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Dear WestCoast Gal,
I have gone through this same exact thing with my current boyfriend! About 6 months in, I started feeling there might be some things I didn’t know about him. At this point, we had just barely became “official”, and so I felt like it was plausible to deepen the relationship a bit. When I would bring this up to him though, he said he felt bad because he believed he had been deep with me and that he thought I knew him pretty well. I reflected back on myself and why I had been feeling this way, and I chalked it up to the fact that in all my past relationships, I had gotten super close super fast. This relationship was different because we had taken the time to go on dates, only see each other a couple times a week, and allow the connection to bloom on its own. So once I was actually his girlfriend, I had felt confused because in my past relationships, 6 months in, I knew all of their trauma and they knew all of mine. I realized that me not knowing absolutely everything about him in 6 months wasn’t a loss and that I should do what I had been doing up until that point: letting the relationship bloom on its own. And it worked! A year later we are best of best friends. In the last year, I gained so much knowledge about him, but in a less controlled way. Either he’d openly come to me about something, or I’d randomly ask a question that lead him to open up.
Obviously, my situation could be a lot different than yours, but I just thought I’d mention it in case you had a similar past to mine. All in all, I think most men have a hard time opening up and it’s not always necessarily because they don’t want to. It could be because they just don’t really think about things like that. As women, we will offer information about ourselves because we want to be understood, but most times men truly could care less about how people perceive them. I’d just try asking things you want to know, after a while, he’ll probably feel comfortable enough just telling you outright. If he has a hard time answering the questions you want to know, and depending on what the question is, that’s when I would begin to feel iffy.