When your boyfriend tells you he had a crush on one of his current friends...

I've been scouring blogs all day, trying to find anything to help me learn the skills to have a productive conversation about jealousy.

I haven't found one that can give me the concrete tools to do this.

I spent an entire week with Jay when we celebrated his graduation this past week. He flew in and spent about 4 days with me before we attended his ceremonies and then his bff's wedding. It was the most time I've ever spent with him. So, I've been in a bit of withdrawal since.

A lot happened last week. I'll save that for another post. The focus of this entry is about his disclosure that he had a crush on his friend while he had been in his last relationship.  Let me rewind...

Over the course of graduation weekend, one of Jay's friend, Connie, came to almost every gathering he had, from his 2 ceremonies, to the post-graduation lunch, breakfast the next day, and then dinner and movie night the following night. In between that time, she even gave him a gift and a card-- something none of his other friends offered him. Sweet, right?

A little excessively sweet. So much so that I noticed it and asked him on our 2.5 hour drive home. My question was initially innocuous because I hadn't expected anything out of the ordinary. I simply said to him, "Wow, I hadn't known you and Connie were so close. She came to every event this weekend and even gave you a gift!" To which he replied that he sees her as one of his top 3 friends from grad school. I was actually a little surprised by that answer, considering I know exactly who Jay's top 2 friends are, and have also felt close to them over the last two years. One of them is a girl, so I had asked him before if anything romantic ever happened between them since they spend so much time together, including sleeping over on vacation trips in large group settings. It didn't feel out-of-the-ordinary to pose this question again, and rather than respond like he did last time (he said "oh, she's like a sister to me"), he actually said, "Yeah, actually I had a crush on her when I was with my last girlfriend."

Huh?
What?
Come again?

There were so many things wrong with this sentence.
1) Had a crush on her
2) While in your last relationship
3) Had a crush? Or still has a crush?
4) In the midst of a relationship? Any relationship? This relationship?

I pushed away the shock factor and tried to ask more questions.
Me: So, why didn't you get together with Connie after you and your ex-girlfriend broke up?
Jay: It just didn't happen
Me: Why didn't you pursue Connie by ending things with your girlfriend? Your relationship fizzled in the end, so why didn't you jump ship if you felt chemistry with Connie?
Jay: We had been together together for 7 years!

I actually flipped out when he responded to my second question. I actually regret how reactive I was because it was not necessary to be so defensive. I said to him that if he EVER thought the grass was greener on the other side, then get the fuck out this relationship because I would not want number-of-years-together (aka loyalty) to be the only reason he feels tied down by me

And then a hot tear barrelled out from one eye so I had to stop the questions because it was too mortifying to let him know how emotionally intense I was feeling.

In essence, the conversation ended because 1) Jay is too dull (versus sharp) to notice how distressful this information was to me, and 2) I did not know how to continue the conversation in a way that would a) be constructive to our relationship and b) where I would be true to my own feelings.

It's been 3 days since this conversation and I still feel conflicted inside. I have a million questions swirling in my brain, none of which I feel confident in asking. The conflict is this: with any question I am asking, whose purpose am I serving? Is it because I want to know certain things for my own curiosity? Or am I asking certain questions to advance our relationship? This is a major distinction because couples do not need to know all the details to one another for a relationship to thrive or even continue. But individuals want to know for their own curiosity, and that curiosity can actually kill a relationship sometimes.

What to do, what to do?