Hello, I am Rafael. Thanks for asking your question - I'm here to support you. (Information posted here is not private or confidential but public).
I am very sorry to know about this situation.
Your relationship is still very young, and past relationships did not end too long ago. Also he has had this history of ending and restating the relationship with his ex-girlfriend, and the fact he has kept the ring and told you he kept it in case they get back together, was not just a red flag but an obvious behavior showing you how attached he is to this person and his expectations and hopes about a possible reunification.
Most times first relationships are very irrational,people get too attached, and easily deny core issues and if the person is not mature enough, then multiple problems could happen. His present behavior around the ring clearly shows what he is still expecting about this person, what obviously does not show any positive thing around the stability and seriousness of your relationship.
If you truly believe this person is worthy as a boyfriend and that he is being totally honest towards you, and are willing to afford challenges and the risk of a broken heart, then you could give him the time he asked for and see what happens. Other people in your shoes would just not feel comfortable nor respected at all when aware of such situation and end the relationship, while other would set a boundary and make it clear that after such period of time, if he is not clear, respectful and responsible in the relationship, it would have to end.
It could be helpful as long as they happen to be mature and assertive people. Most times out of loyalty friends would not say negative things about each other unless they happen to be really assertive. I[d say that it is always useful to get as much feedback and information as you could from those who know him, just be careful not to take everything you hear
Whenever you see a pattern is what you hear, then you could better know there is something concerning abou it
I would say that the bet cautious approach would be to give him this time and then depending not only on his words but on his concrete actions and commitment, you would decided if it is worthy, healthy and something you want, if he really meets your core needs and expectations in the relationship or not.
If he comes back telling you he wants you but continues to present behaviors that do not match his words, like keeping the ring, deep attachment and hopes about her and any other similar behavior, then it would be better for you to reassess if you truly want to stay in a relationship like that, since not even real respect, sensitivity, honesty and caring would be present to build it healthy and in fulfilling ways.
I would say only to those who you know are mature and healthy individuals, who could provide objective suggestions instead of mostly protecting him and whatever he does because of their friendship.
If he truly deserves you and wants to work in the relationship, his consistent actions would show it, otherwise you would know it is not healthy nor worthy.
The communication he keeps with her, things related-from the relationship, fantasizing about past hopes around her, not being truly present and committed in your relationship, no showing real openness and honesty when talking about his feelings and what you are working on building together.
Sounds good. I support you and hope things work for you. Please feel free to contact me as needed, since I am here willing to support you.
You're welcome.(Please do not forget to rate the session. Thank you).