In the beginning of our friendship, Seamus and I started having brunches and games nights with Tim and his then-girlfriend, and Tim and I hit it off right away. The first time Tim and I hung out on our own, we talked for hours, wandered around our city, perused comic books and ate fancy grilled cheese. We became fast friends and I had a fleeting thought that he was perfect for me, but I knew he had a girlfriend. Shortly after Seamus and I started sleeping together, Tim and his girlfriend broke up.
Since then, Seamus and I stopped seeing each/sleeping together/whatever we were doing. My feelings changed, or his did, or maybe they both did. I wanted more, he started pushing me away, and, in the distance, I realized how poorly-matched we really are. We remain friends; we both love our community and have fun hanging out within it, with the occasional coffee here and there.
About two months ago, Tim started dating someone new. It was fast and intense, and Seamus and I watched with our eyebrows just a little raised. Tim says he fell for her right away, but he has explained to me that he feels a little stuck. He doesn’t know what to do now, he says. It all happened so fast, and now he doesn’t know where to go from here. It has been clear from the very beginning that Tim has had feelings for me. Before Seamus and I ever became a thing, Seamus told me that, if it ever became relevant, he would be uncomfortable with Tim and me dating. I know he has told Tim the same thing. I also know that this still holds true. However, it has now become an obstacle.
Since I am no longer with Seamus, Tim has become more vocal about his feelings for me, feelings he apparently still has. We have always had a little bit of a flirty banter going on but, at least on my end, it has never had true sincerity behind it. Now, though, I think back to how he’s always treated me. I think back to that first time we hung out, which, in hindsight, looks like a date. I think about how much I’ve grown to care about this man and I realize I care about him more than the friend I’ve always called him.
This is not simple. I know Tim cares about his girlfriend, and I know he is happy with her, although he has told me that he knows he could be happier. I know that, against all logic, Seamus still feels possessive of me. I know this has “drama” written all over it. But I can’t let it go. I know you’re going to say I should. I know I should. It’s not like I’m going to put my romantic life on hold for a man who is currently unavailable, and nothing has or will happen between us so long as he remains unavailable. But, if he became single and Seamus got over himself, I don’t see what else would hold us back.
I can’t stop thinking about it. I feel guilty for even considering it. Maybe I’ve answered my own question. I’m not even sure what my question is. What do you think? — Double Trouble
What I think is that Tim has much, much more to risk by dating you and disappointing/hurting Seamus than you do. You might lose an acquaintance you have occasional coffee with. Maybe things would be awkward in your mutual community and you might be forced to find a new group to hang out with. Big deal. Tim, on the other hand, would risk losing his best friend. If that were a risk he was really willing to take — if his feelings for you were strong enough to potentially throw away his friendship with Seamus — he probably would have pursued you in the window of time between you ending your fling with Seamus and Tim starting a relationship with his new girlfriend.
Sure, you could argue that the risk might be worth taking for Tim if he had confirmation from you that his advances would be welcome. Maybe if HE didn’t have to be the pursuer, the risk of losing Seamus’ friendship would be even easier to take. But I still say that if Tim felt strongly enough for you, he would have figured out a way by now to act on those feelings. I also think that, if you were to pursue him, either now while he’s with his girlfriend or in the future if they break up, and he was receptive, there’s a good chance he would resent you if being with you cost him his closest friendship.
I’d recommend you hold off on doing anything. Let nature take its course. If things don’t work out between Tim and his current girlfriend and you’re still single and enough time has passed since your FWB situation with Seamus, then maybe the current will pull you two together without much effort on your part. But if it doesn’t go that way, just let it be. There are enough men out there that you don’t have to pursue someone who is unavailable to you in multiple ways, however perfect you might think he is for you.
If you have a relationship/dating question I can help answer, you can send me your letters at email@example.com.