Here are some things to remember. Since, a shy guy hesitates to engage into face-to-face talks, it is preferred to chat with him through mobile instant messages or Social media sites. So clearly, you realise that I am in an extremely demanding job. You really can decipher an incredible amount from what a guy says even on the first few dates. Once you like a profile and he likes you back, you can open up a messaging feature and start chatting.