One of the most tantalizing tropes in pop culture concerns a young protagonist setting his or her sights on a companion much older than they are, and/or vice versa. “The Graduate,” “American Pie,” even the hit song “Stacey’s Mom” all celebrate the scandalous “age is but a number” scenario. And as we’ve learned in our culturally driven world, life often imitates art.

The topic of age gaps in relationships is often a vessel for controversy in society since there are multiple double standards and stigmas attached to the concept. If you’re a young man seeking an older woman, you’re considered a God among men; a young woman in this situation would be viewed in a less than flattering light. If you’re an older woman seeking a younger man, you’re considered a force to be reckoned with; an older man, on the other side of the coin, is viewed as creepy and desperate.

Despite this, we as humans just can’t seem to help ourselves when certain, ahem, opportunities arise. I admit, I myself am at fault. And with the abrupt beginning and even more abrupt end of my casual relationship with an older guy, I learned that age gaps and hookups are not exactly what you see in the movies.

The conversation went something like this:

“I’m into you. Let’s go to my room.”

“You’re drunk.”

“Is it because of my age?”

“What? No, you’re only a couple of years older than me.”

“Alyssa, how old do you think I am?”

“Twenty-four?”

“…I’m thirty years old.”

“…Oh…” Let the record show that I was born in 1995. You do the math.

I pondered into the wee hours of the morning how this would end if I accepted his offer, and at the time didn’t foresee anything too terrible, so I went for it – attention from boys is my kryptonite.

Let the record show that we didn’t have sex, because you know what happens when you assume. In between the sheets and drunkenness he told me to keep him a secret “for now,” as to not ruin his reputation at our workplace. And, of course, I agreed since I was a long-term employee hooking up with an intern —technically not frowned upon, but juicy gossip nonetheless.

The next morning I took my first-ever walk of shame, filled with a sugary sort of regret, shocked and awed at myself, happily embarrassed by the whole thing. Had I really just done that? What was I thinking? And most importantly: did I want to do it again?

The days to follow were filled with multiple text messages from my lack-of-a-better-handle Sugar Daddy, which made me simultaneously blush and wince. Being lusted after was a very rare occurrence in my love life, yet I couldn’t shake the decade between us.

On a more sober occasion we hung out in his room, dishing small talk and obsessing over the S’mores Oreos and Billy Joel, and out of nowhere he goes in for a kiss, at which I protest, the reason being, “I’m not so sure about this.”

“Well we can focus on being really awesome friends then,” he says. And before I decide to completely break it off right then and there I get greedy, and ask “what is it about me?” He gives me this grocery list of qualities that reeled him in, the most interesting one being “forward,” a word I’m all too familiar with.

But from Sugar Daddy “forward” seemed more sincere for some reason, considering he coupled it with “you know what you want” rather than “whom you want.” One of the benefits of shooting for the older fish in the barrel is that they aren’t threatened by ambitious women like some younger guys are. So we saw each other a couple of times after that, keeping quiet and sneaking around — I loved that part; the adrenaline was too sensational to remember that he was born in 1985.

But I noticed he was needy, wanted what I couldn’t give him so not to stray outside my comfort zone. And he noticed I wouldn’t put out, and strung me along for two weeks because of it. I realized during those lackluster weeks of our affair that he had given up trying to get me to bed, but hadn’t exactly communicated this information to yours truly.

This left me questioning and guessing his intentions, a feeling no relationship should entail. Although we were both clear with each other about what was going on in the bedroom, we talked little about what concerned us emotionally. Which brings us to our next tip for those adventurous lovers attempting to jump the age gap: always make sure you know what you want.

So how did it end? Rumors. All good salacious relations end that way, don’t they? Apparently I told one of our co-workers that we had sex (let the record show that those words never left my mouth), and when it got back to him, he didn’t exactly deny that we were seeing each other (like he should have per his previous request of me). Rather, he insisted to everyone who asked that I had made the whole thing up, and proceeded to ignore me at our workplace.

That’s why age really doesn’t matter, kids. Some men never really grow up, no matter how old they actually are. All I can say is tread carefully, be true in your intentions, and remember, life, as surprising and serendipitous as it may be, is no Simon and Garfunkel song.