If he says sorry a lot, then he sounds a bit insecure, and wants you to know that he's sorry, and uses emoticons in a way to flirt. Each person has their own reason behind using smiley faces.
I tend to use them to help convey what I am saying, since not just emotions but tone of voice can be hard to pick up through text alone. If I am being sarcastic, I tend to use a smiley face to show that I am being sarcastic just in case the person was thinking I was being serious. The only time I ever use any kind of smiley face as a way to show I am flirting with a girl is when I use the wink face ;) like that. If I am just using a regular :) face, then I am just trying to get across the tone of voice.
its not lack of manliness as these people say. its this guy likes you and I trying to get to know you more. maybe he feels his emotion smileys will convey his message to you indirectly. sorry isn't a weakness he just probably feels intimidated by you & that you may not like him and therefore reject him. hence forth he playing the Slow but Steady approach :-)
In fact, whenever I'm chatting, almost every single sentence has at least one emoticon at the end.. o.o
That's kinda how it works! :P
...point is, for me, it's a habit, and a means of showing some type of emotion. But it's nothing compared to voice and all. "lol" is sort of neutral if you ask me, most people just reply that to almost anything.