To get to those feelings, you’ll need to have a different kind of conversation. But first, let me offer some context to help you create a space in which your boyfriend might feel more comfortable opening up about his inner world rather than evading the topic altogether with some version of Maybe one day I’ll sell it.
What you two have been doing so far is staying in what therapists call the “content” of the conversation. The content is what the disagreement is ostensibly about. It might be something like You don’t do your share of the laundry, or You need to defend me when your dad criticizes me, or I want you to get rid of your ex’s engagement ring. Just beneath the content is what’s known as the “process,” which is what informs the content. For instance: When I’m left with all the laundry, I feel invisible, unappreciated, and unloved. Or: I don’t defend you when my dad criticizes you because I’m terrified of standing up to him and I freeze, just like I did when I was a kid. Or: I avoid talking to you about the ring because I’m afraid that you don’t want to hear my complicated feelings about it, and I will have no way to convince you that I want to be with you without denying these other feelings that are also very much a part of who I am.
Many couples stay in the content, rehashing the same argument (and getting nowhere), without ever talking about what’s really going on.
Let’s begin with a fundamental truth about being human: Our experiences in life stay with us and shape who we are. Our pasts aren’t magically erased when we meet a new partner; we all show up on Day One of an adult relationship with our own histories, ways of relating, ideas about ourselves and others, insecurities, pain, and losses. It’s unrealistic to expect a new partner to be a clean slate, especially with regard to significant relationships from the past. This means that if you’re going to have a strong relationship with your boyfriend, you’ll need to get acquainted with his losses.
You might be thinking, Wait, this loss happened almost two years ago. She was awful to him, and if he’s happy with me, it’s a gain, right? But some breakups can hit hard and linger because in some ways, they feel like a death—the person who was an integral part of one’s life is no longer there. Even if that person wasn’t the best match, there’s the loss of the good parts of the relationship that will never be replicated in quite the same way with another partner. Additionally, and this seems especially relevant here, the way in which a relationship ends (amicably, angrily, unresolved) affects the way the survivor will grieve, just as how the way in which someone dies can affect their loved ones for years to come.
The conversation you need to have will be made harder if your boyfriend has gotten the sense (and based on your letter, I imagine he has) that this is less a discussion that allows room for his messy feelings and more a means to get him to stop having the feelings he’s having. There’s a big difference between Tell me more about the pain of that relationship so I can understand you better and feel closer to you—this will make it easier for me to not take so personally your wanting to keep the ring (process) and Let’s talk about how we can work together to make any trace or memory of this woman disappear, specifically by selling the ring (content). (By the way, this is also a common dynamic when a person whose spouse died begins dating a new partner. Sometimes the new partner feels threatened by the pieces of the past, while the other person has a deep need to preserve them in daily life.)