Samara O'Shea

Archive for the ‘Other Web sites’ Category

Would You Give a Guy Who Broke Your Heart Another Chance?

Friday, February 5th, 2016

Hi Samara,

I am 42 years old. Divorced twice, no children, 1 dog. Recently, I reconnected with my high school sweetheart. He is divorced with 2 children. We are madly in love once again and I think I want to spend the rest of my life with him.

The problem is that we reconnected once before in our late twenties and it didn’t work out and I was terribly hurt by him. I see many positive changes in him since we started seeing each other again. This is the third time around with him. I am wondering if we both needed to grow up before finding each other again or am I just fooling myself?

Any suggestions on how to approach this relationship this time around. I really want it to work.

Thank you,

Check out my response here.

When to Call it Quits on an Unrequited Crush

Tuesday, March 25th, 2014

Happy theoretical spring everyone! (It is literally still winter here in the northeast). In any case, check out my latest write up: When to Call it Quits on an Unrequited Crush. I can’t promise it will keep you warm, but I hope it makes you smile.

Letter-Writing in the New Year Air

Wednesday, January 4th, 2012

Will this be the year letters take their final curtain call? In 2013 will we be saying, “Remember paper?” I think not! I am encouraged by the letter-writing whispers I heard just yesterday. First, artist Lisa Congdon has announced she’ll take on a letter-a-day challenge in 2012: 365 Days of Hand Lettering. Hats off to Lisa. And The New Yorker has posted an early-year ode to the letter with
Life And Letters. The article speaks the truth:

“If we stop writing letters, who will keep our history or dare venture upon a biography? George Washington, Oscar Wilde, T. E. Lawrence, Virginia Woolf, E. B. White, Oliver Wendell Holmes, Vera Nabokov, J. P. Morgan—if any of these vivid predecessors still belong to us in some fragmented private way, it’s because of their letters or diaries (which are letters to ourselves) or thanks to some strong biography built on a ledge of letters.”

My Dearest Self

Thursday, August 25th, 2011

While catching up on the posts over at, I spotted a link to an article called Writing a Letter to Yourself. This piece celebrates writing to yourself in a time-capsule type of way—taking a picture of your life with words rather than a camera. I haven’t done that. If I write a letter to myself, it’s in an emotional way. I try to step outside myself and be the voice of reason that often times only outsiders can be. In any case, the article offers some great tips for writing to yourself—whatever your reason.

Modern Love Rejects Update

Thursday, August 11th, 2011

When MLR first launched, we posted an essay a day for about a month and a half. It was a great way to start off. Things have waned since then, but the essays still trickle in. Someone with an 1800-2000 word rejected essay always manages to find our site.

We’ve had a good week this week—four fantastic essays have gone up. Stop by and read if you have a chance. Here’s a synopsis of each in reverse chronological order:

When the Married Boyfriend is Dying – The title here is pretty self-explanatory. The writer was involved in an affair that lasted for fifteen years! But when her lover discovered he had stage four liver cancer, she was devastated when she realized she wouldn’t be the one holding his hand in the hospital.

Savior – This is one of the best “The One Who Got Away” stories I’ve heard. The writer and her boyfriend came very close to death while on a bus heading to a free love hippie festival in Arizona. It took her a long time to recover physically and even longer to get over him.

My Freeloading Renaissance Man – This essay had me screaming “Nooooo! Don’t let him move in!” It’s crazy what people will do when they think they’re in love.

Friends with Benevolence – Trying to figure out if and how you can be friends with your ex is difficult. This gal’s ex comes through for her during a dark hour. Warning: A dog chokes to death in this essay. It’s very sad.

Big Things, Small Packages

Thursday, May 19th, 2011

Is this not the cutest thing EVER?!

Almost Back to Business

Tuesday, April 26th, 2011

I hereby solemnly swear that it will not be Modern Love Rejects all the time here on LetterLover, but I ask that you bear with me these first few days. I’m excited and we’re getting a great initial response. Just two more notes on MLR, and then it’s back to letters and the royal wedding (three days to go!) I promise.

1. My co-founder Kiri wrote about us for her blog at Forbes. Check it out: Turning Rejection Into A Business Of Love


2. Please stop by MLR tomorrow because there will be a great essay by Author Alisa Bowman called “I’m Leading This Marriage Dance.”

Okay, that’s all.