It's not like he doesn't have what he sees are good reasons for the lies and they aren't meant to be hurtful. The name/Prince James to protect his mother; the excalibur sword to give Snow confidence; the dreamshade poisoning to keep the mission on Henry; the stroller being new to save money. OK the last one wasn't a very good reason.
But his lies are usually to protect someone or help them. But it is still his dark side.
ETA When Anna thanked Emma for taking care of her sister, I kept thinking that really Emma should be thanking Anna because if Anna hadn't taught David to swordfight, Emma would have been killed by the black knights. Or maybe never born because Snow would have been killed by them in Snow Falls.