Midlife Dating Podcast

EP 28 - Common Sense Dating Guidelies 1-5 for Gen X & Baby Boomers

• Paul Nelson • Episode 28

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Highlights for this episode:

Paul reviews the first five or over 30 Common Sense Dating Guidelines for the Gen X and Baby Boomer generations. The guidelines coalesce around the limited dating options these generations had in their youth compared to what is available today. Combining our life experiences with new dating tools, such as online dating, allows us to avoid the same embarrassing slip-ups we made in our youth. 

Guidelines in this Episode:

  • Thou Shalt Not Fish Off The Company Pier
  • Thou Shalt Not Fish At Thy House of Worship
  • Thou Shalt Not Flirt With A Friend’s Partner
  • Thou Shalt Not Date A Friend’s Ex
  • Thou Shalt Not Date A Friend’s Sibling

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EP 28 Common Sense Dating Guidelines 1-5 For Gen X & Baby Boomers

The transcription below is provided for your convenience. Please excuse any mistakes that the automated service made in translation.

Introduction

Paul Nelson: Midlife Dating Podcast, Episode 28, Common Sense Dating Guidelines 1 5.

Now, as we explore Guidelines 1- 5 in this episode, here are some of the things we're going to learn today. First off, why us Baby Boomers and Gen Xers have the benefit of hindsight and life experience. And that life experience reveals to us that the more things change, the more they stay the same.

We're also going to learn why, in order to avoid making the same mistakes in dating, we need to update our approach. We'll also learn why online dating is an excellent tool for our age groups to have in our dating toolbox and why you should embrace it as a portion of your dating plan. Also, a little bit why on advice for millennial dating coaches should be taken with a grain of salt, and keep in mind that the internet is filled and jam-packed full advice for millennials, and we'll go further into that here shortly.

If you like what you hear, please take a moment and click on the subscribe or follow button. I don't want you to miss out on making your date nights more memorable. So, now, 50 Daters, let's start turning those dating busts into dating bests.

Potpourri Segment

Paul Nelson: Now, I'm going to review some common sense dating guidelines that are a combination of lessons learned from life experience I accumulated going back through my high school days.

Now, I offer these guidelines as a quick look back to what we Baby Boomers and Gen Xers started out with. It will become obvious that the additional optional tool of online dating allows us to avoid repeating many of the same mistakes we made in our teens and 20s. For every one of these guidelines, I'm sure you'll know someone that bucks the odds and makes it work.

So please understand that these people are the exceptions that end up working maybe around five or ten percent of the time. My goal is to paint awareness of what it takes to put you in a position to be successful in online dating and help steer the odds in your favor.

Thou Shalt Not Fish Off The Company Pier

Paul Nelson: Let's start with guideline number one.

Thou shalt not fish off the company pier. In other words, no dating coworkers. I have some lessons from this experience. For me, this began when I worked, uh, in restaurants, dating waitresses. I met my wife and now ex-wife at work. We worked in different departments and crossed paths in the hallways. It felt normal at the time because, because, other couples at the same place of employment where we were at were doing the same thing.

There's a story here. I was working at this tax processing company in Southern California in 1989. We processed tax returns for all kinds of accounting firms in the SoCal metro area. This was this, and this processing company was on the cusp of becoming a dying legacy business as TurboTax had recently become available to the masses, and more and more people could do their own tax returns independently on their PCs, including those from some of these accounting firms.

So I was working these long 12 and 16-hour days and dating my girlfriend at the time, whom I met at the tax processing company. We both, of course, both met on the job. We were seeing each other at work on breaks and at lunch, and we were also spending evenings together outside of work. Later, I learned that there were other couples that were doing the same thing, spending long hours working together, and also a lot of time together away from work.

At the time, this seemed all rosy on the outside, seeing, these other couples in relationships at work.

But I later learned that this wasn't as rosy as it appeared, as they were spending a lot of time together at home, and at work also. 

Anyway, this company attempted to adapt to the times. Everything up to this point was processed on an IBM mainframe, which worked almost flawlessly. To modernize, they went all in on setting up this PC network. Of course, they were in such a rush that they never tested the PC network. All the software that was being written at this point was for the PC network and not for the mainframe.

I worked in the data processing department and I got, I got to witness this slow-motion train wreck firsthand. First, the PC network failed due to these long cable runs, so they had people literally running from one end of the building to the other with floppy disks to transfer data in their rush to set things up.

They did not create a tracking system to see where any of the tax returns were at any point in the system, from the beginning at data entry, all the way to the end, where they got printed. The mainframe had this tracing system and went on to process refiled prior your tax returns at this point in time without a hiccup

Tax return processing is very seasonal. The company went from 30 people off-peak to approximately 300 plus during the peak of the season.

What I'm getting at and what I'll get to my point here in a moment is the PC network basically failed and never worked correctly. They never wrote any parallel software, for the current tax year on the mainframe. So they invested all in on the PC network, and the PC network quickly deteriorated into a complete non-functional mess and never recovered. In an attempt to fix the mounting problems, the executive team literally lived around the clock putting out fire after fire. As these accounting agencies that submitted their returns to them were unable to get their completed returns out of this PC network black hole.

It was so bad that the executives had a motor home in the back. Parking lot where they would go sleep or have a drink after a really bad day, which was literally every day during that tax season. I digress here. My main point here is that my girlfriend and I were literally spending 18 to 22 hours a day together on and off at work, and this was not healthy.

We ended up dodging a relationship bullet. Because the company ended up closing its doors shortly after April 15th, our time together after that became more balanced. However, this ended up only being a temporary silver lining. 

 We ended up both getting different jobs. And I started a business shortly after that. My wife got a job working for a company that specialized in four-color process for offset printing.

The reason I bring this up is this is another analog process that would not survive the advancements in digital printing. And the company she worked for went out of business a few years later. And she came to work for me, which was going to be temporary, as she was looking for another job. That turned into a six-year search.

And seeing each other constantly at work and at home on the weekends, you know, eventually chipped away at our relationship. And resentment crept in, and the damage was done, I think, within a few years at that point in time. And I learned the hard way that what starts out as a great relationship can eventually fall apart when you spend way too much time together and fusion sets in.

Let me talk about Fusion for a second. Esther Perel's book, Mating in Captivity, is a great book regarding how the dynamic between a couple changes when they spend too much time together. And the two terms that she talks about are "Fusion" and "Differentiation." I don't hear these two terms very often.

Basically, Fusion is when a couple spends too much time together. So much so that they lose who they are as individuals in a relationship and cease most of the activities that initially attracted them to each other, outside of the relationship. Both give up on these important things in their lives and expect the other person to fill that in.

So they just basically fuse together, and this creates neediness, dependency, resentment, and boredom. Differentiation is the capacity or discipline to maintain who you are as an individual, in a relationship, when you're naturally compelled to adjust to please the other person. Now, understanding Differentiation is the understanding of balance.

It's maintaining who you are as a person outside of the relationship. Let me give you a couple of examples of this balance. When I was in high school and just out of high school and junior college, I was a car guy. I had a '71 Mustang, I had a '69 Mach 1 also. I hung out with a bunch of car guys. And there were a bunch of other, these other guys had their cars, and some of them would start dating these gals, and they would just totally fall in, head over heels in love with the gal, and they would sell their car.

And then they just went into the full family mode, you know, this is like two years out of high school, went full family mode. Stopped doing things with us as a group. Basically, cut off their social circle and went all in. Sold their car and started a family and then within two years they were basically broken up.

Because Fusion took place, this is an example of Fusion. What he did in the social circle, his car, and his passion for his car, and all the work that he did to it are what made him attractive to the gal that he was dating. And when he gave those up, I have another story that's similar to this. When I lived in Denver, Colorado, I played in several bands.

One of the bands I played in, we had this drummer. He was a really good drummer. And we really started to gel. But he started dating this one gal. And within a few weeks of dating her, he started missing rehearsals. And then stopped coming to rehearsals and quit the band altogether. And then we had to find another drummer, but we kept up with him and what he was doing.

But he just isolated himself with this gal that he was dating. He fell head over heels in love with her. Well, they broke up within three months. And why was that? Well, it was simple because she was attracted to him because of his drumming capabilities and the activities that he was doing as a drummer.

That's what made him initially attractive to her. And he gave all that up and went all in on the relationship. There was no balance. No differentiation. He didn't try and keep and establish things with the band. Those activities that made him an interesting person to her, he basically cut all those off.

So some of the key risks here in dating a coworker are office breakups. When they happen, they can turn into daily awkward encounters, and I've been guilty of this in many cases. So I've experienced it, as I know many of us have also experienced this firsthand. I've also mentioned on the podcast that the reality is when you get out there and date, you're going to learn that 8 or 9 out of every 10 that you meet online are not going to be a realistic compatible match when it comes to dating.

So in my dating experiences in my 50s, as a side note here too, I met several women that started a business together with their now ex, and they still work together every day. Want to talk about awkward? Not only is that awkward in a dating perspective, it's not really that attractive. Why is that? Because you just never know if they decide to rekindle their relationship.

And that possibility is always lurking in the background and you just make it cut loose and never know. Now, millennials are going to give you some really good dating advice, or they're going to think they are, when it comes to dating a coworker. They're going to say, hey, it's fine to date a coworker.

Here's some great tips on how to properly do it. And while their process may be sound, [00:13:00] it's still not a good idea because it lacks life experience. The life experience that you and I have to go with this advice. Because we all know what eventually happens when you date a coworker, you end up spending too much time together.

And when you do break up, and it doesn't work. It's just going to be awkward at the office. For us baby boomers and Gen Xers, there is a risk in retirement also. Too much shared time together can also strain solid marriages or solid relationships. So when a couple is both retired together, you're spending way much more time together and Fusion can take place.

So you need to have activities that give you time away from the relationship to prevent Fusion and maintain balanced Differentiation. So when it comes to online dating versus dating a coworker, online dating wins every time on this. Why? Well, because as we've talked about, the vast majority of the time, things will not work out.

Just look back at your dating history that us Baby Boomers and Gen Xers have. What's great here is, online dating helps you avoid Getting into a situation where you have all the awkwardness of dating a co worker and it didn't work out. 

Guideline #2 - Thou Shalt Not Fish For Dates At Thy House Of Worship

Paul Nelson: All right, guideline number two. Thou shalt not fish for dates at thy house of worship.

Yes, I know I'm going to get some blowback from this. This is very similar to dating a coworker. Even though having a shared faith no doubt increases your odds to a minor extent of potentially making things work. As I mentioned in guideline number one, the reality is most people you encounter, even meeting people in a house of worship, are not going to be suitable dating or relationship partners.

You gotta ask yourself, is the potential for an awkward worship experience worth it? This would be an awkward weekly experience that you're going to go through. You're going to meet every Saturday or every Sunday or whatever at church. It could get awkward if it doesn't work out. And again, most of the time it won't.

And there are some great alternative strategies to taking this path. You know, 30 years ago, when we were in our 20s and 30s, this was a path to take. There weren't a lot of other options. But I'm going to talk about the great option that you have available today. And that is online dating comes to the rescue again.

Platforms like JDate offer great opportunities. People have shared faith to get together. Also, expand your horizons by attending services at similar houses of worship outside your current social circle. Meeting other like-minded singles this way makes more sense in that if it doesn't work out, again, most of the time it won't.

This allows you to bow out without the weekly awkwardness. If it does work out, you can slowly integrate those worship services together. 

Guideline #3 - Thou Shalt Not Flirt With A Friend's Partner

Paul Nelson: Alright, guideline number three, thou shalt not flirt with a friend's partner. You know, this is like performing a high wire act without a net, a tightrope of potential disrespect for your friend.

I've had many personal experiences with this, and I dabbled with this back in my twenties on several occasions. My flirting experiences were pretty worthless, but nevertheless, I still tried this. It was easy in many aspects back at that period of time because I knew whatever buddy I was with, I knew his girlfriend.

I'd been introduced to her. So this played out with several buddies. I would flirt with his girlfriend just playing around. I did this with several buddies over a decade. And all it got me was the stink eye from my buddy and not being invited to any more parties. Or, you know, one of the additional negative bonuses in this also was there were times when I was actually dating someone at the same time, and I would meet my buddy and his girlfriend at a party, and I would flirt with his girlfriend just a little bit, and all that did was piss my buddy off.

And then also, piss my girlfriend off at the same time. It wasn't worth it. So part of the problem here was not understanding where the nuances were and where the lines should be drawn when it came to flirting. You know, I eventually learned that Good friendships were hard to find and that flirting with a buddy's girlfriend was a really bad idea.

Because it just has many potential risks of damaging your friendship with your buddy to some degree, and additionally causing some damage to the relationship between your buddy and his girlfriend. This pans out to women, too. I'm looking at this from a men's perspective, but this can also be flipped 180 degrees from a gal's perspective.

So the key takeaway here is I learned to focus on strengthening my friendships. I could, that way I could sleep better at night, and I didn't have to look over my shoulder if I pissed my buddy off too much. And online dating, I'm going to keep bringing this up because this is the greatest tool. Online dating is a great place to practice your flirting skills, figuring out where the line is without the potential sacrifice of a friendship.

Or causing negative vibes in a relationship. If you really want to practice your flirting skills, Speed Dating. I'm going to have an episode on that one coming up. It's, Speed Dating is just totally awesome for that. For a variety of reasons. I could go on to that for 20 minutes. I digress. 

Guideline #4 - Thou Shalt Not Date A Friend's Ex

Paul Nelson: Guideline number four. Thou shalt not date a friend's ex. Now I have lots of small-town experience on this. I went to a high school in a small farming community in Minnesota in the late 70s. The dating pool there was one high school, so it had a small dating pool. It was like a kiddie pool, a kiddie pool. Very small and crowded.

There just weren't many options, but this was normal. We didn't know any better. And there just wasn't any, again, there weren't any other options. Although the dating pool did expand somewhat when I was going to junior college there, at that period of time, but not much. Anyway, uh, during high school, I personally participated in dating ex-girlfriends of classmates and friends.

I'm going to give you one story that taught me a hard learned lesson. This is the story of John and Mary, and obviously, the names have been changed to protect the family's privacy. John and Mary have been going steady, and they've broken up. Probably steady, I would say, uh, six months to a year. Now, John and I were car guys, and in high school, there were three basic crowds.

You had the freaks, the jocks, and the motorheads. The freaks were the ones that got high. The jocks were obviously the athletes. Then you had the motorheads. The motorheads were us guys that were really into cars and we tweaked and modified our cars and had a lot of fun with them. And John and I were part of the motorhead group.

About a month after the breakup, I ran across Mary at a party. And I ended up asking her out on a date, and we went out on a few of them. Well, turns out John is the jealous type and approached me one day and warned me, to say, that I should be staying away from Mary, and if I didn't, there would be consequences for it.

He said, if I can't date her, nobody can. And this kind of caused this really strange rift within our social circle, kind of a division of the group of car guys. At that point, I told John, you know, you don't own Mary, and since you guys are no longer going steady, that you have no claim on her. And I thought that would be that.

Well, after another date, John accosted me at my locker at high school, in between classes, in preparation to demonstrate what those consequences were going to be. He began to get violent, and I got lucky as a teacher happened to be walking by and restrained John. John had held me pushed up against the locker and had reached back to let me have it with a fist, and that's when the teacher intervened.

And due to what took place there, John got suspended, and I did not. Shortly after John returned to school from his suspension, I asked for a truce. And met him in the parking lot during study hour, and we talked. I told him, John, I give up. You win. I won't date or contact Mary anymore. And in exchange, all I ask is that you just leave me alone.

And we agreed. At that point, I cut off all contact with Mary, and I moved on. A few weeks after that, news of a tragedy struck the town. John and Mary were both killed in a car accident. Nobody knows for sure if they'd gotten back together or not. They were in John's car as he was driving around the lake by our town, and apparently, he was going so fast that he lost control of the car at the spot where there was a lake on both sides of the narrow road, and he lost control and went into the lake, killing both of them.

It was a real tragedy. I still remember the funeral to this day, what it was like. Lesson learned. Dating someone's ex that you know has the potential to create a really messy situation and is not simply just not a good idea, it's a really bad idea. That's what I took away from this. And from that point on I never dated anyone's ex that I knew.

In high school, I also watched other classmates cycle through these same types of dating situations. By the time graduation came along, a lot of my friends had sacrificed many of their friendships with other guys, dating other guys' exes. It was just this crazy, circular firing squad that just was not worth it.

First takeaway from this is that I had a life lesson on attempting to date in a very limited dating pool. If I had lived in the St. Paul-Minneapolis area where I moved there from, our family did, or even in neighboring Sioux Falls, South Dakota, near where our farming community was, I could have dated outside my local dating pool and eliminate many of these issues.

Dating outside your social circle provides a soft landing when Things don't work out, and as we learn, most of the time it won't. I could have easily created more early self-confidence by knowing I could make dating mistakes without affecting friendships. I'm gonna cycle back here to online dating again, because this is one of the many positives of online dating is the ability to date outside your peer group and avoid many potentially messy situations.

Guideline #5 - Thou Shalt Not Date A Friend's Sibling

Paul Nelson: Guideline number five. Thou shalt not date a friend's sibling. Personal story here. Here is another dating faux pas with the potential of creating a lifetime of awkwardness, especially if you live in a smaller [00:24:00] town or maybe even, in some aspects, live in a small retirement community for us baby boomers.

Again, let's acknowledge the reality that most of the time, romantic relationships don't pass the test of time. I'm going to give you a story when I initially moved to this small town from the Minneapolis-St. Paul area. At church, I met a family there. Two brothers, two sisters. One of the brothers was in my same grade.

They invited me out to the family farm, where I helped them out on many weekends and developed a good, fun relationship with them and their social circle. Living in that community was very difficult at first because everybody had been born and raised together, and it was difficult to kind of get into the clique, and this was a welcome relief for me.

To kind of get to meet some of the people there anyway, one of the older sisters, she was like 2 years older than me, and this family would always flirt with me. It was always very friendly, and she was flirting with me to be friendly, but I really hadn't realized that at the time. And so, without even talking to her brothers about it, I asked her out on a date, and she politely turned me down.

I was so embarrassed by this that I stopped doing things with the brothers as friends. I stopped doing things with their social circle. This is purely out of teen embarrassment. So I sacrificed the potential of a good friendship even though nothing bad happened. Just pure teen embarrassment. So some of the risks of dating a sibling are the potential fragile tensions with the rest of the family, especially if it does not work out, and like I've talked about so many times, it usually won't.

You've got to ask yourself, is the embarrassment worth the risk? And the key takeaway here is that in our youth, in many aspects, and the same applies today, that dating your friend's sibling has too many downsides, as it usually won't work out. Guess what? What's the fix to this? Online dating. It's a great alternative to completely avoiding any situation like this.

Lessons Learned

Paul Nelson: So let's talk about some of the lessons learned here. Some real-life wisdom, if you will. The guides that I'm talking about here, they're not just theories. They're real lessons. I learned through trial and error at the cost of bruised and broken friendships. And so let's review here. 

Dating coworkers is not a good idea. Dating directly within your house of worship? It's also not a good idea for the same reason dating a coworker is not a good idea. And again, I know I'm going to get blowback from this. Also, flirting with your friend's partner has way too many drawbacks. Dating a friend's ex or a friend's sibling has got way too many complications.

So the key point here is that online dating is your ticket to a bigger, more dynamic dating pool. It's the best tool for avoiding unnecessary social complications and needs to be an option in your dating toolbox. As I expressed at the beginning, you're always going to be able to find exceptions and I'm not trying to be negative, I'm just trying to be realistic here.

However, things not working out most of the time, generally, is the rule when it comes to romance. All you have to do is look back on your dating life experience to know what I'm saying here has merit. Enabling you to use online dating tools to tip the odds in your favor is what we're all about. The entire Gen X and Baby Boomer community, we didn't have online dating as an option in our youth.

We are so lucky now. So please use this great tool to meet other singles in our age group who are not available to us in the not-so-distant past. It gives us options we never had before. It allows us to avoid potential strain, embarrassment, and potential exclusion from our current social circles. I also want you to be aware of current online dating advice from the millennial generation.

While they provide good advice on using modern dating tools, they lack the life experience of what happens over the long run.

Outro

Paul Nelson: Okay, guys and gals, it's been fun, and I look forward to being with you on the next episode to take your dating experience from a bust to a best, and that's a really good place to be.