I dated a man for 1.5 years who, at the beginning, was everything I wanted. He was divorced and has a son and, it turns out, was more attached to his ex-wife than I knew. There have been some trust concerns in the past six months. I snooped (I know ... ) on his phone and found some hurtful texts between the two of them. I confronted him and he said he was scared, wasn't sure he could move on, etc., so he regressed. Long story short, she has been playing with his head and he has been stuck on her for years. Right around the time this came out, he decided, independently of me, that he was ready to move on. He was in love with me (which took him a long time to say), and was ready to put the past behind him. I was hurt and didn't trust him, so I broke up with him. If it were only that easy – he is now saying everything I want to hear, and I want to believe him. I know he can't change overnight, but I am not done figuring out if it could work.
To complicate things, my parents and other family and friends do not approve. They are protective of me, and I appreciate it, but they see other character flaws that I am having a hard time seeing because I am emotionally invested. This is my journey and I need to figure it out for myself. I am conflicted, but not ready to give up on us. Am I just prolonging the inevitable?
– Wavering in MA
Maybe you're prolonging the inevitable, but you said it best: It's your journey. Your gut is telling you to see what this guy can do, so you might as well try.
But please, pay attention and be honest with yourself about how things go. If you find yourself wanting to break into his phone, ask yourself why. If his actions don't match his words, don't make excuses.
Also, make sure to use your witnesses. You didn't tell us what your friends and family noticed about this guy, but clearly they're worried and don't mind speaking up. As this relationship progresses, ask them whether you seem happy. That's the most important question, and sometimes it's the hardest one to answer on your own.
Readers? Should she try again? Should she listen to friends and family?