Mastering Online Dating: Financial and Personal Insights




online dating lessons learned

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It is no surprise that there are many different opinions and lessons learned when it comes to the topic of online dating.  Toss in the topic of personal finances with online dating, lo and behold you have an award winning Comedy Central headline!

They are two very different things; online dating and personal finance.

Personal finance can be thought of as very distinct boundaries or rules dealing with the relationship a person has with money.  Some people have laxed boundaries or no rules when it comes to money.

online dating lessons learned

On the other hand, online dating is a wildcard.  It is the wild wild west of dating and very different than traditional dating tactics that our parents and grandparents underwent.

It used to be that you would have to actually call a girl up on the phone, court them, and communicate that way.

Today it is different.

Swipe left…swipe right…swipe left.

OMG…we match!

Star that as a “VIP match” meaning you are the ultimate match over all of my other matches (since I can only give that designation out once every 24 hours)!

Additionally, you get a star so you know that!

A few years back I found myself re-entering the dating world after decades of being absent.  I can remember back in the day there was something called AOL Instant Messenger, which at the time, was the cat’s meow of online communication.

Today who even has an AOL email address?!  Seriously do you even know anyone?

Over the course of 18 months, I basically spent around $2,500 in my estimation for 42 dates.   

Although 42 dates sounds like an awful lot, on average, it was only 2-3 a month for the time period.

All of these unique women came from all different walks of life.  Some of their professional backgrounds were:

  • Nurses
  • Police Officer
  • VP of a Nonprofit
  • Hospital Administrator
  • Housekeeper
  • Bank Teller
  • Dental Hygienist
  • Administrative Assistant
  • Teachers
  • Realtor
  • Veterinarian
  • Dentist
  • Public Broadcasting Spokesperson
  • Optometrist Assistant
  • Business Owners

Most of these dates were  similar to my situation; divorced with kids currently in midlife era.

A lot of them played an important role, more than they realize, on lessons learned of how I thought about personal finance as it relates to a partner in my life moving forward.

Over the course of those 18 months, there were a lot of lessons learned that related to online dating, midlife, financial freedom, and personal finances.

Below are some of those lessons learned.

Lesson Learned #1: Online Dating Varies From Traditional Dating

I do think online dating does get a bad rap.  For the most part, most of my experiences were very positive.

I can however understand why people say online dating is horrible.

You do have to take online dating with a grain of salt.  That in and of itself was a lesson learned.  It used to be that you would go to a bar or some type of social setting with your friends and maybe look for a potential mate there.  And that’s not to say that that doesn’t happen these days.  It just doesn’t happen AS MUCH.

Why Can’t You Meet Someone Outside Of Online?

My view is that it has a lot to do with the society that we live in and social instant gratification.

When I say social instant gratification, I don’t mean in a physical sense.

Think of somebody who may not have the best credit and has a hard time not making impulse purchases.

Online dating is no different in the sense that we want to share our lives and experiences with other people and we want to do that instantly.

It’s an instant and immediate addiction to be in a relationship just like the keeping up with the Joneses lifestyle and the purchases we make to live that lifestyle.

With online dating, we can potentially shop for a match much quicker, faster, and precise, (well according to behind the scenes algorithms of online dating apps I suppose) than what we could by chance of running into somebody not online.

My friend Sasha at wrote a post about dating tips for single parents that pertain to online dating and advice.  

Online Dating Apps

Dating today really is done through online dating apps.  According to Statista, online dating in the United States is becoming more socially acceptable.  Roughly 19% of US internet users are using dating sites and dating apps according to their study.

This comes as no surprise since everything else humans do in their daily lives is all done online.

online dating apps

Those tasks include things such as increase retirement savings, paying our bills (we don’t go to post offices), booking vacations (we don’t use travel agents) and shopping in stores (we all shop on Amazon).

Looking for love and dating is no different.

It is through the use of online dating apps that I began my 18 month journey.

There are so many online and mobile dating apps available now a days it was a bit overwhelming which to use.

I selected a couple apps, completed a brief profile, included one or two pictures of me highlighting my best features, and I was off.

Lesson Learned #2: The Good, The Bad, and The Ugly

dating activities

Early on, I was not very good at dating.

Remember I hadn’t been on a date in over 20 years so the whole concept of looking at pictures and trying to decide if you would like to meet somebody or not was very different.

Then there was the whole dating etiquette.

Was I supposed to bring flowers for somebody I had never met in person before?

It was a very steep learning curve in the beginning for me.

I also discovered early on not all pictures are created equal.  This was a big lesson learned. 

The deception of those pictures as well, especially the elusive “heavenly selfie” as I refer to it, was clearly present with some of my potential matches.

The “heavenly selfie” is the picture that is taken from high up above looking down at a person complete with a couple picture filters as well!

And on top of that I recall one particular picture where my date was in a Halloween costume as well dressed as a black cat with whiskers!

Yes it was very difficult to determine if I would like to go out on a date with a black cat. It was a lesson learned of really going out with a date for WHO they were not WHAT they were.

Now there were a couple dates that I had where the picture was no resemblance to my date that showed up.

Or it could’ve been the picture was from so long ago that my date had changed so much that I didn’t really recognize her.  It was a good lesson learned of not judging a book by its cover.

The Bad Date

This elusive heavenly selfie happened to me with one of my dates at Tim Hortons.

My date showed up and there was a significant appearance difference between the picture and in person.

This probably was one of my worst online dating horror stories.

However being the gentleman that I am, I stuck it out for an hour and a half and pretended to be interested in the salvage car title business.

I heard all types and kinds of stories pertaining to salvaged car titles and how her family had run this business and made tons of money with car titles.

I’ll probably write a post about it at some point in my blogging career.

As fascinating as that was learning about a potential side hustle down the road, this date was a bust.

my grandpa

Then there was a date that showed up in a 1989 Burgundy Red Mercury Grand Marquis!

For the most part I tried not to stereotype, but what kind of single woman drives the same car that my grandfather drove 20 years ago?!

The Good Date

Another one of my early on dates involved having lunch with a woman who worked for public television.

This sort of restored a little bit of faith to me on the whole online dating app idea.

  • Did the pictures online match the person in real life? Check
  • What about most of the profile information being somewhat accurate? Check.

Things were off to a great start.  I can say that I was genuinely interested in the background of her life and what she did.  At the time Downton Abbey was really big on TV and ironically I was actually a big fan of it.  I mean who doesn’t want to watch a show about the aristocrats living in an enormous castle?!

We had many conversations where we discussed all of the ins and outs of Downton Abby.

I was actually supposed to get some Downton Abbey bling from her, but unfortunately this never materialized.

We did spend some time talking about marriages and divorces along with children.  This is common with divorces as I learned to share these types of war stories.

The Drunken/Ugly Date

One of my most memorable dates that I can remember involved meeting a woman at a restaurant.

Now, this woman liked to drink.

Don’t get me wrong, I went to the Big 10 school and for those that know me know that I as well liked to have a good time.

However when you’re in your 40’s, things are a little bit different.  I had graduated out of that type of behavior for the most part.

My date however was able to continually pound rum and cokes down; 3 of them within the hour!

During this time I also learned a lot about being Jewish, growing up Jewish, and living in the Jewish culture.  So it was educational in a sense and I consider that a positive.

Another lesson learned was how she spent a lot of time around the holidays looking for this matzah bread.

However after her fourth drink, “check please.”

It was a $58 experience.

Lesson Learned #3: Some Were Living a Jones Lifestyle

A lot of my dates were living a Jones lifestyle.  Sometimes it was apparent right off the bat, but other times it was a little bit more hidden in the details.

One of my most memorable experiences over these 18 months involved a nurse.

What made this experience memorable were all the past similarities my date and I had in common.

  • She had two boys…I had two boys.
  • Her vehicle was a Dodge Caravan…I had a Dodge Caravan.
  • She had a Pulte built house…I had a Pulte built house.

In fact her house was the exact same floor plan as what I had for the last 8 years, except the house was reversed.  So when you walk in her front door, her garage was on the left whereas in my old house, mine would have been on the right.

This really tripped me up for a while.  It was like I had somehow stepped back into my old Jones married lifestyle, but everything was reversed.

I joked with some of my friends in real life (IRL) that I had gone back into the bizarro world!

It would be like going to the upside down parallel universe in Stranger Things.  That’s how creepy it was!  I mean I wasn’t scared of mind flayer coming out but, it was this weird feeling I got every time I went over to that house.

Even though the floor plan was reversed, it still triggered emotional memories for me that I had of being in my own former house.

As our time together progressed, I learned more about her past family life and the struggles they had financially.

Financial over-commitment was a common theme in my past life.  And it was also a theme in hers as well.

The only difference was I made a conscious choice to leave that lifestyle.  My date wasn’t there yet.

Lesson Learned #4: Some Were Financially Burned

Sometimes it can be fun to tell war stories, but other times, not so much.  I heard a lot of stories about how my dates had supported their spouses at the time financially.

Some of them helped pay their spouses student loans off, while others were working jobs while their husbands were going back to school. Some got burned on electric bills. (Know can you put your electric bill in someone else’s name so this does not happen to you!)

And then there were a lot of stay-at-home moms who managed kids and households while their husbands worked and traveled.  Their husbands were absent a lot from the family life.  I heard these types of stories a lot over the last 18 months.

Some of them had extremely large divorce settlements.

Getting divorced financially is a lot like starting over.  Basically everything you have earned, saved, and worked for since being married, gets split down the middle.

You have to restart your financial life.  It’s a financial do-over.

Another date I recall had to deal a lot with the gambling debt of her spouse.

That took a significant toll on her as well both financially and mentally.  I could definitely relate to some of the stories and personal experiences I heard.

Lesson Learned #5: Serial Daters DO Exist

Over time, I came up with the term “serial dater.”  These would be the dates I had that were basically just looking for somebody to go out with and pay for meals and drinks.

dinner date

I could eventually spot a serial dater on date number one.  These serial daters would basically tell stories of themselves or about themselves pretty much the majority of the time.  There was not a lot of two-way interaction.  I could just tell that they were looking for somebody to go out with on a Friday night and pretty much not anything more.

However, there were exceptions where a serial dater became evident, not just on the first date, but also after spending a significant amount of time together. 

I initially didn’t pick this up on my radar.

There was one woman that I did spend significant amount of time with (in the online dating world a couple months is significant time).  She and I had a lot in common.

She had a great career…I had a great career.  Her divorce circumstances were similar to mine; having her lawyer on speed dial.  She made all the financial sacrifices in her marriage as did I in mine.

So it seemed like we were cut from the same cloth and, in theory, we should get along great.

And we did for the most part.

We went on great dates.  We had hundred dollar dinners, did activities together, and hung out on the weekends and took our kids to kids eat free restaurants sometimes.

The problem that developed had to do with financial compromise.  When you have two people that went through the exact same financial struggles together, there is the possibility that it’s much more difficult to reach financial compromises on things because of past experiences.

As such, all of our time together which was not an insignificant amount of time, I pretty much covered all of the expenses on our dates.  Don’t get me wrong I didn’t have a problem with this but, after a while it started to weigh on me.

It became more clear over time that she would be less likely to financially compromise with a partner.

She had made comments to me during our time together that she would never support a man again financially. 

That was even clear on the dates that we had!  The only thing that she did cover for me were 3 bottles of water for my kids that she purchased while we were doing an activity once.

That was it.

So past financial experiences and financial compromise were lessons learned that I started to consider more going forward with dates. 

Lesson Learned #6: There Was No Communication About Money

The number one complaint I heard from my dates about their former spouses was that they were just not on the same page with communication.

Most of their marriages had ended because of communication issues and often times their poor financial conditions were the result of not communicating about other things.

Now it’s not like I showed up on these dates and requested FICO scores or anything like that.  Some were just willing to share more than others were about their issues.

Dating after going through a divorce can be a form of therapeutic entertainment.

Especially if you are going on a date with somebody else who has been divorced.  You can sort of get perspective on things.

My conclusions were that family finances didn’t really rip most of these marriages apart, rather it was communication in general about other issues.

As a result of that, sometimes people let their finances go.  Their finances took a backseat to other issues.

There was one date that I met at a restaurant for lunch and she had talked about all of her credit card payments that were coming due!  All of it was a result of her divorce.  To give her credit though, she did arrive a little bit later so there was an element of nervousness and being frazzled.  In that type of situation, anyone can be rattled, so I didn’t hold it against her.

Meeting somebody in person through online dating the first time is a very nerve-racking experience.

Lesson Learned #7: Online Dating Helped Determine My Financial Values

I never would have thought in 1 million years that online dating would actually help shape my financial philosophies.

But it did just that.

great lakes living

Through these 42 online dates, I realized that a lot of my financial values were not in line with theirs.

One of my dates had lived on one of the Great Lakes.  After her divorce, she moved into an exclusive community no longer on the water, however just as expensive if not more.

Now don’t get me wrong there was no question in my mind that she couldn’t afford it, however it really put in perspective the whole “needs vs wants” scenario for me.

Would my date have to stay at her job for decades in order to pay for her house and exquisite property?

More importantly, did I want to be with somebody who has that type of financial commitment in their life and future?  

I had already gone through a suburban utopia lifestyle which I knew for a fact caused me great financial stress and anxiety.

And I knew that I did not want to return to that part of my financial life ever again.

It was a deal breaker in so many ways.

So financial sustainability became an important factor for me.

A lesson learned this time around was to place a greater importance on financial communication and talking about finances with my partner.  That was something that was exquisitely lacking in my prior relationship.

Not having both partners on the same page when it came to making appropriate money choices is a huge red flag.

Somebody that has $20,000 in a bank account who is partnered with someone that only has $500 and is overextended on all credit card accounts, is also a red flag.

Not being on the same page for personal values and family values also affects financial goals.

Lesson Learned #8: Rebound Relationships, Financial Peace, & Applebee’s

Online dating was both a horror story, comical, and yet the one of the greatest things that ever happened to me.

Clearly there were people that were just looking for a rebound relationship.  I encountered several of those dates as well.

Then there was the topic of “ghosting.”  Many times, I was ghosted and a few times I ghosted some.  Then I made the mistake of talking about ghosting as small talk on a date.  This turned out to be a HUGE mistake because my date was scathing mad about this; almost as if flames or laser beams of fire were shooting out of her eyes due to anger!  I received a major scolding from my date on ghosting.

(NTS: Don’t talk about ghosting…we all do it, yet no one talks about it; like peeing in a pool.)

There were also a lot of single moms that were struggling as well to rebuild their lives with all types of challenges; some of those who had special needs children as well.

Since I had pretty much gotten rid of my expensive suburban house and started my journey to financial freedom, I was at a state of financial peace in my life.

I didn’t really want to go back to worrying about finances.

My online dating journey came to an end at Applebee’s of all places.

It was there I met a wonderful woman in all aspects.  There were a couple things that made this date very memorable.

  • We had an excellent rapport and communication about several different areas of our lives.
  • I would be thinking of something to say in my head and this woman would say what I was thinking.  There is such a thing as being on the same wavelength.
  • The third was that our server came a few inches from spilling ranch dressing all over me.  I tried to play it off all cool all Rico Suave-like, but it sucked!

It was at this point I excused myself to go use the restroom.  When I came back, she had already paid the bill.

I never asked, nor did we even discuss who was paying for it, yet she had taken care of it.  This was utterly fascinating and at first I thought it was a joke.  I though I was being tricked into some type of dine and dash situation!

Not that I would have any problem paying, it was just something I really hadn’t encountered in any of my previous 41 dates!

this is us

So if there was ever a shock at all during those 18 months, this would have been it.

This person is my current partner now and we have been together over two years and still complete each others sentences.

During the early stages of my divorce, I had a very close friend who sort of became my divorce sponsor.

He had been through it and everything he told me in his “divorce prophecy” that would happen during the process came true, including him stating “there’s somebody out there for you.”

Ironically, I am now a divorce sponsor for another one of my friends.  It’s almost like the torch has been passed on.

History repeats.

Online Dating Summary

There is no question that if there was ever a time in my life where I would grow more as a person it was during these 18 months.

While some of my experiences were definitely crazy and bizarre, they were also experiences that defined how the second half of my financial life will be.

Every experience I had, in one way or another, played a role on how I think about family values, financial freedom, family goals, and family finances.

It was the best $2,500 I ever spent!

Looking for Financial Freedom?  

Check out our  Financial Freedom Guide:  Financial Freedom Strategies That Work 

About the author

8 responses to “Mastering Online Dating: Financial and Personal Insights”

  1. Lisa Avatar

    What a great story and I’m so glad it had a happy ending! I’ve learned a lot about finances from dating as well. Mostly it’s about judging whether someone will be intimidated by dating a woman who earns more and/or whether someone is going to squander my money away. And y’know, filling all the other criteria one wants in a mate. Your story gives me hope!

    1. Bryan Avatar

      There’s someone out there for everyone Lisa. Don’t give up hope and keep looking! Thanks for writing in.

  2. Abigail @ipockuppennies Avatar

    $2500 for 42 dates? Yikes! I guess this is why I prefer to just meet for drinks. Much lower money commitment. I go by the rule of whoever asks the other person out pays but I should probably offer to pay more. Usually the guy bellies up to the bar and orders before I have a chance though. I did pay for dessert on my last date because the guy had paid for my drink at the first place we went.

    I haven’t learned all that much financially from dates except one guy I dated had very different financial priorities. I know he was saving for retirement (sexy!) but he also likes expensive cars, bought a $300k house and eats his lunch out every day. That said I plan on keeping my finances separate from any future partner so I’m not too worried about it. I do know that one guy I’m seeing is saving diligently for retirement. But I also found out he makes a little more than half what I do so I’m definitely going to need to pay for our next meal or drinks out! He’s covered drinks the last two times so it’s only fair.

    1. Bryan Avatar

      Saving for retirement is definitely sexy! There may not even be anything more sexy in the PF world! Yea sometimes you just have to feel out the whole who pays situation. It’s just another variable in the whole online dating world for sure.

  3. Gwen @ Fiery Millennials Avatar

    I don’t even want to think about the amount of time spent on dates looking for a partner. Notice I didn’t say the money, because as a woman society expects men to pay for the first date. I hate getting trapped into a dinner with a guy who I have no chemistry with, so I usually suggest meeting up for a coffee or a drink first. If that goes well, then we can move on to more time and money intensive dates! Online dating is a real crapshoot but it is all about the numbers in the end. I’m happy you found someone!

    1. Bryan Avatar

      Hi Gwen, Yea I didn’t even address the whole time factor as well involved! Towards the second part of my journey, I did switch up to mainly coffee dates, but some suggested meeting up more for drinks etc so sometimes I just had to go with the flow.

    2. Kayann Avatar

      I really enjoyed reading your blog Bryan! I’m so happy you found happiness and a lady who will have your back forever! She’s beautiful and a great partner wishing you both eternal peace and happiness.

      1. Bryan Avatar

        Thank You!

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