What Online Dating Taught Me About Online Business

I’ve been single a few times in my life. That will happen when you get married at 18 and can’t stop crying on your 10th anniversary thinking about living another 10 years with the person you married. Ending the marriage was a hard decision, especially when you have two kids under five.

I was thankful for the chance to ‘do over’ finding a more fulfilling relationship. As it turns out, I’ve had a few chances for a relationship ‘do-over’ in my life. And whether I liked it or not, the path to a new relationship was always through dating.

As I reflect on the dating segments of my life, it’s not too much of a stretch to find the correlation with the entrepreneurial journey I’m on today.

  • Both require putting it all out there, sharing the best of you while hoping you’re attracting the right people.
  • You constantly unveil new paths, trying to anticipate where they may lead while listening to your gut so you can stay true to yourself.
  • You persevere, weathering the bumps along the way and focusing on why you're driven to keep going.

As I look back on my relationship journey, I gained some valuable life skills that are useful when building an online business.

The Joys of Dating

In the early 1990s, dating meant putting yourself out there by getting dressed up, going to the bar with friends, and hoping for the best. Your friends and family were entertained by your antics and excited to know you were ‘back on the market.’

There wasn’t much I liked about dating, but knowing it was the path to a real relationship, I forged ahead.

I have some very vivid memories of those early years of dating:

  • Friends and family trying to ‘help’ you by setting you up with anyone they knew who happened to be single. That was the only criterion. You were left to sort out the awkward mess. 
  • A random stranger catches your eye, and you immediately check their ring finger to see if they’re married. If not, scheme how you could get their attention--even if it’s in the grocery store's produce section. 
  • Surviving terrible first dates. Like Billy, who wouldn’t stop talking in the third person. “Billy thinks you’re reeeal cute”, said Billy. I responded, “Jan thinks Billy is creepy”, as I planned my escape.

Marketing skill: Identifying pain points.

I discovered online dating when I found myself single and ready to date in the early 2000s. I was used to working on a computer at work and home. As a relatively early adopter of the Internet, I was intrigued by Google and the immediate answers you could get if you asked the right question.

I didn’t Google ‘hot men near me’ back then, so I’m not sure how I first heard about match.com. On my work-issued IBM ThinkPad, I logged on to match.com and started looking around. I’m unsure what that website said, but I pulled out my credit card, paid the monthly fee, and started setting up my profile.

Marketing: Opting in and purchasing a membership in one visit. Woah. Website goals.

Searching for men online, or in other words, shopping for a man. It sounded perfect to me.

To be clear, I was just shopping. Getting a feel for what was out there. I hesitated to take the next step and meet someone in person. At the time, I remember feeling safe since I was in control of who I ‘winked at’ (the equivalent of a Facebook like) and, more importantly, who I decided to email through the match.com email I was assigned.

Getting started searching on match.com meant sorting my potential mate by gender, age range (number of years younger and older than you), and miles within a zip code. There may have been more filters, but I remember using those.

Marketing skill: Identifying ideal customer demographics

When I saw the results of my search, I was astounded. I don’t remember the exact number of men that came up on my list, but it was in the hundreds. Right before my eyes was a list of over 100 men who lived within 30 miles, were within 10 years of my age, and, most importantly, were ready to date. Jackpot.

It provided much-needed validation that there are people out there, just like me, looking for a relationship, and lots of them. My relationship goals were slowly shifting from looking for a fulfilling relationship to thinking I may be able to find my soulmate.

It made the worst parts of dating; the late nights, lousy dates, and interrogation from my family worth it.

Most importantly, I was in control of my destiny. I had confidence that putting my tech-savviness and research skills to work on finding a man would give me some good options.

My future vision of finding my soulmate looked bright.

Marketing skill: Clarifying goals and busting the scarcity myth.

Piles of Men

It wasn’t long before I quickly scanned the profiles and sorted the men into piles. Do you remember the viral Mitt Romney quote about binders full of women? My version is ‘Piles of Men’.

The first thing that caught my eye was the photos. Most photos were fuzzy (no iPhones back then) or dressed in formal wear (taken at a wedding), and some just flat-out revealed their true colors.

Here are some of the photos that are burned in my mind:

  • Smiling with their shirt off, gut sucked in, showing off their tan in the bathroom mirror (this was pre-selfie, so kind of impressive).
  • Posing in front of their sports car, their really expensive Harley, or with a dead animal and their rifle (a true man's man).
  • Or worse yet, flashing a smile with their arm draped over a beautiful woman. Was that their ex? Their sister? Their daughter? No matter who it was, they gave you a clear message of your role in that relationship (ego-maniac).

Marketing skill: The power of visual content.

If their photo didn’t put me off and I got to the written part of their profile, things got better or worse in a hurry.

I distinctly remember seeing the same pattern in those profiles. Back then, there was a lot of:

  • ‘People tend to notice my eyes and smile’ (while I’m undressing you).
  • ‘I’m laid back, easy-going, and love to have a good time’ (I want to stay in bed all day).
  • ‘I love to travel and take long walks on the beach’ (Wanna have sex on the beach?).
  • ‘I don’t know what to write on one of these things’ (I don’t know what to do in bed either).
  • ‘I’m looking for someone equally as comfortable in jeans and a T-shirt as in a little black dress and heels’ (I’m the sex addict with his arm draped over his woman).

Or my personal favorite. I’m a Renaissance man. What does that mean, and is it even a good thing? My version of Renaissance men were those at the annual festival with a turkey leg in one hand and a mug of warm wine in the other, being excited about the chance to wear tights.

It got pretty boring reading the same clichés repeatedly, and after a while, it became hard to distinguish one profile from another. ‘Which guy was this one again? The one who loves hanging out with his friends on a Friday night?’

When you did run across a profile that didn’t feature the exact tired phrases, it was a breath of fresh air. Maybe some guys thought for a minute about what they were genuinely looking for in another person. Bonus points if they could express it by typing on a keyboard to get the words out (remember, I’m tech-savvy).

There was something sexy about a clever and well-thought-out profile. Those were the profiles that would get a ‘wink’ from me (modern-day call-to-action). If I’ve lost you about winking, it’s still a thing in online dating. You can learn more about winking by Googling, ‘what is a wink on match.com’.

After sending the ‘wink,’ I’d press enter on my laptop 5,000 times to refresh my screen so I wouldn’t miss it when they winked back (this was before notifications).

Marketing skill: Recognizing effective copywriting and segmenting your list.

When the relationship moved past the winking stage, it was time to take the next step on email.

It was exciting to come home at the end of the workday and hear your computer say ‘You’ve got mail’. Which, if I’ve lost you, was a voice that came out of your computer, courtesy of AOL, that was such a part of pop culture at the time that it inspired one of my all-time favorite movies, You’ve got mail.

Most of the guys that made it to the email phase just wanted to meet immediately. They were on the communication fast track. You winked, I winked, I’m on my way over with a bottle of wine type of fast track. Whoa.

When I did engage in conversation using email, it was very revealing. You could quickly figure out: 

  • Whether they had spelling skills, if they were able to form a proper sentence, or if paid attention to punctuation (this was before emojis).
  • If they could ask interesting questions, complete a thought, and keep the conversation going (this was before texting).
  • You could even tell from their emails if they were a coward. Many people suddenly disappeared mid-conversation, only to reappear saying they had to leave town unexpectedly (hotter prospect didn’t work out).

The email conversations were another form of filtering my ‘Pile of Men.’ Those I found intriguing and kept my attention made it to the next level in the relationship.

It was time to meet in person.

Marketing skill: Email marketing, the importance of being authentic online.

Meeting In Person

Even though you got to know this person over email, meeting in person was always nerve-wracking.

The simple act of agreeing to that first meeting in person took courage. You had to get out from behind your keyboard, dress up, and make an excellent first impression. There was also a chance to review the facts again since this was a really easy time to bail.

If I had my way, the first date would be a coffee or lunch date. It was too risky for me to meet for drinks because of the expectation of dinner and an entire evening. Even though I always had an exit plan if the date was going badly, I didn’t completely trust my judgment, especially after a few drinks.

Marketing skill: Getting out of your comfort zone and understanding your options.

I always tried to get to the meeting place early, so I would have a split second to recognize my date before he noticed me. I remember waiting with the mental fuzzy image of the person etched into my mind, hyper-aware of everyone in the room.

The first site of them was a whirl of emotions. You’re trying to reconcile that mental image with all the dimensions standing before you. In 5 microseconds. What is that rush of feelings? Chemistry, nervous excitement, or sheer panic? 

The first impression usually when something like this for me:

  • I’d zero in on the face first. Not to see if they had nice eyes and a great smile as their profile promised, but because the face reveals a lot about a person. It wasn’t a good sign if you couldn’t keep eye contact.
  • Next was observing if they were heavier or lighter than their profile let on, all while pretending not to look. As it turns out, there is room for interpretation when you declare your body style to be athletic. 
  • Your profile also allowed you to declare your height, which many men, especially those who said they were 5’ 8” (short guy minimum declared height), were busted when I towered over them (I’m 5’ 8” in flats). 

The first words spoken were very awkward. Especially when you realize they were comparing their mental image of you with their reality at the same time. There was a lot of nonsensical small talk and stammering.

Once you settled down and started conversing, you’d share a ‘surprised on the first date story, recapping the details of big misses. I laughed along with ‘surprise’ first date stories at the time, the online version of the comparison game that’s so prevalent in social media today.

Marketing skill: The importance of being authentic online and avoiding comparison.

Relationship Building

While that first date can indicate an initial mutual attraction, you quickly realize you need a few more dates to dilute the awkwardness of that first impression. Or if you had a solid first reaction, you used the following few dates to see if that marathon make-out session was as good as you remembered.

Over the next few weeks, as you start doing things together, you quickly determine if you have the same common interests declared before you met. This is when you can tell if they ever had fun before they met you, have hobbies and interests, or have ever walked anywhere, much less on the beach.

If you make it a few months, you are now dating, and as a woman, you start to ask yourself more significant questions about the future. If you’re taking notes, it’s crucial never to acknowledge that you are dating or ask questions about the future out loud. Unless, of course, you’re ready to end the relationship.

It was also when the initial excitement of the relationship would wear off, and you’d get to the good stuff. As they revealed more about themselves as the relationship progressed, you would start to see if their actions lived up to their words.

Here are some of the real-life things I learned about people I dated:

  • The guy who, as it turned out, didn’t like dogs was rude to wait-staff and was overly judgemental about the parenting of my teenager (he never had kids).
  • The guy who ditched me on a Friday night to go to a concert then lied to me about going and let it spill accidentally when we were out with friends (busting himself about unnecessarily lying).
  • The guy who loved hanging out at my house, traveled for work all the time, and finally invited me to his home a few months into the relationship, which looked like an episode of hoarders. (Too much revealed here to sort out).

During this point, I’d intentionally spend some time away from the relationship and get honest with where it was headed. If the future didn’t look bright, I like to think I attempted to work on the differences, but in most cases, I ended it rather abruptly.

There was that 'Pile of Men' waiting after all.

Marketing skill: Identifying ideal customer psychographics, decision-making, and pivoting.

Happy Ending

My latest round of ‘do-over’ in the relationship game happened in 2015.

It was on the heels of my second marriage ending (don’t judge me). This relationship started with an eHarmony introduction, advanced too quickly to marriage, and ended after much careful thought, fueled by a heavy dose of marriage counseling.

There is a lot to unpack there, but rest assured, I came away with increased self-awareness, a drive to make more meaning out of my life, and a very useful stack of books on relationships and love.

During this time, I started to get serious about my entrepreneurial journey, mainly as a side hustle. I had bills to pay, after all. I didn’t even think about dating, and as I continued to work on my self-awareness, I started to visualize my soul mate.

Marketing skill: Goal setting, aligning your path with your goals.

Eventually, my thoughts made me wonder if it was time to return to the dating game. But this time, as tempting as it was, I didn’t return to the ‘Pile of Men.’ It was time to practice my newfound self-awareness about relationships and love.

I confided my dating readiness to my sister on a visit, and soon we were setting up a ‘Plenty of Fish’ profile.’ Letting your sister write your dating profile after you’ve had a few margaritas is never a good idea. There’s that temporary lack of judgment fueled by a few drinks.

My sister, who had 25+ years of a happy marriage, was enjoying her front-row seat in online dating. She was winking at men on my behalf left and right. All while we were debating whether or not the burly biker dude had a soft side or not.

I distinctly remember my sister being astounded when learning that there was one man for every 10 women over 50. It didn’t matter where that stat came from. The idea of ‘Piles of Women’ out there prompted her to call her husband and tell him she missed him.

Later that summer, I had friends at my mountain home for the weekend, and we started talking about online dating. It’s so terrifying for people in a secure, long-term relationship yet they’re willing to offer the opinion that there are great men everywhere you look.

We went to a festival the next day, continuing the debate about the available men everywhere, when a handsome man caught my eye in the beer line. I immediately checked his ring finger to see if he was married. So far, so good. Time to scheme how I could get his attention.

I poured on the charm, and before I knew it I was on a first date with what would become my true soulmate. The initial jitters dissipated quickly, we had a fantastic courtship that transitioned into a fulfilling, happy life together.

I met my soulmate offline, in a beer line. That’s the ending to my relationship journey that none of my friends or family could predict.

Marketing skill: Commitment, self-awareness, and life-long learning.

Lessons Learned

Thanks for following along as I reflect on my personal journey to find my soulmate. As you can see, there are true correlations to the entrepreneurial journey.

  • Both require putting it all out there, sharing the best of you while hoping you’re attracting the right people.
  • You constantly unveil new paths, trying to anticipate where they may lead while listening to your gut so you can stay true to yourself.
  • You persevere, weathering the bumps along the way and focusing on why you're driven to keep going.

The layers of complexity that exist in today’s world are mind-boggling. The connections you make on social media, video, and other nuanced ways of communicating online can be challenging to navigate.

But in the end, as you can see, in the relationship and entrepreneurial journey, it boils down to the belief that one simple connection can make every step of the journey worthwhile.

Jan Golden is a creative entrepreneur and founder of Age-Friendly Vibes, a stationery brand focused on bringing awareness to ageism.

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