Clare
Don't be sorry! I sent my fair share of way too long and rambly but what if I ruin everything messages when I wasn't sure how to handle how I felt about your mom.
Change is scary, but it can be good? Really good. Because as nice as it is to have someone to text at 2 AM when your brain decides to be an asshole it's way nicer to have a person there. I always thought the best relationships are ones that have a really amazing friendship as the foundation, which it sounds like you and Owen do. It might be worth seeing if that friendship is more. He seems like a good guy and if he's taking your 2 AM texts I really can't see him letting something like you coming clean about your feelings be a deal breaker. Yeah maybe it might be a little bumpy for a small blip of time - but holding onto your feelings and always wondering what if won't do you any good either.