Hi Jocelyn,
He may be following up again because he wants to observe your behavior in order to determine whether there is any romantic interest for him on your part.
When he spoke to you on Valentine’s day and asked you about how your day was going, he was most likely trying to get your attention and make himself known to you once more.
Being that he is socially awkward, he finds it hard to truly express himself or be more extemporaneous whenever he is talking to you.
That is one of the reasons why your conversations with him tend to be dull and awkward.
On the one hand, he is interested in you and would like to go out with you again but on the other hand, he is very inexperienced and uncomfortable when it comes to courting a girl.