Using smileys
To smiley or not to smiley, that is the question! Some people love using smiley faces in their texts, others think it looks like an overeager 2-year-old has taken over your phone.
So how do you know if it's going to make him cringe? You just don't, so the answer is to do what you want to do.
If you think a little winky face at the end of your message will do the trick then go for it! And if he doesn't like it, well then maybe you should find someone who can appreciate your inner smiley geek.
Of course another solution is to just wait and see what he does. "Smiley faces can show that you are a relaxed, fun and friendly person. But if you are unsure about using them, wait and see how they text you first. If they send you one then you know they are fine with it," James says.