I had lunch with Rob the day before he died, but a few weeks before that we had breakfast together at the Greek diner near his apartment. Just to refresh your memory, Rob was supposedly in deep shit with a loan shark and owed thousands of dollars, and I just couldn’t deal with the drama anymore. That’s when I decided it was finally time to “detach with love.” In retrospect, it was absolutely the worst timing of anything I’ve ever done in my life, a Homer Simpson “doh!” of monumental proportions.

For those of you who’ve been lucky enough never to have gone to an AA, Al-Anon or Families Anonymous meeting, the concept of “detaching with love” or “tough love” is pretty straightforward. It basically means that you (and by you I mean me) can’t keep saving someone (let’s call him “Rob”) from the consequences of his batshit-crazy actions and foolish decisions because every time you do (meaning me again), it only prevents the fuckin’ idiot from actually learning something from his ludicrous mistakes and prevents him from making any meaningful change that we (me, Caryn, Zach and everyone else who loved him) so desperately want to see the stupid asshole make.

I knew it was the right thing to do because everyone kept telling me it was the right thing to do. Caryn had been suggesting it for months. “Let go, let God,” she’d say, another popular expression you’ll hear in all those meetings that I hope you never have to go to. Julie, the therapist I specifically went to for help navigating the shoals of Rob, agreed, pointing out how he needed to develop coping skills and work the program. “It’s time he put on his big boy pants,” she liked to say. Maura adhered to a similar script, but she was also scared because she knew what was inside my heart, and how I had tried—unsuccessfully—to untether from Rob before.

“Detaching with love” is sort of counterintuitive. You have to watch the person you love run out into heavy traffic and just sit back while that person dodges and weaves as cars whiz by on all sides, and you have to just wait and wait and wait until one of the cars finally plows into the person you love more than anything in the world. And then you’ve done it. You’ve detached with love! Hooray! Don’t forget to send flowers to the hospital.

I just couldn’t do it. I told Maura and Caryn and Julie that I was trying, that I wasn’t going to see Rob every weekend, that I would no longer give him money, that I wouldn’t help him with the countless things I had always helped him with. I told them that they were further down the “tough love” road than I was, but I’d be catching up soon, and I wouldn’t let Rob continue to wreak havoc on our lives. But in my heart, I knew the truth.

It was always about my heart with Rob. My foolish fuckin’ heart. I knew detaching was the right thing to do. It all made perfect sense in my head. It always did. My head was never the problem. I knew bailing him out every time he was in trouble wasn’t the correct answer. If a friend had asked my advice about their child with a drinking or drug problem, I would’ve told them that they had to let their kid hit rock bottom in order for the kid to finally ask for help and want to turn his life around. I knew “What is tough love?” was the right answer to the Jeopardy question. What I didn’t know was that we were in Final Jeopardy and I had wagered everything.

Tough love just never felt right to me—and yes, I’m well aware that’s the way it’s supposed to feel, but I don’t care. And neither does my heart. I was tortured and continue to be tortured about it. If I had helped him the last time he needed help (I changed “asked for” to “needed” because he didn’t ask), he’d still be with us now.

I’m not saying that his life would’ve been any better and I’m not saying that Rob wouldn’t have eventually done what he did. Helping him wouldn’t have solved his larger problems with mental health, depression and addiction, I know that. I know that he was the only one who could have saved himself and he just didn’t want to be saved. I know, I know, I know.

I’m just saying that he’d still be here today. With all of his same fucked-up shit, making us all crazy and miserable, he’d still be here. And he’s not because of my terrible fuckin’ timing. Oh, sorry, I forgot to put it in the form of a question. What is Rob’s not here because of my terrible fuckin’ timing, Alex?