Dear Massimo, I’m Sorry

Gisele Sanchez

When I think of a Mr. Nice Guy, I am immediately inclined to picture the sweet-faced and somewhat ditsy second male lead from The Wedding Planner (2001), Massimo. When I—still under the age of ten and certainly unaware of the complexities of men and dating—was first introduced to Massimo I thought of him as nothing more than a nuisance. Clearly, I thought a little sourly at the time, Jennifer Lopez and the country guy (Matthew McConaughey) were going to end up together, so this poor man needed to just move on. But it’s been more than a decade since I’ve been introduced to him, and my thoughts have changed. I owe this man an apology. Not just because I feel for the guy, but because even my limited experience with men has clued me in on just how genuinely good, albeit incredibly fictional, he was.

Massimo was nice, too nice. When Mary, played by the stunning Jennifer Lopez, suddenly decides that she doesn’t want to marry Massimo, only moments before a priest is about to declare them husband and wife, all he has to say about it is: “I am not the one…I could never forgive myself if ever I got in the way of Mary’s true love.” Aside from Justin Chambers’ questionable Italian accent, which is really ambiguously European at best, the most unbelievable thing about this scene is how un-slighted he is. But that isn’t what I retrospectively appreciate about him—even I would need to throw a rock or something if I was led on and left for Matthew McConaughey the way he was—instead it’s more the fact that I, like Lopez’s character, didn’t appreciate his genuine kindness enough.

This isn’t me coming out as a Mr. Nice Guy sympathizer. Trust me, I am well aware of the consequences of falling into a “girls just don’t like me” trap. Self-proclaimed nice guys aren’t any better than an Andrew Tate podcast listener, who is often subtly misogynistic, awkwardly arrogant, and frustratingly aloof to these qualities. But, recently joining a dating app has me wondering if I am overly critical—the same way I once was toward Massimo—of men who are just trying to be nice. After all, there are perfectly good, outwardly misogynistic, and insufferable men that I could be complaining about instead.

In a lame attempt to start dating for the first time I created a Hinge account. A little bit tipsy off a couple glasses of sangria from Barcelona, not the Spanish city but a dimly lit wine bar in Brookline, and arrogant from the energy of being with my friends, I downloaded the app thinking to myself: how hard could it be? I perched my feet up on the couch, picked out a couple pictures I thought accurately portrayed my current self (because I am deathly afraid of being someone’s “they didn’t look like their pictures” story), and sent it off. While this wasn’t exactly baby’s first dating profile, I was still nervous. After all, Hinge’s claim to fame is that it provides “deeper connections,” but I questioned how far sharing my most irrational fear (bears, by the way) could get me in that respect. And, how do you explain that you don’t want to hook up with strangers, but also aren’t exactly thinking about marriage?

Hinge calls itself “the app that is meant to be deleted,” and I would say my experience has inclined me to agree with that statement, but probably for the wrong reasons. A few weeks have gone by and I fear the only things I’ve gotten are ghosted, twenty screenshots of interesting one-liners, and a newfound sense that I might be a part of the problem. There are some things men do on dating apps that are just blatantly strange. Like when Fabien, 21, responded to the prompt “you should leave a comment if” with “you wanna meet the best person ever.” I have no remorse for not giving things that objectively bad a second thought. But, then there's guys like Ben, 24, who responded to one of my pictures with: “You have the kind of eyes that poets write about.”

As much as I know this man meant well, more than well, my initial reaction was one full of contempt. Why would you say that? I immediately thought as I looked over my phone, a bag full of Trader Joe’s groceries balancing between my feet as I waited for the next C train. Something about being so casually scornful—as if there were nothing wrong with literally X-ing out a person’s existence from in front of me—makes me feel bad. And maybe it has something to do with women feeling like they owe men their time of day in exchange for the bare minimum, but I can’t help but feel like, in my case at least, things go a little bit deeper than that.

I often ask myself, maybe my friends are just trying to make me feel better by agreeing that this guy was coming on too strong? Maybe I am too jaded, too skeptical for all of this dating stuff to work out in the end. Maybe the real person I should be apologizing to isn’t Massimo (who isn’t real) or Ben (who can’t hear my thoughts), but myself, for making it impossible to be more open to new people.

I’m almost 100% sure now that dating apps aren’t for me, but a small part of me is afraid that the entire act of dating is something that I will never be able to embrace. When it comes to love, it might be time for me to return to the basics and start the process of figuring out where it is exactly that I fell out of step with everyone else emotionally. Which is what brings me back to Massimo, the first man I ever unfairly judged. While I’m sure the answer to my interpersonal problems probably lies buried deep somewhere in a therapy session, and it’ll take a lot of time and effort to find it, I owe it to myself to try.