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Dear emberlyn:
It reads to me like your boyfriend cares for you and is forming an emotional attachment to you. His relationship with you may grow more loving and beautiful for him than his previous relationship. The thing is old attachments take time to end. During his relationship with his ex girlfriends, there were times he felt a strong attachment, then a time he fell out of love, then a time the attachment returned, ups and downs. This is a natural process. The texts you read, as unpleasant to read as they were, do not indicate to me that the man is not a good man for you.
You wrote: “the hopeful side of me believes he doesn’t have feelings for her anymore” The hopeful-side when it is not a realistic-side, a side true to reality, will hurt you. Life is often not what we WISH it would be. Wishing will not change reality. If you fit your thinking to reality, it will benefit you.
Reality: he was still attached to her when he sent those texts. When he texted her that “he really missed her and their time together, talking with her and hanging out with her” that means he is still emotionally attached to her, and that he does have feelings for her, at least he did when he sent her those texts. So you thinking that “he doesn’t have feelings for her anymore” is wishful thinking.
Your thinking that he “is just looking out for her as a friend and just feels guilty about hurting her” is also wishful thinking because reality is that he kept texting her without her response: “He has sent her like 5 text messages since with no response from her at all.”
He told you before you found out about the texts that she was possessive of him. Her text to him doesn’t indicate possessiveness: “She told him…she would be fine, and told him not to worry about her and that she just wanted him to be happy even if it couldn’t be with her.” She may have been possessive of him in the past but not from the time she sent him that text you saw to the time she didn’t answer his last text.
If she continues to not answer his texts, it will help him un-attach himself to her. If he feels safe and comfortable with you, growing an attachment to you, it will help him un-attach himself to her, over time. One day, it will happen: he will no longer be attached to her, just like you wish it was already the case.
anita