What I’ve Learned After 15 Years Of Failed Relationships

They’re Like Seasons, How Well Do You Handle Winter?

Everyone loves spring, summer, and fall. Relationships just like the seasons, have their ups and downs where when times are good it can be like a summer’s day at the lake and when things are bad it can be like waking up at 6am to shovel a foot of snow off your driveway in 20 degree temperatures with 30mph wind gusts blowing on your face.

How you handle the bad times will ultimately define how strong your relationship is. They say the number one quality of any effective leader is their ability to be calm and rational in crisis. Relationships are no different. It takes an incredible amount of emotional maturity from both parties to come out of dark times in a positive mindstate.

Also, a healthy relationship should be Santa Barbara, not Chicago. If it continues to snow into June you may want to start asking some tough questions and assess whether it’s best to go your separate ways. The definition of crazy is continuing to do the same thing while expecting different results. Life is too short and if you’re constantly fighting with someone it can be absolutely soul-sucking.

Saying You’re Sorry Is Meaningful Even If It’s Meaningless

Stubbornness is a great quality for certain aspects of your life but when it comes to relationships it makes for a hostile and guarded environment. I’ve come to realize that there were times where even if I truly wasn’t remorseful for something I did or said it would have been useful to just say “I’m sorry”. Instead, I felt the need to defend my positions at all costs, causing friction where it wasn’t necessary – leading to more fights, driving the wedge in a little further with each stand. If you truly love someone you should be willing to say sorry even if you don’t mean it. Even if the apology isn’t 100% heartfelt it shows that you’re at least willing to acknowledge that your actions were hurtful.

Jealousy Snowballs

Trust issues are a major factor in any relationship, romantic or otherwise. If you don’t trust your partner the jealousy continues to spread like an infection without antibiotics.  Before you know it you’re questioning everything the other does and suddenly find yourself anxious when they’re around members of the opposite sex, especially if you’re not there with them.

Sustaining, long-term relationships require separate time apart and if you don’t trust the other person they will resent you for always questioning their activities to the point of where you think, “is this always going to be like this? how much tighter can this leash get? I cannot fathom this person having legal control over me (marriage)”. Once trust is lost it’s hard to get over this hump.

A House Is Nothing Without A Solid Foundation

There is no manual on how to properly start a relationship but there are some commonly accepted wrong ways to go about it:

  • Turning an affair into a relationship: If you start seeing the person while you’re exclusive with someone else there will always be trust issues that linger.
  •  Drunken hookups: It’ll be hard to take it seriously going forward if you’re courtship period consisted of drunken encounters at 3 in the morning. You cannot base an entire relationship on sex. That part usually fades after the initial excitement wears off and you’ll find yourself grasping for straws, wondering how to connect on emotional/spiritual levels.
  • On the rebound: It’s important to find yourself before you dedicate your time to making someone else happy. Jumping from one relationship right into another rarely works out.
  • Convenience: Depending on what stage of life you’re in, it’s never a good idea to start a relationship because it’s easy. I always laugh when people say, “it just seemed like the right thing to do”. That’s not a sufficient enough reason to commit to something as life-involving as a relationship.

If You Build It, They Will Come

For men especially, I can’t stress enough how important it to work on yourself before you dedicate your time and resources to making someone else happy. This includes:

  • Taking care of your physical appearance: Don’t buy into this disturbing trend of women saying they like “dad bods”. This is utter horseshit and goes against years of biological hardwiring – women will always prefer the strong, masculine type who best fits the ideal breeding profile. Women only say this because they want to be the pretty one in the relationship and being with a guy who’s in-shape and takes care of their physical appearance makes them insecure. Learn to eat right and make exercise a part of your daily routine. And if you have the money, PLEASE spend a little extra to get properly fitting clothes, it goes a long ways and lets women know you take yourself seriously.
  • Building your professional profile:  Your 20s should be spent on establishing your career, not getting married and having kids. Unless you look like Brad Pitt no woman is going to want to get with you if you’re a shift manager at Pep Boys.
  • Travelling: Experiences are like social currency, they define your worldview and make you a more interesting person. Women pick up on this and love someone who’s traveled/lived in different places.
  • Growing your social network: And no I’m not talking about FaceBook. Make an effort to attain worthwhile friends who add to, not subtract from your life. It’s also important to recognize toxic friendships and cut those people out of your life…..”the company you keep”.
  • Developing healthy sleep habits: Sleep is paramount. It affects everything from your testosterone levels to serotonin production. People who say they only need “5 hours” of sleep per night are lying to themselves.
  • Addressing mental health issues: There is a social stigma in this country regarding mental health and how it applies to men. “Real men don’t cry” is something douchebags and people born before 1950 say. If you know you have mental health issues SEEK PROFESSIONAL HELP. Most insurance plans cover it and it’s amazing the personal growth that stems from just having someone to talk to.

Focus your energy on being the best possible version of yourself you can be. The results speak for themselves as you’ll find your options and the quality of women willing to date you will greatly increase.

People Don’t Change, Expectations Do

There have been points in past relationships where I thought, “there are things I don’t like about this person (possible deal-breakers) but maybe overtime they will change”.

I consider myself to be an authentic person. While I may not be everyone’s cup of tea I pride myself on being a “what you see is what you get” kind of guy. The older I get though I realize that I am in the minority. Most people let their character flaws trickle out over time and it’s naive to think these things will iron themselves out on their own. Stubbornness only solidifies with age and often times there is little you can do to make someone “see the light”. If you’re dating someone and you’re gut instinct tells you that they’re unfixable, you’re probably right.

After coming to this stark realization the only thing left is to adjust (lower) your expectations and cave in on things that would be absolute deal breakers if you were to start dating someone new, all for the sake of trying to “make it work”.

The Marriage & Kids Talk Should Be One of the First Serious Conversations You Have

Speaking of expectations…..Ladies, if a guy truly wants to get married and have a family they will tell you within the first month or two of your relationship. If entering holy matrimony is one of your ultimate goals then you need to make that clear from the gitgo. Don’t beat around the bush. Saying “I would like to someday” is not enough. Save yourself the heartache and make sure you two are on the level about this.

Many men are backed into marriage because the American dream has been pounded into our head since we were young lads. Personally, I find the idea to be as terrifying as it is archaic. Modern marriage is a losing proposition for most successful men and I can’t for the life of me figure out why bringing the government into my relationship is a good idea (for me).

The only reason to get married is if you want to have kids. A two-parent household is and always will be the preferred environment to raise well-adjusted children. Guys, don’t get married if you are still on the fence about having children. The court system overwhelmingly favors women in divorce proceedings even if there are no kids involved.

Money Is Always An Issue

It can’t buy happiness but it sure doesn’t hurt. Living what’s commonly-accepted as a “good life” is more expensive than it ever been. The cost of living has steadily outpaced inflation since the late 70s and will continue to do so in the foreseeable future.

Unless you’re the fortunate recipient of a trust fund or winning lottery ticket the money you have is the money you’ve earned, whether it be through hard work and determination or deft financial decisions. Inevitably you will be in a relationship where you earn more than the other person, especially if they’re younger and less established. It isn’t their fault, you just happen to be at different stages in your professional life. It takes an incredible amount of empathy and perspective to stick with someone who’s struggling financially. And unless you want to foot the bill for everything it severely limits how/where you travel, things you do on the weekends, and how often you go out to fancy dinners.

Resentment can build up pretty fast in this scenario, especially if you didn’t enjoy the same financial support from your partner when you were their age. And if the relationship begins to go south the resentment grows uglier and even more apparent. Most guys don’t have a problem spending money on a girl if he feels like he’s getting something in return. Men who date younger women have to accept this situation and ultimately decide if the juice is worth the squeeze.

It’s important to find someone who’s at the same stage in their career and can equally contribute to your mutual lifestyle.

Nothing Erodes A Rocky Relationship Faster Than Excessive Alcohol Use

If things are already contentious alcohol only serves to throw more gas on the fire. While at first it may seem like a nice way to loosen your nerves and open up to your partner, often times it’s taken too far and causes escalation to point of where you’re fighting with each other in public and saying things you’d never say when sober. If you both realize that the relationship needs serious work then it’s best to lay off the sauce or if you do drink have a couple glasses of wine with dinner.

Cities Are For Single People

Cities are breeding grounds for illicit behavior. Which is fine if you’re single but presents challenges for couples, especially when both people are outgoing. There are too many options, too many temptations, too much bullshit. A single person thrives in such an environment but for couples it can truly test your commitment, especially when times are bad. I’ve often thought, “I don’t need this, I can walk outside of my door and there are literally thousands of single women in this city, why am I torturing myself by staying in this relationship?”.

There are several reasons why married people move to the suburbs: better schools, bigger houses, less crime…..but there’s one aspect of suburbia that’s often overlooked: there’s less opportunities to go out and make bad decisions. When your options on a Friday night are chain restaurants and bowling you tend to “settle down” a bit. This, coupled with the insular nature of neighborhoods where everyone knows each other, the suburbs make ideal settings for being in and working on relationships. They keep people in line and encourage the perpetuation of the familial unit.

Fostering Relationships With Other Like-Minded Couples Is Healthy, But Hard

Speaking of the suburbs, it’s important that you seek out other couples to hang out with socially. What doesn’t work is hanging out with each other’s single friends. There’s nothing worse than bar-hopping with your girlfriend and five of your single guy friends, especially if you’re going to hole-in-the-wall bars where people’s’ aim is to get as drunk as possible. Your gf WILL get hit on and it gets old really fast.

But, in order to establish and maintain these kind of relationships it takes a lot of scheduling and the willingness to leave your comfort zone. Couples that have been together for years become stuck in their routines and it’s oftentimes difficult to sync up.

Another caveat to this is the division of mutual friends after a breakup. People often have to choose sides and things can get messy real quick. These are the times when you find out who your true friends are.

Parenting Has Deep-Rooted And Long-Lasting Implications

You are your father’s son. She is her mother’s daughter. Don’t underestimate the effect one’s upbringing has on their adult life. The values they learn and behaviors they observe during adolescence are directly applied to future relationships. It’s important to find someone who grew up with a similar background.

If your partner has a strained relationship with their parents – expect turbulence. I’ll leave it at that.

The Binary Approach To Good Times/Bad Times Doesn’t Work

When things are on the brink of falling apart people often will do mental gymnastics to justify the very existence of the relationship. They will take a black and white approach to assess whether they should keep it together. I.E. – Listing out the pros and cons. Most of our lives are spent in the gray area and as much as we’d like to implement common-sense mathematics to our lives this method ultimately falls short. You can’t simply add columns together and say, “well, the good times outweigh the bad times so if we can just hold on to those moments we may be able to make it work.”

Nostalgia Is A Subtle Beast

Ever notice that you always feel the most nostalgic when things aren’t going particularly well? Nostalgia is pain masquerading as fondness. It’s a mental device we use to help us get through the bad times. It’s particularly destructive in the case of breakups where you find yourself looking back at those happy moments.

There’s a reason you’re no longer together and dwelling on what “could have been” will drive you mad.

There Are Two Sides To Every Story, You Mostly Hear The Woman’s Version

As men, we pride ourselves on putting out the public perception of stability. For us, it makes zero sense to tell our friends about our relationship problems. They’re not licensed counselors and revealing flaws about your partner only serves to blow hot air around. I’ve had breakups that to this day still baffle my friends because I never went into the details of what really happened.

Women on the other hand, tend to wear their hearts on their sleeves when it comes to confiding in their friends about their relationships. During a breakup you’re going to hear all kinds of shit about why it happened and who was at fault. Take this with a giant grain of salt.

Social Media Is Toxic for Relationships

Nothing breeds jealousy quite like going through your partner’s past social media history and comparing their “old” life to the one you’re currently trying to build together. Obsessing over the past like this is unhealthy and will ultimately lead to resentment. You’ll find yourself having to justify pictures and status updates you made over 5 years ago. It’s like a time capsule of your life that hundreds of people have access to.

And nothing screams INSECURE like couples who find the need to constantly post pictures of themselves followed by hashtags like #blessed, #truelove, #sohappy, etc. Give me a fucking break. These kind of posts are nothing more than projections that are basically public relations maneuvers operating under the guise of happiness. Is there anything more absurd than the train wreck of a couple who you personally know are going through crisis but post pictures of themselves smiling together like nothing is wrong? At best it’s naive, at worst it’s nefarious – people will post these kind of things as a way of saying, “we’re alright……..see, we went to a baseball game together, nothing to worry about here”.

Also, breakups have never never been more public especially if you’re one of these couples that post together frequently – you have to go through and delete all of your old pictures, erase status updates, and basically rebuild your public profile to give people the impression that you’ve “moved on”. What a circus.

Letting Go Is  A Personal Journey

The nihilist in me says, “she wasn’t yours, it was just your turn” – a phrase that although seems harsh on the surface has personally been a time-proven mantra for me when contextualizing past relationships.

People enter and exit your life with greater frequency the older you get. This applies to not only romantic relationships but friendships as well. You can’t take it personally when you lose touch with someone. Sometimes you have to shed these people to grow as a person and it seems more painful in our adult lives because growing up we enjoyed the cohesion and routines associated with living with a family and seeing the same people at school everyday. The thought of losing touch with your childhood best friend seemed like an impossibility at the age of 13 but when you get older you come to terms with it and accept that part of maturing as a person means having to seek out new friendships.

It’s important to look at these past relationships not as abject failures but rather learning experiences that have shaped you into the person you are today. There is a little piece of me left from everyone who’s come into my life, for better or worse – and I don’t take any of it for granted.

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