Five Four Dressed Me For Three Tinder Dates & I Took Girls On The Lamest Dates Ever To See If They’re Keepers

It’s been a year and a half since I went on my first Tinder date in New York City. I wore my favorite striped-shirt, my tightest pair of boxer briefs and not one thread of Five Four garb on my body. Before the date, I took three shots of Tito’s vodka with my roommates, grabbed a 5-hour energy and a pack of gum, and, in an attempt to silence the fluttering butterflies in my stomach, I told myself I was a “Sex God” in my bathroom mirror. Audibly. That is the first time I’ve admitted that to anyone. And the last. That confession will likely spark a group text between all my exes commiserating over how objectively false that claim is. Just let me have this, girls.

My date’s name was Brittany. She looked like the store brand version of her Tinder pictures, which was initially a bit disappointing until I contextualized the lie I was selling:

She’s probably seen police sketches more closely resemble reality.  The poor thing was expecting a Coach bag and got a Douchebag. Sad.

Upon arrival, we went through that whole charade where we ask the standard questions strangers ask to each other:  “Do you like your job? Have any brothers or sisters? You into butt stuff?” A year and a half later, I can only remember the answer to one of those questions. I’ll let you finger out which one.

Once we settled in, I realized Brittany was way more attractive than I initially gave her credit for. I was positive she was going to make some other guy very happy one day.  But, I was fresh off a breakup and there wasn’t one day I woke up when I wasn’t stressed out about my ex beating me to rebound sex.

I had fun. She had fun. We had agreed to see each other again.

That was the last time I saw Brittany.

Since then, I’ve been on no less than 50 Tinder dates—all races, shapes and sizes, some with an Adam’s Apple, most without. I’ve spent thousands of dollars and have successfully fought off countless farts. Some girls I’ve maintained extended flings with and some I wouldn’t recognize if they showed up to my birthday party with a name tag. I’ve had lots of sex (fist bump me, bro) and learned a lot about what I’m looking for in someone.

But, I’m 29, and believe it or not, writing ‘N/A’ in the +1 section of your friends’ wedding invitations takes a toll on the psyche. Tinder has been a hell of a wing man, but ultimately I’m still spending my Valentine’s Days on PornHub and still trying to convince my grandfather I’m not gay.

Plus, there’s only so much emotionless sex and obligatory cuddling a man can take before the routine loses its luster. The Webster’s Dictionary definition of insanity is swiping right over and over and expecting a different result, so I have made the decision to delete the app to challenge myself to meet people organically and also because I need to make room for the new iOS update.

BUT, like any addict, it’s not always healthy to go clean turkey. So I’ve allowed myself to go on three final Tinder dates before I delete the app forever. Or until next week when I’m bored and thirsty.

I wanted to make these dates more memorable than the last 51, so I decided to bring in the fine folks over at LA-based brand, Five Four. For those unfamiliar, Five Four is a membership-based clothing company who sends its members individually curated clothes monthly based on their style preference and the current season. It has been a godsend for people like me who hate shopping and want to look cool but just don’t know how. Not to play salesman here but if you got an extra $60 a month and want to have grown-up clothes sent directly to your door, I’ve found no better option. BUT, you can get your first month for only $30 using the code BROBIBLE at checkout. Don’t say I never did nothin’ for ya.

So Five Four agreed to dress me in some fresh threads for the three dates, replacing my And 1 t-shirts and JNCO cargo shorts with some grown-up threads that give off the illusion that I have my shit together.

I didn’t want the final three dates of my Tinder career to be the standard “get drinks at an overpriced bar until inhibitions are lowered enough for me to confidently make a move.” I’ve adopted the mantra “If you can’t appreciate me in the worst of situations, you don’t deserve me at a speakeasy bar bankrolling your drinks.”  That’s why I decided to take the girls on the lamest dates imaginable. It’s the only way to decipher what they’re truly made of.

Here are my findings.

DATE 1: Olive Garden – Times Square

Times Square is like Two Girls, One Cup—once you’ve seen it once, you’re good for life. New Yorkers even avoid passing through that cesspool of humanity like we avoid the dude with the cold sore in the blunt circle. If you can make it out of there without suffering from a panic attack or stepping in a homeless man’s doo doo, you’re in the minority. It is the DMV of New York City and I wouldn’t wish it on my worst enemy.

Out of the estimated 8,000 restaurants in New York City, Olive Garden was the easy choice. It is the tuxedo t-shirt of Italian dining. If this girl can shelve her pride and fully immerse herself in some stale breadsticks and artery-clogging pasta dishes, she’s a ride-or-die chick. And that’s something you can’t find out from a night out at Ruth Chris.

 The Girl: A 26-year-old marketing associate who is a self-proclaimed BroBible reader. This is important because if she knows I’m a degenerate off the bat, she won’t be disappointed later.

I hit her with the ‘Super Like,’ which is a thirsty move but is the online equivalent of handing a girl a rose. It’s like swiping with dynamite.

The Outfit: Five Four blue button-down with dark jeans. I’ve spent most of my adult life searching high and low for jeans that fit properly, to no avail. I’m convinced jeans change sizes immediately after your try them on in the store. Either that or I’m getting fatter minute-to-minute. The fact that the ones that fit perfectly showed up on my doorstep before I even tried them on is proof that working hard for what you want is overrated.

The Opening Tinder Line:  “Are we in love?” This line gets a response 100% of the time, 60% 18% of the time.

Date Highlight: I told my date I had to use the restroom, which made complete sense since I just polished off an entire plate of Fettuccine Alfredo. Instead, I found our waiter and told him it was our anniversary and to throw me a solid. Five minutes later, he shows up with a black tie mousse cake and says “Thank you for spending your anniversary with us.” I met her 34 minutes prior. This is my date blushing and probably fighting off the urge to drop her pants right then and there. Power moves only.

Date Lowlight: The Olive Garden is a sneaky shakedown. I’ve spent less money on the suit I wore to my grandfather’s funeral. I may need to start a GoFundMe to pay for rent this month.

Overall Date Grade: B+

My date proved to be a trooper, handling the atmosphere quite well. She did check her phone far too often at the beginning of the night and even muttered the phrase “I can’t believe I’m at an Olive Garden right now,” which I found to be rude. But to her credit, she started to warm up to the place after her fourth glass of wine and turned out to be a cool chick.

Although I learned that sex is physically impossible after eating three plates of Olive Garden, I also learned that you can score a free dessert from any restaurant in America by claiming it’s your anniversary.

Second Date Odds: 70%

Thinking Applebee’s for my encore date with this one.



 DATE 2: The New York Transit Museum 

The New York Transit Museum, believe it or not, is as boring as it sounds. The museum displays historical artifacts of the New York City Subway, bus, commuter rail, and bridge and tunnel systems under the administration of the Metropolitan Transportation Authority. Are you still awake? Why anyone would commemorate something so drab is beyond me, but at this rate, I wouldn’t be surprised if the Time Warner Cable Museum moved in next door.

One thing was for sure: If I could have fun with this girl in a Subway museum, I should probably just propose to her right then and there on the mock subway platform.

The Girl: A 29-year-old high school Math teacher.

The Outfit: Five Four henley with black pants and New Republic chukkas. Aka the ‘Getting Laid’ Starter Pack. The goal with this outfit is to look fresh enough to distract my date from my personality and my unibrow.

Tinder Opening Line: “Can you do me a huge favor and help me solve for ‘x’? U + Me = x” I honestly can’t believe this worked.

Date Highlight: Leaving.

Date Lowlight: The Transit Museum trying to tell us to have fun sober. Let’s be realistic, Transit Museum.

Date Lowlight #2: Realizing a family with two young children witnessed me take this picture and having to stare at the floor as I passed them.

Overall Date Grade: C-

Granted the venue sucked, but my date didn’t do too much to soften the blow. Our personalities didn’t mesh and I found myself more interested in the challenges and labor involved in subway construction during the period 1900-1925 than in our future. She was a nice girl but definitely was expecting someone who doesn’t use the subway turnstiles as a phallic symbol. Sorry I’m not sorry.

Second Date Odds: 15%


Date 3: America’s Oldest Fair

I trekked up to my hometown of Topsfield, Massachusetts for the last date of my three-date Tinder farewell tour. Topsfield is the home of America’s oldest fair (1818) and I spent many-a-trip around the ferris wheel growing up trying to cop an OTPHJ. The fair consists of rickety ass fair rides, diabetes-inducing fried foods, rigged games, farm animals, and toothless carnies.

I made the mistake of bringing my ex-girlfriend to the fair in 2012 in some cheesy, piss-poor attempt to resemble romanticism. She didn’t even pretend to be impressed. I didn’t want to blow my money on the rigged games so for the majority of time, we sat on a bench pointing out particularly ugly people and asking each other how much money it would take to have sex with them. I learned that evening that I am a cheap fuck, in two ways.

BUT HEY! New year, new date, hopefully new results!

The Girl: A 28-year-old underemployed actress. I was a little skeptical on this one at first because I imagine actresses to be really self-centered, but then I realized that she’d probably be really convincing at faking an orgasm, which, at this point, is enough reinforcement for me.

The Outfit: Five Four green flannel with dark jeans and New Republic black chukkas. The flannel says ‘I’m capable of chopping down a Redwood,’ and the jeans say ‘Hopefully these things end up on your floor by the night’s end.’ Calm down, jeans. You’ll get your wish.

The Opening Tinder Line: “Where should I tell your parents we met when you introduce me to them?” Never underestimate the value of blind confidence.

Date Highlight 1: Finally getting the reassurance that if coach ever put me in the game in high school, we would have taken State. How much you wanna bet I can throw this ball over them mountains?

P.S. This video of me scoring is also a metaphor for what happened later that night.

Ain’t that right, Nature Boy?

Highlight #2: Nothing gets you in the mood like watching two pigs 69.

Date Lowlight: Spending $40 to find out I look like a human rat.

I honestly didn’t know whether to give the small Korean man who drew this two twenties or two black eyes.

Lowlight #2: Going 0/13 from the field and getting two free shots because the carnie worker felt bad for me.

Overall Date Grade: B

My date battled the stench of farm animals and carnies and proved herself to be a solid date. She stuck by me as I consistently failed to win her a Hello Kitty stuffed animal, but seeing as I looked like Brad Pitt next to all the mouth-breathing carnies, I guess she had no choice. She also told me she was a sucker for my flannel, which is an upgrade from the turtleneck I would have worn if I wasn’t outfitted with big boy threads.

Second Date Odds: 8%

She lives in a different state so it’s physically not feasible. But am I saying I would totally rule out crossing state lines for some booty? Nah–it certainly wouldn’t be the most pathetic thing I’ve ever done.


Thank you for taking a journey with me on my last three first Tinder dates. Although I probably didn’t meet my soulmate, I ate a shitload of free breadsticks, learned I have a rat face, and now know more useless facts about public transit than I know what to do with. Chalk it up to an overall success. Or somewhere between success and failure. Big shout out to the bros over at Five Four for hooking me up with the threads to instill some confidence in the most trying of times. Don’t forget to take advantage of 50% off your first month over at Five Four using the code BROBIBLE. You owe it to yourself.

Matt Keohan Avatar
Matt’s love of writing was born during a sixth grade assembly when it was announced that his essay titled “Why Drugs Are Bad” had taken first prize in D.A.R.E.’s grade-wide contest. The anti-drug people gave him a $50 savings bond for his brave contribution to crime-fighting, and upon the bond’s maturity 10 years later, he used it to buy his very first bag of marijuana.