say, "That Pope costume…" When the response comes: "What about it?" say, "I MUST HAVE IT!" or, "My greatest respect to you, Your Holiness, for pulling it off…"