Board Thread:Arrow discussions/@comment-9346948-20160407004753/@comment-3423279-20160408042642

The only secret Felicity kept was about her non involvement with Team Arrow during their time away, not exactly the worst thing to keep and the writers played it off for laughs, even Oliver considering how harmless it was to their relationship.

Oliver did a bit more than that.

After Samantha explained to Felicity that it had been an ultimatum she forced Oliver into accepting so he could see and connect with his son Felicity was certainly more understanding than before.

Oliver going behind her back again with something of that nature after he already knew doing such a thing was not a good idea is what finally did it.

Sending that message to William wasn't the problem, it was the fact that Oliver, who was under zero obligation to hide that from Felicity did so anyways.

Instead of walking up to her and saying "I am thinking about sending a message to my son explaining everything that he can watch on his 18th birthday, wanna talk and know about it?" He just did it anyways because he didn't learn from before.

Oliver had no reason to keep that from Felicity and if she hadn't been close enough that she could overhear it do you really think he would've ever told her?

No doubt in real life this wouldn't be an issue as actual humans tend to learn from their mistakes, but the writers apparently wanted Oliver to do the stupidist thing possible with the information and knowledge he had gained after secrets he kept from his Fiancee were found out.

Hey guys we have this thin ice here, wanna jump on it and see if it breaks? No wait... better yet drive a M1 Abrams Tank over it, we really need to make sure it doesn't break.