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*GUEST SUBMISSION* Letter 68: You’re About To Break Your Mama’s Heart

24 Oct

Amber writes:

Dear me at 12,

You are about to break your mama’s heart, and I wish you wouldn’t.

The Author (right) at 12

Things are getting harder with her, I know. You’re almost a teenager, and no one gets along with her mother during middle school. But since your dad is trying to convince you to move in with him, it’s going to be harder than usual. And when you decide he’s right and you begin a two year custody battle… oh honey. You’re in for some heartache.

I know the grass seems greener at Dad’s house. Your stepfamily is super cool, whereas your mom is cramping your style. You don’t understand your new stepdad’s humor. You have to share a room with your little sister since your big sister moved back in, and your baby nephew cries a lot.  Compare that to Dad’s promise of your own room and a puppy if you moved in with him. You’re forgetting something big when you make this decision: Your dad and stepmom can be cool and permissive because they parent you every other weekend. They can’t be that cool all the time.

This is also important, and I don’t think you realize this, but your dad is kind of manipulative. Dad always says, “I never talk bad about your mother, BUT YOUR MOTHER…” and describes some horrible thing she did.  Despite his claim, he’s *always* talking bad about your mom, and usually, in half-truths at best.

Now, I don’t want to talk bad about your dad, but I won’t lie– I’m going to talk bad about him. Just listen to logic instead of arguing, pretty please. Your dad likes to have his way, and manages to get it most of the time. (This is something you get from him– try to use this talent for good, not evil.) Unlike you, however, he doesn’t mind hurting your mom, and he’s using you for that purpose. When this awful custody ordeal is finally over and he loses, he will be hurt instead. You’re going to see an ugly side of him. He and his wife will lash out by screaming obscenities at you. The worst of it will be you can’t protect your little sister, who they insist needs to hear all the screaming and cussing.  Thank your lucky stars that the judge knew what he was doing and saw through the manipulation.

You and your mom will be fine. When you realize you’re turning into her, you smile. You will cover your mouth in a horrified giggle when you automatically blurt out one of your stepdad’s jokes, and you’ll call him your hero. You’ll treasure your sisters, sharing a room or otherwise. Your nephew will grow monstrously huge, but he will still look up to you, as will his sister later on.  Your dad and stepmom G, however, are a little less sturdy. They’ll divorce, he’ll remarry (and divorce again), you won’t talk to your stepmom again after your stepbrother’s graduation party. Your relationship with your dad will never be whole again, but you’ll at least be on speaking terms.

Please ride this out. Give you and your mom time, and whatever angst you have will turn into a beautiful friendship. She loves you, and you love her back. (You know you do.)

Amber, 27, is an educator in East Tennessee. She loves reading (, crafting, and being with family (especially her husband and cat, Cat).

*GUEST SUBMISSION* Letter 65: He’s Not Worth It

6 Sep

Bay writes:

Dear me at 16,

I know you are lonely.

The Author at 16

I know it’s hard that your 16th year, the year you envisioned as being perfect, didn’t turn out anything like you thought it would.

I know it’s not easy that the guy you had crushed on for two years was finally interested in you… but he turned out to be something of a loser.

I know it’s hard that deciding not to date him killed your social life and left you out of the group you had so much fun with.

I know it’s killing you that your best friend, the one who’s more like a sister, is making some terrible decisions that are ruining her life and putting some serious distance between the two of you.

I know.

But please, don’t reply. I know it’s exciting that he just IM’d you, the boy who lives across the country, the one who you haven’t talked to in months and never really knew very well in the first place. I know you secretly thought he was pretty cool last year at competition, and that you may have even had a mini crush on him. I know everyone talked about how much he loved your friend, and you couldn’t help be a teensy bit jealous.
I know.

I know it’s amazing that he’d decide to talk to you out of nowhere, for no real reason, just because he saw your profile online. I know he’s funny, and intelligent, and complimentary right to the edge of being flirty, something you’re completely new to.

I know that no guy has ever really told you that you were pretty before, except the creeper who was way older than you and semi-stalked you a few months ago. I know that everytime you get online the two of you come up with hilarious plans to take over the world and run for president and build a chocolate factory and a million other things.

I know.

I know that he will mention he doesn’t have your number, and you’ll be all to eager to give it to him. I know that in future months you’ll text 24/7 and talk on the phone whenever you get the chance. I know that he will only seem to get better, funnier, smarter, more mature, the whole nine yards. I know that you will meet up again at competition and that the week will be incredible, everything you had wished it was last year. You will talk and laugh and flirt and sit next to each other all the time and be talked about as a ‘couple’.

I know it will be one of the most exciting things you’ve experienced to finally have a ‘boyfriend’, even if nobody knows and it is just over the phone.

But please, stop it now while you can. If he really loved you, he wouldn’t ever ask you to do or talk about things that make you extremely uncomfortable. Ever.

If he really wanted to commit with you, he wouldn’t break it off every few weeks to think about it, then start all over again, jerking your heart around mercilessly.

If he really wanted only the best for you, he wouldn’t be averse to telling your parents. He would have no problem talking to your dad and making it a serious relationship.

And honey, let me tell you from this end, if he really loved you, when the secret came out and everything came crashing down, he would have stuck by you. He wouldn’t have cut it off forever without making any effort to fix things with you and your family.

So here you are, on the eve of your seventeenth birthday, a lonely girl with the exciting prospect of a new friendship and maybe something more. I know how hopeful you are dear, but please. Don’t give him your whole heart. Don’t plan your whole future around him. Don’t cut off ties to friends an family because of him.

He’s not worth it.

Bay is a cynical romantic who spends her time reading, writing, and dazzling the world with her sparkling wit. You can find her rambling’s at, where she continues to write even though no-one is reading. She loves comments!

*GUEST SUBMISSION* Letter 61: You Will Get Through Everything

25 Jul

Lisa Marie writes:

Dear me at 15,

The Author at 15

Although you may not think so now, you are going to get through the obstacles in your life. As you are, sitting all alone late at night in the children’s ward at Oldham Hospital. Sure, you’re in a lot of pain now. But what do you expect? You’ve had surgery on your hip today.

Just remember who was there for you. Yes, you know who I’m talking about. Your best friend. The best friend who you say now will be your best friend forever. I know you think nothing will ever come between you both. You have all these thoughts in your head. That you will always be as close as you are at this very moment. Like sisters. I wish I could tell you that you will always be this close.

But I can’t. I can’t lie to you. That temper you hate about your Dad? Well I’m sorry to tell you, but you’ve inherited it too. That temper will get you into so much bother as you get older. Not only with friends, but men as well. Please don’t bottle things up. Don’t only see the black and white in life.

I will give you some hope. At 27 years old (as I write this letter to you) you will have a better understanding of the person you want to be. It’s not going to be an easy  ride, let me tell you. But everything that happens in your life after today will shape you into the women you want to be. I hate that I can’t warn you about certain places to avoid. I truly do. You will probably hate me for it.  Just trust me. Trust that I know you will get through everything life throws at you.

Here is my last piece of advice: In the time you are recovering from this operation you will get some great enjoyment out of writing your stories. Trust me when I tell you to keep writing. It will help you so much over the years.

Now, put this letter down and get some sleep. You have physio in the morning. It’s gonna hurt like hell, but you need to do it. Go to sleep.

Lisa Marie has a blog ‘Inside My Head’ ( You can also follow her on twitter (!/lisa_m_miller) She values her close friends like an extension to her family.


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Letter 59: Get Off The Elevator

14 Jul

Dear me at 13,

You’re pressing the “close elevator” button as quickly as your little fingers can manage.

“1,2,3,4,5,1,2,3,4,5,1,2,3,4,5…” you count the pushes in your head as you plead with the doors to shut already. People are taking their seats. The ceremony is about to begin. You’re not quite sure where you plan to ride this elevator, but if it doesn’t take you there soon, you’re considering scaling the shaft yourself through the emergency exit. Anything to get you out of here.

Me at 13

As the doors begin to close you can feel the hot sting of tears in your eyes. You’re trying to keep them in there so they don’t smear the makeup that you don’t know how to fix.

You’re standing in the elevator of the Beth Tikvah Synagogue in North York, Ontario. Today is David L.’s Bar Mitzvah, and somewhere between the coat check room in the basement and the main floor you were dumped by your boyfriend of a week and a half.

He said his friends thought you were too controlling and that he needed some time to be single. How you could possibly be controlling through the course of a week and a half in which you only saw each other at school and talked on the phone twice is beyond me (and you). But the ridiculous nature of his logic doesn’t take away from the hurt you’re feeling right now.

Tonight was supposed to be a really big deal. Everyone cool was coming to this Bar Mitzvah. Everyone cool was coming with a date. In fact, coming here with a date was the single largest factor in being considered cool in the first place. For the last week and a half, your life has been consumed with planning for this evening. The dress. The hair. The makeup. Standing in front of the mirror twirling and smiling. Practicing your “Mazel Tov”s so as to sound as authentic as a nerdy suburban shiksa can.

When he first asked you out, you were nearly too shocked to accept. I mean, he was one of the popular boys. One of the boys all the other girls liked. One of the boys who generally didn’t give you the time of day unless they were publicly ridiculing your clothing or your straight A grades. How or why he would come to the conclusion that he wanted to date you was a complete and total mystery. You somehow managed to get your words together and accept.

Instantly, your social standing changed. People who had intentionally avoided you but moments before were now clamouring for your attention. Heads turned as you walked through the hallways. And not in the “Now’s the perfect time to stick the ‘Kick Me’ sign on her back” kind of way you had typically experienced. You could sense your peers re-evaluating your worth.

It was wonderful. You felt as if, for the first time, your classmates were actually understanding who you were. Like they were finally catching onto what you had known about yourself all along. You started to imagine what the remainder of your Junior High career might be like if you could just keep this up. And it felt as though a gigantic weight had been lifted from your shoulders.

And now, travelling in that rickety elevator to goodness-knows-where, that weight is resting firmly once again, although now in the pit of your stomach. You are terrified to face your classmates. To face the popular girls. To face him. You don’t want to leave that elevator, but you know you can’t ride it forever. Your parents might worry. You’ll need to eat eventually.

Here is the thing: This situation is a perfect example of how fickle the popular 13-year-old crowd can be. Kids go from A List to D List and back again in a span of days. And they even do it to themselves! Amanda S. might be popular today, but believe it or not, in a few months, one of her fellow clique members will start a rumour about a naughty dream and her stocks will plummet too.

If I were you, I wouldn’t put so much weight on being accepted by people incapable of acceptance. They are 13. They’re hormonal. They’re insecure. You are an old soul. And deep down inside, you know you’re way beyond this. You will grow up into a successful person who loves her life, who has amazing friends and an incredible family (including a super hot husband, by the way! Yipee!).

The bad news is: You have to exit the elevator. The good news is: This Bar Mitzvah only lasts one night. And you’re already part way through. As your Dad always said, “By this time tomorrow, it will be what it was”. So wipe your eyes, straighten your hair, march on into the sanctuary and watch your classmate become a Man.

And if the popular girls ask any questions, just tell them you’re glad to be single again. After all, he was pretty controlling anyway.


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*GUEST SUBMISSION* Letter 58: It’s Not Always Awful

11 Jul

The Author at 17

Katie writes:

Dear me at 17,

I know how miserable you are right now. You’ve just dropped out of high school. All of your friends deserted you after a slew of rumors were passed around the school. Your heart was broken by so many boys you’ve lost count.

You’re feeling useless, unwanted and forgotten.

I remember that feeling. Not understanding why you’re feeling so depressed. Confused about how people could treat you so cruelly. Trying to find some reason why these injustices were done to you. Wondering what you did wrong.

But I’m here to tell you that you did nothing wrong. The boys are just immature jerks who don’t know the extent of the harm they have done. Your friends don’t realize yet how much you need them or how much they in turn need you.

And most of all, you are not a failure for dropping out. I know it feels that way. And it will for a very long time. But I don’t think it was a mistake.

You are a very smart young woman. Never doubt that. You have enough imagination and creativity to accomplish anything you set your mind to. You are talented in so many ways and you can use those gifts to the benefit of so many people, including yourself.

I don’t want to ruin the future for you. But I will give you a few helpful and hopeful tips.

Don’t be afraid to work. It is the most rewarding thing you can do for yourself. Be dedicated to the things you try, work hard and you will be astonished at the things you will accomplish.

Not all men are jerks. There are so many that are, so be wary. Remember your experiences so far and they will serve you well. However, do not lock your heart away or be afraid to love. There are quite a few good men as well, and you’ll want to be able to give them your heart when the opportunity presents itself.

Take chances. Don’t be afraid to do something because you are afraid you will fail. Setbacks are a part of life. But if you hide yourself away you will never experience anything.

Don’t be afraid to be yourself. Don’t strive to be anyone else. The sooner you learn this, the quicker you realize how wonderful you are when you are just being you; the easier life will be. Don’t live for anyone else. Don’t strive to be what others want you to be. Just be you. You’re wonderful.

And most of all, remember that you are loved. You are so lucky to have people in your life that will never leave you. Your family is your greatest support, and they will always be there for you.

Life won’t always be easy and there is a lot that I don’t know yet. But I’ll tell you that it’s not all hard. It’s not all mean. It’s not all scary. There are so many good times ahead of you.

Don’t let yourself get lost in this hard time.

But then, I already know that you are stronger than you think you are. Trust me.

And one peek at the future: You’re very happy.

The Author Today

Katie is the writer of Simply Kate. She is exploring her life in Las Vegas, is currently editing her first novel, has a wonderful boyfriend and is very happy.


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The Cafeteria: Hindsight Letters Pilot Podcast

26 Jun

Hi Everyone!

Earlier this week I announced some very exciting news regarding The Hindsight Letters producing a Pilot for The CBC. Today, a portion of the pilot will be featured on a wonderful show called Tapestry that airs on CBC Radio 1. Follow the link to be brought to Tapestry’s website, where you can find air times as well as download a podcast of the show. Or you can visit the CBC website to access the online streaming. Thanks again so much to The CBC and particularly to Nicola Luksic for including The Hindsight Letters in the broadcast.

The full Pilot can be found below. Big Thank You’s to former HL team member Brianna Goldberg for hosting and co-producing, as well as to Ari Weinberg for sharing his story with us in such an engaging and dynamic way. I would love to hear any feedback you might have. Press “play” and enjoy!


Letter 55: Being A Teenager Is Awesome

20 Jun

Dear me at 15,

I’m writing you this letter to tell you about an epiphany I had a few nights ago:

Being a teenager is awesome.

Now, I know this sounds contradictory to all the Letters I’ve written to you prior to this one. And it kind of is. Most of my Letters have been addressing all of the anxieties, grievances, confusion and general turmoil that tends to accompany one’s adolescence. But I’m here to tell you that there’s actually a whole lot of awesomeness that’s involved in being your age. And I want for you to recognize it and take advantage of it before it’s too late.

You see, the other night, I was downstairs in your future kitchen, having just put your future daughter to bed. It was one of the first hot days of summer, and the sky had that wonderful warm glow that happens just after the sun sets. I myself was settling down for the evening; teeth brushed, jammies on. But looking at that summer sky, I was overcome with a feeling of anticipation. Excitement. Freedom.

Something about that summer night sky sent me right into a full-force teenaged summer flashback. I was right back into your life again.

I was putting on my makeup and my cutest little punk rock outfit with Amy in the upstairs bathroom of my parents’ house. I was taking the Don Mills bus down to Cliffwood Park. I was singing Sublime into the wee small hours with a 40 oz of Cherry Wine Cooler in my hand and not a care in the world. I was relishing in time wasted without responsibilities, surrounded by friends, feeling the warm summer breeze on my skin. Enjoying the first real kisses with my first real love. Laughing and dancing and falling down.

And as much as I tried to remember all of the uncomfortable, awkward and even downright traumatic things that happened during my teenaged years, I just simply couldn’t. All I could think about was that uncontrollable laughter. The time that Amy and I had a food fight with Betty Crocker frosting at the Lake House in the middle of the night. The way that we were literally rolling around on the ground, holding our stomachs, smears of chocolate in our hair, sore from giggling so hard and trying even harder not to wake Mom.

The luxury of time. Planning for hours about what outfit would be worn to which show. Organizing snacks, travel arrangements and must-see-acts to each years’ Warped Tour with the intensity deserving of a year-long journey. Going to a concert and dancing until hot and sweaty, hair ruined, make-up running, and not caring, because I was having the time of my life moving to the music that truly moved me.

The connection with friends. Such a deep, intimate connection. Sharing every detail of your life with someone, good and bad, unafraid of judgement, and knowing that person cares enough to listen and understand. The feeling of connecting intensely with someone who isn’t either related by blood or legally bound to appreciate you.

The hope for the future. Everything is an unknown. The possibilities are endless. There’s so much to experience. So much to see. So much to look forward to.

My dear girl, you will do a lot of wonderful things in your life. Most of your dreams will actually come true. But I’m here to tell you, in many ways, the dreaming can be almost as good as the fruition. Dreaming about the things you want, not knowing, wondering, questioning, imagining all the possibilities- that’s an incredible feeling. And it’s a feeling you’ll experience less often, the more experiences you gain.

I know that being a teenager can be frustrating. You feel like an adult. You just want to get your life started, already. You want to be in control of your own independence and no longer under your parents’ rule. But, in many ways, you have more freedom now than you will as an adult. All your expenses are covered. There is food on your table without you having to prepare it. Your bills are paid. Your laundry is done. The only person that you need to focus on right now is YOU.

I know that you’re itching to be responsible for your own life. But there is something really, really great about being able to be irresponsible.

You have the ability to write your future. To decide who you want to be and be it. Try on some different hats. Don’t be so serious all the time. Stop worrying about the details of the sequence of events that will follow from every single step of your life. Stop worrying. Stop being so darned responsible and just BE for a while.

And the next time you hop on the Don Mills bus and head down to Cliffwood Park for the evening, do me a favour and give an extra big hug to your friends. Dance a little more. Laugh a little harder. Love those moments as intensely as they deserve and I promise you, you won’t regret it.

And as for me, tonight I’ll raise a special glass of Cherry Wine Cooler to you, my friend. The night is ours. Now hop on that bus and go make me proud.


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