8 Hilarious Things That Happen to Guys with Online Dating


I online dated before. Past tense? Yes, even now I’m still ambivalent about the online dating experience. It can definitely be a useful tool that opens you to a world of potential dates – maybe even something serious.

But it can also just as easily expose you to another side of dating you never thought possible, with hilarious and sad things that might only happen online.

I’m here to talk about those things today…here are 8 that stick out to me:

1) It’s A Picture Game.

This is guaranteed to be a universal problem for guys dating online…”is she hot or not?”

Women, on an order of 2 to 3 times more than men, really know how to work the camera. The average woman on Facebook knows which side is her good side, have their standard smile down, and know where to position their arms and body to achieve maximum photogenic-ness. Most guys don’t know that shit.

Now take that photo-taking ability to the online dating sphere, and you get some interesting results. You get this phenomenon where some girls look deceivingly good in their pictures. I mean, hot damn!

Then she shows up to the date and you barely recognize her. At best, when she steps out of her car it’s 80% of what she looked like in pictures, and by the end of the evening it’s 50% or less.

After a few bad dates, you start to notice a pattern. It almost seems like you cracked Da Vinci’s Dating Code to Analyzing Pictures That Women Take Online. Here’s the battery of tests that you run through upon opening a girl’s profile:

1) Does she fail to show her whole body? (E.g. only shows her face, or keeps cropping out parts of her body)
2) Does she only take photos with weird angles, or obscure lighting?
3) Does she put on a LOT of makeup?
4) Does she not smile, or only smiles with her mouth closed?

The catch-all question: is she consistently obscuring her appearance in some way?

If it even remotely feels like she’s hiding something in her pictures, then you best believe it. I’ll give you the Guy Guides guarantee on that one.

This phenomenon is so prevalent, there’s an entire TV SHOW dedicated to this phenomenon. It’s called Catfish.

2) Girls who have boyfriends

I almost did a double take when I first saw “taken” or “in a relationship” on a girl’s profile. If you’re seriously dating someone, WHY THE HELL ARE YOU ON A DATING SITE? “Looking for friends” my ass.

The real reasons: they’re online for attention and digital validation. Or looking for a backup boy, rebound, or distraction. Whatever the reason, it’s unhealthy.

“Just looking” when you’re dating someone is unhealthy. Dipping into your inbox when you’re feeling down about your significant other is unhealthy.

Let’s all make this pledge: “when I start dating someone, I will deactivate my online dating account(s).”

Please, for your own sanity and that of the one you’re dating, do this.

3) Time Consuming, Addictive and Distracting

Online dating was a HUGE distraction to me. A GuyGuides reader framed it best:

“In the morning, I wake up and open up [dating apps]. I’d lay there for 30 minutes just surfing profiles. During the day I’m constantly checking/replying to texts, online messages, and even snapchat from some of the girls I’m talking to. Before going to sleep, I lay in bed for 30 min – 1 hour, browsing more profiles and messaging girls…”

On the flipside, I also got some interesting, unsolicited advice:

“Dude, you gotta think of free time as an opportunity to message girls. When I’m standing in line for Chipotle, I’m messaging girls. When I have some free time at work, I find funny pictures on the internet, then save them for sending it to girls later. You gotta be on it all the time.”

Man, that sounds tiring. But I’m guilty too – I ended up checking the dating apps on my phone even more than email or Facebook. While I resent the apps for being so addictive, I also admire them for being so well designed. If you haven’t been online dating before, beware – it can hook you and suck a looot of time.

 4) Asian Men and Black Women struggle online.

After reading an article that black women and Asian men are the most racially excluded groups online, I tried an experiment. On OKC, I ticked “White” along with my actual race (to imply I was a halfbreed).

I didn’t change ANYTHING else on my profile. The result? The number or profile views I received, as well as my response-rate, more than doubled.

I can’t make this up, because I’m guilty too: unchecking boxes for certain races, religions, or any number of preferences.

5) It’s a small world

If you’re on more than one dating site, what makes you think others aren’t too? It’s weird seeing double online.

The offline world is also a small one. I’ve bumped into someone IRL who I forgot I spoke to online. We both did double takes. Probably the most awkward “Do I know you?” I ever uttered.

Lastly, there’s the strange thing of seeing people you know on dating sites – coworkers, high school acquaintances, and even exes. Shout out to girls from my home town though – you ladies are fine.

Good reminder to always treat others with dignity and respect. Especially if they work in the same industry as you :p

6) Girls who brag about dating

On more than one occasion, a date has bragged about the number dates she’s been on, or evenly casually dropped that she’s going on another date later. You were so nice online, did you become a d-bag on the drive here?

Please humble yourself and eat the dinner that I regret buying you.

7) Undercover Trannies

There is something worse than a girl lying about her appearance. And that’s one who lies about her gender.

Hot girl messages you first? Be a little suspicious. This is a transcript of a conversation I had with one such T-girl. And it doesn’t mean tattoo girl.

Tgirl: “Hey you, wanna hv some fun?”
Me: “I have to ask you a question. Are you a man?”
Tgirl: “No.”
Me: “Do you have a penis?”
Tgirl: “Yes.”
Me: “Goodnight.”

For some reason, there was an unusually high density of transexuals on the Blendr dating app. It got to such a point that when a “hot girl” would approach me first online, I’d guess with 80% accuracy that she possessed male parts.

This also made me sad. I thought the chips were stacked against guys in this dating game. But T-girls, they must have it worse. Imagine: most of them originally have male parts, then added on female parts. And they like straight men (because psychologically/sexually, they consider themselves women).

How many straight men would be attracted to someone with male genitals? That’s a ridiculously small dating pool. Anyway, my heart goes out to all the T-girls looking for love online.

8) “There’s always someone else” syndrome.

The main appeal of dating sites is to give men and women more options. This can be a good thing on the surface, but it can also encourage non-committal behavior.

By default, almost all dating sites let you browse hundreds upon hundreds of profiles. Blendr presents you an infinitely-scrolling 4 columns by X rows of faces. Tinder presents you just one profile at a time with a quick “like or not button” – and trains the user to quickly think there’s an endless amount of profiles.

Then this very likely scenario occurs: you meet someone and hit it off. You even go on a date and it seems to go well. But you know that neither of your schedules can accommodate a date until a week later.

In that one week, it’s almost guaranteed that both of you will browse other profiles. Maybe you start talking to another person who’s just as interesting and attractive. Maybe the girl you dated last week becomes a lot less responsive. After all, she could just as easily find someone else online (or off), and so can you. So to all the guys who’re wondering why that amazing girl just seemed to disappear off the face of the earth (she’s not texting you back), I feel ya.

There’s a better way

A lot of this above may resonate you, but it’s not all bad news. There’s no magic bullet to solve the woes of  dating, online or off. But one thing that might help is Slow Dating, an idea and mindset to help you get the most out of dating. I lied in the beginning that I used to online date. I just realized that I was actually using a online dating site, but it is so unlike the others – and fits within my budding slow dating philosophy – that I totally endorse it 100%.

I’m still in the midst of developing content for Slow Dating, so subscribe below to be the first to hear about it.


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