Samara O'Shea

Sample Break-up Letter

Sample Break-up Letter

As the saying goes, “Breaking-up is hard to do.” Letters don’t take the pain away but I think they can soften the blow sometimes. I suggest using break-up letters in one of two ways:
1. Use the letter as a starting point. Say the hard stuff in the letter then invite the other person to discuss it further. Most of us need a discussion of some sort.
2. Once the break-up is all said and done give the letter as an act of closure. An, “I’m sorry things didn’t work out but good luck to you” type of thing. (I know not all situations allow for this). I DO NOT recommend using the letter as the only means of breaking-up. However, (Gentlemen!) writing the letter is better than saying nothing at all and I’d be happy to help you do so.

It’s difficult to find a movie in which the featured couple doesn’t end up together, so this is an I’m-flattered-that-you-love-me-but-wish-you-hadn’t-tried-to-break-up-my-engagement letter from My Best Friend’s Wedding.

To: Julianne Poter (Julia Roberts character in My Best Friend’s Wedding)
From: Michael O’Neal
Circa 1997

I’m sorry our goodbye was so rushed. The crowd was a little overwhelming. Actually the whole week was a little overwhelming and, forgive me for being candid, but you weren’t the help I thought you’d be. I needed you Jules—to be my friend and make me laugh the nervousness away. I needed you to mock me while I was getting fitted for my tux. And, above all, I needed you to be there for my bride-to-be, to welcome Kimmie into your life for no other reason than you know how much I love her. That should be enough for you. I know you know this, but again, your attempted manipulation of her was not appreciated. It could have broken up my engagement, but more importantly it could have ended our friendship. To me, that’s not a risk worth taking!

Now of course I can’t be too angry, because you did everything in the name of being with me and, although I hate to say it, your antics are amusing. Plus, you did redeem yourself completely as you ran around the greater Chicago area with me to find my bride hours before the wedding. Kimmie appreciates everything you said to her at the stadium, as do I – it must have been difficult for you.

Julianne, please don’t ever think of this as being a “you vs. Kimmie” situation because it never has been. You were my first love. Savvy. Successful. Did I mention gorgeous? For years I didn’t think anyone could compete, but you made it clear I wasn’t for you and I was happy to hold on to you as a friend. But everyone needs to be loved back at some point. I couldn’t wait forever, and I found someone who loves me back. I’m sorry if she made you realize you had buried feelings for me, but you can’t claim me as your own just because you’re ready now.

Know that part of me will always love you, and I’ll stand-by you at your wedding the way you stood by me at mine (minus the unnecessary drama). Let’s keep this friendship thing going — we’re good at it. I’ll call you soon.

For better or for worse,