6 Men You Meet Speed Dating on Valentine’s Day & Their Underwear



Happy Valentine’s Day! As a way to show your friends you are spontaneous, you decided that you would not be a bitter single this year and try your hand at a Valentine’s date. Six, to be exact.

Yep, this Valentine’s Day you have decided to try your hand at speed dating. Of course, when you entered the event hall at your nearby Marriott in New York, you got a bit nervous. Having perused The Underwear Expert site all morning, you decide that the best way to beat the nerves is to simply imagine your dates in their underwear. This is what happened:


prldWhen you are faced with the challenge of mastering the six wonders of today’s speed dating, you have to be prepared. So, what are you wearing?

Well, if you have been an avid reader of The Underwear Expert, you’ve probably seen our guide to the best love/lust underwear for Valentine’s as well as our take on the 14 best red/pink underwear. Since you are single and not interested in looking for a hookup tonight, you opt for an option from the love category. You want an underwear that says you are flirtatious but not going all the way tonight.

In terms of color, you find yourself drawn to pink this year. Whereas you feel like red is a bit traditional, pink is a bit more playful. Though romance is the objective, you want to have fun here and not take life too seriously.

You end up choosing to wear the Calvin Klein Steel Micro Hip brief. It has always made you feel cute, whether for someone else or yourself. The electric pink with shiny silver waistband shows off your playful mood the best. Also, the fabric is extra comfortable and, tonight, you know you’re going to need to be comfortable.

The 20something Fashionista

The first guy you meet as you sit down in the most awkward version of musical 9491_0285chairs you have experienced (well, if you don’t count the time it was you against Big Bertha at your best friend’s third grade birthday party) approaches you wearing skinny black capris, what appears to be a woman’s blazer, and a tank that leaves you wondering where the rest of his shirt went. His hair is for the most part shaved, except for the patch in front which he brushes back in somewhat of a pompadour fashion.

After he sets down his extremely oversized clutch, he begins to ramble about how he goes to FIT and hopes to be the next great designer. Despite his air of arrogance, you get the uncomfortable feeling that he is reading your plaid shirt, jeans, and broken in vans for filth during the pockets of silence that occur.

As a twenty-something college student who makes fashion statements at weekly Marquee parties in NY, chances are he probably is wearing Andrew Christian underwear. You don’t know a brand this is more youthful and popular than Andrew Christian. It’s definitely a label he wouldn’t mind wearing. And, judging on the tightness of his pants, it’s definitely a jockstrap.


The Guy You Recognize

When you think things could not get worse, you run into the guy you recognize, or, even worse, have gone on a date with. Let’s face it, there are plenty of people in NY who just like the thrill of dating apps. This guy is one of them. You met him garcon_model_black_trunks_iconic_metallic_collection_6after you two swiped yes on Tinder. After a few days of passive exchanges, nothing really materialized. How could it? There comes a time when non stop LOLs just don’t cut it as conversation. You’re funny, but, not that funny.

Anyways, so now you’re stuck somewhat reminiscing with a guy about that one week you chatted and how dating in NY is so hard to do. In the back of your head, as you agree with him, you are thinking that the main reason may just be that he is more committed to the idea of dating around in the digital age then actually being committed to a person.

It’s not too long until he whips out his phone as you are chatting. Only in 2014 can you date while you are on a date right in front of the person you are dating. You come to the conclusion that he’s wearing a simple black trunk from a brand you normally appreciate, but could care less about at the moment, because, let’s face it, nothing says emotionally distant than the color black on Valentine’s Day.

The Hungover Jokester

At the halfway point, you begin to think you chose the wrong Speed Dating event because you’ve come to realize that the only complimentary snacks are hershey headerfeature46kisses and small bottles of water. By the halfway point, you could really use a stiff drink. That is, until a walking PSA for alcoholism becomes your next date.

He smells like whisky and has managed to sneak in a flask. You feel as though you want to make an alliance with him for a swig of his alcohol. Then, you wisely refrain. Who knows where his mouth has been?

He then proceeds to say that he is a stand up comedian. At least, that is what you could make out from his slurred speech. He begins to tell you a raunchy joke about his ex. You amuse him with a polite chuckle, then excuse yourself to the bathroom.

As you stare in the full length mirror of the surprisingly luxurious restroom, you think that the standup comedian prefers jock briefs, like the brightly colored ones from Pistol Pete. Because nothing says funny and blast in a glass like mullets — and jock briefs are the mullets of underwear.


The Socially Awkward Actor

The next guy you meet is an actor because when you live in NY you are destined to dabble with actors at least once. On dating sites, actors usually portray themselves as fun loving, carefree, and blast off witticisms like they’re Lena Dunham preparing for a brand new episode of GIRLS. You can always bet on 3388_1_them posting their head shots as their profile pics. You begin to feel like a casting director at times. Based off of their head shots, you can make a snap judgment as to whether they will be successful or not — and choose to date them.

Unfortunately, when you meet one during speed dating, you have to spend 10 minutes with them after you cut them from the drama/comedy of your life. Sitting with the actor, you come to notice that he is rather socially awkward in person and pretty silent. Understandably, those pics of him having fun are usually taken with groups of other socially awkward actors, and the written word can often be a crutch for some. This guy was the some.

After spending some time in silence, your mind wanders to his underwear choices. You decide that he is most likely wearing a Ginch Gonch boxer from their sporty collection because actors live for irony. Nothing says deliberately ironic than an actor in a football print.

The Space Cadet

prld-1From the guy who doesn’t talk to the guy that can’t stop talking…about Britney Spears. In a date, you try to find the most well rounded person possible. You love a little Britney on occasion, but you appreciate her and your pop culture in small doses. Unfortunately for you, when this guy walked up, he became a living, breathing Star Magazine.

After your ten minutes are up, since you can’t get a word in edge wise, you find out more about Kim Kardashian than you have ever wanted to know. You also find out that he’s wearing Calvin Klein because, well, that’s the brand Justin Bieber wears.

The One

So, we can’t say that you will find the one at speed dating, but, for the sake of a little emotional Valentine’s Day porn, let’s say you do. Of course, it has to happen after surviving the first six circles of hell, when you begin to feel that you have lost all hope in speed dating. Isn’t that the way it usually works? He shows up when you least expect it.

thumb_10634-Baller---Jock---Red---Front-800x1000You guys start to chat at speed dating, and then exchange numbers. The first place he takes you is out for Thai food because you mention it’s one of your favorites during the speed date. You guys begin to open up as each subsequent date takes place. And, dare we say it, you fall in love. It’s mutual. Both of you have a clear respect for each other that other people envy.

When deciding what underwear he’s wearing during your speed date, you actually don’t take time to think about it. You’re so fixated by his eyes and the depth of your conversation. For a moment, all that matters is him and nothing materialistic. That said, you ask him about it a few months later. A Nasty Pig jock, he tells you. Your heart melts. You knew he was your perfect match.

Get The Look

Calvin Klein Underwear

Steel Micro Hip Brief Zinnia Burst


Shop now

Andrew Christian

Trophy Boy Flaunt Bubble Butt Jock


Shop now

Pistol Pete

Nitro Brief


Shop now

Ginch Gonch

Score Sport Brief


Shop now

Calvin Klein Underwear

X Cotton Trunk White


Shop now

Nasty Pig

Baller Jock


Shop now