Here’s Why Dating 4 Guys At The Same Time Is Actually Not Worth Your While

Shutterstock / andrey_l
Shutterstock / andrey_l

A wise woman once told me that until I was older and ready to get super serious, I should always be dating at least three guys at a time, the ‘triad’ if you would. The logic behind this golden rule being that if one or more of them were on a man-period or acting like a little bitch, there was always the one lesser annoying guy for you to spend the night with. Being about 20 years old at the time I figured, why not; men do it all the time. Ladies is pimps too; please excuse me while I spend the next seven years going and brushing my shoulders off.

The danger in this strategy is that you become blissfully numb in all of your relationships with the opposite sex. You are now essentially the emotionally detached dude that all of your female friends spend countless hours crying over, and when they inquire as to if you think he’s ‘only looking for sex’ from them, you awkwardly scrunch your nose and recognize that this scenario sounds all too familiar.

After the inevitable demise of an emotionally draining relationship with a blatant narcissist when I first moved to San Diego, I decided it was time to re-initiate the ‘doing whatever the fuck I want’ sequence that I’d mastered so well in college. Only this time, after months of entertaining awkward Tinder message chains with obvious perverts and convincing countless unsuspecting men at bars to spend their pretty pennies on my newly escalated drinking vice, I found myself dating four different men at the same time. “Why on earth was I wasting so much time in relationships?’ I thought. ‘I’m livin’ the good life now!’

Allow me to introduce the characters in the deliciously hilarious Rom-Com that soon became my life.

Chapter 1: The Era of the Handjob – A Tale of an Emotionally Unstable Navy Seal

Prior to officially dating one of my previous exes, I had regular sexual appointments with a slightly younger member of the military, whom we shall call Panda.

When I met Panda, he was quite easily the most attractive member of the male species I had ever seen stark naked. He used to prance around my apartment holding a fake rifle reenacting sniper scenarios and hanging my blouses off his permanent boner. This allowed me to forgive him for the fact that he was only capable of reading at a first grade level, and had many of the characteristics of a stereotypical meathead douchebag. He did, however, buy me a dozen long-stem roses every time he took me on a date, opened every single door, and never let me carry a thing. But by three months into our fre-lationship, he was convinced that he was in love with me. This likely stemmed from either the fact that I’m fantastic in bed, or that like many other military men, he likes to throw around the word “love” like he’s throwing beads off a Mardi Gras float in New Orleans.

Eventually he deployed for long enough for me to forget about the obvious intellectual differences between us, but never long enough for me to forget the fact that he used to incessantly beg me for overly lubricated handjobs. This is fun for no one, gentlemen. You give yourself a handjob; that’s your job. Women should not be expected to rapid-pace jerk you off past the age of 16. But I digress. This two year era of on again off again performances inevitably ended after my conscience finally felt truly terrible for allowing a human being to obsess over me for so long without any reciprocal feelings surfacing on my end. I felt awful initially, until one day he started calling and texting me so persistently at work that I was forced to block his number, and then after he tried to break into my apartment at 230am that same night, I had to call the police. A shame that it came to that, really.

If you’re reading this, Panda, I want to say thank you for the air conditioner, and also for the arthritis in my left wrist.

Chapter 2: The Silver Fox – An Era of Awkward Dirty Talk

If you haven’t yet dated a significantly older man, I definitely recommend it. Typically they have their lives in order, which may not seem like a huge deal depending on what you’re looking for, but speaks volumes when you compare romantic dinner dates at beautiful restaurants to 2am Taco Surf followed by a pit stop at 7-11 to pick up condoms and a Gatorade.

I met the Silver Fox at a nightclub in downtown San Diego when he was visiting back when I first moved here, and kept up with the small talk on holidays and birthdays for the next couple years. When I became single again, we starting talking more regularly, and eventually he flew out to San Diego to visit me for a long weekend. I was terrified. Usually I spend no more than a few hours with my victims at a time. This was either going to go really well, or really, really horribly. In reality, it went somewhere in the middle.

Through this experience I learned that even if all you desire out of a person is sexual intercourse, it’s still nice when they actually earn it by spoiling you to an extent, and by treating you with respect. Not all of your fuck-buddies need to be hot assholes, but realistically, most of them will be. During that particular weekend I pinpointed two major incompatibilities between the Silver Fox and I. For one, men of this age understandably want to talk about what kind of family you foresee yourself having someday, because they are at a place where they are preparing for things like that, whereas you are likely still struggling with the drink menu to determine what kind of cocktail you want to order next. You guys likely won’t be on the same page, or even reading the same novel.

The other issue was the excessive use of violent dirty talk, which is not an age-related behavior as far as I know, but certainly worth mentioning. Sex is supposed to be hot and kinky and fun, but not to the extent that it sounds like we’re reenacting a Lifetime movie rape scene. I’m not sure I am the “Dirty, dirty little bitch” you speak of as you whisper angrily in my ear, but if you insist. I learned to strategically encourage sex to take place only from behind so I could mask my wildly inappropriate laughter in a pillowcase.

Although his body was cut, he was also one of the most petite men I’d ever slept with, and despite his salt and pepper hair, the ease with which I was able to straddle his waist gave me illusions of pedophilia and made me very uncomfortable. We still touched base daily after this weekend, and the next time we hung out was after he booked me a flight home to New York to see my family at a time when I was having vehicle-induced financial problems. The trouble was that when I got there, the prioritization of my time included very little of him. He talked way too much, and with an inability or lack of desire to pick up on my non-verbal cues, could put me to sleep faster than two Ambien and a stiff Jack n’ Ginger. Things pretty much faded off after that, and I convinced myself that abruptly cutting off all communication without any explanation was the most mature way of letting the situation die of natural causes.

What I realize I did learn from dating this person was that a put-together, motivated and grown ass man (but preferably with bigger bone structure) is attractive, and that sometimes it’s nice to hear from someone regularly, a “Good morning,” and “Good night.”

Chapter 3: The ‘Not Old Enough for Wine’ Waiter – The Era of the Uber-Home-of-Shame

One Sunday Funday after diving balls deep into an unlimited mimosa brunch to nurse a very severe hangover, I found myself bouncing all over downtown San Diego only to eventually land in a Greek Café. Our server was a friendly, dark, young man with delicious arms and a tiny gap-tooth I immediately foresaw myself plugging with my vagina. He was attentively checking me out, but not to the point that it distracted from our service, and I decided immediately that this was as good of a time as ever to make him the first-ever fourth member of what had previously always been a triad of dudes. He told me he was 26, older than I’d expected, so I decided to get his number.

For privacy purposes, we will call him Meze.

Meze and I drank a lot together. In fact, our first few encounters I remember very little of. After spending a few nights at his house, as I never let people know where I reside until after several meet-ups, I began to notice a trend. Meze never offered me a ride home in the morning. I used to sloppily throw my clothes back on come sun-up and lay in a grassy knoll in his neighbors front lawn waiting for either a loyal friend to pick me up, or for my soon to be known as ‘Uber-of-shame’ to arrive and take me home for a mere $7.42.

I wondered why such a seemingly nice guy wouldn’t have the decency to drive a girl home in the morning, especially after she’d put out. Nonetheless, I enjoyed his company and his arms enough to put it out of my mind.

On a later Sunday Funday we were out together with both of our groups of friends and he happened to pull out his license in front of us, which read very clearly 1992 as his birth year. This little shit wasn’t 26 at all! 1992? I’m not a mathematician, but doesn’t that make him 14? 15 tops? I was briefly traumatized.

We also found out this same afternoon that the reason he never offered me a ride home was simply because he didn’t have a car. My friends and I reluctantly agreed to see past these facts as we enjoyed his outgoing personality, but I knew eventually age would start to matter. He called me at 3am a lot after he was getting off work downtown. He’d always claim to be sober, but when he’d come over he’d smell like an Asian sweatshop and I’d have 6 pending Snapchats of him ripping shots at the club right before he came over. I proceeded to give him the benefit of the doubt until one day he actually fell sound asleep while I was giving him a pretty decent blowjob. No wonder it was taking so long!

Soon after, he got a DUI, which sounds impossible for someone without a vehicle, but clearly is not, and I also got sick of not going on all the awesome dates he liked to promise me he’d take me on but realistically couldn’t afford. Eventually I realized all the lost sleep and late-night voicemails asking to come over were not necessarily worth the semi-regular but barely mediocre penetration. Sadly, good looks can’t reach my G-spot. What I’d like to thank Meze for is inspiring this game my friends and I have patented entitled “If he doesn’t have a car, how’s he gonna get here?” And then we go on to list an assortment of hilarious and improbable modes of transportation for example, magic carpet, camelback, roller skates, hot air balloon, and teleportation. It’s totally fun; feel free to try it out.

Chapter 4: The Gentle Giant – The Era of Sarcastic, Witty Banter but a Mystery Penis

Call me old fashioned, but I often like to see the “goods” early on so I know what exactly I’m working with. If I spend more than a few occurrences with an attractive member of the opposite sex and we haven’t yet found ourselves naked, I assume we are “bro-ing out,” 1/2 of the situation is a homosexual, or I’ve completely lost my lady mojo.

A group of my friends and I were out this past February to celebrate “Single’s Awareness Day.” I’ll be the first to admit that I was dressed like a baby prostitute. I drank enough hard alcohol to get the entire starting offensive line of the 49’ers wasted, and therefore blacked out very early on in the evening.

At some point, a tall white guy came up to talk to me, whom I later found out I had verbally assaulted for a great deal of time before he asked for my number against his own better judgment. From my vague drunken memories of him, he was around 8’6” and was wearing a black button-down shirt, and what I remember of our conversation, was…not a Goddamn thing. This has happened to me before on occasion, especially within the past year or two. I’ll get texts from guys following a night of excessive drinking that include things like, ‘hey, thanks for that advice about my grandma’s emphysema, I’ll definitely have her try humidified oxygen!’ or ‘let’s meet up sometime for one of those teriyaki chicken salads we talked about last night.’ I don’t even like lettuce! If these people can punctuate decently and don’t seem super fucking annoying right off the bat, I tend to trust my drunk self enough to let them take me on a date.

The most awkward part of these meet-ups is that I often repeat myself multiple times related to the fact that I remember none of the truths or lies that I’d conjured up on the night we met. The gentle giant and I went on five months worth of dates without laying a hand on each other; something positively unheard of in my little world. He was funny and nice, but texted me very sporadically, which hardly mattered since my inbox was constantly cluttered with messages from my three other dingleberry boyfriends. But as they slowly started weeding themselves out of the picture, the small, but existent attention-seeking/girly lobe of my brain now required more from this particular guy. To cut a long story short, the biggest reason why we hadn’t yet been intimate was because I was acting noticeably awkward and was extremely uncomfortable showing interest in a man who I actually liked, and who genuinely wanted to get to know me before sleeping with me.

The beauty and the beast about superficial sexual relationships, is that people know as little or as much about you as you want them to. And when you have multiple guys in the picture, the weaknesses of some are balanced out by the strengths of the others, so combined you have essentially created the perfect man. Except for not at all, you crazy moron, because in reality, none of those idiots are right for you! After eliminating the distractions aka the rest of the triad, I was able to invest my time overcoming my severe fear of letting my guard down around someone that might, heaven forbid, actually be worthy of my time. The gentle giant is a hot dork with a great dick that laughs at all my jokes and treats me like a queen. He is the last and only man standing, and I wouldn’t have it any other way.

What this promiscuous last year has taught me, and what the take-home for you all should be, is that men that aren’t desperate to shove their junk in your face within five minutes of meeting you are an alien minority. A true gentleman makes us uncomfortable because we’ve likely never seen one in real life before, much like a bald eagle, or a duck-billed platypus circa right before they went extinct, or whatever. Cut me some slack, I’m not a fucking Zoologist. We have been conditioned to keep our expectations low, our guards up high, and to depersonalize sexual intercourse to make this whole dating game easier on our egos, hearts, and private parts. But in order to ever really be completely fulfilled sexually or romantically, we need to be willing to get a little vulnerable. Because when you wait to have sex, the anticipation is deadly good, and when you have sex with someone you actually care about, it makes the experience a whole fuck of a lot better too.

If the man milk I’m currently drinking were to go sour, as it very well might, I’d recover eventually. Heck, I might even work on recruiting a new triad, simply for the entertainment value. But from here on out I will force myself to remember that I have to be willing to take some risks with my heart in order to achieve the real rewards I never knew I wanted all along. Four ‘heads’ (dick joke, ha ha) are not necessarily better than one. Thought Catalog Logo Mark

More From Thought Catalog