Should I confess my feelings … again?

Dear Meredith,

I met "Jason" about three years ago through a friend of his that I was seeing. I ended up introducing him to one of my girlfriends and they started seeing each other. Both relationships ended after about two months but Jason and I continued being friends. We spend that whole summer talking every day and hanging out. Occasionally we'd spend the night sleeping next to each other, platonic and innocent for the most part. He ended up confessing that he had feelings for me, which deep down I kind of knew, but I didn't do anything about it or own up to my feelings for him because I felt guilty (my girlfriend was still bitter about their casual relationship ending).

At the end of the summer, Jason and I had a huge falling out over a complicated situation between our two groups of friends getting into a physical fight during which the police got involved. We didn't really blame each other but decided it would be easier to put some distance between us. We ended up not seeing each other for two years and only speaking very rarely.

About a year ago I realized he was still on my mind a lot and decided to test the waters about reconnecting. He was apprehensive about it, and would often agree and then change his mind. About three months ago we finally met up for drinks and had a great conversation. We talked for about three hours, just catching up. We even joked about how stupid all the drama was surrounding our friends. I was really hoping something would come from that, but he texted me a few days later saying he couldn't start anything between us and wasn't looking for anything serious. I was pretty bummed and confused but tried to move on with no hard feelings.

About a week ago, he was still on my mind a lot, and after a few too many drinks I texted him. He agreed to meet up and we talked again, this time less catching up and more about our feelings for each other. I told him that in three years I never met anyone that I felt that strongly about, and he said that although he was aware of something special between us, he's been in relationships since he was 15 and is not looking for that right now. We ended up staying up all night talking and spent the next night together as well. I was walking on clouds and thought that finally, after three years of bad timing, fights, and wishful thinking, something was finally happening between us.

Since then I've texted him twice and received nothing but a lukewarm response that he's busy. I thought I'd made it clear that I didn't want to push him into a relationship and just enjoyed his company like I always have. What bothers me the most is what could've been, and what I at least think could still be. Should I try once more, being as blunt as possible about my feelings for him, or should I let this one go and after three years try and move on for good? Does the fact that I waited for him and couldn't forget about him for two years mean anything at all?

– Bummed Out in Boston

It sounds like you've been pretty blunt about your feelings, BOIB. You've reached out multiple times. You've told him that you're drawn to him. You've sent texts. You've tried to make plans. His response? "Lukewarm," you say.

This is about unrequited affection as opposed to legit connection. He's one big "what if," and you've written up your own fictional happy ending. Isn't it possible, though, that a relationship with Jason would end with a fizzle just like it did with your friend? And really, if there's such an intense connection between the two of you, why didn't he reach out during the last few years?

Let this one go. No more waiting and pining for Jason. He says he's not looking for a relationship. Meanwhile, it's clear that you want much more than his casual company. At the very least, you want him to be excited to see you, and he can't even get it together to be consistent about that. It's time to find someone who wants to seize the opportunity to spend time with you. That's the point.
Readers? What's up with Jason? Does she need to give another blunt confession? Does he understand where she's coming from? What's happening here? Discuss.

– Meredith