My 4 biggest dating regrets that impacted my life

Everyone is bound to have feelings of sadness, remorse or repentance toward something pertaining to their love life, particularly having dating regrets. I have my own, yet this certainly doesn’t mean I have any regrets about where I now stand or my marriage.

Sure, some may go as far as to say, “Who cares? You’re married and happy, so any regrets you have shouldn’t matter,” or that regrets hold no bearing on my life. But I think we’re misunderstanding something about regret; that it convicts us as in order to change our mind, thinking or way about something. We tend to focus on the fact that we can’t change the past and to just move forward – *no regrets*, we often hear and say.

Here’s the thing: I actually wouldn’t do it all over again if given the opportunity. In fact, I REALLY don’t want to go back and relive it all, only to hope circumstances change or different outcomes when they, ultimately, may not be. In hindsight I’d probably end up with the same regret or making plenty other mistakes, anyway. So it’s more that I’ve acknowledged the lesson learned and greatly accepted this shift in my beliefs as well as the impact it has since had and will continue to have.

Then are we to beat ourselves up about regret for the rest of our lives? No, of course not, though beating ourselves up and feelings of conviction are totally different. That’s not to say I’m not taken back and feel sad or remorseful from time to time; mainly because I am now fully aware of how these dating regrets [choices, beliefs, actions] were more hurtful than beneficial, whereas back then I believed repercussions were inconceivable.

In actuality, my dating regrets have reshaped me as well as transformed my thinking and understanding in such a way that has changed how I view certain things – like dating, relationships, sex, partnership and marriage, in general – though mostly on a personal level (my walk). Alas, these regrets I have may even be deemed controversial today…and because of my very individual and personal journey I’m beginning to see why.

My biggest dating regrets that impacted my life | In actuality, my dating *regrets* have reshaped me as well as transformed my thinking and understanding in such a way that has changed how I view certain things - like dating, relationships, sex, partnership and marriage, in general - though mostly on a personal level (my walk). Alas, these regrets I have may even be deemed controversial today, and because of my very individual and personal journey I'm beginning to truly see why.

My 4 biggest dating regrets that impacted my life


Juggling multiple people at once

Am I saying this is wrong, per say? No, but I guess it also depends on an individual’s heart posture [motives, intentions, way of thinking]. Am I implying that because I juggled multiple people that I did so with ill intent? We have to remember that this can simply mean self-centeredness without direct affliction on another. That said, I wasn’t always being totally honest and forthright when dating multiple people at the same time.

My regret in this case was an underlying fear of rejection or abandonment – I felt a sense of security maintaining some sort of connection with more than one person in the event one fell through. And most of the time, regardless of external satisfaction, this only added more stress.

I also look back and see how I was creating an unfair scenario of comparison between two individuals. Instead of dedicating to one at a time and deciding whether or not we were compatible before moving on, we’re often geared towards a route that is more efficient [rushed, pressured] and effective [timely, calculated] as well as self-convenient [advantageous, favorable].

How has this impacted my life? It’s been my biggest lesson on the real meaning of, “Patience is a virtue.” Dating can be frustrating, and our instinct may be to rush things, create placeholders, limitations, unrealistic expectations and ultimatums against people.

Being patient can mean accepting that things may only take place one at a time or by fully seeing something through before moving onto the next. I struggle with hyper-productivity, taking on too many tasks that remain unfinished and I tend to quickly “give up”/let go/move on when something doesn’t come easy for me.

I *can’t* juggle everything all at once because then my efforts won’t be 100% in it or I will experience complete burn out. I’ve now had to take a step back and realize that IT’S OKAY to focus on one thing at a time and to prioritize my efforts to fewer things – patience doesn’t guarantee checking off all the boxes or getting something done according to my time and my liking.

Not walking away when I should’ve (sooner)

Mostly when I knew it was the right thing to do – I’d tell myself their hurtful behaviors were a one and done. This is not the same as forgiveness or giving second chances. I regret tolerating certain things for the sake of my feelings for them.

Granted, this wasn’t always a negative-case scenario; there were genuinely “boyfriend-material” individuals that I felt close to but had zero romantic connection with, and yet justified staying with them. Therefore, I regret stringing along those longer than I should’ve out of fear of hurting their feelings and that costing me what connection I did have with them.

There were even second chances I took, times I stayed or situations I wrote off that I would never encourage with friends. There’s that struggle to practice what we preach – make it make sense.

There were even times where walking away was literally on the tip of my nose, with the voice screaming at me to see things the right (clearer) way and one foot already out the door, yet I often battled and succumbed to this other voice. It was always tempting and deceiving, and really had a way of making me feel like it had my back though it was only using my weaknesses to gain my dependence.

This voice would have its hand on my shoulder, encouragingly, as it would guide me back down that familiar dark path saying, “But look at the fun you’ll have – you’ll be fine!“, knowing the negative effects thereafter would be continual and lasting.

It really does sound stupid, and there was a point I genuinely thought I was coo-coo for thinking this, but I have never been more convinced that many of us hear and listen to that deceptive yet enticing, regrettable voice more often than not today.

How has this impacted my life? Unfortunately, not walking away from something when I should’ve has taught me self-neglect and to avoid being attuned to how I am feeling (my body, sensations, needs, wants, etc.).

It has also taught me that the goal in life is not to avoid pain – we can’t. Pain and suffering is an inevitable, unavoidable and universal experience, which includes the pain we may unintentionally cause others.

By staying in certain situations with someone as to avoid hurting them, I was ultimately trying to avoid feeling hurt myself, which can actually be selfish and unloving. While we are called to serve others (i.e., in relationships), serving others does not equate to self-neglect nor is serving intended for personal gain.

The Relationship Wellness Journal for Couples | Created by theMRSingLink LLC
The Relationship Wellness Journal Created by theMRSingLink LLC

Dating *casually*

Meaning without marriage in mind (or as the goal). Since that is what casual dating is – without intent for commitment – I did not have any thought or consideration for the long-term, particularly with the end-goal of marriage. And, sure, in high school or college that just wasn’t on my near-future timeline. Otherwise, I probably would have eliminated at least HALF of the total number of people I dated.

But maybe that’s part of the point, because most of my dating regret stems from those I dated casually…not my committed relationships. I had few real, long-term relationships besides my now husband – two, to be precise. Everything outside of those two relationships were pure chaos, and not in a good (beneficial, healthy) way now looking back.

It’s not up to me to tell others whether or not to date casually or to judge those who do, but I can confidently say (as someone who did) that we ought not to by default, and that I advise against it. Why? Mainly because of the lack of or minimal strings casual dating professes while still holding onto the implications of a physical connection. That means casual dating is less about commitment and more about basing connection on chemistry.

How has this impacted my life? Casual dating was a failed attempt of conditioning me to believe it was socially acceptable to have multiple “soulmates” and to find long-term potential without commitment.

“Date as many people as you can!” or “You won’t know until you’ve been around the block a few times,” they say.

The thing is, you do have to *date* to find someone you’re compatible with, but casual dating is dating someone (or multiple people) long-term without commitment. Casual dating, for me, is really about two people simply looking to benefit for an indefinite yet self-appointed time without consequence or consideration for the other. It’s sad, and many will die on their hill justifying it, but that is why commitment is called a Promise and is meant to bring two people together as one to be selfless and serve the other.

With that, I really can’t say I took away [learned] anything from my casual dating experiences like I did my actual committed relationships. And as far as gaining *experience* goes – IM[honest]O – the idea of less is more holds true. The more casual dating *experiences* I had, the more unhealthy behaviors I learned, patterns I continued and enabled, self-control I lost, temptations I succumbed to, poor choices I made, unhealthy bonds I created and overall baggage I ended up carrying through life. Humans are far more complex with a higher morality and are wired for deep, conscious human connection, not a roster.

Sex before marriage

Here we go – the big one – sex before marriage. This section gets a bit particular for me. And while these may not be everyone’s experience or personal beliefs, it’s mine, and they just might strike a cord for some never thought possible. So hear me out.

For starters, youth preaches FOMO/YOLO. I’m starting to think the whole mid-life crisis is either just a farse or is one to thank for the cause. Technology, social media, its advancement and consumerism doesn’t help, either.

This idea of missing out, *living it up while you’re still young*, or YOLO has obviously evolved with the times through subtle differences and trends. Yet sex will always be part of that, and (for me) there came a point in social culture when sex was taking root in social circles pertaining to popularity, commonality, credibility and social acceptability. This began in high school for me, but I fear now it’s much younger.

Dumb and plainly, you weren’t in the *cool* club if you hadn’t crossed that bridge. As for me and my social groups (particularly in grade school/high school) – there was just so much constant subtle and severe pressure surrounding sex, it was almost unavoidable by way of general conversation and being around the same people [friends, groups] day in and day out.

While I would argue that I didn’t give in to that pressure, I still regret not waiting and willfully riding the FOMO/YOLO wave. I don’t regret my *first time* or who it was with – at all, actually. I do, however, regret blindly partaking in this notion that it’s nothing *that* special, and believing that since it wasn’t evident in my social circle.

As a young, dumb teenager my thinking and ways were absolutely defiant, regardless if I still knew and was told (by family, for instance) that I should save sex for marriage. Fact is, I knew I should wait (a part of me probably hoped to) but I didn’t, anyway. As a raging, hot-mess and hormonal teenager and young adult, who was I kidding? Even 30-something year old me probably wouldn’t stand a chance reasoning with 18-year old me.

Still, I regret the influence I allowed lust to have upon my life, and this started much younger than I’m proud to admit.

There’s even the *Test Ride* justification for sex prior to marriage, and yet people still lose their minds over the idea of sleeping with one person (the real version is far more explicit) for the rest of their life. So I think we’ve distorted sex from being special (as in sacred) to being important (as in a *need* fulfilled). Nonetheless, I definitely regret buying into the car salesman tactic.

The Partnership Workbook for Couples | "How to be a better partner" | Created by theMRSingLink LLC
The Partnership Workbook for Couples | Created by theMRSingLink

I fell pretty hard for sex culture’s deceptive advertising. The trickery went as far as equating nerves, hesitancy, regret, and insecurity as simply *that hump* to overcome – it would all be over and you’d be *liberated*.

The older I got the more damage was silently being done. Its like the silent killer phenomenon – you don’t realize what’s happening in the moment behind the scenes, though you’re trying to sort through the confusing mixture of high-highs and low-lows. The difference being those high-highs were just a cover for the damage from the low-lows. I’m talking damage on an emotional, mental and spiritual (soul) level.

Sex, so I thought or was assured by society, was going to produce something or lead me somewhere. And while the initial feel-goods were [always/mostly] nice they only lasted so long and, ultimately, nothing was actually being delivered. In fact, sex stole more than I got from it and, in turn, had this weird sense of [*]dependency on it. [*]Today, we call this many other things to make it sound less serious and more appealing.

How has this impacted my life? Well, I fully believe that having sex before marriage has done more damage than it has “liberated” me. I also feel my previous ways and thinking cheapened my view and treatment of sex – it was no longer “special”.

I built my own adapted framework around sex I thought would serve me. It wasn’t until I got married I began feeling disgusted and gross (dirty). I wasn’t necessarily disgusted in myself, but by how I viewed and treated sex, what little value I had assigned it, the delusion I had fallen into surrounding sex culture, and the overall picture I had painted. I defined sex with lust, not Love. It was so wrong.

It was like I was finally able to witness what had been lost or missing, and it required turning away from and letting go of the framework I had created. Now I am starting to see sex through a whole new lens, including in today’s culture.

That said, I have such a newfound respect and admiration for individuals – especially in today’s youth – that are choosing and desiring to save themselves for marriage (including those who have had sex, repented [changed their mind], and are now making the commitment to wait until marriage). That is such a beautiful thing not given enough credit these days.

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