Strange Bedfellows: Broken Hearts and CL Missing Connections

My Short and Brilliant Career as Lovelorn Columnist on Craigslist

As a divorced woman with three sons, writer/observer of affairs of the heart, I’ve experienced more than one stage of single-hoodness. You know the script: you leave a marriage, you leave a life, things settle and then the self-questions start. It was ‘him’, it was ‘us’ and then one day you realize, maybe some of it was, in fact, ‘you’ and there and then the quest begins — that big, inner journey wherein you tell your friends and your journal You’re Still Healing. My initial single life was launched with the discovery of free, spiritual podcasts of Sounds True and Hay House plus the odd YouTube video, Ted Talks on romance, a few tours of yoga, a dabble in meditation, and a good smattering of new age philosophy. In that same phase, on occasion, I was invited as a cookbook author, local journalist, asked to speak to singles’ groups on Cooking for One: It’s like cooking for 6 but you simply freeze 5 portions, was my advice. And no, I was not asked back. Go figure.

I feigned polite attentiveness as I listened to while well-meaning but clueless couple friends who told me to ‘just be good to yourself’. I’ve never understood what that phrase means? Does it mean more lavender baths, Cronuts or buy that better purse or the authentic pashmina? Or do they mean ‘be good to myself’ via some means and become a poster child for self-actualization. I lumped all this unsolicited advice from married who also suggest to (referring to dating) to “just go out and have a good time” Are they kidding? Where have these people been? Do they fantasize that online dating is also either a candy store/sex fest or Camelot of the heart wherein countless perfect strangers await to meet your authentic self with their own vs. the reality I found: a plethora of Loneliness’ great unwashed who browse Tinder and EHarmony hoping for a person or a brief tonic to mitigate the sting of not being comfortable in their own skin and hoping, as most of us do, the solution is That Someone Else. It’s partly true but it’s not a great strong suit to go hunting with.

Desperate for insight, I inhaled a steady diet of self-help books that had some gems of advice but I noticed many were by authors who, by virtue of: failed celebrity or abusive relationships, recovery programs or huge tragedies (versus garden variety ones) found some Truth and put it into a book.
Overfed and undernourished on a glut of actualization, I segued to daily journaling, faithfully documenting each bit of angst, sundry minutia, rants on being a single parent, writer/entrepreneur, baker-hating-Atkins, infidel agents, disappointing publishers, bad dates, financial trials, and legal battles. All were chronicled in both redundant and abundant detail. Journaling went from noble confessions in a safe place to whine and then simply, the journal became an articulate barf bag. So I stopped. Ditto for the new age digital broadcasts — done. I ignored the spiritual section of the bookstore and fled instead to Jane Austen or to Us Magazine. And mostly, I stopped looking ‘for signs’ such as feathers, pennies in the street, special favorite songs on the radio, fortune cookie fortunes, and rainbows. I was done with the kinder, gentler way of being and gave romance the up-you sign. And then one day, void of affirmations and ‘signs’, and totally out of the blue, I fell in love — wholly and in a ‘then my heart stood still sort of way’. Totally, unequivocally and incredibly amazing. Like in the books — mind, body and soul — I fell. I walked into a legal aid clinic and there he was — my soulmate. He seemed to agree. And? Just as my guard was down and the first I love you was uttered (him to me), it was done. Inexplicably, and with a laser touch. On the outside, you could hardly see the entry wound. Took the tears out of my eyes with the dryness only a merciless tour de force of indifferent weather, emotionally speaking, could deliver. At first, I couldn’t even make a sound.
Love gone awry is like being cured of an illness you wanted to keep. Sometimes the hurt is the only thing that reminds you it once was real. It sits like a little cat on your lap, keeping you warm but stopping you from getting up and moving on.

When I thawed out, I railed against the hurt for some time, trying, with the dubious input of empathetic friends, to figure out what had happened. He this, why that, peppered all my conversations. There was no solace nor rational and my heart wanted either or both. The real answer to these questions is: it was what it was/one never knows/and you have to move on.

I made another pass at the self-help section only to discover that there was not one book written on pining, something that seemed to have gone out with Rumi and Browning. No one tells the truth which is that pining is real (like your appendix: useless but still there) and pining takes whatever time you think it takes and then probably it needs more. How long a time is that? As long as it takes. Then I felt better and in decided I would be a tender conduit for others who had suffered heartache. Thinking myself ‘healed, and seeing I was good at giving romantic advice I decided to add the shingle of lovelorn columnist on my to-do list. I am kinder than Greg Behrendt (He’s Just Not Into You) and the world could use a softer landing. I cyber slummed into discovering Craigslist Missed Connections. Missed Connections was, in its debut was the wishing well of the Internet. Missed Connections is that part of the site wherein if you see a face, a girl, a guy — passing on a subway or coming out of a restaurant and think you missed True Love you can at least try and connect on Missed Connections on Craigslist. It is the cyber version of a note in a bottle. In its early stages, CLMC is also for strangely played out sad little romances that seem half-baked or nonstarters, or thrive on secrecy. Lots of people leave cryptic notes “Miss you. Come Back. You know who you are”.

I decided to launch my lovelorn columnist career here with the same impulsive energy that also made me think we need non-stick hamantashen molds. Nonetheless, at around 4am one morning, a time where I birth all similarly ill-advised great notions, I posted an ad.

(Free) Advice for the Lovelorn — w4m

Free Love and Romance Advice Missed Connection Special Are you fumbling your way through romance? Is the he said/she said stuff a total mystery? Free advice for the love-lorn. Email one brief problem/issue/scenario/relationship angst & free advice doled out in a prompt fashion.

Moi? Single/woman of a certain age with a tender heart and wise spirit. Expertise? I just seem to have an instinct for this sort of thing (at least, for others). No question too trivial (basic dating manners advice also on tap — sometimes it’s just a matter of etiquette). No heartache unheard of. Discretion and compassion assured.

I knew it was quirky but it seemed worth the price of admission. Very quickly my (alternate, private) Hotmail In-box filled up, assuring me that I was filling a gap (and/or people love anything free).

The first letter I got was simply a man saying, bravo, w/hat a good thing, and if we all knew more about romance, the world might turn smoother. The second email was a man who wrote and said: I am a 52-year-old man who is married but has a sexual problem. Do you handle that? I quickly dispatched him to, with a reply that said my expertise only went so far. I am a writer with a romantic heart, not an urologist.

Email 3 was texturally brief: He wrote: I have a BIG problem. Can you help with this? The ‘this’ was an attachment, a photo of a penis about the size of the Sears Tower. At least I think it was — it was quite close-up and the attachment seized my computer and I had to reboot. Delete, delete, delete.

Email 4 was from a man who had an absent father. To repair his childhood neglect he had decided to become the perfect husband to some unmet woman. Although far away (Spain? Africa?) he ‘could come to ‘my town’ since I was HIS DESTINY. He intended to rewrite his personal history via marrying a complete faceless, posing as a lovelorn columnist on Craigslist. His email, entitled YOU ARE MY DESTINY, alas, ended in the Junk file.

Email 5 was from a woman who found out, within the hour of her writing, that her husband of 20 years had an affair and the ‘other woman’ and he had fled to a hotel, and phone calls, tears, and lawsuits were swirling. “I have no one to tell. What should I do? She wailed through the ethers. I had no idea. It was not my business other than I wondered how someone that distraught could email a lovelorn columnist on Craigslist with so much real drama, going on, in real time.

What did you expect? asked a friend. “People are nut cases out there’

But then, emails 6 and 7 showed promise and I settled into my calling.

Number 6 was a nice sounding, 36 year old man in love with a woman he wanted to marry but after 7 months inexplicably wanted to simply be ‘cuddle friends’ and date other men but still stay in touch As Friends. He was heartbroken and wanted to know if he should have hope, stay a ‘cuddle’ friend, and/or sleep/heal his way with other women and have faith his ladylove would return one day. Hold your shoulders up/be a man, and move on, was my advice.

Email 7 was from a 28-year-old woman in Toronto who pined for a summer fling man from Buffalo. She was smitten but he ended it when ‘it got serious” with communications dwindling accordingly. Her question pawed away at the notion that perhaps he simply didn’t appreciate the depth of her feelings, was holding back and simply needed prodding to remember he might care deeply, a fact that seemed to have escaped him on his own.

Emails 8, 9, and 10 were essentially the same thing, as were the pattern of the many (long and detailed!) notes over the course of some 48 hours. The scenario was an unchanging theme with variations. Someone liked someone too soon or too fast and someone was coincidentally absent or ‘distant’ or ‘wanted to be friends’ or not take things ‘so serious’. This happened, without exception, either after one night or a special weekend, a holiday romance, or at the 4–7 month mark of dating.

In these notes, via my Hotmail account, sent by perfect (and hurting) strangers with faceless voices, I heard the same hopeless hope, over and over again. In the face of uncaring lovers and romances that seemed built on foundations fragile as sand, from such small crumbs, such hope lay! It was hard to believe. Any stranger reading these letters could discern, barring a miracle, these were not grand affairs of the heart. These were the look and feel of things that never amount to anything other than they are: the ones that got away which bestowed in them, a false sense of something that was probably never there. More than one man or woman wrote me that they KNEW they were special and HOW COULD someone not see or know that? As if it was all a case of matchy/matchy furniture from the Crate and Barrel catalogue.

The quantity and variety of excuses people had for lazy, insensitive, uncaring lovers was remarkable. No one wrote of his or her own disappointment. Instead, they invented possible explanations or interpretations of the dubious acts and absences of others. A third theme of words, untethered to actions or behavior, also emerged. Lovers promised much and delivered little. Words were freely offered, feelings and charming phrases but when push came to shove — push didn’t. Things stayed flat-line and the hurt party would often write: but you don’t understand. He/she SAID this or that.

My first responses were notes of length, all mindfully and caringly penned out even though the questions were always the same as was the same two answers to the one question which I didn’t have the heart to respond with. The two answers were a) No, he/she doesn’t care for you and you must move on, or B) Yes, you have to face the difficult thing you don’t want to. These were in the fact, the same two answers I had given myself for many months and it was as effective on my anonymous inquirers as it was for me, which is to say — totally ineffective. Who said it? The heart wants what the heart wants. If the heart were any smarter than it is they would have named it the brain, and that name, as we all know, has already been bequeathed to another organ more heartless but more deserving. In the end, I realized no one really wanted advice; they wanted comfort or refutation of the apparent (and painful) truth (as it played out).

Letter by letter, I saw I had no business offering advice on this or any other basis. I felt intrusive and responsible for intervening in the personal lives of total strangers.
Something else, like a small drip from an insistent faucet, began to penetrate my Dear Abby veneer. I saw in those emails my own still slightly broken heart. Removing the judgement from my lofty perch of lovelorn advisor, I heard a replay of my own tales. I recognized that I too, had dined on vapors of love, holding to the myth rather than let my heart let go and allow it to mend once and for all. I could see it in those anonymous people; I suppose it was time to face it in myself.
Heartbreak really demands nothing more than accepting what is, Faith and Time itself — a commodity we all have in great measure but has become a true rarity. Chastened, humbled, I withdrew my CL advertisement and closed my account. I also deleted each and every saved ambivalent email from the man who broke my heart that I used to re-read for clues and trace of love that might still be there, to see if I could blow onto dead embers and make them live again. I donated all my self-help books, stored the Tarot deck and stopped tossing coins in park fountains . I no longer asked the most patient friend for their take on ‘what happened’. Something happened, it felt wonderful and then it didn’t and it simply, whatever it was, needed time and space to work its way out.

As for Love itself, I didn’t stop believing in magic but I stopped trying to create it artificially, if only to give meaning to the hurt, rather than just sit with it. If I see a rainbow, I no longer see it as a ‘sign’ that love will conquer all or true love is just around the corner. If anything, it just means a storm has passed.

I still check Craigslist from time to time. It is where I recently picked up a great, big, caramel-hued antique oak writer’s desk for $50, including delivery, with the perk of the purchaser (me) throwing in a bag of still-warm Tollhouse cookies.

But as for half-baked advice, I am careful about doling romantic counsel in service to the comfort of strangers. Charity, as they say, and after all, begins at home.



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