A Man’s Guide to Online Dating

I love the internet, and I don’t need a Samantha OS to know I can use it to deliver women into my life. I’m 35, have had computers since I was a kid, the Internet since my teens, and dated almost exclusively online for about the last decade.

Everyone else I dated was through proximity growing up, friends, or coworkers. I’ve met a few random women at bars, but online dating is a process I run in the background for the sake of convenience  more than anything at this point.

Here’s a little background on how online dating became a regular thing for me.

“I’m a Terrorist”

When I left Bank of America on January 5, 2011 and the bank’s corporate security called a bomb threat into the police under my name, I was placed on a terrorist watch list. It didn’t help that I had been searching online for everything Assange, Manning, Wikileaks, and Anonymous.

As I built my Twitter following, built my blog, and searched for meaning in my life, I still had 8 months left on my Match.com profile.

Until February, I was afraid to leave my house much, but by April, my neighbors, roommate, friends, and I would keep ourselves occupied at at small Chandler bar called Tom Ryan’s. I went to high school with the bartender, so I survived for months on cheap American beer, fireball whiskey, peanuts, pretzels, and cheese puffs.

When I needed a distraction, I would turn to my Match profile and find comfort in having normal conversations with women I met throughout Arizona.

Optimizing Match

Prior to leaving the bank, I had already put a few months into my online dating profile. I’ve built profiles on quite a few over the years.

The problem with any community website is if you’re a woman, people instantly start interacting with you, but if you’re a man, you have to interact, or you’ll sit stagnant.

Reading a woman’s individual profile is fun for the first few pages, but soon you realize every profile is the same pics of people traveling somewhere, eating something, or smiling with friends/family in some party atmosphere. Each profile has a version of “I’m a unique social butterfly interesting in stuff and looking for friends to do things with. Not looking for a one-night stand.”

Of course, if you’re rich or otherwise desirable, the rules of women apply to a man. Lying about having wealth isn’t advisable, because, like appearances, someone can instantly spot the lie on the first date.

However, I did find a spot to change my luck in June, when I updated my education level from “No Answer” to “Doctorate.”

Nothing else on my profile changed – as a matter of fact, it’s probably still sitting there looking the same right now. The day after I updated my education, women were flocking to me, despite me making under $20k/year at that point with no future.

Conversations became much more interesting, and I was meeting more and more women.

How I did it was to first flip through all the pages and click out anyone I wasn’t physically attracted to after the custom filters. Then I sent a message of “Hi” to every single woman that was left. I sent that message to over 1500 women over the course of a week and heard back from an average of 5 women per day.

Of those 5, I just started a conversation and dropped it when it went nowhere or felt forced.

Some of those 5 women a day, I met with over the span of June through September – I dated a doctoral student, a brain surgeon, a few scientists, an entreprenuerial single mother, multiple teachers and nurses, several doctors and lawyers, and quite a few professional businesswomen.

It happened because I optimized my dating resume to match my professional resume’s formatting.

Learning to Date

I spent most of my 20s in a series of relationships, so dating in my 30s took a little time to get used to. On top of this, as I was barely getting into the swing of things, I lost my job, became, a whistleblower, and was learning to stand on my own in a whole new world.

The Chandler PD had interrogated me in my home as being a terror suspect, and I was scared. I was leaning too heavily on women I had only known for a few weeks.

A few of these women I slept with, and some I only met once or twice, but I retained a level of friendship with each. We left on good terms for the most part, and several of them talked me through some rough times and I’ve reciprocated throughout the years as I travel my roads and they travel theirs.

Most of the sex was awkward. One woman I’ll never forget, we were about to have sex when she yelled out “don’t penetrate me!”

I rolled off her, frustratingly trying to work out how I was going to rub one out to avoid the dreaded blue balls (it’s a real, very painful, thing, I assure you, and it’s the reason guys jerk off all the time).

We met at Tom Ryan’s, where I knew I could afford to get drunk with her in an environment I was comfortable with, and she could tell I was being open and honest because I had a lot to talk about.

I explained how the banks sent the police after me, I’m likely on terrorist watch lists now, and I’m working with the media, Anonymous, and some hackers in the middle of what would later become the Occupy movement.

She walked home with me, and on the mile stroll from the bar to my house, I jokingly asked why she felt so comfortable walking home with me.

“I’m a terrorist. Have you no standards, woman?” I remarked, half-jokingly.

She laughed and I could tell she, like me, was just happy to finally be talking to someone honest in the world. So when she balked at sex at the last possible moment, I wanted to comfort her the way my parents did when I decided at the last minute to avoid riding Magic Mountain at Disneyland as a child.

I was instantly thrust into myself and at a loss for words – that moment of honesty was filled with an awkward void.

Sensing my frustration, she blew me, and I could tell she didn’t do that often. It wasn’t the worst blow job, and I should have been more grateful, but I just wasn’t in the mood anymore.

Looking back, I’m not entirely sure how much I destroyed that woman’s spirit (or how many women, for that matter) with my focus on things other than them.

“I Get You Have More in Common”

Having conversations and meeting different women between Tom Ryan’s in Chandler or Casey Moore’s in Tempe gave me an idea of how to tell when you’re connecting with someone. I started to learn how to maintain confidence and not come off like a jerk.

As I moved back in with my parents, then to Florida and back to Gilbert, AZ, I let my Match account expire, though I remained in contact with quite a few women from the site.

Twitter also became a great dating aid at the time, as I was unleashing my rage against the machine, 140 characters at a time, and attracting a large female following. I also blogged more frequently on other media sites, making friends with other whistleblowers, journalists, marketers, artists, and tech enthusiasts around the world.

My document leak through Anonymous got me in circles of Occupy, Wikileaks, Anonymous, and more. I was a certified gangsta at that point, and quickly becoming an OG at that.

Soon I was travelling throughout the West Coast, living in a van, watching my expenses, and covering a variety of major events.

E3, CES, Super Mobility Week, the NAB Show, VR Fest, Cannabis Cups, PAX Prime, and the decriminalization of marijuana in Oregon, Colorado, and Washington.

As I traveled to each place, I used Tinder for several years to explain that I’m a traveler looking for locals to show me around town. In this manner, women around the west coast would welcome me into their homes as a guest. I was interesting and had some great stories and collectibles as gifts.

In Denver, I learned to sneak into the Cannabis Cup. In Seattle I learned to sneak a friend into the Cannabis Cup (a Cannabis Now reader I connected with through Facebook), and in Oregon, I worked in the cannabis harvest and met with a bluegrass singer/neuroscientist.

These events are related in that I blew a tire out on my way south from Seattle after their Cannabis Cup in 2014 and ended up stopping in Oregon, just south of Portland, to get all my tires replaced.

Without gas money, I settled in a nearby apartment complex in Eugene, Oregon, where there was a Home Depot nearby I could park at for free WiFi to work during the day and plenty of apartment complexes or parking lots to park and sleep in during the night.

The first woman I met was a brain researcher at the University of Oregon. We met up at her house, and she showed me around town with her roommate. We went on a hike through the park, along a creek, up a mountain, and even crossed the river to a diving spot.

Enjoying each other’s company, we smoked some weed together I picked up in Seattle, shared some with everyone who passed by, and enjoyed the sunset view before going back to her place in Springfield to prepare for the band’s gig.

I met at least a dozen people who came in and out while grabbing gear for the gig, and we ended up at a saloon in the middle of downtown Eugene.

I smoked outside for much of the time, allowing her to get ready to go onstage and trying to stay out of the way overall. As she was singing, I came and found the only two of her friends I recognized and sat on a couch next to them to chat and watch the performance.

They were great, and she had a strong voice. Most of my bluegrass knowledge is limited to what I’ve heard from my parent’s country music leanings and George Clooney. It was a lot different atmosphere than the live bands at Tom Ryan’s, and a much different atmosphere than the bikers and cowboys of Arizona’s largest metropolis.

As I enjoyed the atmosphere, one of her friends sat down and started talking to me. I decided to have a cigarette, and she followed me out. We continued talking and drinking together until we ended up in a booth at the back of the club, and she asked me to kiss her.

Forgetting I came here with the woman singing the background music, I fell for her eyes, closed mine, and obliged. Soon we were fully embraced and staring in each other’s eyes.

“Do you wanna get out of here?”

I asked if she had a car and we left, as I started to understand and realize this woman was not with the band, and my van is parked at the singer’s house tonight.

We made out up against, and then inside her parked car, discussing where to go next. I explained I’m living in the van parked at the band’s house, and we decided to park there. We got into my van, but she couldn’t sleep with me in it – instead she complained about needing to go to the bathroom, so I twice…twice…politely walked her into the house, chatted with whoever was in there until she finished, then returned to feeling her up in my van.

For the sake of my own pride, four months prior in the suburbs of Los Angeles, I worked for a week consulting a successful real estate agent’s lawyer and had sex with his secretary in both her office and my van. We also did it in an alley and parking lot before passing out that night in my van.

This Oregon chick, I ended up sleeping with and dating for a few weeks before I found out I had been sued and returned to AZ to go to fight it and go to jail.

She worked in the Pacific Northwest with her friends, trimming cannabis crops during the harvest season. She got me a job (and a place to park my van and sleep) trimming outdoor buds to look like indoor grown. The job paid in product and was located in the most beautiful forested backyard.

She also accompanied me to meet with several medical marijuana businesses that provided interviews for stories I wrote for Cannabis Now, Jim Cramer’s Main Street, and my own website.

By the time I left this woman and returned to AZ, I had much less money than I hoped, but I had plenty of product and stories to sustain me with a woman I went to high school with to take me in as a roommate for over a year.

Although she’s not a woman I met on a dating site, my experiences on Match and Tinder helped me navigate my role in her life and maintain a friend zone while I recovered from the financial hit suffered in the court case.

Having known each other over the course of several decades, we trusted each other and could support each other through some of the deeper things that happen over the course of one’s lifetime.

Now that I’m back on the road, I have Tinder going again, and as soon as I settle down in Tucson for the fall, I’ll have Match going again as well.

I’m already 35 and barely getting my life back on the track it was on when I was 30, but my 40 looks stronger than ever.

I’ve used dating sites and met women as lovers, friends, and girlfriends throughout my 20s and 30s through these sites, at bars and clubs, at work events, in libraries, all over the internet and throughout towns and cities all over the west coast.

If you ever wanna know anything about how online dating works, just ask.

My favorite part of online dating, by the way, is that Tinder invites you to tell your friends every time you have a match. If you’re bothering people by telling them Tinder matched you with someone, you’re taking Tinder waaaay to seriously.

It’s the equivalent of notifying your friends and family every time you rate someone’s pic “Hot” or “Not”…just…no…

cropped-brian-penny-anonymous-gonzo1.jpgBrian Penny is a former Business Analyst and Operations Manager at Bank of America turned whistleblower, troll, and freelance writer/consultant. His work appears in High Times, Huffington Post, Hardcore Droid, The Street, Cannabis Now, and Fast Company.


Dr. Brian Penny is a former Business Analyst and Operations Manager at Bank of America turned whistleblower, troll, and freelance writer. You can find his work in Cracked, High Times, HuffPost, Lifewire, Forbes, Fast Company, and dozens of other places, although much of it is no longer under his name. Dr. Penny loves annoying fake media.

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