The dating game is a delicate one - you've got to think carefully about what you say and how you say it to make sure you don't end up looking like a complete jerk or worse - a creepy weirdo and it seems that it's men who find it most difficult.
Recent research by TSB Magazine shows that men tend to agonise most over when it is appropriate to send a message to their date, not to mention how best to word it.
"There is a major urgency to it. Because guys know one text can make or break your chances with a woman," says TSB Magazine founder Bobbi Rio.
A flirtatious text between dates is seen by most men as a great opportunity, but with the wrong wording you could scare her off.
Too many messages, bad spelling and grammar and misinterpreted meanings can all be dealbreakers and suggest that there is a fine balance at play.
The next most challenging part of dating was knowing how to make a comeback after an awkward moment in conversation with an attractive woman.
Third on the list of challenges for men was knowing when the right moment is to lean in for a kiss.
Initiating conversation didn't pose nearly as much of a problem to most men who took part in the study.
Rio has noted the need for great advice on good communication between those first few dates and has written a book with co-author Rob Judge entitled Magnetic Messaging which offers a few pointers - one of which is to avoid sending messages to the tune of "How's your day going?" or "What you up 2?"
"Most men are simply lost when it comes to using their phones effectively," Rio describes in a blog. "It got to the point where 75 percent of our coaching calls revolved around the topic of texting women."
Using a three-text rule, Rio suggests that appealing to a woman's emotion and being personal are important factors that will help capture her attention.