5 Dating Truths I Learned By Seeing 5 Different Guys In 5 Days

by Sean Abrams
TLA Releasing

During my continuous efforts on Tinder, Hinge, Bumble and essentially every other dating app known to man, I found myself coming off a bit overeager all summer long.

As my notifications boiled over with each continued match, I kept a list of my potential suitors. And before I knew it, I had five dates scheduled back to back to back from Tuesday night to late Saturday afternoon.

But I began to question my motives and wondered if I was truly up for this challenge ahead of me.

Was I the type to talk to so many people, agree to so many hormone-induced encounters, that I was afraid I'd end up confusing their names?

Absolutely not. But that's exactly why I was so excited.

My friends questioned my dating decisions, but never discouraged me from living my life. In fact, they were impressed with my stamina and overall confidence in this ferocious, fast-paced city.

“Who's that one, again? Ray? Oh, tonight is with the guy who's in a frat,” they would guess. Typically, they were never on the right track, but to be honest, I don't blame them for failing to keep up.

In the midst of a long work week and a heavy dance schedule, I barely understood how I managed to pencil in small talk and light bites with a bunch of random strangers.

Was it because of my lust for a boyfriend? I wouldn't say that. Was I craving a random hookup and some quality comfort? Sure, but who isn't? And with the idea of a potential free drink floating in the back of my mind, can you blame me?

I'm certainly no scientific expert, but my experiences and efforts with the following five gentlemen might teach you a thing or two about how to navigate the jagged path we know as dating.

Let's just say I went on this journey without a map... and I sort of wish I had one.

Let's just say I went on this journey without a map... and I sort of wish I had one.

Below, you'll find some valuable life lessons that I was able to gather from going on five dates in five days.

Date 1: A handshake is never, ever a good sign.

I was already hesitant about getting drinks on the sweltering Tuesday night, when all I really wanted to do was lie naked in front of my air conditioner — alone.

I went out on a limb, and despite mediocre conversation via Tinder and texts, I still set up a time and a place. I'm a firm believer in meeting up relatively fast because online conversation always seems to find a place to keel over and die.

And well, if you are in the midst of an in-person date, and you find yourself talking about the weather, pull the cord and jump out of that plane as soon as possible.

I wasn't lucky enough to get the chance, though.

The entire counter was dry with no real spark off the bat. I chugged my beer, hoping he would catch on to my forceful subtleness.

Instead, he took that as a sign to order a second round, and I was out $16, which could've been put toward a quality Seamless order.

As we exited the bar (and by exited, I mean briskly ran because I wanted to GTFO as soon as possible), we awkwardly locked eyes, unsure of each other's respective next move.

He finally went in for the hug... and I stuck out my arm for the handshake. Have a great night! See you never.

Date 2: You're allowed to be horny at 1 pm on a Wednesday.

After setting up my next encounter for a Wednesday afternoon, I wasn't exactly sure what to make of it.

While I certainly have no issue taking a guy home on the first date, at least for a solid make-out session, do these same rules still apply when brunch is being served?

You're damn right they do.

Our conversation held up nicely, the food was enjoyable and my date, who was on a long break between grad school classes, still had some time to kill.

Before I knew it, we were back at my apartment, going at it on my bed before I was even able to remove my shoes.

I kept getting the vibe that sex was an option in the moment, but on top of trying not to be a dirty slut over the next couple days, other thoughts crossed my mind. Could there actually be something there, aside from general interest in each other's erections?

Ultimately, I resisted the temptation, accepted the terrible case of blue balls I'd have later and kissed him goodbye for what I didn't know was the last time.

A few days of texting turned into absolutely nothing, and with that, I was onto the next one.

Date 3: Don't hate yourself if you can't keep your eyes open. 

By mid-week, I was running on fumes.

My dance schedule was cruel, forcing me to remember hours of choreography several days a week, and I yearned to spend whatever free time I had with my face buried under a pillow.

Everyone's allowed to be lazy once in a while, right?

This next date had been a few weeks in the making, and while I was genuinely excited to meet him, I just couldn't bring myself to travel from my apartment to the city. Everyone's allowed to be lazy once in a while, right?

So, I cancelled.

Though he originally seemed to understand (I sent the text from under my covers, claiming I was swamped with work), several failed attempts to reschedule led to me being ghosted.

Usually, I'd wallow in self pity for a day or two, wondering what I did wrong or if I'd ever find love again. But this time, it was different.

I let it ride off my back and appreciated my extra "me" time.

Besides, I had two more dates to go.

Date 4: If you never actually establish it's a date, then it's not a date.

I take most forms of conversation as you trying to get deep in my pants, so when my compliment to a fellow writer via Tinder turned into some back-and-forth DM-sliding, I assumed he was as thirsty as I was.

He was not like anyone I'd ever shown interest in before, mainly because he resided in Boston, had a few oddly-placed piercings and was in the midst of dating a man who was married to a woman, aka polyamorous.

When he announced he'd be visiting New York soon (for a leather fetish event, no less), I took no time in setting up yet another brunch date. The first one worked out decently, so why not dust myself off and try again? If he showed up in some assless chaps, I was golden.

When my compliment turned into some back-and-forth DM-sliding, I assumed he was as thirsty as I was.

As we met, I realized he towered over me, which was an immediate turn-on. And I found myself OK with the hit-it-and-quit-it mentality, at least for this one day.

I deserved to have a little fun, and I was ready to climb him like a tree.

But unfortunately, "fun" didn't end up happening.

Sure, I cleared my eggs Benedict off the plate, but I found myself unsure if either of us was ever going to a make a move.

After we returned to my place and I sprawled out on my couch in my most seductive of poses, he got up to use the bathroom.

I assumed it was to pee, you know, to empty his bladder before he ferociously ripped off my jeans... but nope. Instead, he exited nonchalantly about 15 minutes later, with a fowl smell creeping out after him.

Did this dude come over just to take a shit in my bathroom?

Did this dude come over just to take a shit in my bathroom?

He hugged me goodbye, told me to hit him up next time I'm in Boston (which is, you know, just about zero percent of the time) and headed to his car.

By that point, I had all my eggs left in one testosterone-filled basket.

Date 5: When the date hits hour six, you might as well get married.

You'd have thought my brain — and balls — would be spent from keeping track of the names of all these dates. But to be honest, I had a good feeling this final date would be epic.

He agreed to meet me near a friend's birthday party on the Upper West Side, so I was thankful for being able to dose up on a little liquid courage before our dinner.

Once we met face-to-face, I concluded he would most definitely be called in to a precinct for a line-up if Ryan Reynolds ever got arrested.

In other words, he was absolutely gorgeous.

The night had barely begun by the time we finished throwing back a couple of meatball sliders, and since we were conveniently located near Central Park, we went for a stroll.

Can't get more romantic than that, can ya?

We walked so much, it felt like my feet were bleeding, but the time spent with him was worth it.

With no real reason to split (he didn't have plans until late that night), we made a full circle back to a local bar in the area, where my friend's party had just conveniently shifted to.

In most instances, I would NEVER introduce a date to my friends this early, let alone while we were still on the date. But at the time, I didn't care.

I was eager for a surprise bout of rain to start pouring down, like a gay version of 'The Notebook.'"

In that moment, he was pretty much everything, and I wanted my friends to see that (even if they were blackout at the time).

And by the time he had to leave, I really wished he didn't.

Though out of my way, I walked him to the subway, eager for a surprise bout of rain to start pouring down, like a gay version of "The Notebook."

While the air stayed dry, you can bet he leaned in for a kiss before making his way underground, and I went home swooning like things had finally worked in my favor for once.

Now, I will disclose this: He's not my boyfriend, we're no longer hooking up and I've stopped looking for a nice house for us in the suburbs. But do I regret any part of my time with him? Absolutely not.

Experience is everything. Plus, everyone deserves to date someone like Ryan Reynolds at least once in their lifetime.

Now, would I buy another ticket to this rollercoaster-esque dating adventure I took myself on?


In no other instance do I think I'd have experienced such men from all different walks of life. Though none of them exactly turned out to be boyfriend material, I learned from this that the only way to keep yourself from drowning in self pity is to laugh it off — and just make the best of a truly bad date.