Weep and Learn: Cautionary Tales and Valuable Lessons

I look at the world and I notice it’s turning
While my guitar gently weeps
With every mistake we must surely be learning
Still my guitar gently weeps*

My guitar didn’t weep, but I did. My mistakes were legion.

When I started dating I was naïve and I was hopeful. I was trusting, gave men the benefit of the doubt, and thought the best. I did not grow up surrounded by healthy and well-functioning relationships to inform my choices. My older brother protected me through high school; no one dared hurt me for fear of his wrath. My early years left me unskilled in relationship basics and entirely unprepared to navigate the hearts and minds of men.

Ultimately, it all worked out for me, after many twists and turns on the journey. Here are some cautionary tales and lessons I had to learn along the way. These lessons are likely obvious to many. I share them in case you have blind spots, as I did, and would like to avoid ending relationships in a way that has you ducking into doorways to avoid coming face-to-face with your past on the street.

Some relationship endings were a dagger to the heart, taking months and years to grieve and recover. These aren’t those stories, with these I shed a few tears and moved on. These are experiences that demonstrate how you learn a quick and unequivocal lesson.

  1. You’re in your apartment talking to the new man you have met. There’s only been a couple dates, getting to know each other over dinner and coffee, and for the first time he’s stopping by. Your roommate, Pat, is on the phone, talking to her mother. Her mother hears the conversation in the background and asks about the man she can hear, what’s his name, why is he at the apartment. Pat tells her, it’s someone Carol is dating. Her mom tells her to put you on the phone, where she proceeds to inform you she knows this man, and his family, which includes a wife and three children, one a newborn, from their church. He is married in no uncertain terms. You get off the phone, confront him, and he does not deny it, but asserts that he didn’t lie because you never explicitly asked him if he was married. Apparently you’re the one at fault that in all the conversations getting to know each other these details didn’t happen to come up when he was telling you about himself. You are in the wrong for assuming someone with time to go on dates, stop by and hang out, doesn’t have other commitments like three children. A lie of omission is still a lie. You tell him to get out and never darken your door again, and perhaps spend his time and money on his family, and listen up when he’s in church.

Lesson Learned: Ask early on, directly and explicitly, if he is currently married or in a relationship, does he have children, what are their ages, has he been divorced, how many times, how long ago.

  1. You were close as freshman in college. You even stayed close the next year, when you changed schools, and he took a year off to work on the Alaskan pipeline, knowing he could cover the remaining three years of private school in cash with the earnings. Staying close means you hand-wrote letters and sent them in the mail to stay in touch. He’s back in Oregon, back to school, and you’ve just spent a few days and nights with a group of his friends at a big house on Mt. Hood. He is someone special, no doubt about it. After the time on Mt. Hood, you arrive back at your apartment in Portland, where he plans to stay overnight before driving back to school in Salem the next morning. You turn on the TV for some election night returns, become more and more bewildered/agitated by his political views and the spirited disagreement you’re having. Despite the late hour he decides to leave immediately and drive back to Salem. That is the last time you ever hear from him. A classic election-night breakup.

Lesson Learned: Discuss things that could prove difficult to compromise on – including politics and religion. Don’t wait for election night to understand his political views. Don’t put off meeting his family for months or years, only to find they’ll never accept you because of your different faith or lack of religion.

  1. During the relationship, his tastes exceed his income. You’re working and he’s a student. So you pick up the check most of the time. Against your better judgment, when he asks to borrow money you loan it. He is annoyed that you write “loan” in the memo portion of the check each time. He breaks up with you. You ask for the loan to be repaid. He gives an insolent smirk and tells you that you’ll never collect the debt. So you file a claim in Small Claims Court; this takes the smug look off his face and he agrees to repay you if you’ll agree not to take him to court. But you’re past taking him at his word; you go to court and are awarded a judgment. There’s still the issue of collection, so you go to the library, use the bread crumb trail of information he’s given you to track down his father, mail a copy of the judgment to his father’s office, and receive a note back saying both of you are foolish, but the debt will be repaid. And it is.

Lesson Learned: Never ever loan money or intermingle finances. An income imbalance is not toxic, but constant pressure to loan, gift, or spend money on someone you’re romantically involved with is. Don’t move in before you’ve known someone 12-18 months, and they’ve demonstrated things that are important to you, like financial responsibility and living within their means. Before co-mingling living expenses and financial commitments, understand your new love’s relationship with money, ability to live on what they earn, general level of debt, and expectations around who will pay the bills.

  1. You’ve had some very good times with someone who seems enthusiastically into you. You like him; it feels promising. Things are humming along with the easy back and forth of an established relationship. You are happily oblivious until, after a few calls, one with his bath water running, one with dinner currently cooking and the stovetop needing his constant attention, and one when he’s just walking out the door and can’t possibly be delayed, it finally sinks in. He doesn’t want to talk to you. This relationship is over. The only other time you hear from him is an apologetic call some weeks later informing you he has tested positive for a venereal disease and he’s not sure if there was overlap between you and the woman who gave it to him. Thankfully you dodged that bullet, but from this moment on he’s dead to you.

Lesson Learned: Don’t assume you’re on the same page regarding exclusivity and monogamy. Be clear about using protection and birth control. How will you avoid unplanned pregnancy and sexually transmitted infections? Before you move to intimacy, have these awkward but necessary conversations; don’t risk your health and never assume you’re in an exclusive relationship. Don’t even assume you are in a relationship.

  1. You meet someone and he has an exciting and edgy energy. You spend time talking and dancing and exchange numbers because you might like to see him again. When you get home that night, you have an intense nightmare where he brutally strangles you; you wake up terrified, gasping for breath. A couple days later he calls and invites you to go to the coast for the weekend. You tell him you’re not comfortable with that because you don’t know him well enough. (In your mind giving him control of the transportation and accommodation makes you vulnerable if things take an unpleasant turn.) He’s deeply offended by this, and says if you don’t trust him enough to go, this is over before it starts. And so it is.

Lesson Learned: Do not ignore intuition or dreams. Something in the subconscious is telling you the situation is unsafe. In this case, I’ll never know, he might have been the nicest guy ever. I stick with trusting my intuition, even though it cost me a possible relationship. This experience reinforced something I was starting to understand – anyone who moves too fast, pressures you to push your pace and do something outside your comfort zone, who downplays your need to keep yourself safe – that person is raising a huge red flag. Women have unknowingly crossed paths with sociopaths, malignant narcissists and serial killers, trusted their lives and the lives of their children to men they barely knew, with tragic results. Never be manipulated into ignoring your instincts. Don’t be shamed. Don’t be threatened. Don’t ignore your instincts because you feel embarrassed. The news is full of narratives where people say I had a feeling something was off, but I ignored it. I should have paid attention. Don’t be that person.


These stories may give the impression I always put men at fault. Not so. I’m well aware men might be out there writing cautionary tales about relationships with someone like me.

I never want to give up my trusting nature and my belief in the goodness of people. But I learned to accept the reality of the world we live in. Men (and women) lie, cheat, manipulate, con, hurt, disappoint, prey upon, bully, keep secrets, stalk, exploit, present themselves falsely, and in worst-case-scenarios assault, rape and murder – then minimize, deny, deflect, gaslight, blame others, and cast themselves as the victim while they do it. And it’s not black-and-white – good people end up behaving badly in some situations.

Hope and wanting make you vulnerable to an extent; I never found a way around that other than life experience. In my 25-year** learning curve, I got better in my skills and my selection process. When I made missteps I tried not to dwell on self-recrimination. I tried to remain optimistic despite bitter setbacks. Some experiences left me sad, resentful, disillusioned, distrustful, angry, wary, yet some part of me remained committed to a life with love in it.

There are wonderful potential partners out there who are worth the trouble to find. What kept me from finding one sooner was spending months, sometimes years, with men who were never going to be that partner for me. I reacted to hurt unpredictably – sometimes endlessly accommodating and forgiving nonsense, and at other times instituting a harsh one strike and you’re out policy with men. Over time I found balance. The trick is to evolve and not keep repeating the same hard lesson over and over. Learn and grow. Carry on.

* “While My Guitar Gently Weeps.” The White Album. 1968. Writer: George Harrison
Publisher: Concord Music Publishing LLC. My favorite version: Guitar Heaven: the Greatest Guitar Classics of All Time, performed by Santana and Yo Yo Ma, featuring India Arie.



**I started dating around age 15 and got married at age 40, so spent about 25 years in and out of relationships (including a short first marriage) before entering into marriage with my right partner. This year will be our 25-year anniversary, marking a milestone for me – I’ve now been with one man longer than I was with all the other men put together.

© 2021 Carol Merwin, All Rights Reserved

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