10 Tips for Men Who Want to Date Women and Slay In the Era of Digital Dating

 When your date shows up and he looks nothing like his pics. #fml #tinderfail #heeeeeelp

When your date shows up and he looks nothing like his pics. #fml #tinderfail #heeeeeelp

I re-entered the dating world after a multi-year hiatus and was less than shocked to discover that the dating game had gone almost entirely digital. It's a brave new world out there kids. Here are some tips I've gathered based on my personal experiences and minimal field research that may help men have a leg up on the competition. 

FYI: This post is written for sex-positive, cis-gendered homo sapiens with heterosexual tendencies because that's my scene but hopefully people who identify across the spectrum of diverse, human expression can still glean a little something to take away. Peace and Love. 

1. Don't Hate the Players, Hate the Game... Or You Could Just Stop Hating?

First of all, if you are going digital, you have to know and embrace what the people you are trying to date are using the site or app for. It turns out that most of us are out there searching for, at minimum, a physical connection, and at most, a legitimate, full-blown love affair. Above all, people seem to want chemistry. If you think everyone is on that site or app in search of a loving, committed relationship, they're not. And if you think everyone on there is just looking to get laid (like tonight!), they're not. Being frustrated that the majority of people are not using an app the way you are is a waste of your precious time and energy. It's also poor dinner conversation for a first date! So it's time to let it go. You'll have more fun if you do. I promise. 

2. Photos Say More Than You Think

Pictures are worth a bunch of words or whatever and this is the digital equivalent of catching that special lady's eye at the bar and making sure she notices you. She's trying to get a feel for who you are. Use each photo as an opportunity to communicate a different, awesome quality. You're artistic? Funny? Active? A party animal? Spiritual? Adventurous? Laid back? A proud workaholic? A globetrotter? Show her you're free range. You'll have her wondering "Who is this devilishly handsome man with so much to offer?" in no time.

On the flip side, false advertising will never end well. Your photos should be recent and look like you. They should be in focus. If I can't see your teeth, I'll wonder if you're missing some. If there are kids in your photos, I'll assume they're yours unless otherwise stated. I would not recommend including photos of other women unless you explain who they are. Most people have a tendency to unfairly compare themselves to others and you want ladies to be feeling exclusively good feels while they are checking you out. Am I right? If every picture is a group picture, I don't who you are!! A profile doesn't take that long to assemble so if your pictures say you don't care, then why should I? And I love being in the great outdoors adventuring but if every photo is of you summiting Mount Everest, wrestling sharks with your bare hands, and slack lining across the Grand Canyon I'm probably a bit intimidated and worried that I can't keep up. Remember, only good feels!

3. Due Diligence, YEAH! Pen Pals, NOOOO!

Dating can feel like a chore so pre-date chatting is a must but nobody, and I mean nobody, wants a pen pal. It shouldn't require too much back and forth to weed out the total duds and to decide if you want to meet this new human in person. If you're going to ask her out, get it done. If not, let her move on to the next suitor. Ain't nobody got time for that!

4. Ask Her Out! What's the Worst that Could Happen?

You both swiped right. So you know that she thinks you're hot. She's basically already said 'yes'. What the heck are you waiting for? 

Yeah, but what if it's, like, IRL? Rejection is the worst... Or is it? Let's build some perspective. It's Tuesday, you're grocery shopping, and your plans tonight involve catching up on the latest episodes of Mr. Robot after, that's right, nachos baby! You turn down aisle 4 to get your favorite can of chunky chili and lo' and behold! There is a woman sizing up different tuna brands. She exudes that special something that lights up your radar in just the right way. What do you do?! Humor me while I run through a few scenarios. 

  • A) You choose not to ask her out. She picks the dolphin-friendly albacore. And your day continues along exactly how you planned it. F Society is still the vanguard of the revolution! It was a good day.
  • B) You choose to go for it and ask her out. She says 'no'. Shucks. And your day continues along exactly how you planned it. Rami Malek still kills it because that kid sure can act! It was a good day.
  • C) You ask her out, you badass you. She says 'yes'. All of a sudden Tuesday has turned into your own personal holiday because, damn boi, you da man. It was a great day.

So there really isn't all that much to lose, is there? In the dating game, the only action you can take that guarantees that she'll have the opportunity to say 'yes' is daring to ask her out. You got this bruv. #yolo #butforrealyouonlyliveoncesowhynot

5. Do Something You're Great At!

There is nothing sexier than watching a man do something he loves, especially when he's good at it. Whether it's ping-pong or popping bottles, if you're good at it, you'll be confident and confidence is the most tried and true panty-dropper of all time, because science. One of my favorite dates so far was when a guy asked me to go to the driving range. I don't golf, I was awful, and I did not discover some latent passion for hitting up the green but damn it was attractive to watch him do something he killed at. Like woah.

6. Big Brains Are Sexier Than Big Wallets. Can I get an 'Amen'?!

I totally appreciate getting treated to a fancy dinner. Duh! And yet in my experience I have been way more impressed by dates that have small price tags but stand apart because they are unique and creative. If you're tired of predictable dates with predictable conversations, then so is she. Consider making your date an opportunity to do something you've always wanted to do, like go mushroom hunting, learn how to surf, attend an air guitar championship, or eat a picnic on the hood of your car (I swoon for a good PB&J) while watching a meteor shower. Nostalgia and romance? Yes, please! Resourcefulness and originality are beaucoup hawt!

7. Be Curious and Listen. For Reals.

I fundamentally believe that men have interesting stories to tell. If I truly pay attention, I can often pick out their most deeply held values, experiences, and ideas. Yes, even on the first date. It's pretty cool. But because I am a great listener, I have spent many first (and only) dates listening, and listening, and listening. I don't want your resumé. I want a connection with you. If a man hasn't shown any curiosity about my world, I think it's safe to assume that zero chemistry has been generated. 

8. Take The Reigns. It's Crazy Hot. (Especially if you are good at #7!)

The question I dread the most when I first start seeing a guy is "What do you want to do?". If this was 90's Nickelodeon, you just got slimed. Yuck. The last thing I want is for a guy to ask me out only to turn around and delegate all the work to me. Know what you want to do and invite her to do it with you. I think your male role models would agree: don't ask her out and then make her plan it. If however, you want to create space for her to imagine rad dates in the future, why not offer to pull off an awesome, mind-blowing first date. If you succeed, then she's in charge of trying to top it for hang out number two. And so on. Cue the adventures please!

9. Beware of Convenience. It's Not Your Friend.

You're driven, intelligent, and you probably have a killer sense of humor. Everybody says you cut a mean silhouette in a suit. You, sir, are a total catch! So beware of taking her on a date at the bar across the street from your apartment complex, even if it really is a great bar! I know we all go on a lot of these dates, and it can become a bit of a grind so convenience becomes more and more alluring. BUT! Be mindful that choosing something that requires basically zero effort or imagination can read as lazy. And you're not lazy! And I don't want to accidentally think you are! So just follow tips 2 and 3 and you'll slay. Plus, you can save that bar for date number 3 or 5, depending on your steez (wink and nudge). It'll still be there.

10. Learn How to Eat Pussy: Did I just go there? Yes. Yes I did.

It's 2017 people! Y2K did not happen and consenting adults are having sex on the regular. It's the age of female sexual enlightenment, which means everyone is getting laid at unprecedented rates. You're Welcome! [insert Blushy Smiley Face Emoji] 

I've surveyed all the single ladies - all of them, everywhere - and they all agree that it is a huge turn off for sexual pleasure to be one-sided. There just isn't a compelling reason for either party not to be able to deliver the goods. With as little as 20 minutes of research on the internet, you could be a better lover than 85-90% of your competition. If you don't have 20 minutes to spare, how about three? You DEFINITELY have 3 minutes to watch my good friends Key & Peele help a homie out.

For the more studious out there, there are entire books on the subject matter! I can attest to the power of a well read gentleman. I started seeing a guy and stumbled upon one such book while I was perusing his library. I mean the guy had gone through and highlighted entire sections! Knowing that he took pleasuring a woman seriously won him plus one thousand points towards us doing the nasty. I'm happy to report that his homework paid off handsomely for the both of us. 


If I've done my job, and done it well, then you've learned everything you'll ever need to know about Mr. Robot, hard science, my affinity for nostalgic references to bygone pop culture, as well as the power of a well-made peanut butter, and jelly sandwich. Good luck my gorgeous padawans and may the odds be ever in your favor.